# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1586812'
_audit_update_record             
;
2017-11-21 deposited with the CCDC.
2018-11-26 downloaded from the CCDC.
;
_audit_creation_date             2017-11-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H11 Cl N6 Na2 O13 U, H2 O'
_chemical_formula_sum            'C15 H13 Cl N6 Na2 O14 U'
_chemical_formula_weight         820.77
_chemical_melting_point          ?
_chemical_oxdiff_formula         c12h12n2u1
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'
Cl Cl 0.1484 0.1585 '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'
Na Na 0.0362 0.0249 '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'
U U -9.6767 9.6646 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 1 2/n 1'
_space_group_name_Hall           '-P 2yac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z-1/2'

_cell_length_a                   15.1242(3)
_cell_length_b                   7.06510(10)
_cell_length_c                   23.2973(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.600(2)
_cell_angle_gamma                90
_cell_volume                     2409.02(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3761
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.8400
_cell_measurement_theta_min      3.1330
_shelx_estimated_absorpt_T_max   0.229
_shelx_estimated_absorpt_T_min   0.194
_exptl_absorpt_coefficient_mu    6.968
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60425
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    2.263
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            10946
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.373
_diffrn_reflns_theta_min         2.912
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00  19.20   0.70    3.50    --  -14.97 -99.00 150.00   56
  2  ω    -37.00  72.20   0.70    3.50    --   16.69   0.00-120.00  156
  3  ω     12.00  85.50   0.70    3.50    --   16.69  38.00 -90.00  105
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0107795000
_diffrn_orient_matrix_UB_12      0.0221305000
_diffrn_orient_matrix_UB_13      -0.0271437000
_diffrn_orient_matrix_UB_21      0.0462241000
_diffrn_orient_matrix_UB_22      -0.0251114000
_diffrn_orient_matrix_UB_23      0.0126097000
_diffrn_orient_matrix_UB_31      -0.0097372000
_diffrn_orient_matrix_UB_32      -0.0946909000
_diffrn_orient_matrix_UB_33      -0.0096892000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4089
_reflns_number_total             4917
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.842
_refine_diff_density_min         -1.558
_refine_diff_density_rms         0.135
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         4917
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0334
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0333P)²+2.5865P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0711
_refine_ls_wR_factor_ref         0.0768
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 O13-H13B = O13-H13A
 0.86 with sigma of 0.02
 O13-H13B
 0.86 with sigma of 0.02
3.a Free rotating group:
 O14(H14A,H14B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
U1 U 0.77684(2) 0.71579(3) 0.48404(2) 0.02729(8) Uani 1 1 d . . . . .
O1 O 0.7836(3) 0.7108(6) 0.58661(16) 0.0419(10) Uani 1 1 d . . . . .
O2 O 0.8509(3) 0.6961(7) 0.68277(17) 0.0531(12) Uani 1 1 d . . . . .
O3 O 0.8601(3) 0.7195(6) 0.41467(17) 0.0432(10) Uani 1 1 d . . . . .
O4 O 0.8111(3) 0.6923(6) 0.31613(17) 0.0406(10) Uani 1 1 d . . . . .
O5 O 0.6592(3) 0.6984(5) 0.39628(16) 0.0351(9) Uani 1 1 d . . . . .
O6 O 0.5187(3) 0.6584(6) 0.34170(17) 0.0486(11) Uani 1 1 d . . . . .
O7 O 0.7735(3) 0.9596(6) 0.48509(15) 0.0413(10) Uani 1 1 d . . . . .
O8 O 0.7797(3) 0.4664(6) 0.48758(16) 0.0418(10) Uani 1 1 d . . . . .
N1 N 0.9394(3) 0.7388(6) 0.55831(19) 0.0311(11) Uani 1 1 d . . . . .
N2 N 1.0158(3) 0.7583(7) 0.5400(2) 0.0410(12) Uani 1 1 d . . . . .
N3 N 0.9826(3) 0.7053(7) 0.3043(2) 0.0380(11) Uani 1 1 d . . . . .
N4 N 1.0667(4) 0.7202(9) 0.2966(2) 0.0558(16) Uani 1 1 d . . . . .
