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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H20 Cl N2 O8 U'
_chemical_formula_weight         665.84

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1480 0.1590 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
U U -9.6770 9.6650 '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                   9.7918(7)
_cell_length_b                   9.9454(7)
_cell_length_c                   12.7361(9)
_cell_angle_alpha                84.216(4)
_cell_angle_beta                 76.642(5)
_cell_angle_gamma                64.070(4)
_cell_volume                     1085.25(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    6537
_cell_measurement_theta_min      2.591
_cell_measurement_theta_max      23.842

_exptl_crystal_description       block
_exptl_crystal_colour            color
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.038
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             630
_exptl_absorpt_coefficient_mu    7.647
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.4140
_exptl_absorpt_correction_T_max  0.7010
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
   'SADABS,Scheldrick G.M., Bruker-Siemens Area Detector 
Absorption and Other Correction, Version 2006/1, Gottingen Germany (2006).'
;

_diffrn_ambient_temperature      273(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23817
_diffrn_reflns_av_R_equivalents  0.0570
_diffrn_reflns_av_sigmaI/netI    0.0423
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.81
_diffrn_reflns_theta_max         25.64
_reflns_number_total             4069
_reflns_number_gt                3666
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART/SAINT'
_computing_data_reduction        'Bruker SMART/SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0268P)²+0.7857P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4069
_refine_ls_number_parameters     266
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0272
_refine_ls_wR_factor_ref         0.0597
_refine_ls_wR_factor_gt          0.0582
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.055
_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 0.55948(2) 0.991669(19) 0.274885(14) 0.02114(7) Uani 1 1 d . A .
Cl Cl 0.81630(19) 0.9250(2) 0.35229(15) 0.0613(5) Uani 1 1 d . . .
O1 O 0.6430(5) 1.1858(4) 0.1880(3) 0.0409(10) Uani 1 1 d . A .
O2 O 0.4603(5) 1.1672(4) 0.1283(3) 0.0428(10) Uani 1 1 d . A .
O3 O 0.4772(4) 1.1786(4) 0.4053(3) 0.0305(8) Uani 1 1 d . . .
O4 O 0.7335(4) 0.7221(4) 0.2363(3) 0.0380(9) Uani 1 1 d . A .
O5 O 0.7496(5) 0.8801(4) 0.1068(3) 0.0411(10) Uani 1 1 d . A .
O6 O 0.4971(4) 0.8640(4) 0.4240(3) 0.0298(8) Uani 1 1 d . . .
O7 O 0.4433(4) 0.8752(4) 0.1899(3) 0.0375(9) Uani 1 1 d . . .
O8 O 0.2765(4) 1.1159(5) 0.3196(3) 0.0460(10) Uani 1 1 d D . .
N1 N 0.2371(5) 0.8652(5) 0.1482(4) 0.0374(11) Uani 1 1 d . . .
C1 C 0.4955(5) 1.3635(5) 0.4968(4) 0.0217(10) Uani 1 1 d . . .
C2 C 0.4922(6) 1.2153(5) 0.4923(4) 0.0237(11) Uani 1 1 d . . .
C3 C 0.5187(6) 1.4400(5) 0.4019(4) 0.0253(11) Uani 1 1 d . . .
H3 H 0.5317 1.3989 0.3358 0.030 Uiso 1 1 calc R . .
C4 C 0.4774(6) 1.4240(5) 0.5951(4) 0.0255(11) Uani 1 1 d . . .
H4 H 0.4626 1.3728 0.6588 0.031 Uiso 1 1 calc R . .
C5 C 0.7885(6) 0.7519(7) 0.1403(4) 0.0351(13) Uani 1 1 d . . .
C6 C 0.9012(6) 0.6221(6) 0.0676(4) 0.0365(13) Uani 1 1 d . A .
C7 C 0.9428(8) 0.6443(7) -0.0407(5) 0.0526(18) Uani 1 1 d . . .
H7 H 0.9054 0.7405 -0.0690 0.063 Uiso 1 1 calc R A .
C8 C 0.9591(8) 0.4771(7) 0.1087(5) 0.0523(17) Uani 1 1 d . . .
H8 H 0.9319 0.4612 0.1822 0.063 Uiso 1 1 calc R A .
C9 C 0.5219(7) 1.3710(6) 0.0617(4) 0.0351(13) Uani 1 1 d . A .
C10 C 0.5404(7) 1.2327(6) 0.1299(4) 0.0315(13) Uani 1 1 d . . .
C11 C 0.4161(7) 1.4202(6) -0.0051(5) 0.0385(14) Uani 1 1 d . . .
H11 H 0.3598 1.3666 -0.0089 0.046 Uiso 1 1 calc R A .
C12 C 0.6068(7) 1.4503(7) 0.0669(5) 0.0427(15) Uani 1 1 d . . .
H12 H 0.6786 1.4175 0.1112 0.051 Uiso 1 1 calc R A .
C13 C 0.3389(6) 0.9197(6) 0.1365(4) 0.0324(13) Uani 1 1 d . . .
H13 H 0.3338 0.9952 0.0861 0.039 Uiso 1 1 calc R . .
C14 C 0.2391(8) 0.7474(8) 0.2272(6) 0.068(2) Uani 1 1 d . . .
H14A H 0.1348 0.7685 0.2646 0.102 Uiso 1 1 d R . .
H14B H 0.2996 0.7431 0.2781 0.102 Uiso 1 1 d R . .
H14C H 0.2843 0.6530 0.1907 0.102 Uiso 1 1 d R . .
C15 C 0.1175(7) 0.9172(8) 0.0834(5) 0.0525(17) Uani 1 1 d . . .
