# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 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_1-98K
_database_code_depnum_ccdc_archive 'CCDC 1472437'
_audit_update_record             
;
2016-04-05 deposited with the CCDC.
2016-05-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H11 O16 P4 U2, C4 H12 N'
_chemical_formula_sum            'C16 H23 N O16 P4 U2'
_chemical_formula_weight         1085.29

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'
P P 0.1023 0.0942 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   19.7287(17)
_cell_length_b                   15.1632(14)
_cell_length_c                   9.0568(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2709.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    98(2)
_cell_measurement_reflns_used    9686
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      27.54

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.661
_exptl_crystal_F_000             1992
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    12.251
_shelx_estimated_absorpt_T_min   0.193
_shelx_estimated_absorpt_T_max   0.640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.561
_exptl_absorpt_correction_T_max  0.613
_exptl_absorpt_process_details   'Bruker, SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      98(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Aperx II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            63489
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.463
_diffrn_reflns_theta_max         27.547
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3245
_reflns_number_gt                2825
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'SMART (Bruker)'
_computing_cell_refinement       'SMART (Bruker)'
_computing_data_reduction        'SMART (Bruker)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0299P)²+8.3388P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3245
_refine_ls_number_parameters     205
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0245
_refine_ls_R_factor_gt           0.0190
_refine_ls_wR_factor_ref         0.0595
_refine_ls_wR_factor_gt          0.0564
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.002
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
U1 U 0.13238(2) 0.03776(2) 0.50298(2) 0.00855(6) Uani 1 1 d . . . . .
P1 P 0.20758(4) 0.06590(6) 0.86816(10) 0.01152(17) Uani 1 1 d . . . . .
P2 P 0.01508(4) -0.06843(6) 0.25515(9) 0.01101(17) Uani 1 1 d . . . . .
O1 O 0.19244(12) 0.08427(16) 0.7077(3) 0.0161(5) Uani 1 1 d . . . . .
O2 O 0.27095(12) 0.01210(16) 0.8926(3) 0.0160(5) Uani 1 1 d . . . . .
O3 O 0.14950(13) 0.01247(17) 0.9437(3) 0.0189(5) Uani 1 1 d . . . . .
H3 H 0.1122 0.0264 0.9057 0.028 Uiso 1 1 calc R U . . .
O4 O 0.06585(12) 0.00162(16) 0.3019(3) 0.0142(5) Uani 1 1 d . . . . .
O5 O -0.03901(12) -0.08723(15) 0.3699(3) 0.0139(5) Uani 1 1 d . . . . .
O6 O -0.02031(12) -0.04234(16) 0.1081(3) 0.0150(5) Uani 1 1 d . . . . .
H6 H 0.0092 -0.0298 0.0446 0.022 Uiso 0.5 1 calc R U P . .
O7 O 0.11991(13) -0.06864(16) 0.5799(3) 0.0177(5) Uani 1 1 d . . . . .
O8 O 0.14378(12) 0.14346(16) 0.4243(3) 0.0154(5) Uani 1 1 d . . . . .
C1 C 0.2059(2) 0.2500 0.8879(5) 0.0118(9) Uani 1 2 d S T P . .
H1 H 0.1943 0.2500 0.7861 0.014 Uiso 1 2 calc R U P . .
C2 C 0.21448(17) 0.1697(2) 0.9626(4) 0.0128(6) Uani 1 1 d . . . . .
C3 C 0.23008(18) 0.1708(2) 1.1127(4) 0.0166(7) Uani 1 1 d . . . . .
H3A H 0.2360 0.1167 1.1640 0.020 Uiso 1 1 calc R U . . .
C4 C 0.2371(3) 0.2500 1.1882(6) 0.0178(10) Uani 1 2 d S T P . .
H4 H 0.2467 0.2500 1.2910 0.021 Uiso 1 2 calc R U P . .
C5 C 0.0273(2) -0.2500 0.2470(5) 0.0127(9) Uani 1 2 d S T P . .
H5 H -0.0190 -0.2500 0.2757 0.015 Uiso 1 2 calc R U P . .
C6 C 0.06036(17) -0.1701(2) 0.2265(4) 0.0121(6) Uani 1 1 d . . . . .
