# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016

####################################################################### 
# 
# 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 1413776'
_audit_update_record             
;
2016-04-14 deposited with the CCDC.
2016-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H22 N2 O18 U2'
_chemical_formula_weight         1150.54

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   13.7812(13)
_cell_length_b                   7.5010(8)
_cell_length_c                   15.1787(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.5980(10)
_cell_angle_gamma                90.00
_cell_volume                     1547.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5138
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      30.92

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.470
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1064
_exptl_absorpt_coefficient_mu    10.544
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2527
_exptl_absorpt_correction_T_max  0.4186
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            7532
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.85
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2711
_reflns_number_gt                2458
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0170P)²+0.5630P] 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         2711
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0215
_refine_ls_R_factor_gt           0.0181
_refine_ls_wR_factor_ref         0.0434
_refine_ls_wR_factor_gt          0.0425
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
U1 U 0.821280(9) 0.075007(18) 0.030164(8) 0.02370(6) Uani 1 1 d . . .
C1 C 1.0522(3) -0.0135(5) 0.1319(2) 0.0269(8) Uani 1 1 d . . .
C2 C 1.0677(3) -0.0303(5) 0.2311(3) 0.0277(9) Uani 1 1 d . . .
C3 C 1.1624(3) -0.0795(6) 0.2713(3) 0.0408(11) Uani 1 1 d . . .
H3 H 1.2120 -0.0858 0.2367 0.049 Uiso 1 1 calc R . .
C4 C 1.1841(3) -0.1191(7) 0.3613(3) 0.0473(12) Uani 1 1 d . . .
H4 H 1.2476 -0.1527 0.3867 0.057 Uiso 1 1 calc R . .
C5 C 1.1118(3) -0.1085(6) 0.4130(3) 0.0381(10) Uani 1 1 d . . .
H5 H 1.1258 -0.1339 0.4738 0.046 Uiso 1 1 calc R . .
C6 C 1.0182(3) -0.0598(5) 0.3738(3) 0.0307(9) Uani 1 1 d . . .
H6 H 0.9694 -0.0527 0.4092 0.037 Uiso 1 1 calc R . .
C7 C 0.9941(2) -0.0210(5) 0.2835(2) 0.0239(8) Uani 1 1 d . . .
C8 C 0.8900(3) 0.0352(5) 0.2483(3) 0.0263(8) Uani 1 1 d . . .
C9 C 0.5917(3) 0.1164(5) -0.0941(3) 0.0305(9) Uani 1 1 d . . .
C10 C 0.5294(3) 0.0547(5) -0.1797(3) 0.0289(9) Uani 1 1 d . . .
C11 C 0.4296(3) 0.0386(5) -0.1828(3) 0.0303(9) Uani 1 1 d . . .
H11 H 0.4014 0.0666 -0.1330 0.036 Uiso 1 1 calc R . .
C12 C 0.4080(3) -0.0546(5) -0.3315(3) 0.0375(10) Uani 1 1 d . . .
H12 H 0.3654 -0.0923 -0.3822 0.045 Uiso 1 1 calc R . .
C13 C 0.5059(3) -0.0377(6) -0.3335(3) 0.0411(11) Uani 1 1 d . . .
H13 H 0.5311 -0.0602 -0.3855 0.049 Uiso 1 1 calc R . .
C14 C 0.5673(3) 0.0142(6) -0.2553(3) 0.0370(10) Uani 1 1 d . . .
H14 H 0.6348 0.0216 -0.2544 0.044 Uiso 1 1 calc R . .
N1 N 0.3735(2) -0.0173(5) -0.2575(2) 0.0324(8) Uani 1 1 d . . .
H1 H 0.3114 -0.0298 -0.2576 0.039 Uiso 1 1 calc R . .
O1 O 0.87343(19) 0.2781(4) 0.00475(17) 0.0370(7) Uani 1 1 d . . .
O2 O 0.76745(18) -0.1281(4) 0.05661(18) 0.0327(6) Uani 1 1 d . . .
O3 O 0.68414(18) 0.1033(4) -0.08852(18) 0.0360(7) Uani 1 1 d . . .
O4 O 0.69310(19) 0.2371(4) 0.08556(19) 0.0484(8) Uani 1 1 d . . .
H4A H 0.6992 0.2779 0.1384 0.073 Uiso 1 1 d R . .
H4B H 0.6350 0.2579 0.0587 0.073 Uiso 1 1 d R . .
O5 O 0.87428(17) 0.1401(4) 0.18236(16) 0.0269(6) Uani 1 1 d . . .
O6 O 0.97272(18) -0.0636(3) 0.08715(17) 0.0293(6) Uani 1 1 d . . .
O7 O 1.12415(19) 0.0412(4) 0.09781(17) 0.0327(7) Uani 1 1 d . . .
O8 O 0.8230(2) -0.0212(5) 0.2875(2) 0.0474(8) Uani 1 1 d . . .
O9 O 0.5477(2) 0.1727(5) -0.03554(19) 0.0473(8) 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 1.755(3) . ?
U1 O2 1.770(3) . ?
U1 O5 2.355(2) . ?
U1 O6 2.363(2) . ?
U1 O7 2.364(3) 3_755 ?
U1 O3 2.393(2) . ?
U1 O4 2.408(3) . ?
C1 O6 1.247(4) . ?
C1 O7 1.261(5) . ?
C1 C2 1.490(5) . ?
C2 C7 1.392(5) . ?
C2 C3 1.395(5) . ?
C3 C4 1.382(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.369(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.377(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.387(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.505(5) . ?
C8 O8 1.252(5) . ?
C8 O5 1.263(4) . ?
C9 O9 1.232(5) . ?
C9 O3 1.267(4) . ?
C9 C10 1.506(5) . ?
C10 C14 1.372(6) . ?
C10 C11 1.374(5) . ?
C11 N1 1.328(5) . ?
C11 H11 0.9300 . ?
C12 N1 1.322(6) . ?
C12 C13 1.360(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.393(6) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
N1 H1 0.8600 . ?
O4 H4A 0.8501 . ?
O4 H4B 0.8496 . ?
O7 U1 2.363(3) 3_755 ?

