# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_U1
_database_code_depnum_ccdc_archive 'CCDC 1822958'
_audit_update_record             
;
2018-02-08 deposited with the CCDC.
2018-03-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
BS-II-U-69 2,3,5,6-Me4-pyrazine-1-oxide, urea
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H12 N2 O, C H4 N2 O'

_chemical_formula_sum            'C9 H16 N4 O2'
_chemical_formula_weight         212.26

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           Orthorhombic
_symmetry_space_group_name_H-M   Pbca
_space_group_name_Hall           '-P 2ac 2ab'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   12.646(13)
_cell_length_b                   7.002(7)
_cell_length_c                   22.75(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2014(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2222
_cell_measurement_theta_min      6.33
_cell_measurement_theta_max      31.40

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9584
_exptl_absorpt_correction_T_max  0.9919
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9231
_diffrn_reflns_av_R_equivalents  0.0650
_diffrn_reflns_av_sigmaI/netI    0.0751
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         6.33
_diffrn_reflns_theta_max         31.67
_reflns_number_total             3171
_reflns_number_gt                2069
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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 > 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)+(0.0850P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3171
_refine_ls_number_parameters     152
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0933
_refine_ls_R_factor_gt           0.0586
_refine_ls_wR_factor_ref         0.1694
_refine_ls_wR_factor_gt          0.1505
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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
N11 N 0.31829(10) 0.59806(16) 0.35661(5) 0.0246(3) Uani 1 1 d . . .
O11 O 0.41504(8) 0.59179(15) 0.34099(5) 0.0306(3) Uani 1 1 d . . .
C12 C 0.29340(12) 0.6302(2) 0.41324(7) 0.0271(3) Uani 1 1 d . . .
C13 C 0.18855(13) 0.6378(2) 0.42714(7) 0.0285(3) Uani 1 1 d . . .
N14 N 0.11375(10) 0.61503(18) 0.38806(6) 0.0279(3) Uani 1 1 d . . .
C15 C 0.14073(12) 0.58231(19) 0.33287(7) 0.0253(3) Uani 1 1 d . . .
C16 C 0.24353(12) 0.5714(2) 0.31571(7) 0.0248(3) Uani 1 1 d . . .
C22 C 0.38139(14) 0.6567(2) 0.45360(8) 0.0349(4) Uani 1 1 d . . .
H22A H 0.3544 0.6682 0.4938 0.052 Uiso 1 1 calc R . .
H22B H 0.4200 0.7731 0.4431 0.052 Uiso 1 1 calc R . .
H22C H 0.4290 0.5466 0.4511 0.052 Uiso 1 1 calc R . .
C23 C 0.15458(15) 0.6694(3) 0.48853(7) 0.0357(4) Uani 1 1 d . . .
H23A H 0.0773 0.6785 0.4901 0.054 Uiso 1 1 calc R . .
H23B H 0.1857 0.7884 0.5032 0.054 Uiso 1 1 calc R . .
H23C H 0.1782 0.5625 0.5130 0.054 Uiso 1 1 calc R . .
C25 C 0.05396(13) 0.5572(2) 0.29083(7) 0.0315(4) Uani 1 1 d . . .
H25A H -0.0134 0.5873 0.3100 0.047 Uiso 1 1 calc R . .
H25B H 0.0528 0.4245 0.2771 0.047 Uiso 1 1 calc R . .
H25C H 0.0645 0.6428 0.2573 0.047 Uiso 1 1 calc R . .
C26 C 0.28006(13) 0.5364(2) 0.25583(7) 0.0299(3) Uani 1 1 d . . .
H26A H 0.2196 0.5030 0.2309 0.045 Uiso 1 1 calc R . .
H26B H 0.3310 0.4310 0.2559 0.045 Uiso 1 1 calc R . .
H26C H 0.3141 0.6519 0.2405 0.045 Uiso 1 1 calc R . .
C31 C 0.66995(12) 0.57382(19) 0.37990(6) 0.0253(3) Uani 1 1 d . . .
N31 N 0.61549(12) 0.41246(19) 0.37643(7) 0.0319(3) Uani 1 1 d . . .
H31A H 0.5484(19) 0.415(3) 0.3685(9) 0.038 Uiso 1 1 d . . .
H31B H 0.6502(18) 0.308(3) 0.3846(8) 0.038 Uiso 1 1 d . . .
O31 O 0.76417(9) 0.57337(14) 0.39253(5) 0.0281(3) Uani 1 1 d . . .
N32 N 0.61965(12) 0.73470(19) 0.36787(6) 0.0289(3) Uani 1 1 d . . .
H32A H 0.5516(19) 0.730(3) 0.3639(8) 0.035 Uiso 1 1 d . . .
H32B H 0.6510(17) 0.843(3) 0.3757(8) 0.035 Uiso 1 1 d . . .


