# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_IL-13pbp-2
_audit_block_doi                 10.5517/cc1jdxvp
_database_code_depnum_ccdc_archive 'CCDC 1412603'
_audit_update_record             
;
2015-07-14 deposited with the CCDC.
2015-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ' 2(C6 H6 O9 P2 U), 2(C2.50 N0.50)'
_chemical_formula_sum            ' C17 H12 N O18 P4 U2'
_chemical_formula_weight         1118.22

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'
F F 0.0171 0.0103 '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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 2/c'
_space_group_name_Hall           '-I 2yc'

_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, y, -z+1/2'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   17.6906(12)
_cell_length_b                   9.2409(6)
_cell_length_c                   19.8228(13)
_cell_angle_alpha                90
_cell_angle_beta                 114.697(6)
_cell_angle_gamma                90
_cell_volume                     2944.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       TABLET
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_meas      NONE
_exptl_crystal_density_method    NONE
_exptl_crystal_density_diffrn    2.523
_exptl_crystal_F_000             2036
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.070
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    11.283
_shelx_estimated_absorpt_T_min   0.224
_shelx_estimated_absorpt_T_max   0.581
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.472
_exptl_absorpt_correction_T_max  0.798
_exptl_absorpt_process_details   'Bruker, SADABS'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24949
_diffrn_reflns_av_unetI/netI     0.0143
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.262
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3359
_reflns_number_gt                3051
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014 (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)+(0.0525P)²+6.5655P] 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         3359
_refine_ls_number_parameters     209
_refine_ls_number_restraints     144
_refine_ls_R_factor_all          0.0288
_refine_ls_R_factor_gt           0.0218
_refine_ls_wR_factor_ref         0.0974
_refine_ls_wR_factor_gt          0.0810
_refine_ls_goodness_of_fit_ref   1.389
_refine_ls_restrained_S_all      1.388
_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_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 0.17607(2) -0.00979(2) -0.01558(2) 0.02218(10) Uani 1 1 d . U . . .
P1 P 0.17700(8) 0.31372(14) 0.08641(7) 0.0239(3) Uani 1 1 d . U . . .
P2 P -0.11575(7) 0.34415(14) 0.11774(7) 0.0226(3) Uani 1 1 d . U . . .
O1 O 0.1452(2) 0.1670(4) 0.0580(2) 0.0341(9) Uani 1 1 d . U . . .
O2 O 0.2201(2) 0.3978(4) 0.0491(2) 0.0384(9) Uani 1 1 d . U . . .
O3 O 0.2397(2) 0.2934(4) 0.16848(19) 0.0312(8) Uani 1 1 d . U . . .
H3 H 0.2667 0.2192 0.1724 0.047 Uiso 1 1 d R U . . .
O4 O -0.1095(2) 0.1851(4) 0.1106(2) 0.0301(8) Uani 1 1 d . U . . .
O5 O -0.1951(2) 0.4158(5) 0.0713(2) 0.0397(10) Uani 1 1 d . U . . .
O6 O -0.1005(2) 0.3725(4) 0.19954(19) 0.0299(8) Uani 1 1 d . U . . .
H6 H -0.0728 0.3062 0.2257 0.045 Uiso 1 1 calc R U . . .
O7 O 0.1589(3) 0.1251(4) -0.0829(2) 0.0371(9) Uani 1 1 d . U . . .
O8 O 0.1896(3) -0.1463(4) 0.0499(2) 0.0361(9) Uani 1 1 d . U . . .
O1W O 0.0322(3) -0.0134(4) -0.0413(3) 0.0360(11) Uani 1 1 d . U . . .
C1 C 0.0971(3) 0.4185(5) 0.0949(3) 0.0228(10) Uani 1 1 d . U . . .
C2 C 0.0331(3) 0.3522(6) 0.1052(3) 0.0248(10) Uani 1 1 d . U . . .