N5 N 0.6054(3) 0.7294(6) 0.49446(19) 0.0298(10) Uani 1 1 d . . . . .
N6 N 0.5825(4) 0.7553(7) 0.5459(2) 0.0394(12) Uani 1 1 d . . . . .
C1 C 0.9434(4) 0.7397(7) 0.6158(2) 0.0294(12) Uani 1 1 d . . . . .
C2 C 1.0242(4) 0.7669(8) 0.6590(3) 0.0418(15) Uani 1 1 d . . . . .
H2 H 1.0249 0.7712 0.6990 0.050 Uiso 1 1 calc R . . . .
C3 C 1.1022(4) 0.7871(8) 0.6409(3) 0.0424(15) Uani 1 1 d . . . . .
H3 H 1.1584 0.8044 0.6680 0.051 Uiso 1 1 calc R . . . .
C4 C 1.0946(4) 0.7807(8) 0.5802(3) 0.0390(14) Uani 1 1 d . . . . .
H4 H 1.1475 0.7928 0.5671 0.047 Uiso 1 1 calc R . . . .
C5 C 0.8532(4) 0.7147(8) 0.6305(2) 0.0356(13) Uani 1 1 d . . . . .
C6 C 0.9692(4) 0.7304(7) 0.3580(2) 0.0260(11) Uani 1 1 d . . . . .
C7 C 1.0406(4) 0.7706(8) 0.4075(3) 0.0358(13) Uani 1 1 d . . . . .
H7 H 1.0300 0.7848 0.4449 0.043 Uiso 1 1 calc R . . . .
C8 C 1.1261(4) 0.7883(8) 0.3994(3) 0.0393(14) Uani 1 1 d . . . . .
H8 H 1.1760 0.8164 0.4308 0.047 Uiso 1 1 calc R . . . .
C9 C 1.1359(5) 0.7628(9) 0.3425(3) 0.0495(17) Uani 1 1 d . . . . .
H9 H 1.1938 0.7762 0.3360 0.059 Uiso 1 1 calc R . . . .
C10 C 0.8717(4) 0.7125(8) 0.3617(2) 0.0305(12) Uani 1 1 d . . . . .
C11 C 0.5398(4) 0.7184(7) 0.4440(2) 0.0302(12) Uani 1 1 d . . . . .
C12 C 0.4474(4) 0.7338(8) 0.4421(3) 0.0416(15) Uani 1 1 d . . . . .
H12 H 0.4028 0.7252 0.4064 0.050 Uiso 1 1 calc R . . . .
C13 C 0.4246(5) 0.7620(8) 0.4945(3) 0.0454(16) Uani 1 1 d . . . . .
H13 H 0.3640 0.7746 0.4960 0.054 Uiso 1 1 calc R . . . .
C14 C 0.4952(5) 0.7712(8) 0.5453(3) 0.0439(15) Uani 1 1 d . . . . .
H14 H 0.4804 0.7898 0.5813 0.053 Uiso 1 1 calc R . . . .
C15 C 0.5737(4) 0.6902(8) 0.3888(2) 0.0321(13) Uani 1 1 d . . . . .
Cl1 Cl 0.62462(10) 1.1896(2) 0.31927(6) 0.0380(3) Uani 1 1 d . . . . .
O9 O 0.6664(4) 1.1937(9) 0.3804(2) 0.091(2) Uani 1 1 d . . . . .
O10 O 0.6488(5) 1.3491(7) 0.2910(2) 0.0827(18) Uani 1 1 d . . . . .
O11 O 0.6511(4) 1.0286(7) 0.2912(2) 0.0849(18) Uani 1 1 d . . . . .
O12 O 0.5294(4) 1.1881(10) 0.3104(3) 0.091(2) Uani 1 1 d . . . . .
O13 O 0.6660(4) 0.6938(12) 0.6720(3) 0.0858(19) Uani 1 1 d D . . . .
H13A H 0.671(8) 0.727(12) 0.638(2) 0.12(4) Uiso 1 1 d D . . . .
H13B H 0.679(19) 0.577(12) 0.681(11) 0.49(18) Uiso 1 1 d D . . . .
O14 O 0.6641(5) 1.132(2) 0.7019(4) 0.191(5) Uani 1 1 d . . . . .
H14A H 0.6210 1.0911 0.7161 0.287 Uiso 1 1 d G . . . .
H14B H 0.6541 1.0999 0.6657 0.287 Uiso 1 1 d G . . . .
Na1 Na 0.65348(14) 0.6893(3) 0.28519(9) 0.0334(5) Uani 1 1 d . . . . .
Na2 Na 0.9215(2) 0.5445(4) 0.77612(10) 0.0684(9) Uani 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
U1 O1 2.366(4) . ?
U1 O3 2.286(4) . ?
U1 O5 2.351(4) . ?
U1 O7 1.723(5) . ?
U1 O8 1.764(4) . ?
U1 N1 2.630(5) . ?
U1 N5 2.666(5) . ?
O1 C5 1.270(7) . ?
O2 C5 1.235(7) . ?
O2 Na2 2.418(5) . ?
O3 C10 1.291(6) . ?
O4 C10 1.223(6) . ?
O4 Na1 2.548(4) 2_655 ?
O4 Na1 2.311(4) . ?
O5 C15 1.261(7) . ?
O5 Na1 2.568(4) . ?
O6 C15 1.220(6) . ?
O6 Na1 2.700(5) . ?
O6 Na2 2.327(5) 4_565 ?
N1 N2 1.336(7) . ?
N1 C1 1.325(7) . ?
N2 C4 1.327(8) . ?
N3 N4 1.332(7) . ?
N3 C6 1.328(7) . ?
N3 Na1 2.536(5) 2_655 ?
N4 C9 1.330(8) . ?
N4 Na2 2.559(6) 3_766 ?
N5 N6 1.342(6) . ?
N5 C11 1.337(7) . ?
N6 C14 1.321(8) . ?
C1 C2 1.387(8) . ?
C1 C5 1.498(8) . ?
C2 H2 0.9300 . ?
C2 C3 1.357(9) . ?
C3 H3 0.9300 . ?
C3 C4 1.391(8) . ?
C4 H4 0.9300 . ?
C6 C7 1.397(7) . ?
C6 C10 1.503(8) . ?
C7 H7 0.9300 . ?
C7 C8 1.359(8) . ?
C8 H8 0.9300 . ?
C8 C9 1.381(9) . ?
C9 H9 0.9300 . ?
C11 C12 1.391(8) . ?
C11 C15 1.512(8) . ?
C12 H12 0.9300 . ?
C12 C13 1.365(9) . ?
C13 H13 0.9300 . ?
C13 C14 1.381(10) . ?
C14 H14 0.9300 . ?
Cl1 O9 1.404(5) . ?
Cl1 O10 1.400(5) . ?
Cl1 O11 1.419(5) . ?
Cl1 O12 1.402(6) . ?
O10 Na1 2.409(5) 1_565 ?
O11 Na1 2.402(5) . ?
O12 Na2 2.493(7) 4_575 ?
O13 H13A 0.85(2) . ?
O13 H13B 0.864(15) . ?
O13 Na2 2.266(7) 2_656 ?
O14 H14A 0.8496 . ?
O14 H14B 0.8500 . ?
Na1 O4 2.548(4) 2_655 ?
Na1 N3 2.537(5) 2_655 ?
Na1 O10 2.409(5) 1_545 ?
Na1 Na1 3.691(4) 2_655 ?
Na1 Na2 3.835(3) 4_565 ?
Na2 O6 2.327(5) 4_666 ?
Na2 N4 2.559(6) 3_766 ?
Na2 O12 2.493(7) 4_676 ?
Na2 O13 2.266(7) 2_656 ?
Na2 Na1 3.835(3) 4_666 ?