_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
N11 O11 1.275(2) . ?
N11 C16 1.339(2) . ?
N11 C12 1.345(2) . ?
C12 C13 1.364(3) . ?
C12 C22 1.454(2) . ?
C13 N14 1.308(2) . ?
C13 C23 1.478(3) . ?
N14 C15 1.321(2) . ?
C15 C16 1.360(2) . ?
C15 C25 1.466(2) . ?
C16 C26 1.459(2) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C31 O31 1.226(2) . ?
C31 N32 1.322(2) . ?
C31 N31 1.326(2) . ?
N31 H31A 0.87(2) . ?
N31 H31B 0.87(2) . ?
N32 H32A 0.87(2) . ?
N32 H32B 0.87(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
O11 N11 C16 118.61(14) . . ?
O11 N11 C12 119.83(12) . . ?
C16 N11 C12 121.56(14) . . ?
N11 C12 C13 117.12(14) . . ?
N11 C12 C22 116.54(15) . . ?
C13 C12 C22 126.33(16) . . ?
N14 C13 C12 122.74(16) . . ?
N14 C13 C23 116.77(16) . . ?
C12 C13 C23 120.49(15) . . ?
C13 N14 C15 118.71(15) . . ?
N14 C15 C16 121.97(14) . . ?
N14 C15 C25 116.58(15) . . ?
C16 C15 C25 121.45(15) . . ?
N11 C16 C15 117.88(15) . . ?
N11 C16 C26 116.65(15) . . ?
C15 C16 C26 125.46(14) . . ?
C12 C22 H22A 109.5 . . ?
C12 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C12 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C13 C23 H23A 109.5 . . ?
C13 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C13 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C15 C25 H25A 109.5 . . ?
C15 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C15 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C16 C26 H26A 109.5 . . ?
C16 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C16 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O31 C31 N32 121.22(13) . . ?
O31 C31 N31 121.12(14) . . ?
N32 C31 N31 117.64(16) . . ?
C31 N31 H31A 120.4(13) . . ?
C31 N31 H31B 116.1(14) . . ?
H31A N31 H31B 123(2) . . ?
C31 N32 H32A 118.0(13) . . ?
C31 N32 H32B 118.6(14) . . ?
H32A N32 H32B 120.2(19) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O11 N11 C12 C13 179.18(12) . . . . ?
C16 N11 C12 C13 -1.08(19) . . . . ?
O11 N11 C12 C22 0.15(19) . . . . ?
C16 N11 C12 C22 179.89(13) . . . . ?
N11 C12 C13 N14 0.1(2) . . . . ?
C22 C12 C13 N14 179.01(15) . . . . ?
N11 C12 C13 C23 179.02(14) . . . . ?
C22 C12 C13 C23 -2.1(2) . . . . ?
C12 C13 N14 C15 0.4(2) . . . . ?
C23 C13 N14 C15 -178.58(14) . . . . ?
C13 N14 C15 C16 0.1(2) . . . . ?
C13 N14 C15 C25 179.79(13) . . . . ?
O11 N11 C16 C15 -178.72(12) . . . . ?
C12 N11 C16 C15 1.54(19) . . . . ?
O11 N11 C16 C26 0.15(18) . . . . ?
C12 N11 C16 C26 -179.59(13) . . . . ?
N14 C15 C16 N11 -1.0(2) . . . . ?
C25 C15 C16 N11 179.29(13) . . . . ?
N14 C15 C16 C26 -179.81(14) . . . . ?
C25 C15 C16 C26 0.5(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
N31 H31A O11 0.87(2) 2.19(2) 2.941(3) 145.4(17) .
N32 H32A O11 0.87(2) 2.05(2) 2.841(3) 151.8(18) .
N31 H31B O31 0.87(2) 1.98(2) 2.844(3) 172.7(19) 8_755
N32 H32B O31 0.87(2) 1.97(2) 2.845(3) 174(2) 8_765

_diffrn_measured_fraction_theta_max 0.931
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_measured_fraction_theta_full 'ACTA 50'
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.056
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_U4
_database_code_depnum_ccdc_archive 'CCDC 1822961'
_audit_update_record             
;
2018-02-08 deposited with the CCDC.
2018-03-12 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C6 H5 N O3, C H4 N2 O'
_chemical_formula_sum            'C7 H9 N3 O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         199.17

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.2016(19)
_cell_length_b                   26.812(6)
_cell_length_c                   9.497(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.392(13)
_cell_angle_gamma                90
_cell_volume                     1776.2(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9185
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      25.54
_cell_measurement_temperature    130.(2)

_exptl_crystal_description       Plates
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.522
_exptl_crystal_size_mid          0.384
_exptl_crystal_size_min          0.062
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832

_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   TWINABS

_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      130.(2)

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'Fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            3273
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_av_unetI/netI     0.0530
_diffrn_reflns_theta_min         1.52
_diffrn_reflns_theta_max         25.80
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measured_fraction_theta_full 'ACTA 50'
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11

_refine_special_details          
;
;

_reflns_number_total             3273
_reflns_number_gt                2360
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0517
_refine_ls_wR_factor_gt          0.1260
_refine_ls_wR_factor_ref         0.1399
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_number_reflns         3273
_refine_ls_number_parameters     293
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0777P)²+0.2722P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.369
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