H6A H 0.0327 0.2520 0.1094 0.030 Uiso 1 1 calc R U . . .
C3 C -0.0309(3) 0.4330(6) 0.1096(3) 0.0235(10) Uani 1 1 d . U . . .
C4 C -0.0302(3) 0.5830(6) 0.1030(3) 0.0302(12) Uani 1 1 d . U . . .
H4 H -0.0730 0.6378 0.1057 0.036 Uiso 1 1 calc R U . . .
C5 C 0.0338(4) 0.6510(6) 0.0924(3) 0.0333(12) Uani 1 1 d . U . . .
H3A H 0.0339 0.7512 0.0882 0.040 Uiso 1 1 calc R U . . .
C6 C 0.0970(3) 0.5709(6) 0.0880(3) 0.0292(11) Uani 1 1 d . U . . .
H2 H 0.1396 0.6169 0.0806 0.035 Uiso 1 1 calc R U . . .
C7 C 0.2751(10) 0.5771(12) 0.2886(7) 0.071(4) Uani 0.5 1 d G U P . .
C8 C 0.2198(9) 0.6958(17) 0.2753(9) 0.093(7) Uani 0.5 1 d G U P . .
C10 C 0.2425(8) 0.8030(12) 0.2359(8) 0.062(4) Uani 0.5 1 d G U P . .
C9 C 0.3120(8) 0.7506(14) 0.2249(7) 0.092(6) Uani 0.5 1 d G U P . .
N1 N 0.3321(7) 0.6109(14) 0.2574(7) 0.095(5) Uani 0.5 1 d G U P . .
C11 C 0.391(3) 0.522(3) 0.2665(19) 0.122(10) Uani 0.5 1 d . U 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 1.753(4) . ?
U1 O7 1.758(4) . ?
U1 O2 2.358(3) 4_544 ?
U1 O5 2.374(4) 8 ?
U1 O1W 2.378(4) . ?
U1 O4 2.388(4) 5 ?
U1 O1 2.399(4) . ?
P1 O2 1.485(4) . ?
P1 O1 1.486(4) . ?
P1 O3 1.551(4) . ?
P1 C1 1.778(5) . ?
P2 O5 1.476(4) . ?
P2 O4 1.486(4) . ?
P2 O6 1.551(3) . ?
P2 C3 1.776(5) . ?
O2 U1 2.358(3) 4_554 ?
O3 H3 0.8199 . ?
O4 U1 2.388(4) 5 ?
O5 U1 2.374(4) 8_455 ?
O6 H6 0.8200 . ?
C1 C2 1.377(7) . ?
C1 C6 1.415(8) . ?
C2 C3 1.388(7) . ?
C2 H6A 0.9300 . ?
C3 C4 1.393(8) . ?
C4 C5 1.386(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.373(8) . ?
C5 H3A 0.9300 . ?
C6 H2 0.9300 . ?
C7 C10 1.20(2) 7_565 ?
C7 N1 1.4200 . ?
C7 C8 1.4200 . ?
C8 C9 0.75(3) 7_565 ?
C8 C10 0.79(2) 7_565 ?
C8 C10 1.4200 . ?
C8 N1 1.99(3) 7_565 ?
C8 C8 2.01(2) 7_565 ?
C10 C8 0.79(3) 7_565 ?
C10 C10 1.10(2) 7_565 ?
C10 C7 1.20(2) 7_565 ?
C10 C9 1.4200 . ?
C10 C9 1.55(3) 7_565 ?
C10 N1 1.59(2) 7_565 ?
C9 C8 0.75(3) 7_565 ?
C9 N1 1.4200 . ?
C9 C10 1.55(2) 7_565 ?
N1 C11 1.28(4) . ?
N1 C10 1.59(2) 7_565 ?
N1 C8 1.99(2) 7_565 ?

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 178.02(18) . . ?
O8 U1 O2 93.82(17) . 4_544 ?
O7 U1 O2 87.17(17) . 4_544 ?