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 O2 179.15(13) . . ?
O1 U1 O5 87.95(11) . . ?
O2 U1 O5 91.67(11) . . ?
O1 U1 O6 95.35(11) . . ?
O2 U1 O6 85.21(10) . . ?
O5 U1 O6 67.76(8) . . ?
O1 U1 O7 86.64(11) . 3_755 ?
O2 U1 O7 94.12(11) . 3_755 ?
O5 U1 O7 142.52(9) . 3_755 ?
O6 U1 O7 75.87(9) . 3_755 ?
O1 U1 O3 93.35(11) . . ?
O2 U1 O3 86.49(11) . . ?
O5 U1 O3 142.83(9) . . ?
O6 U1 O3 148.56(9) . . ?
O7 U1 O3 74.55(9) 3_755 . ?
O1 U1 O4 89.41(12) . . ?
O2 U1 O4 89.75(12) . . ?
O5 U1 O4 71.24(9) . . ?
O6 U1 O4 138.49(9) . . ?
O7 U1 O4 145.64(9) 3_755 . ?
O3 U1 O4 71.63(9) . . ?
O6 C1 O7 123.6(3) . . ?
O6 C1 C2 119.4(3) . . ?
O7 C1 C2 116.9(3) . . ?
C7 C2 C3 118.8(4) . . ?
C7 C2 C1 125.3(3) . . ?
C3 C2 C1 115.5(3) . . ?
C4 C3 C2 121.4(4) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C5 C4 C3 119.8(4) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 119.1(4) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C7 122.4(4) . . ?
C5 C6 H6 118.8 . . ?
C7 C6 H6 118.8 . . ?
C6 C7 C2 118.5(3) . . ?
C6 C7 C8 117.9(3) . . ?
C2 C7 C8 123.6(3) . . ?
O8 C8 O5 123.0(3) . . ?
O8 C8 C7 118.1(3) . . ?
O5 C8 C7 118.9(3) . . ?
O9 C9 O3 126.1(4) . . ?
O9 C9 C10 116.7(3) . . ?
O3 C9 C10 117.2(4) . . ?
C14 C10 C11 118.1(4) . . ?
C14 C10 C9 123.2(3) . . ?
C11 C10 C9 118.7(4) . . ?
N1 C11 C10 119.6(4) . . ?
N1 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
N1 C12 C13 119.8(4) . . ?
N1 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C12 C13 C14 118.1(4) . . ?
C12 C13 H13 120.9 . . ?
C14 C13 H13 120.9 . . ?
C10 C14 C13 120.8(4) . . ?
C10 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C12 N1 C11 123.5(3) . . ?
C12 N1 H1 118.3 . . ?
C11 N1 H1 118.3 . . ?
C9 O3 U1 135.8(3) . . ?
U1 O4 H4A 123.3 . . ?
U1 O4 H4B 127.7 . . ?
H4A O4 H4B 108.9 . . ?
C8 O5 U1 129.2(2) . . ?
C1 O6 U1 135.2(2) . . ?
C1 O7 U1 126.7(2) . 3_755 ?

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
O4 H4A O8 0.85 1.93 2.682(4) 146.0 2_655
C12 H12 O2 0.93 2.58 3.347(5) 139.8 4
N1 H1 O8 0.86 1.87 2.686(4) 157.2 3_655

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.598
_refine_diff_density_rms         0.106
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1413777'
_audit_update_record             
;
2016-04-14 deposited with the CCDC.
2016-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H12 N2 O8 U'
_chemical_formula_weight         550.27

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   5.6911(5)
_cell_length_b                   7.4024(6)
_cell_length_c                   9.8667(8)
_cell_angle_alpha                106.5610(10)
_cell_angle_beta                 105.8970(10)
_cell_angle_gamma                99.9480(10)
_cell_volume                     368.73(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2366
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      30.38