H15A H 0.1261 0.8339 0.0458 0.079 Uiso 1 1 d R . .
H15B H 0.1316 0.9900 0.0321 0.079 Uiso 1 1 d R . .
H15C H 0.0166 0.9615 0.1298 0.079 Uiso 1 1 d R . .
N2A N 0.0325(14) 1.2826(15) 0.3921(9) 0.058(2) Uiso 0.460(9) 1 d PD A 1
C16A C 0.1831(16) 1.2335(17) 0.3668(12) 0.057(3) Uiso 0.460(9) 1 d PD A 1
H16A H 0.2243 1.2934 0.3863 0.068 Uiso 0.460(9) 1 calc PR A 1
C17A C -0.030(3) 1.173(2) 0.3843(19) 0.094(4) Uiso 0.460(9) 1 d PD A 1
H17A H -0.0829 1.1523 0.4528 0.141 Uiso 0.460(9) 1 d PR A 1
H17B H 0.0528 1.0822 0.3529 0.141 Uiso 0.460(9) 1 d PR A 1
H17C H -0.1021 1.2180 0.3372 0.141 Uiso 0.460(9) 1 d PR A 1
C18A C -0.078(3) 1.435(2) 0.435(2) 0.137(6) Uiso 0.460(9) 1 d PD A 1
H18A H -0.0768 1.4344 0.5105 0.205 Uiso 0.460(9) 1 d PR A 1
H18B H -0.1809 1.4545 0.4280 0.205 Uiso 0.460(9) 1 d PR A 1
H18C H -0.0499 1.5106 0.3987 0.205 Uiso 0.460(9) 1 d PR A 1
N2B N 0.0205(13) 1.2276(13) 0.3999(9) 0.058(2) Uiso 0.540(9) 1 d PD A 2
C16B C 0.1704(13) 1.1781(16) 0.3898(10) 0.057(3) Uiso 0.540(9) 1 d PD A 2
H16B H 0.1988 1.1956 0.4500 0.068 Uiso 0.540(9) 1 calc PR A 2
C17B C -0.040(2) 1.203(2) 0.3100(14) 0.094(4) Uiso 0.540(9) 1 d PD A 2
H17D H 0.0427 1.1746 0.2471 0.141 Uiso 0.540(9) 1 d PR A 2
H17E H -0.1232 1.2959 0.2966 0.141 Uiso 0.540(9) 1 d PR A 2
H17F H -0.0769 1.1269 0.3263 0.141 Uiso 0.540(9) 1 d PR A 2
C18B C -0.098(2) 1.325(3) 0.4907(16) 0.137(6) Uiso 0.540(9) 1 d PD A 2
H18D H -0.1281 1.2610 0.5426 0.205 Uiso 0.540(9) 1 d PR A 2
H18E H -0.1866 1.3976 0.4651 0.205 Uiso 0.540(9) 1 d PR A 2
H18F H -0.0542 1.3753 0.5241 0.205 Uiso 0.540(9) 1 d PR A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
U1 O6 2.291(3) . ?
U1 O3 2.358(3) . ?
U1 O7 2.404(4) . ?
U1 O8 2.439(4) . ?
U1 O5 2.472(3) . ?
U1 O1 2.480(4) . ?
U1 O2 2.485(4) . ?
U1 O4 2.493(4) . ?
U1 Cl 2.7001(16) . ?
U1 C5 2.833(5) . ?
U1 C10 2.840(5) . ?
O1 C10 1.280(6) . ?
O2 C10 1.223(6) . ?
O3 C2 1.259(6) . ?
O4 C5 1.278(6) . ?
O5 C5 1.223(7) . ?
O6 C2 1.256(6) 2_676 ?
O7 C13 1.253(6) . ?
O8 C16B 1.175(11) . ?
O8 C16A 1.232(13) . ?
N1 C13 1.302(7) . ?
N1 C14 1.462(8) . ?
N1 C15 1.467(7) . ?
C1 C4 1.385(6) . ?
C1 C3 1.390(7) . ?
C1 C2 1.495(6) . ?
C2 O6 1.256(6) 2_676 ?
C3 C4 1.375(6) 2_686 ?
C4 C3 1.375(6) 2_686 ?
C5 C6 1.505(7) . ?
C6 C7 1.370(8) . ?
C6 C8 1.394(8) . ?
C7 C8 1.393(8) 2_765 ?
C8 C7 1.393(8) 2_765 ?
C9 C11 1.385(8) . ?
C9 C12 1.389(8) . ?
C9 C10 1.514(7) . ?
C11 C12 1.397(7) 2_685 ?
C12 C11 1.397(7) 2_685 ?
N2A C16A 1.303(14) . ?
N2A C17A 1.482(15) . ?
N2A C18A 1.491(15) . ?
N2B C16B 1.306(13) . ?
N2B C17B 1.488(14) . ?
N2B C18B 1.497(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O6 U1 O3 81.55(11) . . ?
O6 U1 O7 83.53(12) . . ?
O3 U1 O7 137.56(13) . . ?
O6 U1 O8 76.75(14) . . ?
O3 U1 O8 70.38(13) . . ?
O7 U1 O8 67.58(13) . . ?
O6 U1 O5 126.29(12) . . ?
O3 U1 O5 143.55(13) . . ?
O7 U1 O5 74.77(13) . . ?
O8 U1 O5 133.01(13) . . ?
O6 U1 O1 151.53(12) . . ?
O3 U1 O1 72.98(12) . . ?
O7 U1 O1 124.04(13) . . ?
O8 U1 O1 105.53(14) . . ?