C7 C 0.12818(16) -0.1706(2) 0.1818(4) 0.0147(7) Uani 1 1 d . . . . .
H7 H 0.1516 -0.1165 0.1674 0.018 Uiso 1 1 calc R U . . .
C8 C 0.1612(2) -0.2500 0.1585(5) 0.0153(10) Uani 1 2 d S T P . .
H8 H 0.2070 -0.2500 0.1262 0.018 Uiso 1 2 calc R U P . .
C10 C 0.4889(3) 0.2500 0.1089(6) 0.0322(14) Uani 1 2 d S T P A .
H10A H 0.5296 0.2811 0.0753 0.048 Uiso 0.5 1 calc R U P . .
H10B H 0.4485 0.2798 0.0705 0.048 Uiso 0.5 1 calc R U P . .
H10C H 0.4899 0.1891 0.0729 0.048 Uiso 0.5 1 calc R U P . .
C9 C 0.4300(6) 0.1886(8) 0.3284(10) 0.042(3) Uani 0.5 1 d . . P A -1
H9A H 0.4331 0.1821 0.4358 0.063 Uiso 0.5 1 calc R U P A -1
H9B H 0.4348 0.1307 0.2815 0.063 Uiso 0.5 1 calc R U P A -1
H9C H 0.3859 0.2140 0.3023 0.063 Uiso 0.5 1 calc R U P A -1
C11 C 0.5529(5) 0.2103(6) 0.3389(9) 0.034(2) Uani 0.5 1 d . . P A -1
H11A H 0.5506 0.2112 0.4470 0.052 Uiso 0.5 1 calc R U P A -1
H11B H 0.5918 0.2452 0.3058 0.052 Uiso 0.5 1 calc R U P A -1
H11C H 0.5580 0.1493 0.3049 0.052 Uiso 0.5 1 calc R U P A -1
C12 C 0.4796(8) 0.3367(6) 0.3237(10) 0.044(3) Uani 0.5 1 d . . P A -1
H12A H 0.5151 0.3735 0.2795 0.066 Uiso 0.5 1 calc R U P A -1
H12B H 0.4838 0.3382 0.4315 0.066 Uiso 0.5 1 calc R U P A -1
H12C H 0.4350 0.3592 0.2948 0.066 Uiso 0.5 1 calc R U P A -1
N1 N 0.4868(2) 0.2500 0.2741(5) 0.0185(9) Uani 1 2 d S T P . .


_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 O8 1.768(2) . ?
U1 O7 1.775(2) . ?
U1 O2 2.282(2) 4_554 ?
U1 O5 2.298(2) 5_556 ?
U1 O1 2.311(2) . ?
U1 O4 2.311(2) . ?
P1 O2 1.509(2) . ?
P1 O1 1.510(2) . ?
P1 O3 1.561(3) . ?
P1 C2 1.797(4) . ?
P2 O5 1.517(2) . ?
P2 O4 1.520(2) . ?
P2 O6 1.555(3) . ?
P2 C6 1.801(3) . ?
O2 U1 2.282(2) 4 ?
O3 H3 0.8400 . ?
O5 U1 2.298(2) 5_556 ?
O6 H6 0.8400 . ?
C1 C2 1.403(4) . ?
C1 C2 1.403(4) 7_565 ?
C1 H1 0.9500 . ?
C2 C3 1.395(5) . ?
C3 C4 1.389(4) . ?
C3 H3A 0.9500 . ?
C4 C3 1.389(4) 7_565 ?
C4 H4 0.9500 . ?
C5 C6 1.388(4) 7 ?
C5 C6 1.388(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.398(5) . ?
C7 C8 1.385(4) . ?
C7 H7 0.9500 . ?
C8 C7 1.385(4) 7 ?
C8 H8 0.9500 . ?
C10 N1 1.497(7) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C9 N1 1.537(9) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C11 N1 1.552(9) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 N1 1.396(8) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

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
O8 U1 O7 179.11(12) . . ?
O8 U1 O2 91.00(10) . 4_554 ?
O7 U1 O2 89.23(10) . 4_554 ?
O8 U1 O5 90.46(10) . 5_556 ?
O7 U1 O5 89.37(10) . 5_556 ?