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
O1 U1 N1 62.70(14) . . ?
O1 U1 N5 72.77(14) . . ?
O3 U1 O1 145.39(14) . . ?
O3 U1 O5 79.45(14) . . ?
O3 U1 N1 82.78(14) . . ?
O3 U1 N5 141.79(14) . . ?
O5 U1 O1 135.06(13) . . ?
O5 U1 N1 162.23(14) . . ?
O5 U1 N5 62.67(13) . . ?
O7 U1 O1 89.69(15) . . ?
O7 U1 O3 91.24(15) . . ?
O7 U1 O5 92.65(15) . . ?
O7 U1 O8 176.43(16) . . ?
O7 U1 N1 87.40(15) . . ?
O7 U1 N5 86.00(15) . . ?
O8 U1 O1 86.76(15) . . ?
O8 U1 O3 91.91(16) . . ?
O8 U1 O5 89.57(16) . . ?
O8 U1 N1 91.34(16) . . ?
O8 U1 N5 92.55(16) . . ?
N1 U1 N5 134.98(14) . . ?
C5 O1 U1 128.9(4) . . ?
C5 O2 Na2 144.9(4) . . ?
C10 O3 U1 155.2(4) . . ?
C10 O4 Na1 139.5(4) . . ?
C10 O4 Na1 121.2(4) . 2_655 ?
Na1 O4 Na1 98.75(15) . 2_655 ?
U1 O5 Na1 134.70(17) . . ?
C15 O5 U1 130.3(3) . . ?
C15 O5 Na1 95.0(3) . . ?
C15 O6 Na1 89.8(4) . . ?
C15 O6 Na2 151.5(4) . 4_565 ?
Na2 O6 Na1 99.15(16) 4_565 . ?
N2 N1 U1 122.5(3) . . ?
C1 N1 U1 117.6(4) . . ?
C1 N1 N2 119.9(5) . . ?
C4 N2 N1 118.8(5) . . ?
N4 N3 Na1 119.8(4) . 2_655 ?
C6 N3 N4 119.7(5) . . ?
C6 N3 Na1 119.6(4) . 2_655 ?
N3 N4 Na2 105.1(4) . 3_766 ?
C9 N4 N3 119.5(5) . . ?
C9 N4 Na2 121.8(5) . 3_766 ?
N6 N5 U1 124.2(3) . . ?
C11 N5 U1 116.2(4) . . ?
C11 N5 N6 119.5(5) . . ?
C14 N6 N5 119.0(5) . . ?
N1 C1 C2 122.8(5) . . ?
N1 C1 C5 114.7(5) . . ?
C2 C1 C5 122.5(5) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 C1 117.7(6) . . ?
C3 C2 H2 121.1 . . ?
C2 C3 H3 121.4 . . ?
C2 C3 C4 117.2(5) . . ?
C4 C3 H3 121.4 . . ?
N2 C4 C3 123.5(6) . . ?
N2 C4 H4 118.3 . . ?
C3 C4 H4 118.3 . . ?
O1 C5 C1 115.9(5) . . ?
O2 C5 O1 124.6(6) . . ?
O2 C5 C1 119.5(5) . . ?
N3 C6 C7 122.3(5) . . ?
N3 C6 C10 115.4(5) . . ?
C7 C6 C10 122.4(5) . . ?
C6 C7 H7 121.0 . . ?
C8 C7 C6 118.0(5) . . ?
C8 C7 H7 121.0 . . ?
C7 C8 H8 121.4 . . ?
C7 C8 C9 117.2(5) . . ?
C9 C8 H8 121.4 . . ?
N4 C9 C8 123.3(6) . . ?
N4 C9 H9 118.3 . . ?
C8 C9 H9 118.3 . . ?
O3 C10 C6 115.0(5) . . ?
O4 C10 O3 125.5(5) . . ?
O4 C10 C6 119.4(5) . . ?
N5 C11 C12 122.7(5) . . ?
N5 C11 C15 114.8(5) . . ?
C12 C11 C15 122.5(5) . . ?
C11 C12 H12 121.3 . . ?
C13 C12 C11 117.5(6) . . ?
C13 C12 H12 121.3 . . ?
C12 C13 H13 121.3 . . ?
C12 C13 C14 117.3(6) . . ?
C14 C13 H13 121.3 . . ?
N6 C14 C13 124.0(6) . . ?
N6 C14 H14 118.0 . . ?
C13 C14 H14 118.0 . . ?
O5 C15 C11 115.6(5) . . ?
O6 C15 O5 125.2(5) . . ?
O6 C15 C11 119.2(5) . . ?
O9 Cl1 O11 112.1(4) . . ?
O10 Cl1 O9 110.9(4) . . ?
O10 Cl1 O11 106.9(3) . . ?
O10 Cl1 O12 108.5(4) . . ?
O12 Cl1 O9 109.4(4) . . ?
O12 Cl1 O11 108.9(4) . . ?
Cl1 O10 Na1 147.6(4) . 1_565 ?
Cl1 O11 Na1 146.8(3) . . ?
Cl1 O12 Na2 127.3(4) . 4_575 ?
H13A O13 H13B 115(10) . . ?
Na2 O13 H13A 146(8) 2_656 . ?
Na2 O13 H13B 63(10) 2_656 . ?
H14A O14 H14B 109.5 . . ?
O4 Na1 O4 81.24(15) . 2_655 ?
O4 Na1 O5 85.16(14) . . ?
O4 Na1 O5 166.28(15) 2_655 . ?
O4 Na1 O6 144.38(14) 2_655 . ?
O4 Na1 O6 134.06(15) . . ?
O4 Na1 N3 144.67(17) . 2_655 ?
O4 Na1 O10 92.0(2) . 1_545 ?
O4 Na1 O11 90.1(2) . . ?
O4 Na1 Na1 43.03(11) . 2_655 ?
O4 Na1 Na1 38.22(10) 2_655 2_655 ?
O4 Na1 Na2 151.51(14) . 4_565 ?
O4 Na1 Na2 110.81(11) 2_655 4_565 ?
O5 Na1 O6 49.34(12) . . ?
O5 Na1 Na1 128.18(13) . 2_655 ?
O5 Na1 Na2 82.19(11) . 4_565 ?
O6 Na1 Na1 174.59(12) . 2_655 ?
O6 Na1 Na2 36.81(10) . 4_565 ?
N3 Na1 O4 63.56(15) 2_655 2_655 ?
N3 Na1 O5 129.88(16) 2_655 . ?
N3 Na1 O6 81.27(15) 2_655 . ?
N3 Na1 Na1 101.76(14) 2_655 2_655 ?
N3 Na1 Na2 55.41(12) 2_655 4_565 ?
O10 Na1 O4 94.37(17) 1_545 2_655 ?
O10 Na1 O5 87.85(17) 1_545 . ?
O10 Na1 O6 81.70(19) 1_545 . ?
O10 Na1 N3 93.5(2) 1_545 2_655 ?
O10 Na1 Na1 93.60(16) 1_545 2_655 ?
O10 Na1 Na2 62.21(17) 1_545 4_565 ?
O11 Na1 O4 93.19(17) . 2_655 ?
O11 Na1 O5 85.03(17) . . ?
O11 Na1 O6 91.59(18) . . ?
O11 Na1 N3 89.0(2) . 2_655 ?
O11 Na1 O10 172.4(2) . 1_545 ?
O11 Na1 Na1 92.93(14) . 2_655 ?
O11 Na1 Na2 113.97(17) . 4_565 ?
Na1 Na1 Na2 142.23(8) 2_655 4_565 ?
O2 Na2 N4 79.48(19) . 3_766 ?
O2 Na2 O12 93.3(2) . 4_676 ?
O2 Na2 Na1 115.54(14) . 4_666 ?
O6 Na2 O2 157.82(19) 4_666 . ?
O6 Na2 N4 81.16(19) 4_666 3_766 ?
O6 Na2 O12 90.2(2) 4_666 4_676 ?
O6 Na2 Na1 44.04(12) 4_666 4_666 ?
N4 Na2 Na1 60.41(14) 3_766 4_666 ?
O12 Na2 N4 128.1(2) 4_676 3_766 ?
O12 Na2 Na1 78.06(16) 4_676 4_666 ?
O13 Na2 O2 95.1(2) 2_656 . ?
O13 Na2 O6 107.1(2) 2_656 4_666 ?
O13 Na2 N4 147.2(3) 2_656 3_766 ?
O13 Na2 O12 84.2(3) 2_656 4_676 ?
O13 Na2 Na1 145.16(18) 2_656 4_666 ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.316
_oxdiff_exptl_absorpt_empirical_full_min 0.782
####################################################################### 
# 
# 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_180613_s2_yyq_u-pz2
_database_code_depnum_ccdc_archive 'CCDC 1865674'
_audit_update_record             
;
2018-09-04 deposited with the CCDC.
2018-11-26 downloaded from the CCDC.
;
_audit_creation_date             2018-06-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C10 H8 N4 O7 U'
_chemical_formula_sum            'C10 H8 N4 O7 U'
_chemical_formula_weight         534.23
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         c12h12n2o3u1
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'
U U -9.6767 9.6646 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   26.1101(17)
_cell_length_b                   7.7452(5)
_cell_length_c                   6.8023(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1375.61(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1268
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.6100
_cell_measurement_theta_min      3.9850
_shelx_estimated_absorpt_T_max   0.200
_shelx_estimated_absorpt_T_min   0.088
_exptl_absorpt_coefficient_mu    11.842
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37301
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    2.580
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0547
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3779
_diffrn_reflns_point_group_measured_fraction_full 0.813
_diffrn_reflns_point_group_measured_fraction_max 0.796
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.058
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -82.00  -18.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -      -15.1231  -57.0000   30.0000 64