loop_
_atom_site_type_symbol
_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_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.7098(3) 0.72227(8) 0.7599(2) 0.0254(5) Uani d . . . 1 . .
H H1A 0.734(3) 0.7456(9) 0.819(3) 0.018(7) Uiso d . . . 1 . .
H H1B 0.809(4) 0.7080(9) 0.731(3) 0.035(7) Uiso d . . . 1 . .
C C2 0.5426(3) 0.69844(8) 0.7334(2) 0.0175(5) Uani d . . . 1 . .
H H3A 0.417(3) 0.7447(10) 0.826(3) 0.025(7) Uiso d . . . 1 . .
H H3B 0.288(4) 0.7032(9) 0.760(3) 0.032(7) Uiso d . . . 1 . .
N N3 0.4028(3) 0.71692(8) 0.7877(2) 0.0242(5) Uani d . . . 1 . .
O O4 0.5171(2) 0.65885(5) 0.65852(16) 0.0212(4) Uani d . . . 1 . .
H H5A 0.187(3) 0.5661(10) 0.696(3) 0.031(7) Uiso d . . . 1 . .
H H5B 0.287(4) 0.6115(9) 0.678(2) 0.025(7) Uiso d . . . 1 . .
N N5 0.1899(3) 0.59635(8) 0.6882(2) 0.0239(5) Uani d . . . 1 . .
C C6 0.0314(3) 0.62203(8) 0.6848(2) 0.0175(5) Uani d . . . 1 . .
H H7A -0.130(4) 0.5671(10) 0.688(3) 0.035(8) Uiso d . . . 1 . .
H H7B -0.238(4) 0.6145(9) 0.683(2) 0.026(6) Uiso d . . . 1 . .
N N7 -0.1272(3) 0.59737(8) 0.6895(2) 0.0254(5) Uani d . . . 1 . .
O O8 0.0291(2) 0.66936(5) 0.67564(15) 0.0197(4) Uani d . . . 1 . .
C C9 0.5060(3) 0.64350(8) 0.2947(2) 0.0192(5) Uani d . . . 1 . .
C C10 0.4652(3) 0.59634(7) 0.3360(2) 0.0193(5) Uani d . . . 1 . .
H H10 0.4535 0.5898 0.4318 0.023 Uiso calc U . R 1 . .
C C11 0.4417(3) 0.55880(7) 0.2335(2) 0.0198(5) Uani d . . . 1 . .
C C12 0.4543(3) 0.56638(8) 0.0922(2) 0.0238(6) Uani d . . . 1 . .
H H12 0.438 0.5397 0.0245 0.029 Uiso calc U . R 1 . .
C C13 0.4915(3) 0.61428(8) 0.0531(3) 0.0232(5) Uani d . . . 1 . .
H H13 0.4992 0.6208 -0.0436 0.028 Uiso calc U . R 1 . .
C C14 0.5176(3) 0.65276(8) 0.1529(2) 0.0227(6) Uani d . . . 1 . .
H H14 0.5435 0.6855 0.1247 0.027 Uiso calc U . R 1 . .
H H15 0.523(4) 0.6742(11) 0.478(3) 0.058(9) Uiso d . . . 1 . .
O O15 0.5392(2) 0.68256(5) 0.39054(18) 0.0258(4) Uani d . . . 1 . .
N N16 0.3976(3) 0.50898(7) 0.2773(2) 0.0259(5) Uani d . . . 1 . .
O O17 0.4374(3) 0.47278(6) 0.2108(2) 0.0403(5) Uani d . . . 1 . .
O O18 0.3216(2) 0.50513(6) 0.37906(19) 0.0343(5) Uani d . . . 1 . .
C C19 1.0062(3) 0.66997(8) 0.3021(2) 0.0202(5) Uani d . . . 1 . .
C C20 0.9677(3) 0.62045(8) 0.3251(2) 0.0197(5) Uani d . . . 1 . .
H H20 0.9492 0.6096 0.4159 0.024 Uiso calc U . R 1 . .
C C21 0.9568(3) 0.58725(8) 0.2122(2) 0.0199(5) Uani d . . . 1 . .
C C22 0.9791(3) 0.60103(8) 0.0770(2) 0.0246(6) Uani d . . . 1 . .
H H22 0.9712 0.5773 0.0014 0.03 Uiso calc U . R 1 . .
C C23 1.0132(3) 0.65090(9) 0.0569(3) 0.0273(6) Uani d . . . 1 . .
H H23 1.0278 0.6618 -0.0349 0.033 Uiso calc U . R 1 . .
C C24 1.0266(3) 0.68521(8) 0.1670(2) 0.0240(6) Uani d . . . 1 . .
H H24 1.0498 0.7193 0.1505 0.029 Uiso calc U . R 1 . .
H H25 1.017(4) 0.6928(10) 0.494(3) 0.052(9) Uiso d . . . 1 . .
O O25 1.0222(2) 0.70562(6) 0.40732(19) 0.0285(4) Uani d . . . 1 . .
N N26 0.9173(3) 0.53490(7) 0.2380(2) 0.0259(5) Uani d . . . 1 . .
O O27 0.9265(3) 0.50432(6) 0.14342(19) 0.0430(5) Uani d . . . 1 . .
O O28 0.8774(2) 0.52333(6) 0.35147(18) 0.0311(4) Uani d . . . 1 . .