O2 U1 O5 175.89(9) 4_554 5_556 ?
O8 U1 O1 88.94(10) . . ?
O7 U1 O1 91.91(11) . . ?
O2 U1 O1 91.37(9) 4_554 . ?
O5 U1 O1 84.81(9) 5_556 . ?
O8 U1 O4 88.25(10) . . ?
O7 U1 O4 90.88(10) . . ?
O2 U1 O4 92.92(9) 4_554 . ?
O5 U1 O4 90.97(8) 5_556 . ?
O1 U1 O4 174.91(8) . . ?
O2 P1 O1 113.89(15) . . ?
O2 P1 O3 105.26(15) . . ?
O1 P1 O3 111.85(15) . . ?
O2 P1 C2 109.94(15) . . ?
O1 P1 C2 108.15(15) . . ?
O3 P1 C2 107.57(16) . . ?
O5 P2 O4 113.84(14) . . ?
O5 P2 O6 108.60(14) . . ?
O4 P2 O6 110.88(14) . . ?
O5 P2 C6 106.67(14) . . ?
O4 P2 C6 108.16(15) . . ?
O6 P2 C6 108.49(15) . . ?
P1 O1 U1 144.85(15) . . ?
P1 O2 U1 159.34(16) . 4 ?
P1 O3 H3 109.5 . . ?
P2 O4 U1 139.40(14) . . ?
P2 O5 U1 147.77(14) . 5_556 ?
P2 O6 H6 109.5 . . ?
C2 C1 C2 120.4(5) . 7_565 ?
C2 C1 H1 119.8 . . ?
C2 C1 H1 119.8 7_565 . ?
C3 C2 C1 119.1(3) . . ?
C3 C2 P1 119.4(3) . . ?
C1 C2 P1 121.4(3) . . ?
C4 C3 C2 120.8(3) . . ?
C4 C3 H3A 119.6 . . ?
C2 C3 H3A 119.6 . . ?
C3 C4 C3 119.7(5) 7_565 . ?
C3 C4 H4 120.1 7_565 . ?
C3 C4 H4 120.1 . . ?
C6 C5 C6 121.5(4) 7 . ?
C6 C5 H5 119.3 7 . ?
C6 C5 H5 119.3 . . ?
C5 C6 C7 119.0(3) . . ?
C5 C6 P2 119.6(3) . . ?
C7 C6 P2 121.4(3) . . ?
C8 C7 C6 119.9(3) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C7 C8 C7 120.8(5) . 7 ?
C7 C8 H8 119.6 . . ?
C7 C8 H8 119.6 7 . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C12 N1 C10 108.9(4) . . ?
C12 N1 C9 113.2(9) . . ?
C10 N1 C9 109.8(5) . . ?
C12 N1 C11 109.2(7) . . ?
C10 N1 C11 110.8(5) . . ?
C9 N1 C11 104.9(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
O2 P1 O1 U1 95.1(3) . . . . ?
O3 P1 O1 U1 -24.1(3) . . . . ?
C2 P1 O1 U1 -142.4(2) . . . . ?
O1 P1 O2 U1 146.5(4) . . . 4 ?
O3 P1 O2 U1 -90.6(5) . . . 4 ?
C2 P1 O2 U1 25.0(5) . . . 4 ?
O5 P2 O4 U1 47.4(3) . . . . ?
O6 P2 O4 U1 170.21(19) . . . . ?
C6 P2 O4 U1 -71.0(2) . . . . ?
O4 P2 O5 U1 68.2(3) . . . 5_556 ?
O6 P2 O5 U1 -55.9(3) . . . 5_556 ?
C6 P2 O5 U1 -172.6(3) . . . 5_556 ?
C2 C1 C2 C3 1.4(6) 7_565 . . . ?
C2 C1 C2 P1 -177.2(2) 7_565 . . . ?
O2 P1 C2 C3 -53.5(3) . . . . ?
O1 P1 C2 C3 -178.4(3) . . . . ?
O3 P1 C2 C3 60.6(3) . . . . ?
O2 P1 C2 C1 125.1(3) . . . . ?
O1 P1 C2 C1 0.2(4) . . . . ?
O3 P1 C2 C1 -120.8(3) . . . . ?