O8 U1 O5 86.15(17) . 8 ?
O7 U1 O5 95.79(18) . 8 ?
O2 U1 O5 73.31(14) 4_544 8 ?
O8 U1 O1W 87.22(18) . . ?
O7 U1 O1W 90.99(18) . . ?
O2 U1 O1W 145.51(14) 4_544 . ?
O5 U1 O1W 141.03(14) 8 . ?
O8 U1 O4 88.05(16) . 5 ?
O7 U1 O4 90.57(17) . 5 ?
O2 U1 O4 73.61(13) 4_544 5 ?
O5 U1 O4 145.91(12) 8 5 ?
O1W U1 O4 71.97(13) . 5 ?
O8 U1 O1 92.02(17) . . ?
O7 U1 O1 88.15(17) . . ?
O2 U1 O1 145.01(13) 4_544 . ?
O5 U1 O1 72.72(13) 8 . ?
O1W U1 O1 69.19(13) . . ?
O4 U1 O1 141.11(12) 5 . ?
O2 P1 O1 118.7(2) . . ?
O2 P1 O3 107.1(2) . . ?
O1 P1 O3 106.2(2) . . ?
O2 P1 C1 110.9(2) . . ?
O1 P1 C1 110.1(2) . . ?
O3 P1 C1 102.4(2) . . ?
O5 P2 O4 118.3(2) . . ?
O5 P2 O6 106.3(2) . . ?
O4 P2 O6 106.2(2) . . ?
O5 P2 C3 110.9(2) . . ?
O4 P2 C3 110.4(2) . . ?
O6 P2 C3 103.4(2) . . ?
P1 O1 U1 134.9(2) . . ?
P1 O2 U1 162.3(3) . 4_554 ?
P1 O3 H3 109.4 . . ?
P2 O4 U1 135.6(2) . 5 ?
P2 O5 U1 172.6(3) . 8_455 ?
P2 O6 H6 109.5 . . ?
C2 C1 C6 119.3(4) . . ?
C2 C1 P1 120.5(4) . . ?
C6 C1 P1 120.2(3) . . ?
C1 C2 C3 120.9(5) . . ?
C1 C2 H6A 119.6 . . ?
C3 C2 H6A 119.6 . . ?
C2 C3 C4 119.3(4) . . ?
C2 C3 P2 120.0(4) . . ?
C4 C3 P2 120.6(3) . . ?
C5 C4 C3 120.3(4) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C6 C5 C4 120.3(5) . . ?
C6 C5 H3A 119.9 . . ?
C4 C5 H3A 119.9 . . ?
C5 C6 C1 119.9(4) . . ?
C5 C6 H2 120.0 . . ?
C1 C6 H2 120.0 . . ?
C10 C7 N1 74.5(10) 7_565 . ?
C10 C7 C8 33.6(10) 7_565 . ?
N1 C7 C8 108.0 . . ?
C9 C8 C10 136(4) 7_565 7_565 ?
C9 C8 C7 166(3) 7_565 . ?
C10 C8 C7 57.5(15) 7_565 . ?
C9 C8 C10 85(3) 7_565 . ?
C10 C8 C10 50.7(15) 7_565 . ?
C7 C8 C10 108.0 . . ?
C9 C8 N1 32.9(15) 7_565 7_565 ?
C10 C8 N1 103(2) 7_565 7_565 ?
C7 C8 N1 160.5(13) . 7_565 ?
C10 C8 N1 52.6(13) . 7_565 ?
C9 C8 C8 103(2) 7_565 7_565 ?
C10 C8 C8 33.1(15) 7_565 7_565 ?
C7 C8 C8 90.5(7) . 7_565 ?
C10 C8 C8 17.6(7) . 7_565 ?
N1 C8 C8 70.1(9) 7_565 7_565 ?
C8 C10 C10 96.0(18) 7_565 7_565 ?
C8 C10 C7 88.9(18) 7_565 7_565 ?