#__ type_ start__ end____ width___ exp.time_
  2 omega   -2.00   24.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -      -15.1231  -99.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega  -13.00   34.00   1.0000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       16.8419  -57.0000 -120.0000 47
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0244870000
_diffrn_orient_matrix_UB_12      -0.0363073000
_diffrn_orient_matrix_UB_13      0.0183013000
_diffrn_orient_matrix_UB_21      -0.0110153000
_diffrn_orient_matrix_UB_22      0.0836928000
_diffrn_orient_matrix_UB_23      -0.0018986000
_diffrn_orient_matrix_UB_31      -0.0041400000
_diffrn_orient_matrix_UB_32      -0.0079813000
_diffrn_orient_matrix_UB_33      -0.1026324000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.467
_reflns_Friedel_fraction_full    0.592
_reflns_Friedel_fraction_max     0.555
_reflns_number_gt                1862
_reflns_number_total             2244
_reflns_odcompleteness_completeness 99.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.729
_refine_diff_density_min         -2.167
_refine_diff_density_rms         0.200
_refine_ls_abs_structure_details 
;
 Flack x determined using 503 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.43(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         2244
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0437
_refine_ls_restrained_S_all      1.102
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0412P)²+0.3348P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0904
_refine_ls_wR_factor_ref         0.0960
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C1) = Uanis(C2) = Uanis(C3) = Uanis(C4) = Uanis(C5) = Uanis(C6) =
Uanis(C7) = Uanis(C8) = Uanis(C9) = Uanis(C10)
Uanis(N1) = Uanis(N2) = Uanis(N3) = Uanis(N4)
3.a Rotating group:
 O7(H7A,H7B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C9(H9)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
U1 U 0.63668(2) 0.14008(6) 0.6925(6) 0.02680(19) Uani 1 1 d . . . . .
O1 O 0.5563(4) 0.2610(12) 0.682(5) 0.036(3) Uani 1 1 d . . . . .
O2 O 0.4702(4) 0.2650(14) 0.673(5) 0.043(4) Uani 1 1 d . . . . .
O3 O 0.6741(3) 0.4111(12) 0.710(5) 0.033(3) Uani 1 1 d . . . . .
O4 O 0.7385(4) 0.5956(11) 0.690(6) 0.049(3) Uani 1 1 d . . . . .
O5 O 0.6366(10) 0.136(3) 0.446(4) 0.039(7) Uani 1 1 d . . . . .
O6 O 0.6359(10) 0.144(3) 0.963(3) 0.038(7) Uani 1 1 d . . . . .
O7 O 0.6635(4) -0.1574(12) 0.708(6) 0.045(4) Uani 1 1 d . . . . .
H7A H 0.6861 -0.1840 0.6084 0.067 Uiso 1 1 d GR . . . .
H7B H 0.6369 -0.2310 0.6804 0.067 Uiso 1 1 d GR . . . .
N1 N 0.5587(4) -0.0735(14) 0.693(6) 0.0343(16) Uani 1 1 d . . . . .
N2 N 0.5656(5) -0.2432(14) 0.674(3) 0.0343(16) Uani 1 1 d . . . . .
N3 N 0.7340(4) 0.1446(13) 0.696(7) 0.0343(16) Uani 1 1 d . . . . .
N4 N 0.7614(4) -0.0047(13) 0.697(6) 0.0343(16) Uani 1 1 d . . . . .
C1 C 0.5119(5) -0.0032(17) 0.692(6) 0.0321(12) Uani 1 1 d . . . . .
C2 C 0.4683(5) -0.1043(17) 0.701(6) 0.0321(12) Uani 1 1 d . . . . .
H2 H 0.4358 -0.0550 0.6980 0.038 Uiso 1 1 calc R . . . .
C3 C 0.4745(5) -0.2751(18) 0.714(3) 0.0321(12) Uani 1 1 d . . . . .
H3 H 0.4463 -0.3486 0.7128 0.038 Uiso 1 1 calc R . . . .
C4 C 0.5241(6) -0.341(2) 0.729(2) 0.0321(12) Uani 1 1 d . . . . .
H4 H 0.5291 -0.4527 0.7765 0.038 Uiso 1 1 calc R . . . .
C5 C 0.5110(5) 0.1926(18) 0.712(4) 0.0321(12) Uani 1 1 d . . . . .
C6 C 0.7572(5) 0.2977(17) 0.694(7) 0.0321(12) Uani 1 1 d . . . . .
C7 C 0.8092(5) 0.3133(17) 0.689(6) 0.0321(12) Uani 1 1 d . . . . .
H7 H 0.8244 0.4204 0.6695 0.038 Uiso 1 1 calc R . . . .
C8 C 0.8387(5) 0.1664(17) 0.713(4) 0.0321(12) Uani 1 1 d . . . . .
H8 H 0.8739 0.1716 0.7346 0.038 Uiso 1 1 calc R . . . .
C9 C 0.8125(5) 0.0116(18) 0.704(5) 0.0321(12) Uani 1 1 d . . . . .
H9 H 0.8319 -0.0892 0.7029 0.038 Uiso 1 1 calc R . . . .
C10 C 0.7210(5) 0.4494(18) 0.683(4) 0.0321(12) Uani 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
U1 O1 2.300(10) . ?
U1 O3 2.318(9) . ?
U1 O5 1.68(3) . ?
U1 O6 1.84(2) . ?
U1 O7 2.411(10) . ?
U1 N1 2.624(11) . ?
U1 N3 2.541(11) . ?
O1 C5 1.311(16) . ?
O2 C5 1.231(18) . ?
O3 C10 1.271(16) . ?
O4 C10 1.223(16) . ?
N1 N2 1.333(16) . ?
N1 C1 1.336(16) . ?
N2 C4 1.374(18) . ?
N3 N4 1.359(14) . ?
N3 C6 1.332(16) . ?
N4 C9 1.343(16) . ?
C1 C2 1.384(17) . ?
C1 C5 1.522(19) . ?
C2 C3 1.336(18) . ?
C3 C4 1.398(18) . ?
C6 C7 1.362(17) . ?
C6 C10 1.511(19) . ?
C7 C8 1.385(18) . ?
C8 C9 1.381(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
O1 U1 O3 91.0(3) . . ?
O1 U1 O7 131.0(3) . . ?
O1 U1 N1 63.1(3) . . ?
O1 U1 N3 155.2(3) . . ?
O3 U1 O7 137.8(4) . . ?
O3 U1 N1 153.9(4) . . ?
O3 U1 N3 64.2(3) . . ?
O5 U1 O1 88.5(12) . . ?
O5 U1 O3 93.9(11) . . ?
O5 U1 O6 179.2(4) . . ?
O5 U1 O7 91.6(12) . . ?
O5 U1 N1 89.3(12) . . ?
O5 U1 N3 90.7(13) . . ?
O6 U1 O1 90.9(12) . . ?
O6 U1 O3 86.6(10) . . ?
O6 U1 O7 88.4(12) . . ?
O6 U1 N1 90.0(12) . . ?
O6 U1 N3 90.1(13) . . ?
O7 U1 N1 67.8(3) . . ?
O7 U1 N3 73.9(3) . . ?
N3 U1 N1 141.7(3) . . ?
C5 O1 U1 130.8(9) . . ?
C10 O3 U1 127.6(9) . . ?
N2 N1 U1 121.1(9) . . ?
N2 N1 C1 121.6(11) . . ?
C1 N1 U1 116.9(9) . . ?
N1 N2 C4 114.4(14) . . ?
N4 N3 U1 120.9(8) . . ?
C6 N3 U1 117.9(9) . . ?
C6 N3 N4 121.2(11) . . ?
C9 N4 N3 116.3(11) . . ?
N1 C1 C2 121.4(12) . . ?
N1 C1 C5 114.8(12) . . ?
C2 C1 C5 123.1(13) . . ?
C3 C2 C1 117.6(13) . . ?
C2 C3 C4 118.8(14) . . ?
N2 C4 C3 120.5(14) . . ?
O1 C5 C1 112.0(13) . . ?
O2 C5 O1 124.2(16) . . ?
O2 C5 C1 116.7(15) . . ?
N3 C6 C7 122.2(13) . . ?
N3 C6 C10 114.1(12) . . ?
C7 C6 C10 123.6(13) . . ?
C6 C7 C8 118.6(14) . . ?
C9 C8 C7 115.6(14) . . ?
N4 C9 C8 125.2(13) . . ?
O3 C10 C6 114.4(12) . . ?
O4 C10 O3 124.8(15) . . ?
O4 C10 C6 118.9(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
U1 O1 C5 O2 -169(2) . . . . ?
U1 O1 C5 C1 -20(4) . . . . ?
U1 O3 C10 O4 179(3) . . . . ?
U1 O3 C10 C6 -17(4) . . . . ?
U1 N1 N2 C4 163.3(18) . . . . ?
U1 N1 C1 C2 -177(3) . . . . ?
U1 N1 C1 C5 -6(4) . . . . ?
U1 N3 N4 C9 -178(3) . . . . ?
U1 N3 C6 C7 -178(3) . . . . ?
U1 N3 C6 C10 -2(5) . . . . ?
N1 N2 C4 C3 29(3) . . . . ?
N1 C1 C2 C3 1(6) . . . . ?
N1 C1 C5 O1 14(4) . . . . ?
N1 C1 C5 O2 166(3) . . . . ?
N2 N1 C1 C2 10(6) . . . . ?
N2 N1 C1 C5 -179(3) . . . . ?
N3 N4 C9 C8 1(6) . . . . ?
N3 C6 C7 C8 -9(7) . . . . ?
N3 C6 C10 O3 11(5) . . . . ?
N3 C6 C10 O4 176(4) . . . . ?
N4 N3 C6 C7 1(8) . . . . ?
N4 N3 C6 C10 177(3) . . . . ?
C1 N1 N2 C4 -24(4) . . . . ?
C1 C2 C3 C4 4(5) . . . . ?
C2 C1 C5 O1 -174(4) . . . . ?
C2 C1 C5 O2 -23(5) . . . . ?
C2 C3 C4 N2 -19(4) . . . . ?
C5 C1 C2 C3 -169(3) . . . . ?
C6 N3 N4 C9 3(7) . . . . ?
C6 C7 C8 C9 12(5) . . . . ?
C7 C6 C10 O3 -173(4) . . . . ?
C7 C6 C10 O4 -8(7) . . . . ?
C7 C8 C9 N4 -8(5) . . . . ?
C10 C6 C7 C8 176(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_171122_s4_yyq_16
_database_code_depnum_ccdc_archive 'CCDC 1865676'
_audit_update_record             
;
2018-09-04 deposited with the CCDC.
2018-11-26 downloaded from the CCDC.
;
_audit_creation_date             2017-11-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C10 H8 N4 O7 U, H2 O'
_chemical_formula_sum            'C10 H10 N4 O8 U'
_chemical_formula_weight         552.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         c12h12n2o3u1
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'
U U -9.6767 9.6646 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   25.7342(9)
_cell_length_b                   6.8614(3)
_cell_length_c                   16.7222(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.750(3)
_cell_angle_gamma                90
_cell_volume                     2932.2(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2751
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.0500
_cell_measurement_theta_min      3.3390
_shelx_estimated_absorpt_T_max   0.470
_shelx_estimated_absorpt_T_min   0.168
_exptl_absorpt_coefficient_mu    11.121
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62439
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    2.502
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2032
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6360
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         3.074
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -2.00   85.60   0.6000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6856   38.0000  -60.0000 146