O5 U1 O1 73.40(13) . . ?
O6 U1 O2 145.42(13) . . ?
O3 U1 O2 95.49(13) . . ?
O7 U1 O2 75.60(13) . . ?
O8 U1 O2 69.93(14) . . ?
O5 U1 O2 74.38(14) . . ?
O1 U1 O2 52.11(13) . . ?
O6 U1 O4 74.09(12) . . ?
O3 U1 O4 142.10(12) . . ?
O7 U1 O4 68.24(13) . . ?
O8 U1 O4 128.93(13) . . ?
O5 U1 O4 52.30(12) . . ?
O1 U1 O4 119.91(13) . . ?
O2 U1 O4 120.94(13) . . ?
O6 U1 Cl 83.76(10) . . ?
O3 U1 Cl 76.26(10) . . ?
O7 U1 Cl 140.83(10) . . ?
O8 U1 Cl 143.31(10) . . ?
O5 U1 Cl 83.47(11) . . ?
O1 U1 Cl 78.12(10) . . ?
O2 U1 Cl 129.26(10) . . ?
O4 U1 Cl 72.66(10) . . ?
O6 U1 C5 100.79(15) . . ?
O3 U1 C5 153.27(15) . . ?
O7 U1 C5 68.75(14) . . ?
O8 U1 C5 136.27(15) . . ?
O5 U1 C5 25.52(14) . . ?
O1 U1 C5 96.53(15) . . ?
O2 U1 C5 96.97(16) . . ?
O4 U1 C5 26.80(14) . . ?
Cl U1 C5 77.53(12) . . ?
O6 U1 C10 159.62(14) . . ?
O3 U1 C10 82.53(13) . . ?
O7 U1 C10 99.94(15) . . ?
O8 U1 C10 85.97(16) . . ?
O5 U1 C10 73.66(14) . . ?
O1 U1 C10 26.75(14) . . ?
O2 U1 C10 25.45(14) . . ?
O4 U1 C10 125.96(13) . . ?
Cl U1 C10 104.68(13) . . ?
C5 U1 C10 99.16(16) . . ?
C10 O1 U1 92.5(3) . . ?
C10 O2 U1 93.8(3) . . ?
C2 O3 U1 147.7(3) . . ?
C5 O4 U1 91.6(3) . . ?
C5 O5 U1 93.9(3) . . ?
C2 O6 U1 161.0(3) 2_676 . ?
C13 O7 U1 135.5(3) . . ?
C16B O8 C16A 30.9(9) . . ?
C16B O8 U1 142.7(7) . . ?
C16A O8 U1 132.9(8) . . ?
C13 N1 C14 120.6(5) . . ?
C13 N1 C15 122.3(5) . . ?
C14 N1 C15 117.2(5) . . ?
C4 C1 C3 119.8(4) . . ?
C4 C1 C2 120.3(4) . . ?
C3 C1 C2 119.9(4) . . ?
O6 C2 O3 124.2(4) 2_676 . ?
O6 C2 C1 117.9(4) 2_676 . ?
O3 C2 C1 118.0(4) . . ?
C4 C3 C1 120.5(4) 2_686 . ?
C3 C4 C1 119.7(5) 2_686 . ?
O5 C5 O4 122.1(5) . . ?
O5 C5 C6 120.4(5) . . ?
O4 C5 C6 117.5(5) . . ?
O5 C5 U1 60.5(3) . . ?
O4 C5 U1 61.6(3) . . ?
C6 C5 U1 176.0(4) . . ?
C7 C6 C8 119.1(5) . . ?
C7 C6 C5 120.3(5) . . ?
C8 C6 C5 120.5(5) . . ?
C6 C7 C8 120.1(6) . 2_765 ?
C7 C8 C6 120.7(6) 2_765 . ?
C11 C9 C12 119.8(5) . . ?
C11 C9 C10 119.1(5) . . ?
C12 C9 C10 121.1(5) . . ?
O2 C10 O1 121.2(5) . . ?
O2 C10 C9 120.7(5) . . ?
O1 C10 C9 118.2(5) . . ?
O2 C10 U1 60.8(3) . . ?
O1 C10 U1 60.7(3) . . ?
C9 C10 U1 174.6(4) . . ?
C9 C11 C12 120.6(5) . 2_685 ?
C9 C12 C11 119.7(5) . 2_685 ?
O7 C13 N1 123.2(5) . . ?
C16A N2A C17A 116.4(14) . . ?
C16A N2A C18A 125.1(15) . . ?
C17A N2A C18A 118.3(16) . . ?
O8 C16A N2A 126.6(14) . . ?
C16B N2B C17B 118.9(12) . . ?
C16B N2B C18B 124.1(13) . . ?
C17B N2B C18B 116.6(14) . . ?
O8 C16B N2B 132.8(13) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.64
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.944
_refine_diff_density_min         -0.771
_refine_diff_density_rms         0.130
_database_code_depnum_ccdc_archive 'CCDC 1017513'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H20 Cl N2 O8 U'
_chemical_formula_weight         665.84

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1480 0.1590 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
U U -9.6770 9.6650 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_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                   17.4025(3)
_cell_length_b                   9.9887(2)
_cell_length_c                   25.5946(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.5680(10)
_cell_angle_gamma                90.00
_cell_volume                     4399.41(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9965
_cell_measurement_theta_min      2.358
_cell_measurement_theta_max      28.372

_exptl_crystal_description       Block
_exptl_crystal_colour            Green
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.011
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2520
_exptl_absorpt_coefficient_mu    7.547
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.489
_exptl_absorpt_correction_T_max  0.547
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
  'SADABS,Scheldrick G.M., Bruker-Siemens Area Detector 
Absorption and Other Correction, Version 2006/1, Gottingen Germany (2006).'