C10 C10 C7 173(2) 7_565 7_565 ?
C8 C10 C9 21.6(16) 7_565 . ?
C10 C10 C9 74.7(10) 7_565 . ?
C7 C10 C9 110.5(10) 7_565 . ?
C8 C10 C8 129.3(16) 7_565 . ?
C10 C10 C8 33.4(11) 7_565 . ?
C7 C10 C8 141.5(10) 7_565 . ?
C9 C10 C8 108.0 . . ?
C8 C10 C9 158(2) 7_565 7_565 ?
C10 C10 C9 62.0(13) 7_565 7_565 ?
C7 C10 C9 112.7(15) 7_565 7_565 ?
C9 C10 C9 136.7(13) . 7_565 ?
C8 C10 C9 28.7(13) . 7_565 ?
C8 C10 N1 148(2) 7_565 7_565 ?
C10 C10 N1 116(2) 7_565 7_565 ?
C7 C10 N1 59.1(15) 7_565 7_565 ?
C9 C10 N1 169.5(18) . 7_565 ?
C8 C10 N1 82.4(18) . 7_565 ?
C9 C10 N1 53.6(9) 7_565 7_565 ?
C8 C9 C10 22.8(16) 7_565 . ?
C8 C9 N1 130.5(16) 7_565 . ?
C10 C9 N1 108.0 . . ?
C8 C9 C10 65.8(14) 7_565 7_565 ?
C10 C9 C10 43.3(8) . 7_565 ?
N1 C9 C10 64.7(8) . 7_565 ?
C11 N1 C7 118(2) . . ?
C11 N1 C9 133(2) . . ?
C7 N1 C9 108.0 . . ?
C11 N1 C10 164(2) . 7_565 ?
C7 N1 C10 46.4(7) . 7_565 ?
C9 N1 C10 61.7(7) . 7_565 ?
C11 N1 C8 150(2) . 7_565 ?
C7 N1 C8 91.4(7) . 7_565 ?
C9 N1 C8 16.6(7) . 7_565 ?
C10 N1 C8 45.0(5) 7_565 7_565 ?

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 21.0(4) . . . . ?
O3 P1 O1 U1 -99.6(3) . . . . ?
C1 P1 O1 U1 150.3(3) . . . . ?
O1 P1 O2 U1 -86.0(9) . . . 4_554 ?
O3 P1 O2 U1 34.1(9) . . . 4_554 ?
C1 P1 O2 U1 145.1(8) . . . 4_554 ?
O5 P2 O4 U1 26.1(4) . . . 5 ?
O6 P2 O4 U1 145.3(3) . . . 5 ?
C3 P2 O4 U1 -103.1(3) . . . 5 ?
O2 P1 C1 C2 159.2(4) . . . . ?
O1 P1 C1 C2 25.8(5) . . . . ?
O3 P1 C1 C2 -86.8(5) . . . . ?
O2 P1 C1 C6 -18.2(5) . . . . ?
O1 P1 C1 C6 -151.6(4) . . . . ?
O3 P1 C1 C6 95.8(4) . . . . ?
C6 C1 C2 C3 -0.5(8) . . . . ?
P1 C1 C2 C3 -177.9(4) . . . . ?
C1 C2 C3 C4 0.3(8) . . . . ?
C1 C2 C3 P2 176.5(4) . . . . ?
O5 P2 C3 C2 -139.2(4) . . . . ?
O4 P2 C3 C2 -6.1(5) . . . . ?
O6 P2 C3 C2 107.2(4) . . . . ?
O5 P2 C3 C4 36.9(5) . . . . ?
O4 P2 C3 C4 170.0(4) . . . . ?
O6 P2 C3 C4 -76.7(4) . . . . ?
C2 C3 C4 C5 -0.1(7) . . . . ?
P2 C3 C4 C5 -176.3(5) . . . . ?
C3 C4 C5 C6 0.2(8) . . . . ?