#__ type_ start__ end____ width___ exp.time_
  2 omega  -55.00   37.40   0.6000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6856  -19.0000  120.0000 154

#__ type_ start__ end____ width___ exp.time_
  3 omega   14.00   41.00   0.6000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6856  -77.0000  150.0000 45
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0233620000
_diffrn_orient_matrix_UB_12      -0.0293259000
_diffrn_orient_matrix_UB_13      0.0152361000
_diffrn_orient_matrix_UB_21      0.0119340000
_diffrn_orient_matrix_UB_22      0.0167722000
_diffrn_orient_matrix_UB_23      0.0398583000
_diffrn_orient_matrix_UB_31      -0.0090337000
_diffrn_orient_matrix_UB_32      0.0977038000
_diffrn_orient_matrix_UB_33      -0.0021830000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2514
_reflns_number_total             3000
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.579
_refine_diff_density_min         -0.619
_refine_diff_density_rms         0.125
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3000
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0233
_refine_ls_restrained_S_all      0.996
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0137P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0397
_refine_ls_wR_factor_ref         0.0426
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Free rotating group:
 O8(H8A)
2.b Rotating group:
 O7(H7A)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C9(H9)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
U1 U 0.38877(2) 0.79612(2) 0.21465(2) 0.02591(6) Uani 1 1 d . . . . .
O1 O 0.33777(11) 0.7903(5) 0.32200(18) 0.0358(8) Uani 1 1 d . . . . .
O2 O 0.26404(12) 0.7932(5) 0.3800(2) 0.0466(9) Uani 1 1 d . . . . .
O3 O 0.44678(11) 0.7385(5) 0.3313(2) 0.0454(9) Uani 1 1 d . . . . .
O4 O 0.39485(11) 1.0482(4) 0.22765(19) 0.0407(9) Uani 1 1 d . . . . .
O5 O 0.38256(12) 0.5436(5) 0.1991(2) 0.0476(10) Uani 1 1 d . . . . .
O6 O 0.46847(11) 0.7858(5) 0.16098(19) 0.0446(9) Uani 1 1 d . . . . .
O7 O 0.37146(13) 0.8559(6) 0.0727(2) 0.0419(10) Uani 1 1 d . . . . .
H7A H 0.3592 0.9732 0.0643 0.063 Uiso 1 1 d GR . . . .
H7B H 0.3936(19) 0.836(7) 0.050(3) 0.050(18) Uiso 1 1 d . . . . .
N1 N 0.28720(13) 0.8103(5) 0.1777(2) 0.0302(9) Uani 1 1 d . . . . .
N2 N 0.26540(15) 0.8129(6) 0.1012(2) 0.0430(11) Uani 1 1 d . . . . .
N3 N 0.54034(14) 0.7770(5) 0.5005(2) 0.0296(9) Uani 1 1 d . . . . .
N4 N 0.54661(16) 0.7694(6) 0.5815(2) 0.0417(11) Uani 1 1 d . . . . .
C1 C 0.25807(15) 0.7997(6) 0.2382(3) 0.0259(10) Uani 1 1 d . . . . .
C2 C 0.20363(16) 0.7942(6) 0.2250(3) 0.0327(11) Uani 1 1 d . . . . .
H2 H 0.1835 0.7889 0.2677 0.039 Uiso 1 1 calc R . . . .
C3 C 0.18118(18) 0.7970(7) 0.1478(3) 0.0416(13) Uani 1 1 d . . . . .
H3 H 0.1450 0.7921 0.1357 0.050 Uiso 1 1 calc R . . . .
C4 C 0.21346(18) 0.8075(7) 0.0867(3) 0.0469(14) Uani 1 1 d . . . . .
H4 H 0.1981 0.8108 0.0335 0.056 Uiso 1 1 calc R . . . .
C5 C 0.28785(16) 0.7936(6) 0.3208(3) 0.0300(11) Uani 1 1 d . . . . .
C6 C 0.49289(17) 0.7528(5) 0.4605(3) 0.0258(10) Uani 1 1 d . . . . .
C7 C 0.44792(18) 0.7229(6) 0.4983(3) 0.0335(12) Uani 1 1 d . . . . .
H7 H 0.4152 0.7072 0.4689 0.040 Uiso 1 1 calc R . . . .
C8 C 0.4544(2) 0.7177(7) 0.5801(3) 0.0402(13) Uani 1 1 d . . . . .
H8 H 0.4261 0.6996 0.6092 0.048 Uiso 1 1 calc R . . . .
C9 C 0.5048(2) 0.7406(6) 0.6188(3) 0.0420(13) Uani 1 1 d . . . . .
H9 H 0.5094 0.7352 0.6747 0.050 Uiso 1 1 calc R . . . .
C10 C 0.49032(16) 0.7601(6) 0.3697(3) 0.0244(10) Uani 1 1 d . . . . .
O8 O 0.32520(15) 1.2009(7) 0.0306(3) 0.0554(12) Uani 1 1 d . . . . .
H8A H 0.3094 1.2363 0.0701 0.083 Uiso 1 1 d G . . . .
H8B H 0.308(2) 1.187(9) -0.013(4) 0.08(2) 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
U1 O1 2.345(3) . ?
U1 O3 2.346(3) . ?
U1 O4 1.748(3) . ?
U1 O5 1.756(3) . ?
U1 O6 2.334(3) . ?
U1 O7 2.398(3) . ?
U1 N1 2.616(3) . ?
O1 C5 1.283(5) . ?
O2 C5 1.225(5) . ?
O3 C10 1.233(5) . ?
O6 C10 1.244(5) 2_655 ?
O7 H7A 0.8702 . ?
O7 H7B 0.73(4) . ?
N1 N2 1.335(5) . ?
N1 C1 1.330(5) . ?
N2 C4 1.331(5) . ?
N3 N4 1.346(5) . ?
N3 C6 1.332(5) . ?
N4 C9 1.321(6) . ?
C1 C2 1.393(6) . ?
C1 C5 1.499(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.351(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.392(6) . ?
C4 H4 0.9300 . ?
C6 C7 1.398(6) . ?
C6 C10 1.513(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.359(7) . ?
C8 H8 0.9300 . ?
C8 C9 1.387(7) . ?
C9 H9 0.9300 . ?
C10 O6 1.244(5) 2_655 ?
O8 H8A 0.8502 . ?
O8 H8B 0.81(6) . ?