;

_diffrn_ambient_temperature      293(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            74345
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_av_sigmaI/netI    0.0514
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         2.75
_diffrn_reflns_theta_max         32.69
_reflns_number_total             8045
_reflns_number_gt                5802
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART/SAINT'
_computing_data_reduction        'Bruker SMART/SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0252P)²+0.5248P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8045
_refine_ls_number_parameters     273
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0327
_refine_ls_wR_factor_ref         0.0661
_refine_ls_wR_factor_gt          0.0601
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_restrained_S_all      1.143
_refine_ls_shift/su_max          0.006
_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 0.533307(7) 0.438260(11) 0.860604(4) 0.02059(4) Uani 1 1 d . A .
Cl1 Cl 0.66411(6) 0.37908(13) 0.81975(4) 0.0548(3) Uani 1 1 d . . .
O2 O 0.49395(15) 0.2854(2) 0.79253(9) 0.0318(6) Uani 1 1 d . . .
O3 O 0.50614(17) 0.5900(2) 0.79340(9) 0.0361(6) Uani 1 1 d . . .
O4 O 0.56690(17) 0.2165(2) 0.89977(9) 0.0393(6) Uani 1 1 d . . .
O5 O 0.47564(16) 0.6136(3) 0.90561(10) 0.0398(6) Uani 1 1 d . . .
O6 O 0.62537(17) 0.4735(3) 0.94230(10) 0.0394(6) Uani 1 1 d . . .
O7 O 0.39204(17) 0.4325(3) 0.84071(12) 0.0558(9) Uani 1 1 d D . .
O8 O 0.62303(15) 0.6308(2) 0.88213(9) 0.0349(6) Uani 1 1 d . . .
O9 O 0.47918(17) 0.3275(3) 0.93391(11) 0.0489(7) Uani 1 1 d . . .
C1 C 0.5000 0.6491(4) 0.7500 0.0203(9) Uani 1 2 d S . .
C2 C 0.5000 0.2270(4) 0.7500 0.0230(10) Uani 1 2 d S . .
C3 C 0.6477(2) 0.5866(3) 0.92780(14) 0.0299(8) Uani 1 1 d . A .
C4 C 0.5186(2) 0.2234(3) 0.93165(14) 0.0310(8) Uani 1 1 d . A .
C5 C 0.4238(2) 0.6347(4) 0.93304(14) 0.0334(8) Uani 1 1 d . . .
H5 H 0.4224 0.5802 0.9623 0.040 Uiso 1 1 calc R . .
C6 C 0.7311(2) 0.7875(4) 0.94785(15) 0.0437(10) Uani 1 1 d . . .
H6 H 0.7183 0.8134 0.9127 0.052 Uiso 1 1 calc R . .
C7 C 0.5000 0.7990(4) 0.7500 0.0189(9) Uani 1 2 d S . .
C8 C 0.5000 0.0762(4) 0.7500 0.0226(10) Uani 1 2 d S . .
C9 C 0.7017(2) 0.6695(3) 0.96525(13) 0.0306(8) Uani 1 1 d . . .
C10 C 0.3714(3) 0.8156(6) 0.8781(2) 0.0802(18) Uani 1 1 d . . .
H10A H 0.3960 0.8988 0.8894 0.120 Uiso 1 1 calc R . .
H10B H 0.3188 0.8322 0.8620 0.120 Uiso 1 1 calc R . .
H10C H 0.3993 0.7735 0.8529 0.120 Uiso 1 1 calc R . .
C11 C 0.5085(2) 0.1079(3) 0.96760(14) 0.0320(8) Uani 1 1 d . . .
C12 C 0.3144(3) 0.7540(5) 0.95767(18) 0.0605(13) Uani 1 1 d . . .
H12A H 0.3215 0.6927 0.9869 0.091 Uiso 1 1 calc R . .
H12B H 0.2632 0.7427 0.9381 0.091 Uiso 1 1 calc R . .
H12C H 0.3203 0.8441 0.9707 0.091 Uiso 1 1 calc R . .
C13 C 0.5526(3) -0.0090(4) 0.96405(16) 0.0421(10) Uani 1 1 d . . .
H13 H 0.5878 -0.0144 0.9401 0.051 Uiso 1 1 calc R . .
C14 C 0.5172(2) 0.8681(3) 0.79726(12) 0.0270(7) Uani 1 1 d . . .
H14 H 0.5289 0.8216 0.8289 0.032 Uiso 1 1 calc R . .
C15 C 0.5170(2) 0.0075(3) 0.79710(13) 0.0275(8) Uani 1 1 d . . .
H15 H 0.5283 0.0543 0.8287 0.033 Uiso 1 1 calc R . .
C16 C 0.4572(2) 0.1157(4) 1.00319(15) 0.0413(10) Uani 1 1 d . . .
H16 H 0.4286 0.1937 1.0053 0.050 Uiso 1 1 calc R . .
C17 C 0.7207(3) 0.6338(4) 1.01749(15) 0.0457(11) Uani 1 1 d . . .
H17 H 0.7007 0.5551 1.0295 0.055 Uiso 1 1 calc R . .
C18B C 0.3442(5) 0.3551(9) 0.8204(3) 0.0418(15) Uiso 0.50 1 d PD A 1
H18B H 0.3593 0.2696 0.8117 0.050 Uiso 0.50 1 calc PR A 1
N1 N 0.37138(19) 0.7276(3) 0.92370(12) 0.0420(8) Uani 1 1 d . . .