C4 C5 C6 C1 -0.4(8) . . . . ?
C2 C1 C6 C5 0.6(7) . . . . ?
P1 C1 C6 C5 178.0(5) . . . . ?
C10 C7 C8 C9 -162(16) 7_565 . . 7_565 ?
N1 C7 C8 C9 -166(15) . . . 7_565 ?
N1 C7 C8 C10 -3.8(19) . . . 7_565 ?
C10 C7 C8 C10 3.8(19) 7_565 . . . ?
N1 C7 C8 C10 0.0 . . . . ?
C10 C7 C8 N1 0(4) 7_565 . . 7_565 ?
N1 C7 C8 N1 -4(5) . . . 7_565 ?
C10 C7 C8 C8 2.6(16) 7_565 . . 7_565 ?
N1 C7 C8 C8 -1.3(8) . . . 7_565 ?
C9 C8 C10 C8 172(5) 7_565 . . 7_565 ?
C10 C8 C10 C8 0(2) 7_565 . . 7_565 ?
C7 C8 C10 C8 -4(3) . . . 7_565 ?
N1 C8 C10 C8 174(4) 7_565 . . 7_565 ?
C9 C8 C10 C10 172(5) 7_565 . . 7_565 ?
C7 C8 C10 C10 -4(2) . . . 7_565 ?
N1 C8 C10 C10 174(4) 7_565 . . 7_565 ?
C8 C8 C10 C10 0(2) 7_565 . . 7_565 ?
C9 C8 C10 C7 0(2) 7_565 . . 7_565 ?
C10 C8 C10 C7 -172(4) 7_565 . . 7_565 ?
C7 C8 C10 C7 -176.6(19) . . . 7_565 ?
N1 C8 C10 C7 1.8(8) 7_565 . . 7_565 ?
C8 C8 C10 C7 -172(4) 7_565 . . 7_565 ?
C9 C8 C10 C9 177(3) 7_565 . . . ?
C10 C8 C10 C9 4(2) 7_565 . . . ?
C7 C8 C10 C9 0.0 . . . . ?
N1 C8 C10 C9 178(2) 7_565 . . . ?
C8 C8 C10 C9 4(3) 7_565 . . . ?
C10 C8 C10 C9 -172(5) 7_565 . . 7_565 ?
C7 C8 C10 C9 -177(3) . . . 7_565 ?
N1 C8 C10 C9 1.8(18) 7_565 . . 7_565 ?
C8 C8 C10 C9 -172(5) 7_565 . . 7_565 ?
C9 C8 C10 N1 -1.8(18) 7_565 . . 7_565 ?
C10 C8 C10 N1 -174(4) 7_565 . . 7_565 ?
C7 C8 C10 N1 -178(2) . . . 7_565 ?
C8 C8 C10 N1 -174(4) 7_565 . . 7_565 ?
C10 C10 C9 C8 -169(6) 7_565 . . 7_565 ?
C7 C10 C9 C8 7(5) 7_565 . . 7_565 ?
C8 C10 C9 C8 -171(5) . . . 7_565 ?
C9 C10 C9 C8 -169(7) 7_565 . . 7_565 ?
N1 C10 C9 C8 0(9) 7_565 . . 7_565 ?
C8 C10 C9 N1 171(5) 7_565 . . . ?
C10 C10 C9 N1 2.4(12) 7_565 . . . ?
C7 C10 C9 N1 177.7(13) 7_565 . . . ?
C8 C10 C9 N1 0.0 . . . . ?
C9 C10 C9 N1 2(2) 7_565 . . . ?
N1 C10 C9 N1 171(11) 7_565 . . . ?
C8 C10 C9 C10 169(6) 7_565 . . 7_565 ?
C7 C10 C9 C10 175(2) 7_565 . . 7_565 ?
C8 C10 C9 C10 -2.4(12) . . . 7_565 ?
C9 C10 C9 C10 0.0(15) 7_565 . . 7_565 ?