C1 C2 C3 C4 0.0(6) . . . . ?
P1 C2 C3 C4 178.7(3) . . . . ?
C2 C3 C4 C3 -1.4(7) . . . 7_565 ?
C6 C5 C6 C7 1.1(7) 7 . . . ?
C6 C5 C6 P2 -179.8(3) 7 . . . ?
O5 P2 C6 C5 29.0(4) . . . . ?
O4 P2 C6 C5 151.8(3) . . . . ?
O6 P2 C6 C5 -87.8(3) . . . . ?
O5 P2 C6 C7 -151.9(3) . . . . ?
O4 P2 C6 C7 -29.1(3) . . . . ?
O6 P2 C6 C7 91.3(3) . . . . ?
C5 C6 C7 C8 0.1(6) . . . . ?
P2 C6 C7 C8 -179.0(3) . . . . ?
C6 C7 C8 C7 -1.3(7) . . . 7 ?

_refine_diff_density_max         0.945
_refine_diff_density_min         -1.356
_refine_diff_density_rms         0.256

####################################################################### 
# 
# 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_1-298K
_database_code_depnum_ccdc_archive 'CCDC 1472440'
_audit_update_record             
;
2016-04-05 deposited with the CCDC.
2016-05-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H11 O16 P4 U2, C4 H12 N'
_chemical_formula_sum            'C16 H23 N O16 P4 U2'
_chemical_formula_weight         1085.29

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.6374(18)
_cell_length_b                   15.312(3)
_cell_length_c                   18.465(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2724.8(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9080
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      27.53

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.646
_exptl_crystal_F_000             1992
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    12.181
_shelx_estimated_absorpt_T_min   0.376
_shelx_estimated_absorpt_T_max   0.442
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.323
_exptl_absorpt_correction_T_max  0.377
_exptl_absorpt_process_details   SADABS,Bruker
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Aperx II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            62820
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_av_R_equivalents  0.0691
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.384
_diffrn_reflns_theta_max         27.588
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6315
_reflns_number_gt                5812
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.780
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'SMART (Bruker)'
_computing_cell_refinement       'SMART (Bruker)'
_computing_data_reduction        'SMART (Bruker)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0414P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.387(8)
_chemical_absolute_configuration AD
_refine_ls_number_reflns         6315
_refine_ls_number_parameters     360
_refine_ls_number_restraints     234
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0242
_refine_ls_wR_factor_ref         0.0708
_refine_ls_wR_factor_gt          0.0616
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.079
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
U1 U 0.44921(3) 0.78603(2) 0.61276(2) 0.01488(9) Uani 1 1 d . U . . .
U2 U 0.55594(3) 0.70879(2) 0.89767(2) 0.01400(9) Uani 1 1 d . U . . .
P1 P 0.2861(2) 0.81586(14) 0.79272(11) 0.0161(5) Uani 1 1 d . U . . .
P2 P 0.2931(2) 1.17627(14) 0.77927(11) 0.0167(5) Uani 1 1 d . U . . .
P3 P 0.0877(2) 0.81389(14) 0.55787(12) 0.0198(5) Uani 1 1 d . U . . .
P4 P 0.0746(2) 1.17991(14) 0.56494(11) 0.0176(5) Uani 1 1 d . U . . .
O1 O 0.3676(7) 0.8304(4) 0.7237(3) 0.0249(14) Uani 1 1 d . U . . .
O2 O 0.3456(7) 0.7520(4) 0.8453(3) 0.0253(14) Uani 1 1 d . U . . .
O3 O 0.1376(6) 0.7837(4) 0.7698(3) 0.0212(12) Uani 1 1 d . U . . .
H3 H 0.1010 0.7582 0.8039 0.032 Uiso 1 1 calc R U . . .
O4 O 0.3837(7) 1.1543(4) 0.7150(3) 0.0225(14) Uani 1 1 d . U . . .
O5 O 0.1489(6) 1.2092(4) 0.7564(3) 0.0274(14) Uani 1 1 d . U . . .
H5 H 0.1541 1.2324 0.7164 0.041 Uiso 1 1 calc R U . . .