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.478
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             254
_exptl_absorpt_coefficient_mu    11.050
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3506
_exptl_absorpt_correction_T_max  0.7328
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            1866
_diffrn_reflns_av_R_equivalents  0.0123
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.29
_diffrn_reflns_theta_max         24.98
_reflns_number_total             1293
_reflns_number_gt                1293
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0331P)²+0.1414P] 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         1293
_refine_ls_number_parameters     106
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0167
_refine_ls_R_factor_gt           0.0167
_refine_ls_wR_factor_ref         0.0431
_refine_ls_wR_factor_gt          0.0431
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_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
U1 U 0.5000 0.5000 0.5000 0.02420(9) Uani 1 2 d S . .
C1 C 0.4819(8) 0.3374(6) 0.1952(4) 0.0283(8) Uani 1 1 d . . .
C2 C 0.4791(8) 0.2558(6) 0.0376(4) 0.0261(8) Uani 1 1 d . . .
C6 C 0.2656(8) 0.1212(6) -0.0744(5) 0.0296(8) Uani 1 1 d . . .
H6 H 0.1243 0.0818 -0.0491 0.036 Uiso 1 1 calc R . .
N1 N 0.2519(7) 0.0445(5) -0.2177(4) 0.0341(8) Uani 1 1 d . . .
C5 C 0.4563(9) 0.1043(6) -0.2517(5) 0.0348(9) Uani 1 1 d . . .
H5 H 0.4491 0.0533 -0.3509 0.042 Uiso 1 1 calc R . .
C3 C 0.6909(8) 0.3144(6) 0.0004(5) 0.0314(8) Uani 1 1 d . . .
H3 H 0.8384 0.4034 0.0734 0.038 Uiso 1 1 calc R . .
O1 O 0.3185(6) 0.6590(5) 0.4514(3) 0.0346(6) Uani 1 1 d . . .
O2 O 0.1216(6) 0.2437(5) 0.4546(3) 0.0385(7) Uani 1 1 d . . .
H2A H 0.0864 0.2620 0.5349 0.058 Uiso 1 1 d R . .
H2B H -0.0027 0.2484 0.3856 0.058 Uiso 1 1 d R . .
O3 O 0.2972(6) 0.2729(5) 0.2322(3) 0.0366(7) Uani 1 1 d . . .
O4 O 0.6702(6) 0.4731(5) 0.2920(3) 0.0379(7) Uani 1 1 d . . .
C4 C 0.6776(8) 0.2376(7) -0.1475(5) 0.0347(9) Uani 1 1 d . . .
H4 H 0.8154 0.2753 -0.1762 0.042 Uiso 1 1 calc R . .


_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 1.775(3) 2_666 ?
U1 O1 1.775(3) . ?
U1 O2 2.452(3) . ?
U1 O2 2.452(3) 2_666 ?
U1 O4 2.472(3) 2_666 ?
U1 O4 2.472(3) . ?
U1 O3 2.503(3) 2_666 ?
U1 O3 2.503(3) . ?
U1 C1 2.868(4) 2_666 ?
C1 O4 1.261(5) . ?
C1 O3 1.266(5) . ?
C1 C2 1.494(6) . ?
C2 C6 1.382(6) . ?
C2 C3 1.389(6) . ?
C6 N1 1.339(6) . ?
C6 H6 0.9300 . ?
N1 C5 1.335(6) . ?
C5 C4 1.378(7) . ?
C5 H5 0.9300 . ?
C3 C4 1.382(6) . ?
C3 H3 0.9300 . ?
O2 H2A 0.8500 . ?
O2 H2B 0.8500 . ?
C4 H4 0.9300 . ?

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 O1 179.999(1) 2_666 . ?
O1 U1 O2 87.20(13) 2_666 . ?
O1 U1 O2 92.80(13) . . ?
O1 U1 O2 92.80(13) 2_666 2_666 ?
O1 U1 O2 87.20(13) . 2_666 ?
O2 U1 O2 180.0 . 2_666 ?
O1 U1 O4 93.60(13) 2_666 2_666 ?
O1 U1 O4 86.40(13) . 2_666 ?
O2 U1 O4 62.80(10) . 2_666 ?
O2 U1 O4 117.20(10) 2_666 2_666 ?
O1 U1 O4 86.40(13) 2_666 . ?
O1 U1 O4 93.60(13) . . ?
O2 U1 O4 117.20(10) . . ?
O2 U1 O4 62.80(10) 2_666 . ?
O4 U1 O4 180.0 2_666 . ?
O1 U1 O3 87.77(13) 2_666 2_666 ?
O1 U1 O3 92.23(13) . 2_666 ?
O2 U1 O3 114.15(10) . 2_666 ?
O2 U1 O3 65.85(10) 2_666 2_666 ?
O4 U1 O3 52.12(10) 2_666 2_666 ?
O4 U1 O3 127.88(10) . 2_666 ?
O1 U1 O3 92.23(13) 2_666 . ?
O1 U1 O3 87.76(13) . . ?
O2 U1 O3 65.85(10) . . ?
O2 U1 O3 114.15(10) 2_666 . ?
O4 U1 O3 127.88(10) 2_666 . ?
O4 U1 O3 52.12(10) . . ?
O3 U1 O3 180.0 2_666 . ?
O1 U1 C1 90.92(13) 2_666 2_666 ?
O1 U1 C1 89.08(13) . 2_666 ?
O2 U1 C1 88.42(11) . 2_666 ?
O2 U1 C1 91.58(11) 2_666 2_666 ?
O4 U1 C1 25.98(12) 2_666 2_666 ?
O4 U1 C1 154.02(12) . 2_666 ?
O3 U1 C1 26.14(11) 2_666 2_666 ?
O3 U1 C1 153.86(12) . 2_666 ?
O4 C1 O3 119.8(4) . . ?
O4 C1 C2 119.4(4) . . ?
O3 C1 C2 120.8(4) . . ?
C6 C2 C3 118.6(4) . . ?
C6 C2 C1 120.8(4) . . ?
C3 C2 C1 120.7(4) . . ?
N1 C6 C2 123.3(4) . . ?
N1 C6 H6 118.4 . . ?
C2 C6 H6 118.4 . . ?
C5 N1 C6 117.3(4) . . ?
N1 C5 C4 123.5(4) . . ?
N1 C5 H5 118.2 . . ?
C4 C5 H5 118.2 . . ?
C4 C3 C2 118.5(4) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
U1 O2 H2A 109.4 . . ?
U1 O2 H2B 109.4 . . ?
H2A O2 H2B 109.5 . . ?
C1 O3 U1 93.2(2) . . ?
C1 O4 U1 94.8(3) . . ?
C5 C4 C3 118.8(4) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?