_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
N1 C2 . 1.331(3) ?
N1 H1A . 0.83(2) ?
N1 H1B . 0.91(3) ?
C2 O4 . 1.265(2) ?
C2 N3 . 1.336(3) ?
N3 H3A . 0.82(3) ?
N3 H3B . 0.88(3) ?
N5 C6 . 1.327(3) ?
N5 H5A . 0.82(3) ?
N5 H5B . 0.83(2) ?
C6 O8 . 1.272(2) ?
C6 N7 . 1.330(3) ?
N7 H7A . 0.81(3) ?
N7 H7B . 0.91(2) ?
C9 O15 . 1.369(3) ?
C9 C10 . 1.377(3) ?
C9 C14 . 1.393(3) ?
C10 C11 . 1.381(3) ?
C10 H10 . 0.95 ?
C11 C12 . 1.383(3) ?
C11 N16 . 1.457(3) ?
C12 C13 . 1.382(3) ?
C12 H12 . 0.95 ?
C13 C14 . 1.382(3) ?
C13 H13 . 0.95 ?
C14 H14 . 0.95 ?
O15 H15 . 0.90(3) ?
N16 O18 . 1.228(2) ?
N16 O17 . 1.230(2) ?
C19 O25 . 1.367(3) ?
C19 C20 . 1.385(3) ?
C19 C24 . 1.388(3) ?
C20 C21 . 1.381(3) ?
C20 H20 . 0.95 ?
C21 C22 . 1.383(3) ?
C21 N26 . 1.465(3) ?
C22 C23 . 1.381(3) ?
C22 H22 . 0.95 ?
C23 C24 . 1.378(3) ?
C23 H23 . 0.95 ?
C24 H24 . 0.95 ?
O25 H25 . 0.90(3) ?
N26 O28 . 1.222(2) ?
N26 O27 . 1.230(2) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 N1 H1A . . 121.2(16) ?
C2 N1 H1B . . 118.9(16) ?
H1A N1 H1B . . 118.(2) ?
O4 C2 N1 . . 120.5(2) ?
O4 C2 N3 . . 120.7(2) ?
N1 C2 N3 . . 118.8(2) ?
C2 N3 H3A . . 118.8(17) ?
C2 N3 H3B . . 118.1(16) ?
H3A N3 H3B . . 121.(2) ?
C6 N5 H5A . . 118.4(17) ?
C6 N5 H5B . . 119.0(16) ?
H5A N5 H5B . . 123.(2) ?
O8 C6 N5 . . 121.07(19) ?
O8 C6 N7 . . 120.1(2) ?
N5 C6 N7 . . 118.8(2) ?
C6 N7 H7A . . 120.8(18) ?
C6 N7 H7B . . 119.4(14) ?
H7A N7 H7B . . 119.(2) ?
O15 C9 C10 . . 121.86(19) ?
O15 C9 C14 . . 117.65(19) ?
C10 C9 C14 . . 120.5(2) ?
C9 C10 C11 . . 117.8(2) ?
C9 C10 H10 . . 121.1 ?
C11 C10 H10 . . 121.1 ?
C10 C11 C12 . . 123.4(2) ?
C10 C11 N16 . . 117.67(19) ?
C12 C11 N16 . . 118.90(19) ?
C13 C12 C11 . . 117.5(2) ?
C13 C12 H12 . . 121.3 ?
C11 C12 H12 . . 121.3 ?
C14 C13 C12 . . 120.8(2) ?
C14 C13 H13 . . 119.6 ?
C12 C13 H13 . . 119.6 ?
C13 C14 C9 . . 120.0(2) ?
C13 C14 H14 . . 120.0 ?
C9 C14 H14 . . 120.0 ?
C9 O15 H15 . . 112.6(19) ?
O18 N16 O17 . . 122.95(19) ?
O18 N16 C11 . . 118.23(18) ?
O17 N16 C11 . . 118.82(19) ?
O25 C19 C20 . . 122.6(2) ?
O25 C19 C24 . . 117.4(2) ?
C20 C19 C24 . . 120.0(2) ?
C21 C20 C19 . . 118.1(2) ?
C21 C20 H20 . . 121.0 ?
C19 C20 H20 . . 121.0 ?
C20 C21 C22 . . 123.5(2) ?
C20 C21 N26 . . 117.63(19) ?
C22 C21 N26 . . 118.90(19) ?
C23 C22 C21 . . 116.9(2) ?
C23 C22 H22 . . 121.5 ?
C21 C22 H22 . . 121.5 ?
C24 C23 C22 . . 121.5(2) ?
C24 C23 H23 . . 119.3 ?
C22 C23 H23 . . 119.3 ?
C23 C24 C19 . . 120.1(2) ?
C23 C24 H24 . . 120.0 ?
C19 C24 H24 . . 120.0 ?
C19 O25 H25 . . 112.6(17) ?
O28 N26 O27 . . 122.81(19) ?
O28 N26 C21 . . 119.25(18) ?
O27 N26 C21 . . 117.9(2) ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O15 C9 C10 C11 . . . . -177.32(19) ?
C14 C9 C10 C11 . . . . 1.7(3) ?
C9 C10 C11 C12 . . . . -1.0(3) ?
C9 C10 C11 N16 . . . . -179.71(19) ?
C10 C11 C12 C13 . . . . -0.3(3) ?
N16 C11 C12 C13 . . . . 178.40(19) ?
C11 C12 C13 C14 . . . . 0.9(3) ?
C12 C13 C14 C9 . . . . -0.2(3) ?
O15 C9 C14 C13 . . . . 177.9(2) ?
C10 C9 C14 C13 . . . . -1.1(3) ?
C10 C11 N16 O18 . . . . 24.0(3) ?
C12 C11 N16 O18 . . . . -154.7(2) ?
C10 C11 N16 O17 . . . . -156.2(2) ?
C12 C11 N16 O17 . . . . 25.0(3) ?
O25 C19 C20 C21 . . . . -179.17(19) ?
C24 C19 C20 C21 . . . . 2.1(3) ?
C19 C20 C21 C22 . . . . -1.2(3) ?
C19 C20 C21 N26 . . . . 179.60(18) ?
C20 C21 C22 C23 . . . . -0.2(3) ?
N26 C21 C22 C23 . . . . 179.0(2) ?
C21 C22 C23 C24 . . . . 0.7(3) ?
C22 C23 C24 C19 . . . . 0.2(3) ?
O25 C19 C24 C23 . . . . 179.6(2) ?
C20 C19 C24 C23 . . . . -1.6(3) ?
C20 C21 N26 O28 . . . . 6.9(3) ?
C22 C21 N26 O28 . . . . -172.30(19) ?
C20 C21 N26 O27 . . . . -172.8(2) ?
C22 C21 N26 O27 . . . . 7.9(3) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1A O15 4_576 0.83(2) 2.57(2) 3.212(3) 134.9(19) ?
N1 H1A O25 4_576 0.83(2) 2.42(2) 3.032(3) 131.2(19) ?
N1 H1B O8 1_655 0.91(3) 2.07(3) 2.976(3) 174.(2) ?
N3 H3A O15 4_576 0.82(3) 2.16(3) 2.950(3) 159.(2) ?
N3 H3B O8 . 0.88(3) 2.05(3) 2.929(3) 174.(2) ?
N5 H5A O28 3_666 0.82(3) 2.46(3) 3.253(3) 164.(2) ?
N5 H5B O4 . 0.83(2) 2.13(3) 2.962(3) 172.(2) ?
N7 H7A O18 3_566 0.81(3) 2.37(3) 3.079(3) 146.(2) ?
N7 H7B O4 1_455 0.91(2) 2.09(3) 2.998(3) 175.(2) ?
O15 H15 O4 . 0.90(3) 1.77(3) 2.666(2) 174.(3) ?
O25 H25 O8 1_655 0.90(3) 1.82(3) 2.716(2) 175.(3) ?