N2 N 0.2672(4) 0.3912(8) 0.8096(3) 0.0522(14) Uiso 0.50 1 d PD A 1
C19B C 0.2222(6) 0.2413(11) 0.7836(4) 0.066(2) Uiso 0.50 1 d PD A 2
H19A H 0.2137 0.1547 0.7979 0.098 Uiso 0.50 1 calc PR A 2
H19B H 0.2286 0.2322 0.7471 0.098 Uiso 0.50 1 calc PR A 2
H19C H 0.1784 0.2979 0.7863 0.098 Uiso 0.50 1 calc PR A 2
C20 C 0.2328(8) 0.5141(11) 0.8265(5) 0.093(4) Uiso 0.50 1 d PD A 1
H20A H 0.1778 0.5132 0.8148 0.139 Uiso 0.50 1 calc PR A 1
H20B H 0.2556 0.5898 0.8115 0.139 Uiso 0.50 1 calc PR A 1
H20C H 0.2425 0.5201 0.8644 0.139 Uiso 0.50 1 calc PR A 1
C1A C 0.3194(10) 0.1736(13) 0.8366(7) 0.152(7) Uani 0.50 1 d PD A 2
H1AA H 0.2803 0.1051 0.8312 0.228 Uiso 0.50 1 calc PR A 2
H1AB H 0.3343 0.1884 0.8738 0.228 Uiso 0.50 1 calc PR A 2
H1AC H 0.3639 0.1458 0.8213 0.228 Uiso 0.50 1 calc PR A 2
N3 N 0.2883(4) 0.2976(8) 0.8115(3) 0.0522(14) Uiso 0.50 1 d PD A 2
C19A C 0.2121(6) 0.3039(10) 0.7797(4) 0.066(2) Uiso 0.50 1 d PD A 1
H19D H 0.1613 0.3436 0.7761 0.098 Uiso 0.50 1 calc PR A 1
H19E H 0.2115 0.2195 0.7976 0.098 Uiso 0.50 1 calc PR A 1
H19F H 0.2264 0.2901 0.7453 0.098 Uiso 0.50 1 calc PR A 1
C18A C 0.3334(5) 0.4023(9) 0.8141(4) 0.0418(15) Uiso 0.50 1 d PD A 2
H18A H 0.3153 0.4678 0.7894 0.050 Uiso 0.50 1 calc PR A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
U1 O3 2.288(2) . ?
U1 O2 2.341(2) . ?
U1 O5 2.397(2) . ?
U1 O7 2.436(3) . ?
U1 O6 2.463(3) . ?
U1 O4 2.466(2) . ?
U1 O9 2.482(2) . ?
U1 O8 2.487(2) . ?
U1 Cl1 2.7081(10) . ?
U1 C3 2.845(4) . ?
U1 C4 2.849(3) . ?
O2 C2 1.253(3) . ?
O3 C1 1.249(3) . ?
O4 C4 1.258(4) . ?
O5 C5 1.241(4) . ?
O6 C3 1.267(4) . ?
O7 C18A 1.179(8) . ?
O7 C18B 1.197(8) . ?
O8 C3 1.263(4) . ?
O9 C4 1.251(4) . ?
C1 O3 1.249(3) 2_656 ?
C1 C7 1.498(6) . ?
C2 O2 1.253(3) 2_656 ?
C2 C8 1.506(6) . ?
C3 C9 1.490(5) . ?
C4 C11 1.502(5) . ?
C5 N1 1.298(5) . ?
C6 C17 1.373(5) 7_667 ?
C6 C9 1.385(5) . ?
C7 C14 1.386(4) . ?
C7 C14 1.386(4) 2_656 ?
C8 C15 1.380(4) 2_656 ?
C8 C15 1.380(4) . ?
C9 C17 1.376(5) . ?
C10 N1 1.461(5) . ?
C11 C16 1.369(5) . ?
C11 C13 1.409(5) . ?
C12 N1 1.438(5) . ?
C13 C16 1.382(5) 5_657 ?
C14 C15 1.392(4) 1_565 ?
C15 C14 1.392(4) 1_545 ?
C16 C13 1.382(5) 5_657 ?
C17 C6 1.373(5) 7_667 ?
C18B N2 1.375(9) . ?
N2 C20 1.459(11) . ?
N2 C19A 1.431(10) . ?
C19B N3 1.380(10) . ?
C1A N3 1.462(12) . ?
N3 C18A 1.303(9) . ?

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
O3 U1 O2 82.39(8) . . ?
O3 U1 O5 79.81(9) . . ?
O2 U1 O5 137.49(9) . . ?
O3 U1 O7 76.67(11) . . ?
O2 U1 O7 69.80(9) . . ?
O5 U1 O7 68.65(9) . . ?
O3 U1 O6 125.37(9) . . ?
O2 U1 O6 143.75(8) . . ?
O5 U1 O6 75.72(9) . . ?
O7 U1 O6 133.59(10) . . ?
O3 U1 O4 155.57(8) . . ?
O2 U1 O4 75.04(8) . . ?
O5 U1 O4 123.50(9) . . ?
O7 U1 O4 103.56(10) . . ?
O6 U1 O4 72.46(9) . . ?
O3 U1 O9 143.55(10) . . ?
O2 U1 O9 99.79(9) . . ?
O5 U1 O9 74.28(9) . . ?
O7 U1 O9 70.28(10) . . ?
O6 U1 O9 72.19(9) . . ?
O4 U1 O9 52.10(8) . . ?
O3 U1 O8 72.96(9) . . ?
O2 U1 O8 140.69(8) . . ?