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
O4 C1 C2 C6 -173.5(4) . . . . ?
O3 C1 C2 C6 6.0(6) . . . . ?
O4 C1 C2 C3 6.2(6) . . . . ?
O3 C1 C2 C3 -174.3(4) . . . . ?
C3 C2 C6 N1 -0.3(6) . . . . ?
C1 C2 C6 N1 179.4(4) . . . . ?
C2 C6 N1 C5 -0.5(6) . . . . ?
C6 N1 C5 C4 0.6(7) . . . . ?
C6 C2 C3 C4 0.9(6) . . . . ?
C1 C2 C3 C4 -178.8(4) . . . . ?
O4 C1 O3 U1 -0.6(4) . . . . ?
C2 C1 O3 U1 179.8(3) . . . . ?
O1 U1 O3 C1 -83.3(3) 2_666 . . . ?
O1 U1 O3 C1 96.7(3) . . . . ?
O2 U1 O3 C1 -169.3(3) . . . . ?
O2 U1 O3 C1 10.7(3) 2_666 . . . ?
O4 U1 O3 C1 -179.6(2) 2_666 . . . ?
O4 U1 O3 C1 0.4(2) . . . . ?
O3 U1 O3 C1 97(9) 2_666 . . . ?
C1 U1 O3 C1 180.0 2_666 . . . ?
O3 C1 O4 U1 0.6(4) . . . . ?
C2 C1 O4 U1 -179.8(3) . . . . ?
O1 U1 O4 C1 95.3(3) 2_666 . . . ?
O1 U1 O4 C1 -84.7(3) . . . . ?
O2 U1 O4 C1 10.3(3) . . . . ?
O2 U1 O4 C1 -169.7(3) 2_666 . . . ?
O4 U1 O4 C1 -74(33) 2_666 . . . ?
O3 U1 O4 C1 179.6(2) 2_666 . . . ?
O3 U1 O4 C1 -0.4(2) . . . . ?
C1 U1 O4 C1 180.0 2_666 . . . ?
N1 C5 C4 C3 0.1(7) . . . . ?
C2 C3 C4 C5 -0.8(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        24.98
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         1.249
_refine_diff_density_min         -0.926
_refine_diff_density_rms         0.108
####################################################################### 
# 
# 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 1413778'
_audit_update_record             
;
2015-07-20 deposited with the CCDC.
2016-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H29 N O8 U'
_chemical_formula_weight         757.56

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   20.379(3)
_cell_length_b                   11.7334(18)
_cell_length_c                   12.529(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.340(2)
_cell_angle_gamma                90.00
_cell_volume                     2915.1(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3962
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      24.66