N1 C10 C9 C10 169(12) 7_565 . . 7_565 ?
C10 C7 N1 C11 174(2) 7_565 . . . ?
C8 C7 N1 C11 176.3(19) . . . . ?
C10 C7 N1 C9 -2.2(11) 7_565 . . . ?
C8 C7 N1 C9 0.0 . . . . ?
C8 C7 N1 C10 2.2(11) . . . 7_565 ?
C10 C7 N1 C8 -0.9(9) 7_565 . . 7_565 ?
C8 C7 N1 C8 1.3(8) . . . 7_565 ?
C8 C9 N1 C11 -171(3) 7_565 . . . ?
C10 C9 N1 C11 -176(2) . . . . ?
C10 C9 N1 C11 -174(2) 7_565 . . . ?
C8 C9 N1 C7 4(3) 7_565 . . . ?
C10 C9 N1 C7 0.0 . . . . ?
C10 C9 N1 C7 1.8(9) 7_565 . . . ?
C8 C9 N1 C10 3(2) 7_565 . . 7_565 ?
C10 C9 N1 C10 -1.8(9) . . . 7_565 ?
C10 C9 N1 C8 -4(3) . . . 7_565 ?
C10 C9 N1 C8 -3(2) 7_565 . . 7_565 ?

_refine_diff_density_max         1.594
_refine_diff_density_min         -2.136
_refine_diff_density_rms         0.675

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 'ionothermal reactions'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_IL-13pbp-3
_audit_block_doi                 10.5517/cc1jdxwq
_database_code_depnum_ccdc_archive 'CCDC 1412604'
_audit_update_record             
;
2015-07-14 deposited with the CCDC.
2015-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H6 F O8 P2 U, C7 H10 N'
_chemical_formula_sum            ' C13 H16 F N O8 P2 U'
_chemical_formula_weight         633.24

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'
F F 0.0171 0.0103 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   9.7194(9)
_cell_length_b                   10.3787(9)
_cell_length_c                   10.4643(9)
_cell_angle_alpha                110.067(2)
_cell_angle_beta                 103.971(2)
_cell_angle_gamma                105.105(2)
_cell_volume                     891.27(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       NEEDLE-LIKE
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_meas      NONE
_exptl_crystal_density_method    NONE
_exptl_crystal_density_diffrn    2.360
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    9.337
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.516
_exptl_absorpt_correction_T_max  0.830
_exptl_absorpt_process_details   'SADABS, BRUKER'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker,Apex 2,CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30504
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_av_R_equivalents  0.0623
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.225
_diffrn_reflns_theta_max         27.545
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4118
_reflns_number_gt                3738
_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
_computing_data_reduction        SMART
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014 (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)+(0.0001P)²+93.6017P] 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         4108
_refine_ls_number_parameters     238
_refine_ls_number_restraints     161
_refine_ls_R_factor_all          0.0788
_refine_ls_R_factor_gt           0.0719
_refine_ls_wR_factor_ref         0.2090
_refine_ls_wR_factor_gt          0.2064
_refine_ls_goodness_of_fit_ref   1.203
_refine_ls_restrained_S_all      1.186
_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_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 0.72171(7) 0.57242(8) 0.03623(8) 0.0177(2) Uani 1 1 d . U . . .
P1 P 0.8808(5) 0.2766(5) -0.0556(5) 0.0201(9) Uani 1 1 d . U . . .
P2 P 0.9045(6) -0.0400(5) 0.2783(5) 0.0223(9) Uani 1 1 d . U . . .
F1 F 0.5073(13) 0.6301(13) 0.0526(14) 0.032(3) Uani 1 1 d . U . . .
O1 O 0.7646(15) 0.3520(15) -0.0529(16) 0.029(3) Uani 1 1 d . U . . .
O2 O 1.0172(14) 0.3552(14) -0.0861(15) 0.023(3) Uani 1 1 d . U . . .