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_U3
_database_code_depnum_ccdc_archive 'CCDC 1822960'
_audit_update_record             
;
2018-02-08 deposited with the CCDC.
2018-03-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
BS-II-U-5 (urea)2, citric acid
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H8 O7, 2(C H4 N2 O)'

_chemical_formula_sum            'C8 H16 N4 O9'
_chemical_formula_weight         312.25

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           Triclinic
_symmetry_space_group_name_H-M   P-1
_space_group_name_Hall           '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.5395(5)
_cell_length_b                   6.7758(5)
_cell_length_c                   15.2596(11)
_cell_angle_alpha                81.525(2)
_cell_angle_beta                 85.861(2)
_cell_angle_gamma                74.230(2)
_cell_volume                     643.24(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9985
_cell_measurement_theta_min      3.15
_cell_measurement_theta_max      32.61

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.36
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.612
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             328
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9408
_exptl_absorpt_correction_T_max  0.9490
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19260
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_sigmaI/netI    0.0204
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.35
_diffrn_reflns_theta_max         32.61
_reflns_number_total             4243
_reflns_number_gt                3790
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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 > 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)+(0.0600P)²+0.1500P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4243
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.1013
_refine_ls_wR_factor_gt          0.0980
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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
C11 C 0.28441(14) 0.50096(13) 0.41634(6) 0.01313(16) Uani 1 1 d . . .
O11 O 0.23654(12) 0.54227(11) 0.49869(4) 0.01748(14) Uani 1 1 d . . .
H11 H 0.230(2) 0.432(2) 0.5324(10) 0.021 Uiso 1 1 d . . .
O12 O 0.30821(12) 0.33194(10) 0.39380(5) 0.01928(15) Uani 1 1 d . . .
C12 C 0.30048(14) 0.69234(13) 0.35533(6) 0.01273(15) Uani 1 1 d . . .
H12A H 0.3776 0.7684 0.3857 0.015 Uiso 1 1 calc R . .
H12B H 0.1551 0.7826 0.3450 0.015 Uiso 1 1 calc R . .
C13 C 0.41165(13) 0.65503(12) 0.26564(5) 0.01115(15) Uani 1 1 d . . .
O13 O 0.62817(10) 0.54455(10) 0.27365(4) 0.01256(13) Uani 1 1 d . . .
H13 H 0.688(2) 0.617(2) 0.2978(9) 0.015 Uiso 1 1 d . . .
C14 C 0.38766(14) 0.87179(13) 0.21107(6) 0.01371(16) Uani 1 1 d . . .
H14A H 0.2413 0.9250 0.1893 0.016 Uiso 1 1 calc R . .
H14B H 0.4096 0.9682 0.2501 0.016 Uiso 1 1 calc R . .
C15 C 0.54366(14) 0.86644(13) 0.13336(6) 0.01301(16) Uani 1 1 d . . .
O14 O 0.50099(11) 0.77629(11) 0.06840(4) 0.01548(13) Uani 1 1 d . . .
H14 H 0.600(2) 0.768(2) 0.0272(10) 0.019 Uiso 1 1 d . . .
O15 O 0.69620(11) 0.93710(11) 0.13158(5) 0.01721(14) Uani 1 1 d . . .
C16 C 0.29748(14) 0.53582(13) 0.21741(6) 0.01270(15) Uani 1 1 d . . .
O16 O 0.42215(10) 0.38633(10) 0.17684(4) 0.01455(13) Uani 1 1 d . . .
H16 H 0.346(2) 0.342(2) 0.1433(9) 0.017 Uiso 1 1 d . . .
O17 O 0.10549(11) 0.58749(12) 0.21488(5) 0.01951(15) Uani 1 1 d . . .
C21 C 0.23723(14) 0.05206(13) 0.61604(6) 0.01307(16) Uani 1 1 d . . .
N21 N 0.24297(14) -0.01710(13) 0.53810(5) 0.01837(16) Uani 1 1 d . . .
H21A H 0.252(2) 0.070(2) 0.4906(10) 0.022 Uiso 1 1 d . . .
H21B H 0.243(2) -0.141(2) 0.5343(10) 0.022 Uiso 1 1 d . . .
N22 N 0.22995(14) -0.07707(13) 0.69059(5) 0.01763(16) Uani 1 1 d . . .
H22A H 0.236(2) -0.028(2) 0.7404(10) 0.021 Uiso 1 1 d . . .
H22B H 0.263(2) -0.209(2) 0.6896(10) 0.021 Uiso 1 1 d . . .
O21 O 0.23101(11) 0.23864(10) 0.61923(4) 0.01530(14) Uani 1 1 d . . .
C31 C 0.97288(14) 0.71826(13) -0.06014(6) 0.01244(15) Uani 1 1 d . . .
N31 N 1.05220(13) 0.76342(13) 0.00993(5) 0.01599(15) Uani 1 1 d . . .
H31A H 0.966(2) 0.812(2) 0.0488(10) 0.019 Uiso 1 1 d . . .
H31B H 1.182(2) 0.756(2) 0.0103(9) 0.019 Uiso 1 1 d . . .
O31 O 0.77430(10) 0.73601(10) -0.06232(4) 0.01403(13) Uani 1 1 d . . .
N32 N 1.10155(13) 0.65629(13) -0.12829(5) 0.01689(16) Uani 1 1 d . . .
H32A H 1.056(2) 0.591(2) -0.1648(10) 0.020 Uiso 1 1 d . . .
H32B H 1.234(2) 0.645(2) -0.1258(9) 0.020 Uiso 1 1 d . . .