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.726
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1464
_exptl_absorpt_coefficient_mu    5.617
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4313
_exptl_absorpt_correction_T_max  0.7293
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            13781
_diffrn_reflns_av_R_equivalents  0.1006
_diffrn_reflns_av_sigmaI/netI    0.0992
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.02
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5126
_reflns_number_gt                3441
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0200P)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         5126
_refine_ls_number_parameters     354
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.0859
_refine_ls_wR_factor_gt          0.0773
_refine_ls_goodness_of_fit_ref   0.909
_refine_ls_restrained_S_all      0.909
_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
U1 U 0.129499(13) 0.04261(2) 0.34832(2) 0.03764(11) Uani 1 1 d . . .
C1 C 0.2132(4) 0.1678(6) 0.5204(6) 0.0388(18) Uani 1 1 d . . .
C2 C -0.0137(3) 0.0344(6) 0.3360(5) 0.0375(17) Uani 1 1 d . . .
C3 C 0.1840(4) -0.0660(7) 0.1855(6) 0.051(2) Uani 1 1 d . . .
C4 C 0.2582(4) 0.2348(6) 0.6078(6) 0.0425(19) Uani 1 1 d . . .
H4 H 0.2394 0.2746 0.6576 0.051 Uiso 1 1 calc R . .
C5 C 0.3236(4) 0.2401(6) 0.6174(6) 0.0441(19) Uani 1 1 d . . .
H5 H 0.3402 0.1993 0.5656 0.053 Uiso 1 1 calc R . .
C6 C 0.3735(4) 0.3020(6) 0.6990(6) 0.0426(18) Uani 1 1 d . . .
C7 C 0.4383(4) 0.3101(8) 0.6842(7) 0.067(2) Uani 1 1 d . . .
H7 H 0.4492 0.2745 0.6242 0.080 Uiso 1 1 calc R . .
C8 C 0.4884(4) 0.3713(9) 0.7585(8) 0.082(3) Uani 1 1 d . . .
H8 H 0.5320 0.3764 0.7479 0.099 Uiso 1 1 calc R . .
C9 C 0.4720(5) 0.4224(8) 0.8452(8) 0.079(3) Uani 1 1 d . . .
H9 H 0.5043 0.4645 0.8939 0.095 Uiso 1 1 calc R . .
C10 C 0.4081(4) 0.4132(7) 0.8623(7) 0.065(2) Uani 1 1 d . . .
H10 H 0.3981 0.4461 0.9242 0.078 Uiso 1 1 calc R . .
C11 C 0.3590(4) 0.3556(6) 0.7887(6) 0.053(2) Uani 1 1 d . . .
H11 H 0.3154 0.3526 0.7995 0.063 Uiso 1 1 calc R . .
C12 C -0.0861(3) 0.0416(6) 0.3293(5) 0.0407(18) Uani 1 1 d . . .
H12 H -0.1011 0.0836 0.3818 0.049 Uiso 1 1 calc R . .
C13 C -0.1309(4) -0.0099(6) 0.2505(6) 0.0447(19) Uani 1 1 d . . .
H13 H -0.1134 -0.0516 0.2003 0.054 Uiso 1 1 calc R . .
C14 C -0.2046(4) -0.0097(6) 0.2324(6) 0.0435(19) Uani 1 1 d . . .
C15 C -0.2379(4) 0.0525(6) 0.2977(6) 0.051(2) Uani 1 1 d . . .
H15 H -0.2135 0.0965 0.3551 0.061 Uiso 1 1 calc R . .
C16 C -0.3069(4) 0.0490(7) 0.2775(7) 0.063(2) Uani 1 1 d . . .
H16 H -0.3290 0.0900 0.3221 0.076 Uiso 1 1 calc R . .
C17 C -0.3435(4) -0.0140(7) 0.1926(7) 0.064(2) Uani 1 1 d . . .
H17 H -0.3903 -0.0145 0.1791 0.077 Uiso 1 1 calc R . .
C18 C -0.3118(4) -0.0760(7) 0.1276(7) 0.065(2) Uani 1 1 d . . .
H18 H -0.3365 -0.1197 0.0703 0.077 Uiso 1 1 calc R . .
C19 C -0.2428(4) -0.0728(7) 0.1479(6) 0.056(2) Uani 1 1 d . . .
H19 H -0.2211 -0.1147 0.1032 0.068 Uiso 1 1 calc R . .
C20 C 0.2163(4) -0.1254(7) 0.1084(6) 0.052(2) Uani 1 1 d . . .
H20 H 0.1907 -0.1728 0.0552 0.063 Uiso 1 1 calc R . .
C21 C 0.2814(4) -0.1125(6) 0.1134(6) 0.0463(19) Uani 1 1 d . . .
H21 H 0.3040 -0.0608 0.1653 0.056 Uiso 1 1 calc R . .
C22 C 0.3220(4) -0.1695(6) 0.0475(6) 0.047(2) Uani 1 1 d . . .
C23 C 0.2981(4) -0.2508(6) -0.0303(6) 0.054(2) Uani 1 1 d . . .
H23 H 0.2528 -0.2709 -0.0439 0.065 Uiso 1 1 calc R . .
C24 C 0.3382(5) -0.3029(8) -0.0883(7) 0.073(3) Uani 1 1 d . . .
H24 H 0.3205 -0.3571 -0.1413 0.088 Uiso 1 1 calc R . .
C25 C 0.4055(5) -0.2744(8) -0.0675(8) 0.074(3) Uani 1 1 d . . .
H25 H 0.4334 -0.3105 -0.1062 0.089 Uiso 1 1 calc R . .
C26 C 0.4321(5) -0.1931(8) 0.0098(8) 0.076(3) Uani 1 1 d . . .
H26 H 0.4774 -0.1730 0.0225 0.092 Uiso 1 1 calc R . .
C27 C 0.3900(4) -0.1417(8) 0.0682(7) 0.066(2) Uani 1 1 d . . .
H27 H 0.4076 -0.0881 0.1218 0.079 Uiso 1 1 calc R . .
C28 C -0.0303(4) 0.2895(7) 0.5881(7) 0.069(3) Uani 1 1 d . . .
H28A H -0.0304 0.3642 0.6193 0.103 Uiso 1 1 calc R . .
H28B H -0.0341 0.2333 0.6421 0.103 Uiso 1 1 calc R . .
H28C H -0.0678 0.2823 0.5260 0.103 Uiso 1 1 calc R . .
C29 C 0.0462(5) 0.3640(7) 0.4811(7) 0.079(3) Uani 1 1 d . . .
H29A H 0.0109 0.3658 0.4154 0.119 Uiso 1 1 calc R . .
H29B H 0.0886 0.3504 0.4625 0.119 Uiso 1 1 calc R . .
H29C H 0.0478 0.4357 0.5185 0.119 Uiso 1 1 calc R . .
N1 N 0.0327(3) 0.2720(5) 0.5530(5) 0.0495(16) Uani 1 1 d . . .
H1A H 0.0306 0.2052 0.5172 0.059 Uiso 1 1 calc R . .
H1B H 0.0671 0.2680 0.6127 0.059 Uiso 1 1 calc R . .
O1 O 0.1409(2) -0.0824(4) 0.4273(4) 0.0450(12) Uani 1 1 d . . .
O2 O 0.1155(2) 0.1673(4) 0.2678(4) 0.0482(13) Uani 1 1 d . . .
O3 O 0.2381(2) 0.1153(5) 0.4494(4) 0.0523(14) Uani 1 1 d . . .
O4 O 0.1503(2) 0.1622(4) 0.5144(4) 0.0424(12) Uani 1 1 d . . .
O5 O 0.0268(2) 0.0883(4) 0.4139(4) 0.0466(13) Uani 1 1 d . . .
O6 O 0.0114(2) -0.0199(4) 0.2688(4) 0.0505(14) Uani 1 1 d . . .
O7 O 0.1211(2) -0.0745(5) 0.1797(4) 0.0559(15) Uani 1 1 d . . .
O8 O 0.2188(2) -0.0057(5) 0.2617(4) 0.0595(15) 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 1.755(4) . ?
U1 O2 1.763(4) . ?
U1 O8 2.392(5) . ?
U1 O3 2.436(5) . ?
U1 O4 2.464(4) . ?
U1 O5 2.477(4) . ?
U1 O7 2.493(5) . ?
U1 O6 2.494(5) . ?
C1 O4 1.270(7) . ?
C1 O3 1.279(8) . ?
C1 C4 1.481(9) . ?
C2 O6 1.255(8) . ?
C2 O5 1.289(7) . ?
C2 C12 1.460(9) . ?
C3 O8 1.266(8) . ?
C3 O7 1.271(8) . ?
C3 C20 1.465(9) . ?
C4 C5 1.312(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.459(9) . ?
C5 H5 0.9300 . ?
C6 C7 1.378(9) . ?
C6 C11 1.379(9) . ?
C7 C8 1.409(11) . ?
C7 H7 0.9300 . ?
C8 C9 1.349(12) . ?
C8 H8 0.9300 . ?
C9 C10 1.371(11) . ?
C9 H9 0.9300 . ?
C10 C11 1.373(10) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.326(9) . ?
C12 H12 0.9300 . ?
C13 C14 1.465(9) . ?
C13 H13 0.9300 . ?
C14 C19 1.376(9) . ?
C14 C15 1.385(9) . ?
C15 C16 1.371(10) . ?
C15 H15 0.9300 . ?
C16 C17 1.367(11) . ?
C16 H16 0.9300 . ?
C17 C18 1.361(10) . ?
C17 H17 0.9300 . ?
C18 C19 1.371(10) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.322(9) . ?
C20 H20 0.9300 . ?
C21 C22 1.459(9) . ?
C21 H21 0.9300 . ?
C22 C23 1.371(9) . ?
C22 C27 1.389(10) . ?
C23 C24 1.359(9) . ?
C23 H23 0.9300 . ?
C24 C25 1.377(11) . ?
C24 H24 0.9300 . ?
C25 C26 1.378(12) . ?
C25 H25 0.9300 . ?
C26 C27 1.386(10) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 N1 1.465(8) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 N1 1.472(8) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
N1 H1A 0.9000 . ?
N1 H1B 0.9000 . ?