O6 O 0.3539(7) 1.2440(3) 0.8300(3) 0.0225(13) Uani 1 1 d . U . . .
O7 O 0.0474(7) 0.7588(4) 0.4944(3) 0.0295(14) Uani 1 1 d . U . . .
O8 O 0.0325(8) 0.7628(4) 0.6255(3) 0.0357(17) Uani 1 1 d . U . . .
H8 H -0.0382 0.7361 0.6145 0.054 Uiso 1 1 calc R U . . .
O9 O 0.2407(6) 0.8320(4) 0.5648(3) 0.0243(14) Uani 1 1 d . U . . .
O10 O 0.2303(6) 1.1654(4) 0.5610(3) 0.0226(14) Uani 1 1 d . U . . .
O11 O 0.0292(7) 1.2157(4) 0.6386(3) 0.0294(15) Uani 1 1 d . U . . .
O12 O 0.0193(6) 1.2379(4) 0.5050(3) 0.0266(15) Uani 1 1 d . U . . .
O13 O 0.3767(7) 0.6804(4) 0.6266(4) 0.0317(16) Uani 1 1 d . U . . .
O14 O 0.5170(6) 0.8916(4) 0.5986(3) 0.0260(14) Uani 1 1 d . U . . .
O15 O 0.4851(7) 0.6060(3) 0.9202(3) 0.0263(15) Uani 1 1 d . U . . .
O16 O 0.6251(7) 0.8128(4) 0.8730(3) 0.0284(15) Uani 1 1 d . U . . .
C1 C 0.2592(10) 0.9207(5) 0.8350(5) 0.0204(19) Uani 1 1 d . U . . .
C2 C 0.1980(10) 0.9242(6) 0.9035(5) 0.025(2) Uani 1 1 d . U . . .
H2 H 0.1758 0.8730 0.9279 0.030 Uiso 1 1 calc R U . . .
C3 C 0.1707(9) 1.0043(6) 0.9350(5) 0.028(2) Uani 1 1 d . U . . .
H3A H 0.1316 1.0066 0.9810 0.034 Uiso 1 1 calc R U . . .
C4 C 0.2010(10) 1.0812(6) 0.8984(5) 0.024(2) Uani 1 1 d . U . . .
H4 H 0.1812 1.1349 0.9197 0.029 Uiso 1 1 calc R U . . .
C5 C 0.2615(9) 1.0778(5) 0.8296(5) 0.0189(18) Uani 1 1 d . U . . .
C6 C 0.2899(8) 0.9963(6) 0.7980(4) 0.0193(17) Uani 1 1 d . U . . .
H6 H 0.3295 0.9934 0.7521 0.023 Uiso 1 1 calc R U . . .
C7 C -0.0034(9) 0.9165(5) 0.5537(5) 0.021(2) Uani 1 1 d . U . . .
C8 C 0.0657(8) 0.9966(5) 0.5602(4) 0.0210(17) Uani 1 1 d . U . . .
H8A H 0.1609 0.9977 0.5683 0.025 Uiso 1 1 calc R U . . .
C9 C -0.0074(9) 1.0741(5) 0.5545(5) 0.021(2) Uani 1 1 d . U . . .
C10 C -0.1489(10) 1.0709(6) 0.5423(5) 0.027(2) Uani 1 1 d . U . . .
H10 H -0.1983 1.1228 0.5375 0.033 Uiso 1 1 calc R U . . .
C11 C -0.2183(9) 0.9923(7) 0.5371(5) 0.030(2) Uani 1 1 d . U . . .
H11 H -0.3138 0.9916 0.5303 0.036 Uiso 1 1 calc R U . . .
C12 C -0.1458(10) 0.9149(6) 0.5421(6) 0.028(2) Uani 1 1 d . U . . .
H12 H -0.1921 0.8619 0.5378 0.034 Uiso 1 1 calc R U . . .
C13 C 0.361(2) 0.5802(8) 0.2512(10) 0.101(6) Uani 1 1 d . U . . .
H13A H 0.4590 0.5761 0.2416 0.152 Uiso 1 1 calc R U . . .
H13B H 0.3462 0.5838 0.3025 0.152 Uiso 1 1 calc R U . . .
H13C H 0.3246 0.6314 0.2282 0.152 Uiso 1 1 calc R U . . .