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
O1 U1 O3 73.70(11) . . ?
O1 U1 O7 134.82(11) . . ?
O1 U1 N1 63.13(11) . . ?
O3 U1 O7 151.36(11) . . ?
O3 U1 N1 136.31(11) . . ?
O4 U1 O1 88.38(12) . . ?
O4 U1 O3 91.39(13) . . ?
O4 U1 O5 178.62(15) . . ?
O4 U1 O6 90.46(12) . . ?
O4 U1 O7 87.56(14) . . ?
O4 U1 N1 93.73(13) . . ?
O5 U1 O1 92.71(12) . . ?
O5 U1 O3 89.71(14) . . ?
O5 U1 O6 88.95(13) . . ?
O5 U1 O7 91.08(14) . . ?
O5 U1 N1 86.02(13) . . ?
O6 U1 O1 152.84(11) . . ?
O6 U1 O3 79.20(11) . . ?
O6 U1 O7 72.19(11) . . ?
O6 U1 N1 143.99(12) . . ?
O7 U1 N1 72.28(11) . . ?
C5 O1 U1 129.6(3) . . ?
C10 O3 U1 149.6(3) . . ?
C10 O6 U1 173.3(3) 2_655 . ?
U1 O7 H7A 109.9 . . ?
U1 O7 H7B 114(4) . . ?
H7A O7 H7B 112.3 . . ?
N2 N1 U1 121.5(3) . . ?
C1 N1 U1 117.1(3) . . ?
C1 N1 N2 121.2(4) . . ?
C4 N2 N1 118.3(4) . . ?
C6 N3 N4 119.7(4) . . ?
C9 N4 N3 118.2(4) . . ?
N1 C1 C2 121.8(4) . . ?
N1 C1 C5 115.4(4) . . ?
C2 C1 C5 122.7(4) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 C1 117.4(4) . . ?
C3 C2 H2 121.3 . . ?
C2 C3 H3 120.8 . . ?
C2 C3 C4 118.5(4) . . ?
C4 C3 H3 120.8 . . ?
N2 C4 C3 122.8(5) . . ?
N2 C4 H4 118.6 . . ?
C3 C4 H4 118.6 . . ?
O1 C5 C1 114.7(4) . . ?
O2 C5 O1 125.6(5) . . ?
O2 C5 C1 119.7(4) . . ?
N3 C6 C7 123.3(5) . . ?
N3 C6 C10 115.5(4) . . ?
C7 C6 C10 121.2(4) . . ?
C6 C7 H7 121.7 . . ?
C8 C7 C6 116.7(5) . . ?
C8 C7 H7 121.7 . . ?
C7 C8 H8 121.2 . . ?
C7 C8 C9 117.6(4) . . ?
C9 C8 H8 121.2 . . ?
N4 C9 C8 124.5(5) . . ?
N4 C9 H9 117.8 . . ?
C8 C9 H9 117.8 . . ?
O3 C10 O6 124.7(4) . 2_655 ?
O3 C10 C6 116.6(4) . . ?
O6 C10 C6 118.6(4) 2_655 . ?
H8A O8 H8B 118.4 . . ?