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 O2 178.3(2) . . ?
O1 U1 O8 92.4(2) . . ?
O2 U1 O8 88.7(2) . . ?
O1 U1 O3 90.75(19) . . ?
O2 U1 O3 90.86(19) . . ?
O8 U1 O3 67.91(17) . . ?
O1 U1 O4 91.45(19) . . ?
O2 U1 O4 89.11(18) . . ?
O8 U1 O4 121.17(16) . . ?
O3 U1 O4 53.36(15) . . ?
O1 U1 O5 90.35(19) . . ?
O2 U1 O5 88.42(19) . . ?
O8 U1 O5 172.39(16) . . ?
O3 U1 O5 119.17(15) . . ?
O4 U1 O5 65.81(15) . . ?
O1 U1 O7 89.5(2) . . ?
O2 U1 O7 90.11(19) . . ?
O8 U1 O7 52.83(16) . . ?
O3 U1 O7 120.69(16) . . ?
O4 U1 O7 173.98(15) . . ?
O5 U1 O7 120.14(15) . . ?
O1 U1 O6 88.24(19) . . ?
O2 U1 O6 90.09(19) . . ?
O8 U1 O6 120.96(16) . . ?
O3 U1 O6 171.11(15) . . ?
O4 U1 O6 117.82(15) . . ?
O5 U1 O6 52.02(14) . . ?
O7 U1 O6 68.15(15) . . ?
O4 C1 O3 119.4(7) . . ?
O4 C1 C4 121.1(6) . . ?
O3 C1 C4 119.6(6) . . ?
O6 C2 O5 118.0(6) . . ?
O6 C2 C12 123.5(6) . . ?
O5 C2 C12 118.5(6) . . ?
O8 C3 O7 118.0(7) . . ?
O8 C3 C20 120.3(7) . . ?
O7 C3 C20 121.7(8) . . ?
C5 C4 C1 122.3(7) . . ?
C5 C4 H4 118.8 . . ?
C1 C4 H4 118.8 . . ?
C4 C5 C6 128.1(7) . . ?
C4 C5 H5 115.9 . . ?
C6 C5 H5 115.9 . . ?
C7 C6 C11 118.2(7) . . ?
C7 C6 C5 118.3(7) . . ?
C11 C6 C5 123.5(7) . . ?
C6 C7 C8 121.0(8) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C9 C8 C7 118.9(8) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C8 C9 C10 120.8(9) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C9 C10 C11 120.3(8) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C10 C11 C6 120.8(8) . . ?
C10 C11 H11 119.6 . . ?
C6 C11 H11 119.6 . . ?
C13 C12 C2 122.0(6) . . ?
C13 C12 H12 119.0 . . ?
C2 C12 H12 119.0 . . ?
C12 C13 C14 128.3(7) . . ?
C12 C13 H13 115.8 . . ?
C14 C13 H13 115.8 . . ?
C19 C14 C15 118.1(7) . . ?
C19 C14 C13 119.7(7) . . ?
C15 C14 C13 122.2(7) . . ?
C16 C15 C14 119.8(8) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C17 C16 C15 120.9(8) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C18 C17 C16 120.3(8) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C19 118.9(8) . . ?
C17 C18 H18 120.6 . . ?
C19 C18 H18 120.6 . . ?
C18 C19 C14 122.1(8) . . ?
C18 C19 H19 119.0 . . ?
C14 C19 H19 119.0 . . ?
C21 C20 C3 120.8(8) . . ?
C21 C20 H20 119.6 . . ?
C3 C20 H20 119.6 . . ?
C20 C21 C22 127.9(7) . . ?
C20 C21 H21 116.0 . . ?
C22 C21 H21 116.0 . . ?
C23 C22 C27 118.2(7) . . ?
C23 C22 C21 124.5(7) . . ?
C27 C22 C21 117.4(7) . . ?
C24 C23 C22 122.3(8) . . ?
C24 C23 H23 118.8 . . ?
C22 C23 H23 118.8 . . ?
C23 C24 C25 119.0(9) . . ?
C23 C24 H24 120.5 . . ?
C25 C24 H24 120.5 . . ?
C24 C25 C26 121.0(9) . . ?
C24 C25 H25 119.5 . . ?
C26 C25 H25 119.5 . . ?
C25 C26 C27 118.8(9) . . ?
C25 C26 H26 120.6 . . ?
C27 C26 H26 120.6 . . ?
C26 C27 C22 120.8(8) . . ?
C26 C27 H27 119.6 . . ?
C22 C27 H27 119.6 . . ?
N1 C28 H28A 109.5 . . ?
N1 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
N1 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N1 C29 H29A 109.5 . . ?
N1 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
N1 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 N1 C29 112.4(6) . . ?
C28 N1 H1A 109.1 . . ?
C29 N1 H1A 109.1 . . ?
C28 N1 H1B 109.1 . . ?
C29 N1 H1B 109.1 . . ?
H1A N1 H1B 107.8 . . ?
C1 O3 U1 94.2(4) . . ?
C1 O4 U1 93.1(4) . . ?
C2 O5 U1 94.9(4) . . ?
C2 O6 U1 95.0(4) . . ?
C3 O7 U1 92.1(4) . . ?
C3 O8 U1 97.0(4) . . ?