_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
C11 O12 1.2106(11) . ?
C11 O11 1.3248(11) . ?
C11 C12 1.5045(12) . ?
O11 H11 0.853(16) . ?
C12 C13 1.5245(11) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 O13 1.4150(10) . ?
C13 C16 1.5276(12) . ?
C13 C14 1.5518(12) . ?
O13 H13 0.843(14) . ?
C14 C15 1.5054(12) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 O15 1.2153(11) . ?
C15 O14 1.3208(10) . ?
O14 H14 0.865(15) . ?
C16 O17 1.2102(11) . ?
C16 O16 1.3180(10) . ?
O16 H16 0.874(14) . ?
C21 O21 1.2618(10) . ?
C21 N22 1.3354(12) . ?
C21 N21 1.3357(11) . ?
N21 H21A 0.876(16) . ?
N21 H21B 0.851(15) . ?
N22 H22A 0.881(15) . ?
N22 H22B 0.866(15) . ?
C31 O31 1.2737(11) . ?
C31 N31 1.3299(11) . ?
C31 N32 1.3327(12) . ?
N31 H31A 0.831(15) . ?
N31 H31B 0.837(15) . ?
N32 H32A 0.872(15) . ?
N32 H32B 0.851(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
O12 C11 O11 123.99(8) . . ?
O12 C11 C12 125.13(8) . . ?
O11 C11 C12 110.86(7) . . ?
C11 O11 H11 109.6(10) . . ?
C11 C12 C13 115.45(7) . . ?
C11 C12 H12A 108.4 . . ?
C13 C12 H12A 108.4 . . ?
C11 C12 H12B 108.4 . . ?
C13 C12 H12B 108.4 . . ?
H12A C12 H12B 107.5 . . ?
O13 C13 C12 112.31(7) . . ?
O13 C13 C16 109.36(7) . . ?
C12 C13 C16 109.72(7) . . ?
O13 C13 C14 111.21(7) . . ?
C12 C13 C14 106.25(7) . . ?
C16 C13 C14 107.86(7) . . ?
C13 O13 H13 106.9(9) . . ?
C15 C14 C13 112.20(7) . . ?
C15 C14 H14A 109.2 . . ?
C13 C14 H14A 109.2 . . ?
C15 C14 H14B 109.2 . . ?
C13 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
O15 C15 O14 123.42(8) . . ?
O15 C15 C14 122.56(8) . . ?
O14 C15 C14 114.02(8) . . ?
C15 O14 H14 110.7(9) . . ?
O17 C16 O16 124.50(8) . . ?
O17 C16 C13 119.95(8) . . ?
O16 C16 C13 115.45(7) . . ?
C16 O16 H16 109.3(9) . . ?
O21 C21 N22 120.43(8) . . ?
O21 C21 N21 120.49(8) . . ?
N22 C21 N21 119.04(8) . . ?
C21 N21 H21A 116.6(10) . . ?
C21 N21 H21B 122.2(10) . . ?
H21A N21 H21B 121.1(14) . . ?
C21 N22 H22A 116.1(10) . . ?
C21 N22 H22B 120.5(10) . . ?
H22A N22 H22B 120.0(14) . . ?
O31 C31 N31 120.02(8) . . ?
O31 C31 N32 120.20(8) . . ?
N31 C31 N32 119.78(8) . . ?
C31 N31 H31A 116.8(10) . . ?
C31 N31 H31B 119.7(10) . . ?
H31A N31 H31B 123.1(14) . . ?
C31 N32 H32A 117.6(9) . . ?
C31 N32 H32B 119.0(9) . . ?
H32A N32 H32B 120.4(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O12 C11 C12 C13 -17.02(13) . . . . ?
O11 C11 C12 C13 164.10(7) . . . . ?
C11 C12 C13 O13 -64.21(9) . . . . ?
C11 C12 C13 C16 57.64(9) . . . . ?
C11 C12 C13 C14 173.99(7) . . . . ?
O13 C13 C14 C15 39.71(9) . . . . ?
C12 C13 C14 C15 162.21(7) . . . . ?
C16 C13 C14 C15 -80.20(9) . . . . ?
C13 C14 C15 O15 -107.37(10) . . . . ?
C13 C14 C15 O14 71.84(9) . . . . ?
O13 C13 C16 O17 169.31(8) . . . . ?
C12 C13 C16 O17 45.70(11) . . . . ?
C14 C13 C16 O17 -69.62(10) . . . . ?
O13 C13 C16 O16 -14.08(10) . . . . ?
C12 C13 C16 O16 -137.68(8) . . . . ?
C14 C13 C16 O16 106.99(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
O11 H11 O21 0.853(16) 1.718(16) 2.5559(10) 166.5(14) .
O14 H14 O31 0.865(15) 1.716(15) 2.5746(9) 171.7(14) .
O13 H13 O21 0.843(14) 1.892(14) 2.7090(9) 163.0(13) 2_666
O16 H16 O31 0.874(14) 1.727(14) 2.5926(9) 170.0(13) 2_665
N21 H21A O12 0.876(16) 2.227(16) 3.0825(11) 165.4(13) .
N21 H21B O11 0.851(15) 2.301(15) 3.1429(11) 170.3(13) 1_545
N22 H22A O15 0.881(15) 2.240(15) 3.1134(11) 170.8(13) 2_666
N22 H22B O13 0.866(15) 2.186(15) 3.0262(10) 163.3(13) 2_656
N31 H31A O15 0.831(15) 2.144(15) 2.9634(11) 168.8(13) .
N31 H31B O14 0.837(15) 2.370(15) 3.1555(11) 156.5(13) 1_655
N32 H32A O17 0.872(15) 2.062(15) 2.9025(11) 161.5(13) 2_665
N32 H32B O16 0.851(15) 2.291(15) 3.0943(11) 157.5(13) 2_765