O5 U1 O8 67.82(9) . . ?
O7 U1 O8 130.20(9) . . ?
O6 U1 O8 52.67(8) . . ?
O4 U1 O8 120.12(9) . . ?
O9 U1 O8 118.28(9) . . ?
O3 U1 Cl1 86.89(8) . . ?
O2 U1 Cl1 74.92(7) . . ?
O5 U1 Cl1 141.37(7) . . ?
O7 U1 Cl1 142.60(7) . . ?
O6 U1 Cl1 83.17(7) . . ?
O4 U1 Cl1 78.39(7) . . ?
O9 U1 Cl1 129.06(7) . . ?
O8 U1 Cl1 73.63(7) . . ?
O3 U1 C3 99.04(10) . . ?
O2 U1 C3 152.91(9) . . ?
O5 U1 C3 68.55(10) . . ?
O7 U1 C3 137.05(10) . . ?
O6 U1 C3 26.39(9) . . ?
O4 U1 C3 96.89(10) . . ?
O9 U1 C3 94.89(10) . . ?
O8 U1 C3 26.32(8) . . ?
Cl1 U1 C3 78.14(8) . . ?
O3 U1 C4 161.88(11) . . ?
O2 U1 C4 86.54(9) . . ?
O5 U1 C4 99.18(10) . . ?
O7 U1 C4 86.07(11) . . ?
O6 U1 C4 71.03(9) . . ?
O4 U1 C4 26.13(9) . . ?
O9 U1 C4 25.99(9) . . ?
O8 U1 C4 123.67(9) . . ?
Cl1 U1 C4 104.05(8) . . ?
C3 U1 C4 97.35(10) . . ?
C2 O2 U1 153.8(2) . . ?
C1 O3 U1 164.3(2) . . ?
C4 O4 U1 94.2(2) . . ?
C5 O5 U1 142.0(2) . . ?
C3 O6 U1 93.9(2) . . ?
C18A O7 C18B 25.5(6) . . ?
C18A O7 U1 152.4(5) . . ?
C18B O7 U1 136.1(5) . . ?
C3 O8 U1 92.9(2) . . ?
C4 O9 U1 93.6(2) . . ?
O3 C1 O3 123.5(4) . 2_656 ?
O3 C1 C7 118.24(19) . . ?
O3 C1 C7 118.24(19) 2_656 . ?
O2 C2 O2 124.5(4) 2_656 . ?
O2 C2 C8 117.8(2) 2_656 . ?
O2 C2 C8 117.8(2) . . ?
O6 C3 O8 120.4(3) . . ?
O6 C3 C9 119.9(3) . . ?
O8 C3 C9 119.7(3) . . ?
O6 C3 U1 59.74(18) . . ?
O8 C3 U1 60.80(17) . . ?
C9 C3 U1 174.8(3) . . ?
O9 C4 O4 120.0(3) . . ?
O9 C4 C11 119.7(3) . . ?
O4 C4 C11 120.4(3) . . ?
O9 C4 U1 60.38(18) . . ?
O4 C4 U1 59.68(17) . . ?
C11 C4 U1 177.9(3) . . ?
O5 C5 N1 124.6(4) . . ?
C17 C6 C9 119.9(3) 7_667 . ?
C14 C7 C14 120.3(4) . 2_656 ?
C14 C7 C1 119.9(2) . . ?
C14 C7 C1 119.9(2) 2_656 . ?
C15 C8 C15 120.4(4) 2_656 . ?
C15 C8 C2 119.8(2) 2_656 . ?
C15 C8 C2 119.8(2) . . ?
C17 C9 C6 119.1(3) . . ?
C17 C9 C3 121.2(3) . . ?
C6 C9 C3 119.6(3) . . ?
C16 C11 C13 120.4(3) . . ?
C16 C11 C4 120.8(3) . . ?
C13 C11 C4 118.8(3) . . ?
C16 C13 C11 118.8(4) 5_657 . ?
C7 C14 C15 119.7(3) . 1_565 ?
C8 C15 C14 120.0(3) . 1_545 ?
C11 C16 C13 120.8(4) . 5_657 ?
C6 C17 C9 121.0(4) 7_667 . ?
O7 C18B N2 120.8(8) . . ?
C5 N1 C12 123.3(4) . . ?
C5 N1 C10 119.6(4) . . ?
C12 N1 C10 117.1(4) . . ?
C18B N2 C20 126.3(9) . . ?
C18B N2 C19A 120.2(8) . . ?
C20 N2 C19A 113.6(9) . . ?
C18A N3 C19B 143.4(9) . . ?
C18A N3 C1A 118.5(10) . . ?
C19B N3 C1A 96.2(9) . . ?
O7 C18A N3 134.2(9) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        32.69
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         1.526
_refine_diff_density_min         -1.505
_refine_diff_density_rms         0.176
_database_code_depnum_ccdc_archive 'CCDC 1017514'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_shelx

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H22 N2 O10 U'
_chemical_formula_weight         712.45

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   'C 1 2/c 1'

loop_
_symmetry_equiv_pos_as_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                   15.2600(7)
_cell_length_b                   11.4841(5)
_cell_length_c                   13.4499(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.490(2)
_cell_angle_gamma                90.00
_cell_volume                     2309.82(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9972
_cell_measurement_theta_min      2.235
_cell_measurement_theta_max      35.4985

__exptl_crystal_description      block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.128
_exptl_crystal_size_mid          0.077
_exptl_crystal_size_min          0.052
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.049
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1360
_exptl_absorpt_coefficient_mu    7.081
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6121
_exptl_absorpt_correction_T_max  0.692
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            31667
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_sigmaI/netI    0.0251
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.56
_diffrn_reflns_theta_max         36.40
_reflns_number_total             5622
_reflns_number_gt                5072
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0247P)²+0.7669P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5622
_refine_ls_number_parameters     161
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0251
_refine_ls_R_factor_gt           0.0196
_refine_ls_wR_factor_ref         0.0470
_refine_ls_wR_factor_gt          0.0451
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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 0.0000 0.371494(6) 0.2500 0.01411(2) Uani 1 2 d S . .