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
N1 H1A O5 0.90 1.87 2.757(7) 166.3 .
N1 H1B O2 0.90 2.11 2.915(7) 148.8 4_566

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         2.072
_refine_diff_density_min         -1.591
_refine_diff_density_rms         0.137
####################################################################### 
# 
# 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 1413779'
_audit_update_record             
;
2016-04-14 deposited with the CCDC.
2016-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C2 H6 O13 U2'
_chemical_formula_weight         714.13

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'
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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   5.5561(4)
_cell_length_b                   15.2520(11)
_cell_length_c                   13.3506(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.9740(10)
_cell_angle_gamma                90.00
_cell_volume                     1128.63(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3599
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      28.22

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    4.203
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1224
_exptl_absorpt_coefficient_mu    28.725
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.0581
_exptl_absorpt_correction_T_max  0.1300
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            6942
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         28.23
_reflns_number_total             2725
_reflns_number_gt                2466
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0284P)²+0.6772P] 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     SHELXL
_refine_ls_extinction_coef       0.0071(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2725
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0269
_refine_ls_wR_factor_ref         0.0649
_refine_ls_wR_factor_gt          0.0630
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_restrained_S_all      1.109
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
U1 U 0.28005(4) 0.460666(15) 0.714064(17) 0.01169(10) Uani 1 1 d . . .
U2 U 0.96903(4) 0.185308(15) 0.957874(17) 0.01088(9) Uani 1 1 d . . .
C1 C 0.6308(12) 0.3528(4) 0.8817(5) 0.0145(13) Uani 1 1 d . . .
C2 C 0.6046(12) 0.2888(4) 0.7931(5) 0.0125(12) Uani 1 1 d . . .
O1 O 0.0247(10) 0.4086(4) 0.7593(4) 0.0247(12) Uani 1 1 d . . .
O1W O 0.8153(14) 0.5584(4) 0.9539(6) 0.056(2) Uani 1 1 d . . .
H1WA H 0.9354 0.5684 0.9195 0.084 Uiso 1 1 d R . .
H1WB H 0.7321 0.5166 0.9275 0.084 Uiso 1 1 d R . .
O2 O 0.5363(9) 0.5151(3) 0.6722(3) 0.0181(10) Uani 1 1 d . . .
O3 O 0.7241(9) 0.1392(3) 1.0175(4) 0.0216(11) Uani 1 1 d . . .
O4 O 1.2139(9) 0.2312(3) 0.8992(4) 0.0225(11) Uani 1 1 d . . .
O5 O 0.2370(9) 0.3968(3) 0.5573(4) 0.0169(10) Uani 1 1 d . . .
O6 O 0.0187(9) 0.5626(3) 0.6428(4) 0.0171(10) Uani 1 1 d . . .
O7 O 0.4744(9) 0.3137(3) 0.7181(4) 0.0184(11) Uani 1 1 d . . .
O8 O 0.5154(10) 0.4240(3) 0.8713(4) 0.0216(11) Uani 1 1 d . . .
O9 O 0.7161(9) 0.2177(3) 0.8030(3) 0.0179(10) Uani 1 1 d . . .
O10 O 0.7599(9) 0.3295(3) 0.9573(4) 0.0216(11) Uani 1 1 d . . .
O11 O 1.1011(11) 0.2776(3) 1.1043(4) 0.0310(14) Uani 1 1 d . . .
H11B H 1.0714 0.2510 1.1581 0.047 Uiso 1 1 d R . .
H11C H 1.2514 0.2872 1.1040 0.047 Uiso 1 1 d R . .
O12 O 0.2817(11) 0.5833(3) 0.8364(4) 0.0310(14) Uani 1 1 d . . .
H12A H 0.2749 0.6318 0.8052 0.046 Uiso 1 1 d R . .
H12C H 0.4105 0.5812 0.8746 0.046 Uiso 1 1 d R . .