_diffrn_measured_fraction_theta_max 0.904
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_measured_fraction_theta_full 'ACTA 50'
_refine_diff_density_max         0.487
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.059
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_U2
_database_code_depnum_ccdc_archive 'CCDC 1822959'
_audit_update_record             
;
2018-02-08 deposited with the CCDC.
2018-03-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
BS-II-U-79 urea, 2,3,5,6-Me4-pyrazine-1,4-dioxide
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H12 N2 O2, C H4 N2 O'

_chemical_formula_sum            'C9 H16 N4 O3'
_chemical_formula_weight         228.26

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   P2(1)/c
_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                   11.6812(10)
_cell_length_b                   13.2376(12)
_cell_length_c                   6.9737(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.298(4)
_cell_angle_gamma                90.00
_cell_volume                     1060.98(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9255
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      32.49

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9556
_exptl_absorpt_correction_T_max  0.9892
_exptl_absorpt_process_details   TWINABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5593
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0345
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.77
_diffrn_reflns_theta_max         32.94
_reflns_number_total             5593
_reflns_number_gt                4089
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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 > 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)+(0.0900P)²+0.1000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5593
_refine_ls_number_parameters     162
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0749
_refine_ls_R_factor_gt           0.0529
_refine_ls_wR_factor_ref         0.1607
_refine_ls_wR_factor_gt          0.1456
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_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
N11 N 0.21128(9) 0.17441(7) 0.30352(15) 0.0190(2) Uani 1 1 d . . .
O11 O 0.18146(8) 0.07945(6) 0.29756(14) 0.0253(2) Uani 1 1 d . . .
C12 C 0.12651(10) 0.24658(8) 0.28924(16) 0.0186(2) Uani 1 1 d . . .
C13 C 0.15685(10) 0.34678(8) 0.29577(18) 0.0190(2) Uani 1 1 d . . .
N14 N 0.27222(9) 0.37311(7) 0.31845(15) 0.0205(2) Uani 1 1 d . . .
O14 O 0.30012(8) 0.46741(7) 0.32817(14) 0.0335(2) Uani 1 1 d . . .
C15 C 0.35652(11) 0.30052(9) 0.33089(18) 0.0208(3) Uani 1 1 d . . .
C16 C 0.32602(11) 0.20040(9) 0.32316(18) 0.0206(3) Uani 1 1 d . . .
C22 C 0.00537(11) 0.20744(9) 0.2668(2) 0.0266(3) Uani 1 1 d . . .
H22A H -0.0005 0.1610 0.3740 0.040 Uiso 1 1 calc R . .
H22B H -0.0146 0.1715 0.1424 0.040 Uiso 1 1 calc R . .
H22C H -0.0485 0.2640 0.2691 0.040 Uiso 1 1 calc R . .
C23 C 0.07374(11) 0.43296(9) 0.2786(2) 0.0257(3) Uani 1 1 d . . .
H23A H -0.0061 0.4070 0.2569 0.039 Uiso 1 1 calc R . .
H23B H 0.0845 0.4758 0.1687 0.039 Uiso 1 1 calc R . .
H23C H 0.0881 0.4727 0.3991 0.039 Uiso 1 1 calc R . .
C25 C 0.47859(11) 0.33708(11) 0.3517(2) 0.0295(3) Uani 1 1 d . . .
H25A H 0.5207 0.2959 0.2704 0.044 Uiso 1 1 calc R . .
H25B H 0.5168 0.3317 0.4884 0.044 Uiso 1 1 calc R . .
H25C H 0.4787 0.4078 0.3101 0.044 Uiso 1 1 calc R . .
C26 C 0.40908(12) 0.11422(10) 0.3342(2) 0.0293(3) Uani 1 1 d . . .
H26A H 0.4888 0.1402 0.3509 0.044 Uiso 1 1 calc R . .
H26B H 0.3920 0.0747 0.2136 0.044 Uiso 1 1 calc R . .
H26C H 0.4011 0.0711 0.4453 0.044 Uiso 1 1 calc R . .
N31 N 0.25204(12) -0.11811(9) 0.48425(17) 0.0265(3) Uani 1 1 d . . .
H31A H 0.2385(14) -0.0563(13) 0.476(2) 0.032 Uiso 1 1 d . . .
H31B H 0.2675(14) -0.1480(12) 0.594(2) 0.032 Uiso 1 1 d . . .
C32 C 0.26240(10) -0.16971(8) 0.32302(18) 0.0181(2) Uani 1 1 d . . .
O32 O 0.28951(7) -0.26099(6) 0.33025(12) 0.0218(2) Uani 1 1 d . . .
N33 N 0.23831(10) -0.12020(8) 0.15184(16) 0.0222(2) Uani 1 1 d . . .
H33A H 0.2277(13) -0.0580(13) 0.1541(19) 0.027 Uiso 1 1 d . . .
H33B H 0.2534(14) -0.1509(11) 0.055(2) 0.027 Uiso 1 1 d . . .