O1 O 0.05249(10) 0.36555(11) 0.08394(13) 0.0254(3) Uani 1 1 d . . .
O2 O 0.02537(11) 0.17803(11) 0.33240(12) 0.0270(3) Uani 1 1 d . . .
O3 O -0.04686(11) 0.56796(12) 0.30168(13) 0.0305(3) Uani 1 1 d . . .
O4 O 0.14392(10) 0.30093(14) 0.21859(11) 0.0293(3) Uani 1 1 d . . .
C1 C 0.0000 0.1237(2) 0.2500 0.0231(5) Uani 1 2 d S . .
O5 O 0.11907(10) 0.41925(15) 0.38431(12) 0.0303(3) Uani 1 1 d . . .
C2 C 0.0000 0.6217(2) 0.2500 0.0223(4) Uani 1 2 d S . .
C3 C 0.0000 -0.0065(2) 0.2500 0.0241(5) Uani 1 2 d S . .
C4 C 0.01926(17) -0.06656(17) 0.16752(18) 0.0308(4) Uani 1 1 d . . .
H4 H 0.0304 -0.0260 0.1115 0.037 Uiso 1 1 calc R . .
C5 C 0.02185(17) -0.18738(17) 0.16868(18) 0.0307(4) Uani 1 1 d . . .
H5 H 0.0381 -0.2279 0.1153 0.037 Uiso 1 1 calc R . .
N1 N 0.22412(12) 0.41677(17) 0.52662(15) 0.0299(4) Uani 1 1 d . . .
C6 C 0.2477(2) 0.4202(3) 0.6372(2) 0.0501(7) Uani 1 1 d . . .
H6A H 0.3116 0.4207 0.6585 0.075 Uiso 1 1 calc R . .
H6B H 0.2236 0.3529 0.6646 0.075 Uiso 1 1 calc R . .
H6C H 0.2233 0.4894 0.6613 0.075 Uiso 1 1 calc R . .
C7 C 0.0000 0.7524(2) 0.2500 0.0231(5) Uani 1 2 d S . .
C8 C 0.29612(18) 0.4211(3) 0.4710(3) 0.0513(7) Uani 1 1 d . . .
H8A H 0.3525 0.4212 0.5179 0.077 Uiso 1 1 calc R . .
H8B H 0.2909 0.4908 0.4307 0.077 Uiso 1 1 calc R . .
H8C H 0.2927 0.3544 0.4274 0.077 Uiso 1 1 calc R . .
C9 C 0.14077(13) 0.41591(17) 0.47880(16) 0.0246(3) Uani 1 1 d . . .
H9 H 0.0959 0.4127 0.5165 0.029 Uiso 1 1 calc R . .
C10 C 0.12544(12) 0.31867(15) 0.12431(15) 0.0205(3) Uani 1 1 d . . .
C11 C 0.19027(12) 0.28271(15) 0.06053(14) 0.0203(3) Uani 1 1 d . . .
C12 C 0.27040(14) 0.22910(19) 0.10388(16) 0.0268(4) Uani 1 1 d . . .
H12 H 0.2844 0.2157 0.1734 0.032 Uiso 1 1 calc R . .
C13 C 0.17047(13) 0.30441(17) -0.04307(15) 0.0241(3) Uani 1 1 d . . .
H13 H 0.1173 0.3416 -0.0719 0.029 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
U1 O5 2.3575(15) 2 ?
U1 O5 2.3575(16) . ?
U1 O4 2.4552(14) . ?
U1 O4 2.4552(14) 2 ?
U1 O2 2.4786(14) 2 ?
U1 O2 2.4786(14) . ?
U1 O3 2.5066(14) . ?
U1 O3 2.5066(14) 2 ?
U1 O1 2.5194(15) 2 ?
U1 O1 2.5194(15) . ?
U1 C1 2.846(2) . ?
U1 C10 2.8600(16) . ?
O1 C10 1.258(2) . ?
O2 C1 1.2637(18) . ?
O3 C2 1.2544(18) . ?
O4 C10 1.260(2) . ?
C1 O2 1.2637(18) 2 ?
C1 C3 1.495(3) . ?
O5 C9 1.248(3) . ?
C2 O3 1.2544(18) 2 ?
C2 C7 1.501(3) . ?
C3 C4 1.387(2) . ?
C3 C4 1.387(2) 2 ?
C4 C5 1.388(3) . ?
C5 C7 1.389(2) 1_545 ?
N1 C9 1.306(3) . ?
N1 C8 1.448(3) . ?
N1 C6 1.460(3) . ?
C7 C5 1.389(2) 2_565 ?
C7 C5 1.389(2) 1_565 ?
C10 C11 1.491(2) . ?
C11 C12 1.389(3) . ?
C11 C13 1.388(3) . ?
C12 C13 1.388(3) 7 ?
C13 C12 1.388(3) 7 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 U1 O5 153.10(8) 2 . ?
O5 U1 O4 121.62(5) 2 . ?
O5 U1 O4 68.24(5) . . ?
O5 U1 O4 68.24(5) 2 2 ?