_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 1.768(5) . ?
U1 O2 1.772(5) . ?
U1 O6 2.289(5) . ?
U1 O5 2.306(5) . ?
U1 O8 2.460(5) . ?
U1 O12 2.482(5) . ?
U1 O7 2.487(5) . ?
U2 O4 1.762(5) . ?
U2 O3 1.769(5) . ?
U2 O5 2.296(5) 4_666 ?
U2 O6 2.308(5) 2_646 ?
U2 O9 2.468(5) . ?
U2 O11 2.479(5) . ?
U2 O10 2.487(5) . ?
C1 O10 1.250(8) . ?
C1 O8 1.262(8) . ?
C1 C2 1.533(9) . ?
C2 O9 1.251(8) . ?
C2 O7 1.253(8) . ?
O1W H1WA 0.8501 . ?
O1W H1WB 0.8495 . ?
O5 U2 2.296(5) 4_465 ?
O6 U2 2.308(5) 2_656 ?
O11 H11B 0.8504 . ?
O11 H11C 0.8484 . ?
O12 H12A 0.8494 . ?
O12 H12C 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 O2 178.1(2) . . ?
O1 U1 O6 86.9(2) . . ?
O2 U1 O6 92.9(2) . . ?
O1 U1 O5 94.9(2) . . ?
O2 U1 O5 87.0(2) . . ?
O6 U1 O5 83.50(17) . . ?
O1 U1 O8 89.9(2) . . ?
O2 U1 O8 89.1(2) . . ?
O6 U1 O8 142.53(17) . . ?
O5 U1 O8 133.96(16) . . ?
O1 U1 O12 94.6(2) . . ?
O2 U1 O12 83.6(2) . . ?
O6 U1 O12 74.64(17) . . ?
O5 U1 O12 155.62(17) . . ?
O8 U1 O12 68.43(16) . . ?
O1 U1 O7 86.9(2) . . ?
O2 U1 O7 94.1(2) . . ?
O6 U1 O7 152.03(17) . . ?
O5 U1 O7 69.91(16) . . ?
O8 U1 O7 64.66(15) . . ?
O12 U1 O7 133.06(16) . . ?
O4 U2 O3 179.7(2) . . ?
O4 U2 O5 89.1(2) . 4_666 ?
O3 U2 O5 90.7(2) . 4_666 ?
O4 U2 O6 90.5(2) . 2_646 ?
O3 U2 O6 89.7(2) . 2_646 ?
O5 U2 O6 81.39(17) 4_666 2_646 ?
O4 U2 O9 87.7(2) . . ?
O3 U2 O9 92.6(2) . . ?
O5 U2 O9 154.44(16) 4_666 . ?
O6 U2 O9 73.29(17) 2_646 . ?
O4 U2 O11 85.9(2) . . ?
O3 U2 O11 93.8(2) . . ?
O5 U2 O11 73.09(16) 4_666 . ?
O6 U2 O11 154.27(17) 2_646 . ?
O9 U2 O11 131.86(16) . . ?
O4 U2 O10 91.3(2) . . ?
O3 U2 O10 88.8(2) . . ?
O5 U2 O10 140.18(16) 4_666 . ?
O6 U2 O10 138.41(17) 2_646 . ?
O9 U2 O10 65.28(15) . . ?
O11 U2 O10 67.22(16) . . ?
O10 C1 O8 126.3(6) . . ?
O10 C1 C2 117.4(6) . . ?
O8 C1 C2 116.3(6) . . ?
O9 C2 O7 127.0(6) . . ?
O9 C2 C1 116.8(6) . . ?
O7 C2 C1 116.2(6) . . ?
H1WA O1W H1WB 109.5 . . ?
U2 O5 U1 141.0(2) 4_465 . ?
U1 O6 U2 138.5(2) . 2_656 ?
C2 O7 U1 121.1(4) . . ?
C1 O8 U1 121.6(4) . . ?
C2 O9 U2 120.7(4) . . ?
C1 O10 U2 119.8(4) . . ?
U2 O11 H11B 109.3 . . ?
U2 O11 H11C 109.4 . . ?
H11B O11 H11C 109.6 . . ?
U1 O12 H12A 109.6 . . ?
U1 O12 H12C 109.3 . . ?
H12A O12 H12C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        28.23
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         1.891
_refine_diff_density_min         -1.720
_refine_diff_density_rms         0.322