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
U1 O1 C5 O2 -178.8(3) . . . . ?
U1 O1 C5 C1 0.9(6) . . . . ?
U1 O3 C10 O6 -27.7(9) . . . 2_655 ?
U1 O3 C10 C6 152.8(4) . . . . ?
U1 N1 N2 C4 175.7(3) . . . . ?
U1 N1 C1 C2 -176.1(3) . . . . ?
U1 N1 C1 C5 3.7(5) . . . . ?
N1 N2 C4 C3 -0.7(8) . . . . ?
N1 C1 C2 C3 1.0(7) . . . . ?
N1 C1 C5 O1 -3.1(6) . . . . ?
N1 C1 C5 O2 176.5(4) . . . . ?
N2 N1 C1 C2 -1.1(7) . . . . ?
N2 N1 C1 C5 178.7(4) . . . . ?
N3 N4 C9 C8 -0.2(7) . . . . ?
N3 C6 C7 C8 -0.5(6) . . . . ?
N3 C6 C10 O3 -179.8(4) . . . . ?
N3 C6 C10 O6 0.6(6) . . . 2_655 ?
N4 N3 C6 C7 1.3(6) . . . . ?
N4 N3 C6 C10 -178.9(3) . . . . ?
C1 N1 N2 C4 1.0(7) . . . . ?
C1 C2 C3 C4 -0.8(7) . . . . ?
C2 C1 C5 O1 176.8(4) . . . . ?
C2 C1 C5 O2 -3.6(7) . . . . ?
C2 C3 C4 N2 0.7(8) . . . . ?
C5 C1 C2 C3 -178.8(4) . . . . ?
C6 N3 N4 C9 -0.9(6) . . . . ?
C6 C7 C8 C9 -0.6(6) . . . . ?
C7 C6 C10 O3 0.0(6) . . . . ?
C7 C6 C10 O6 -179.5(4) . . . 2_655 ?
C7 C8 C9 N4 0.9(7) . . . . ?
C10 C6 C7 C8 179.7(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_170623_s2_yyq
_database_code_depnum_ccdc_archive 'CCDC 1586814'
_audit_update_record             
;
2017-11-21 deposited with the CCDC.
2018-11-26 downloaded from the CCDC.
;
_audit_creation_date             2017-06-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '2(C10 H8 N4 O7 U), 2(H2 O)'
_chemical_formula_sum            'C20 H20 N8 O16 U2'
_chemical_formula_weight         1104.50
_chemical_melting_point          ?
_chemical_oxdiff_formula         c12h12n2o3u1
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'
U U -9.6767 9.6646 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8240(5)
_cell_length_b                   8.0617(6)
_cell_length_c                   11.9538(7)
_cell_angle_alpha                87.484(5)
_cell_angle_beta                 75.764(6)
_cell_angle_gamma                88.380(6)
_cell_volume                     730.01(9)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2471
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.8770
_cell_measurement_theta_min      3.7110
_shelx_estimated_absorpt_T_max   0.135
_shelx_estimated_absorpt_T_min   0.112
_exptl_absorpt_coefficient_mu    11.167
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.19494
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    2.512
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_av_unetI/netI     0.0791
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5942
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         3.026
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -82.00    2.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -57.0000   30.0000 84

#__ type_ start__ end____ width___ exp.time_
  2 omega  -25.00   24.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000   60.0000 49

#__ type_ start__ end____ width___ exp.time_
  3 omega  -32.00   49.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669   57.0000 -180.0000 81

#__ type_ start__ end____ width___ exp.time_
  4 omega  -58.00  -23.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -38.0000  -30.0000 35

#__ type_ start__ end____ width___ exp.time_
  5 omega  -15.00   19.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000 -180.0000 34

#__ type_ start__ end____ width___ exp.time_
  6 omega  -50.00   44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       16.8419  -77.0000  -60.0000 94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0785129000
_diffrn_orient_matrix_UB_12      -0.0448060000
_diffrn_orient_matrix_UB_13      0.0053505000
_diffrn_orient_matrix_UB_21      0.0434953000
_diffrn_orient_matrix_UB_22      -0.0738485000
_diffrn_orient_matrix_UB_23      0.0134430000
_diffrn_orient_matrix_UB_31      -0.0263523000
_diffrn_orient_matrix_UB_32      0.0172473000
_diffrn_orient_matrix_UB_33      0.0595284000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2676
_reflns_number_total             2982
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.904
_refine_diff_density_min         -1.746
_refine_diff_density_rms         0.219
_refine_ls_extinction_coef       0.0245(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2982
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0400
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0261P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0755
_refine_ls_wR_factor_ref         0.0806
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2. Restrained distances
 O7-H7B
 0.86 with sigma of 0.02
3.a Free rotating group:
 O8(H8A,H8B)
3.b Rotating group:
 O7(H7A)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C9(H9)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
U1 U 0.38342(3) 0.30574(3) 0.25269(2) 0.02282(15) Uani 1 1 d . . . . .
O1 O 0.0879(7) 0.3894(7) 0.2942(5) 0.0338(15) Uani 1 1 d . . . . .
O2 O -0.1463(7) 0.5445(7) 0.3709(5) 0.0344(14) Uani 1 1 d . . . . .
O3 O 0.5412(7) 0.0746(7) 0.1787(5) 0.0369(15) Uani 1 1 d . . . . .
O4 O 0.5881(8) -0.1635(8) 0.0898(6) 0.053(2) Uani 1 1 d . . . . .
O5 O 0.3635(8) 0.2210(7) 0.3936(5) 0.0378(15) Uani 1 1 d . . . . .
O6 O 0.4099(8) 0.3981(7) 0.1137(5) 0.0366(15) Uani 1 1 d . . . . .
O7 O 0.6638(7) 0.4062(8) 0.2462(6) 0.0366(14) Uani 1 1 d D . . . .
H7A H 0.7036 0.4605 0.1818 0.055 Uiso 1 1 d GR . . . .
H7B H 0.734(8) 0.434(10) 0.287(6) 0.03(3) Uiso 1 1 d D . . . .
N1 N 0.3042(8) 0.5896(8) 0.3549(6) 0.0256(15) Uani 1 1 d . . . . .
N2 N 0.1799(10) 0.8732(9) 0.4773(7) 0.041(2) Uani 1 1 d . . . . .
N3 N 0.2035(8) 0.0695(8) 0.1931(6) 0.0291(16) Uani 1 1 d . . . . .
N4 N 0.0496(9) -0.1942(9) 0.1117(7) 0.0392(19) Uani 1 1 d . . . . .
C1 C 0.1328(9) 0.6348(9) 0.3818(6) 0.0189(16) Uani 1 1 d . . . . .
C2 C 0.0714(11) 0.7731(11) 0.4421(7) 0.034(2) Uani 1 1 d . . . . .
H2 H -0.0487 0.7984 0.4591 0.041 Uiso 1 1 calc R . . . .
C3 C 0.3491(12) 0.8259(11) 0.4523(9) 0.043(2) Uani 1 1 d . . . . .
H3 H 0.4280 0.8887 0.4786 0.052 Uiso 1 1 calc R . . . .
C4 C 0.4128(11) 0.6888(11) 0.3895(8) 0.036(2) Uani 1 1 d . . . . .
H4 H 0.5333 0.6651 0.3711 0.043 Uiso 1 1 calc R . . . .
C5 C 0.0117(10) 0.5136(10) 0.3455(7) 0.0237(17) Uani 1 1 d . . . . .
C6 C 0.2987(10) -0.0597(10) 0.1439(7) 0.0239(17) Uani 1 1 d . . . . .
C7 C 0.2245(11) -0.1915(11) 0.1023(7) 0.032(2) Uani 1 1 d . . . . .
H7 H 0.2963 -0.2783 0.0677 0.039 Uiso 1 1 calc R . . . .
C8 C -0.0434(12) -0.0673(12) 0.1592(8) 0.044(3) Uani 1 1 d . . . . .
H8 H -0.1642 -0.0649 0.1653 0.053 Uiso 1 1 calc R . . . .
C9 C 0.0307(11) 0.0648(12) 0.2010(9) 0.044(3) Uani 1 1 d . . . . .
H9 H -0.0419 0.1514 0.2352 0.053 Uiso 1 1 calc R . . . .
C10 C 0.4931(10) -0.0535(9) 0.1367(7) 0.0266(18) Uani 1 1 d . . . . .
O8 O 0.8184(8) 0.5505(7) 0.0550(6) 0.0419(16) Uani 1 1 d . . . . .
H8A H 0.9159 0.5884 0.0611 0.063 Uiso 1 1 d G . . . .
H8B H 0.7531 0.6301 0.0398 0.063 Uiso 1 1 d G . . . .