C14 C 0.350(2) 0.4231(9) 0.2484(9) 0.104(6) Uani 1 1 d . U . . .
H14A H 0.3079 0.3746 0.2238 0.156 Uiso 1 1 calc R U . . .
H14B H 0.3336 0.4180 0.2995 0.156 Uiso 1 1 calc R U . . .
H14C H 0.4480 0.4231 0.2393 0.156 Uiso 1 1 calc R U . . .
C15 C 0.2999(15) 0.5056(9) 0.1422(6) 0.069(4) Uani 1 1 d . U . . .
H15A H 0.2637 0.4523 0.1223 0.103 Uiso 1 1 calc R U . . .
H15B H 0.3950 0.5123 0.1278 0.103 Uiso 1 1 calc R U . . .
H15C H 0.2466 0.5541 0.1245 0.103 Uiso 1 1 calc R U . . .
C16 C 0.1435(15) 0.5037(10) 0.2390(10) 0.091(5) Uani 1 1 d . U . . .
H16A H 0.0918 0.4871 0.1967 0.137 Uiso 1 1 calc R U . . .
H16B H 0.1168 0.5615 0.2535 0.137 Uiso 1 1 calc R U . . .
H16C H 0.1244 0.4634 0.2776 0.137 Uiso 1 1 calc R U . . .
N1 N 0.2911(8) 0.5024(6) 0.2225(4) 0.0301(17) Uani 1 1 d . U . . .


_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 O14 1.763(5) . ?
U1 O13 1.780(6) . ?
U1 O6 2.265(6) 3_646 ?
U1 O1 2.297(6) . ?
U1 O7 2.298(6) 4_566 ?
U1 O9 2.306(6) . ?
U2 O15 1.765(5) . ?
U2 O16 1.785(6) . ?
U2 O12 2.262(6) 2_575 ?
U2 O10 2.296(6) 3_646 ?
U2 O4 2.316(5) 3_646 ?
U2 O2 2.341(6) . ?
P1 O2 1.493(6) . ?
P1 O1 1.513(6) . ?
P1 O3 1.572(6) . ?
P1 C1 1.803(9) . ?
P2 O4 1.511(6) . ?
P2 O6 1.516(6) . ?
P2 O5 1.538(6) . ?
P2 C5 1.797(8) . ?
P3 O7 1.495(6) . ?
P3 O9 1.506(6) . ?
P3 O8 1.567(6) . ?
P3 C7 1.801(9) . ?
P4 O12 1.516(6) . ?
P4 O10 1.518(6) . ?
P4 O11 1.530(6) . ?
P4 C9 1.813(9) . ?
O4 U2 2.316(5) 3_656 ?
O6 U1 2.265(6) 3_656 ?
O7 U1 2.298(6) 4_466 ?
O10 U2 2.296(6) 3_656 ?
O12 U2 2.262(6) 2_574 ?
C1 C6 1.377(13) . ?
C1 C2 1.398(12) . ?
C2 C3 1.381(12) . ?
C3 C4 1.389(12) . ?
C4 C5 1.400(12) . ?
C5 C6 1.405(13) . ?
C7 C12 1.390(12) . ?
C7 C8 1.401(11) . ?
C8 C9 1.384(11) . ?
C9 C10 1.383(13) . ?
C10 C11 1.380(13) . ?
C11 C12 1.379(13) . ?
C13 N1 1.468(14) . ?
C14 N1 1.423(14) . ?
C15 N1 1.487(14) . ?
C16 N1 1.455(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O14 U1 O13 178.6(3) . . ?
O14 U1 O6 91.1(3) . 3_646 ?
O13 U1 O6 90.2(3) . 3_646 ?
O14 U1 O1 89.3(2) . . ?
O13 U1 O1 90.4(3) . . ?
O6 U1 O1 87.4(2) 3_646 . ?
O14 U1 O7 89.6(2) . 4_566 ?
O13 U1 O7 90.8(3) . 4_566 ?
O6 U1 O7 88.4(2) 3_646 4_566 ?
O1 U1 O7 175.6(2) . 4_566 ?
O14 U1 O9 89.2(3) . . ?