O5 U1 O4 121.62(5) . 2 ?
O4 U1 O4 141.45(8) . 2 ?
O5 U1 O2 80.68(6) 2 2 ?
O5 U1 O2 125.38(6) . 2 ?
O4 U1 O2 72.10(5) . 2 ?
O4 U1 O2 73.48(5) 2 2 ?
O5 U1 O2 125.38(6) 2 . ?
O5 U1 O2 80.68(5) . . ?
O4 U1 O2 73.48(5) . . ?
O4 U1 O2 72.10(5) 2 . ?
O2 U1 O2 52.63(7) 2 . ?
O5 U1 O3 77.54(6) 2 . ?
O5 U1 O3 78.29(6) . . ?
O4 U1 O3 131.24(5) . . ?
O4 U1 O3 86.27(5) 2 . ?
O2 U1 O3 154.56(6) 2 . ?
O2 U1 O3 135.29(5) . . ?
O5 U1 O3 78.29(6) 2 2 ?
O5 U1 O3 77.54(6) . 2 ?
O4 U1 O3 86.27(5) . 2 ?
O4 U1 O3 131.24(5) 2 2 ?
O2 U1 O3 135.29(5) 2 2 ?
O2 U1 O3 154.56(6) . 2 ?
O3 U1 O3 51.66(7) . 2 ?
O5 U1 O1 110.67(5) 2 2 ?
O5 U1 O1 70.10(5) . 2 ?
O4 U1 O1 126.64(5) . 2 ?
O4 U1 O1 52.07(5) 2 2 ?
O2 U1 O1 108.85(5) 2 2 ?
O2 U1 O1 68.18(5) . 2 ?
O3 U1 O1 67.66(5) . 2 ?
O3 U1 O1 115.40(5) 2 2 ?
O5 U1 O1 70.10(5) 2 . ?
O5 U1 O1 110.67(5) . . ?
O4 U1 O1 52.07(5) . . ?
O4 U1 O1 126.64(5) 2 . ?
O2 U1 O1 68.18(5) 2 . ?
O2 U1 O1 108.85(5) . . ?
O3 U1 O1 115.40(5) . . ?
O3 U1 O1 67.66(5) 2 . ?
O1 U1 O1 176.89(6) 2 . ?
O5 U1 C1 103.45(4) 2 . ?
O5 U1 C1 103.45(4) . . ?
O4 U1 C1 70.73(4) . . ?
O4 U1 C1 70.73(4) 2 . ?
O2 U1 C1 26.31(4) 2 . ?
O2 U1 C1 26.31(4) . . ?
O3 U1 C1 154.17(3) . . ?
O3 U1 C1 154.17(3) 2 . ?
O1 U1 C1 88.45(3) 2 . ?
O1 U1 C1 88.45(3) . . ?
O5 U1 C10 95.79(5) 2 . ?
O5 U1 C10 89.87(5) . . ?
O4 U1 C10 26.01(5) . . ?
O4 U1 C10 139.35(5) 2 . ?
O2 U1 C10 66.98(5) 2 . ?
O2 U1 C10 90.62(5) . . ?
O3 U1 C10 128.05(5) . . ?
O3 U1 C10 76.44(5) 2 . ?
O1 U1 C10 152.46(5) 2 . ?
O1 U1 C10 26.08(5) . . ?
C1 U1 C10 77.75(3) . . ?
C10 O1 U1 92.25(12) . . ?
C1 O2 U1 93.29(12) . . ?
C2 O3 U1 93.65(12) . . ?
C10 O4 U1 95.24(11) . . ?
O2 C1 O2 120.8(2) . 2 ?
O2 C1 C3 119.60(11) . . ?
O2 C1 C3 119.60(11) 2 . ?
O2 C1 U1 60.40(11) . . ?
O2 C1 U1 60.40(11) 2 . ?
C3 C1 U1 180.0 . . ?
C9 O5 U1 141.31(14) . . ?
O3 C2 O3 121.1(2) 2 . ?
O3 C2 C7 119.47(11) 2 . ?
O3 C2 C7 119.47(11) . . ?
O3 C2 U1 60.53(11) 2 . ?
O3 C2 U1 60.53(11) . . ?
C7 C2 U1 180.0 . . ?
C4 C3 C4 120.4(2) . 2 ?
C4 C3 C1 119.82(12) . . ?
C4 C3 C1 119.82(12) 2 . ?
C5 C4 C3 119.89(19) . . ?
C4 C5 C7 119.69(19) . 1_545 ?
C9 N1 C8 120.7(2) . . ?
C9 N1 C6 121.3(2) . . ?
C8 N1 C6 117.9(2) . . ?
C5 C7 C5 120.3(2) 2_565 1_565 ?
C5 C7 C2 119.83(12) 2_565 . ?
C5 C7 C2 119.83(12) 1_565 . ?
O5 C9 N1 122.41(19) . . ?
O1 C10 O4 120.33(16) . . ?
O1 C10 C11 120.11(18) . . ?
O4 C10 C11 119.56(17) . . ?
O1 C10 U1 61.67(10) . . ?
O4 C10 U1 58.75(9) . . ?
C11 C10 U1 176.15(12) . . ?
C12 C11 C13 119.88(16) . . ?
C12 C11 C10 120.70(17) . . ?
C13 C11 C10 119.41(16) . . ?
C13 C12 C11 119.79(19) 7 . ?
C12 C13 C11 120.32(17) 7 . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        36.40
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.327
_refine_diff_density_min         -0.732
_refine_diff_density_rms         0.129
_database_code_depnum_ccdc_archive 'CCDC 1017515'