_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
U1 O1 2.329(5) . ?
U1 O3 2.292(5) . ?
U1 O5 1.762(6) . ?
U1 O6 1.757(6) . ?
U1 O7 2.342(6) . ?
U1 N1 2.628(6) . ?
U1 N3 2.623(6) . ?
O1 C5 1.255(9) . ?
O2 C5 1.219(9) . ?
O3 C10 1.274(9) . ?
O4 C10 1.206(9) . ?
O7 H7A 0.8617 . ?
O7 H7B 0.86(2) . ?
N1 C1 1.344(9) . ?
N1 C4 1.332(10) . ?
N2 C2 1.339(10) . ?
N2 C3 1.332(11) . ?
N3 C6 1.334(9) . ?
N3 C9 1.333(10) . ?
N4 C7 1.346(10) . ?
N4 C8 1.305(11) . ?
C1 C2 1.364(11) . ?
C1 C5 1.527(10) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C3 C4 1.375(12) . ?
C4 H4 0.9300 . ?
C6 C7 1.392(11) . ?
C6 C10 1.504(11) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C8 C9 1.395(12) . ?
C9 H9 0.9300 . ?
O8 H8A 0.8499 . ?
O8 H8B 0.8501 . ?

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
O1 U1 O7 141.17(19) . . ?
O1 U1 N1 63.45(18) . . ?
O1 U1 N3 72.02(19) . . ?
O3 U1 O1 135.65(18) . . ?
O3 U1 O7 83.0(2) . . ?
O3 U1 N1 160.5(2) . . ?
O3 U1 N3 63.64(19) . . ?
O5 U1 O1 92.3(2) . . ?
O5 U1 O3 89.9(2) . . ?
O5 U1 O7 91.4(3) . . ?
O5 U1 N1 84.8(2) . . ?
O5 U1 N3 94.0(2) . . ?
O6 U1 O1 88.7(2) . . ?
O6 U1 O3 91.3(2) . . ?
O6 U1 O5 177.1(2) . . ?
O6 U1 O7 86.2(3) . . ?
O6 U1 N1 93.3(2) . . ?
O6 U1 N3 88.9(2) . . ?
O7 U1 N1 78.4(2) . . ?
O7 U1 N3 146.1(2) . . ?
N3 U1 N1 135.33(19) . . ?
C5 O1 U1 130.6(5) . . ?
C10 O3 U1 130.6(5) . . ?
U1 O7 H7A 109.8 . . ?
U1 O7 H7B 145(6) . . ?
H7A O7 H7B 102.7 . . ?
C1 N1 U1 116.3(4) . . ?
C4 N1 U1 127.4(5) . . ?
C4 N1 C1 116.1(6) . . ?
C3 N2 C2 115.5(7) . . ?
C6 N3 U1 115.6(5) . . ?
C9 N3 U1 128.5(5) . . ?
C9 N3 C6 115.8(7) . . ?
C8 N4 C7 116.8(8) . . ?
N1 C1 C2 122.5(7) . . ?
N1 C1 C5 114.5(6) . . ?
C2 C1 C5 122.9(7) . . ?
N2 C2 C1 121.6(8) . . ?
N2 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
N2 C3 H3 118.3 . . ?
N2 C3 C4 123.3(8) . . ?
C4 C3 H3 118.3 . . ?
N1 C4 C3 120.8(8) . . ?
N1 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
O1 C5 C1 115.1(7) . . ?
O2 C5 O1 127.1(7) . . ?
O2 C5 C1 117.7(7) . . ?
N3 C6 C7 122.7(7) . . ?
N3 C6 C10 115.2(6) . . ?
C7 C6 C10 122.0(7) . . ?
N4 C7 C6 120.5(8) . . ?
N4 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
N4 C8 H8 118.6 . . ?
N4 C8 C9 122.8(8) . . ?
C9 C8 H8 118.6 . . ?
N3 C9 C8 121.3(8) . . ?
N3 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
O3 C10 C6 114.8(6) . . ?
O4 C10 O3 126.3(8) . . ?
O4 C10 C6 118.8(7) . . ?
H8A O8 H8B 109.5 . . ?

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
U1 O1 C5 O2 -174.9(6) . . . . ?
U1 O1 C5 C1 3.3(10) . . . . ?
U1 O3 C10 O4 172.8(7) . . . . ?
U1 O3 C10 C6 -4.6(12) . . . . ?
U1 N1 C1 C2 175.4(6) . . . . ?
U1 N1 C1 C5 -1.3(8) . . . . ?
U1 N1 C4 C3 -173.5(7) . . . . ?
U1 N3 C6 C7 -176.9(7) . . . . ?
U1 N3 C6 C10 3.4(9) . . . . ?
U1 N3 C9 C8 176.4(7) . . . . ?
N1 C1 C2 N2 0.5(14) . . . . ?
N1 C1 C5 O1 -0.8(10) . . . . ?
N1 C1 C5 O2 177.5(7) . . . . ?
N2 C3 C4 N1 -3.5(16) . . . . ?
N3 C6 C7 N4 -0.8(14) . . . . ?
N3 C6 C10 O3 0.0(11) . . . . ?
N3 C6 C10 O4 -177.6(8) . . . . ?
N4 C8 C9 N3 1.0(17) . . . . ?
C1 N1 C4 C3 2.0(13) . . . . ?
C2 N2 C3 C4 3.2(15) . . . . ?
C2 C1 C5 O1 -177.5(8) . . . . ?
C2 C1 C5 O2 0.8(12) . . . . ?
C3 N2 C2 C1 -1.8(14) . . . . ?
C4 N1 C1 C2 -0.6(12) . . . . ?
C4 N1 C1 C5 -177.3(7) . . . . ?
C5 C1 C2 N2 177.0(8) . . . . ?
C6 N3 C9 C8 -0.5(14) . . . . ?
C7 N4 C8 C9 -1.3(15) . . . . ?
C7 C6 C10 O3 -179.8(8) . . . . ?
C7 C6 C10 O4 2.6(13) . . . . ?
C8 N4 C7 C6 1.2(14) . . . . ?
C9 N3 C6 C7 0.4(13) . . . . ?
C9 N3 C6 C10 -179.3(8) . . . . ?
C10 C6 C7 N4 179.0(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