_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
N11 O11 1.3030(12) . ?
N11 C12 1.3667(14) . ?
N11 C16 1.3668(16) . ?
C12 C13 1.3716(15) . ?
C12 C22 1.4887(17) . ?
C13 N14 1.3735(15) . ?
C13 C23 1.4889(16) . ?
N14 O14 1.2888(12) . ?
N14 C15 1.3675(15) . ?
C15 C16 1.3710(17) . ?
C15 C25 1.4881(18) . ?
C16 C26 1.4905(17) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
N31 C32 1.3395(16) . ?
N31 H31A 0.833(17) . ?
N31 H31B 0.849(16) . ?
C32 O32 1.2477(13) . ?
C32 N33 1.3467(15) . ?
N33 H33A 0.834(16) . ?
N33 H33B 0.836(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
O11 N11 C12 119.08(10) . . ?
O11 N11 C16 119.85(10) . . ?
C12 N11 C16 121.07(10) . . ?
N11 C12 C13 119.60(11) . . ?
N11 C12 C22 115.28(10) . . ?
C13 C12 C22 125.11(11) . . ?
C12 C13 N14 119.45(10) . . ?
C12 C13 C23 125.27(11) . . ?
N14 C13 C23 115.29(10) . . ?
O14 N14 C15 120.32(10) . . ?
O14 N14 C13 119.05(10) . . ?
C15 N14 C13 120.64(10) . . ?
N14 C15 C16 119.85(11) . . ?
N14 C15 C25 116.37(11) . . ?
C16 C15 C25 123.78(11) . . ?
N11 C16 C15 119.37(11) . . ?
N11 C16 C26 115.48(11) . . ?
C15 C16 C26 125.15(12) . . ?
C12 C22 H22A 109.5 . . ?
C12 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C12 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C13 C23 H23A 109.5 . . ?
C13 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C13 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C15 C25 H25A 109.5 . . ?
C15 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C15 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C16 C26 H26A 109.5 . . ?
C16 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C16 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C32 N31 H31A 119.1(10) . . ?
C32 N31 H31B 118.6(11) . . ?
H31A N31 H31B 121.9(15) . . ?
O32 C32 N31 121.35(11) . . ?
O32 C32 N33 121.22(11) . . ?
N31 C32 N33 117.38(11) . . ?
C32 N33 H33A 118.2(9) . . ?
C32 N33 H33B 116.2(10) . . ?
H33A N33 H33B 123.4(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O11 N11 C12 C13 179.86(11) . . . . ?
C16 N11 C12 C13 -0.37(17) . . . . ?
O11 N11 C12 C22 -0.27(16) . . . . ?
C16 N11 C12 C22 179.50(12) . . . . ?
N11 C12 C13 N14 -0.61(18) . . . . ?
C22 C12 C13 N14 179.53(12) . . . . ?
N11 C12 C13 C23 178.92(11) . . . . ?
C22 C12 C13 C23 -0.9(2) . . . . ?
C12 C13 N14 O14 -178.69(11) . . . . ?
C23 C13 N14 O14 1.73(17) . . . . ?
C12 C13 N14 C15 1.21(18) . . . . ?
C23 C13 N14 C15 -178.37(11) . . . . ?
O14 N14 C15 C16 179.08(11) . . . . ?
C13 N14 C15 C16 -0.82(19) . . . . ?
O14 N14 C15 C25 -1.16(17) . . . . ?
C13 N14 C15 C25 178.94(11) . . . . ?
O11 N11 C16 C15 -179.47(11) . . . . ?
C12 N11 C16 C15 0.76(18) . . . . ?
O11 N11 C16 C26 0.64(17) . . . . ?
C12 N11 C16 C26 -179.13(11) . . . . ?
N14 C15 C16 N11 -0.16(19) . . . . ?
C25 C15 C16 N11 -179.91(11) . . . . ?
N14 C15 C16 C26 179.72(12) . . . . ?
C25 C15 C16 C26 0.0(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
N31 H31A O11 0.833(17) 2.219(17) 2.9716(15) 150.3(13) .
N33 H33A O11 0.834(16) 2.189(16) 2.9496(15) 151.6(12) .
N31 H31B O32 0.849(16) 2.022(16) 2.8632(15) 170.3(15) 4_556
N33 H33B O32 0.836(16) 2.054(16) 2.8880(15) 174.5(14) 4

_diffrn_measured_fraction_theta_max 0.905
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.072