O13 U1 O9 89.4(3) . . ?
O6 U1 O9 174.7(2) 3_646 . ?
O1 U1 O9 87.4(2) . . ?
O7 U1 O9 96.9(2) 4_566 . ?
O15 U2 O16 178.7(3) . . ?
O15 U2 O12 89.5(3) . 2_575 ?
O16 U2 O12 91.2(3) . 2_575 ?
O15 U2 O10 90.6(2) . 3_646 ?
O16 U2 O10 90.4(3) . 3_646 ?
O12 U2 O10 95.8(2) 2_575 3_646 ?
O15 U2 O4 89.3(2) . 3_646 ?
O16 U2 O4 89.9(2) . 3_646 ?
O12 U2 O4 175.8(2) 2_575 3_646 ?
O10 U2 O4 88.2(2) 3_646 3_646 ?
O15 U2 O2 90.8(3) . . ?
O16 U2 O2 88.1(3) . . ?
O12 U2 O2 89.0(2) 2_575 . ?
O10 U2 O2 175.1(2) 3_646 . ?
O4 U2 O2 87.0(2) 3_646 . ?
O2 P1 O1 116.4(4) . . ?
O2 P1 O3 108.7(3) . . ?
O1 P1 O3 106.9(3) . . ?
O2 P1 C1 110.9(4) . . ?
O1 P1 C1 108.0(4) . . ?
O3 P1 C1 105.4(4) . . ?
O4 P2 O6 114.5(4) . . ?
O4 P2 O5 112.3(3) . . ?
O6 P2 O5 107.1(4) . . ?
O4 P2 C5 108.5(4) . . ?
O6 P2 C5 108.6(4) . . ?
O5 P2 C5 105.3(4) . . ?
O7 P3 O9 115.1(4) . . ?
O7 P3 O8 104.8(4) . . ?
O9 P3 O8 110.9(4) . . ?
O7 P3 C7 109.4(4) . . ?
O9 P3 C7 108.7(4) . . ?
O8 P3 C7 107.7(4) . . ?
O12 P4 O10 113.4(4) . . ?
O12 P4 O11 109.8(4) . . ?
O10 P4 O11 112.2(4) . . ?
O12 P4 C9 107.0(4) . . ?
O10 P4 C9 107.2(4) . . ?
O11 P4 C9 106.8(4) . . ?
P1 O1 U1 152.3(4) . . ?
P1 O2 U2 141.8(4) . . ?
P2 O4 U2 140.4(3) . 3_656 ?
P2 O6 U1 143.8(4) . 3_656 ?
P3 O7 U1 161.9(4) . 4_466 ?
P3 O9 U1 146.1(4) . . ?
P4 O10 U2 145.9(4) . 3_656 ?
P4 O12 U2 164.5(4) . 2_574 ?
C6 C1 C2 120.5(8) . . ?
C6 C1 P1 120.2(7) . . ?
C2 C1 P1 119.2(6) . . ?
C3 C2 C1 119.7(8) . . ?
C2 C3 C4 120.6(8) . . ?
C3 C4 C5 119.8(8) . . ?
C4 C5 C6 119.5(7) . . ?
C4 C5 P2 120.6(6) . . ?
C6 C5 P2 119.8(7) . . ?
C1 C6 C5 119.9(7) . . ?
C12 C7 C8 119.8(8) . . ?
C12 C7 P3 118.2(7) . . ?
C8 C7 P3 121.9(7) . . ?
C9 C8 C7 120.2(7) . . ?
C10 C9 C8 119.0(8) . . ?
C10 C9 P4 118.6(7) . . ?
C8 C9 P4 122.4(7) . . ?
C11 C10 C9 121.3(9) . . ?
C12 C11 C10 120.0(8) . . ?
C11 C12 C7 119.7(9) . . ?
C14 N1 C16 109.4(12) . . ?
C14 N1 C13 112.8(11) . . ?
C16 N1 C13 111.4(12) . . ?
C14 N1 C15 109.9(10) . . ?
C16 N1 C15 105.3(11) . . ?
C13 N1 C15 107.9(10) . . ?

_refine_diff_density_max         1.071
_refine_diff_density_min         -2.255
_refine_diff_density_rms         0.413