O3 O 0.7973(15) 0.1146(15) -0.1778(16) 0.028(3) Uani 1 1 d . U . . .
H3 H 0.8605 0.0828 -0.2016 0.042 Uiso 1 1 calc R U . . .
O4 O 0.8088(15) -0.1660(15) 0.1280(15) 0.028(3) Uani 1 1 d . U . . .
O5 O 1.0566(16) -0.0466(16) 0.3519(15) 0.028(3) Uani 1 1 d . U . . .
O6 O 0.8088(16) -0.0286(18) 0.3782(17) 0.034(3) Uani 1 1 d . U . . .
H6 H 0.8665 0.0157 0.4641 0.050 Uiso 1 1 calc R U . . .
O7 O 0.6825(17) 0.5677(17) -0.1426(15) 0.032(3) Uani 1 1 d . U . . .
O8 O 0.7619(17) 0.5770(19) 0.208(2) 0.045(4) Uani 1 1 d . U . . .
C1 C 0.942(2) 0.269(2) 0.115(2) 0.024(4) Uani 1 1 d . U . . .
C2 C 0.909(2) 0.133(2) 0.124(2) 0.026(4) Uani 1 1 d . U . . .
H2 H 0.8624 0.0440 0.0399 0.031 Uiso 1 1 calc R U . . .
C3 C 0.947(2) 0.132(2) 0.262(2) 0.024(4) Uani 1 1 d . U . . .
C4 C 1.024(3) 0.264(3) 0.384(2) 0.036(5) Uani 1 1 d . U . . .
H4 H 1.0520 0.2628 0.4754 0.043 Uiso 1 1 calc R U . . .
C5 C 1.063(3) 0.398(3) 0.376(3) 0.040(5) Uani 1 1 d . U . . .
H5 H 1.1156 0.4862 0.4609 0.048 Uiso 1 1 calc R U . . .
C6 C 1.020(2) 0.398(2) 0.239(2) 0.032(4) Uani 1 1 d . U . . .
H6A H 1.0445 0.4877 0.2318 0.038 Uiso 1 1 calc R U . . .
N1 N 0.495(4) 0.217(3) 0.350(4) 0.107(12) Uani 1 1 d . U . . .
C7 C 0.407(4) 0.269(3) 0.409(5) 0.084(11) Uani 1 1 d . U . . .
H7 H 0.3348 0.2909 0.3528 0.100 Uiso 1 1 calc R U . . .
C8 C 0.409(4) 0.292(3) 0.534(4) 0.081(10) Uani 1 1 d . U . . .
H8 H 0.3435 0.3332 0.5692 0.097 Uiso 1 1 calc R U . . .
C9 C 0.501(4) 0.258(4) 0.615(4) 0.073(9) Uani 1 1 d . U . . .
H9 H 0.4989 0.2703 0.7070 0.087 Uiso 1 1 calc R U . . .
C10 C 0.603(5) 0.203(4) 0.566(5) 0.086(11) Uani 1 1 d . U . . .
H10 H 0.6679 0.1742 0.6216 0.103 Uiso 1 1 calc R U . . .
C11 C 0.605(5) 0.191(4) 0.431(5) 0.090(12) Uani 1 1 d . U . . .
H11 H 0.6796 0.1663 0.3972 0.108 Uiso 1 1 calc R U . . .
C12 C 0.459(6) 0.170(6) 0.181(7) 0.15(2) Uani 1 1 d D U . . .
H12A H 0.4450 0.0675 0.1262 0.183 Uiso 1 1 calc R U . . .
H12B H 0.3760 0.1930 0.1342 0.183 Uiso 1 1 calc R U . . .
C13 C 0.603(5) 0.271(5) 0.217(6) 0.117(16) Uani 1 1 d D U . . .
H13A H 0.6069 0.3693 0.2665 0.175 Uiso 1 1 calc R U . . .
H13B H 0.6247 0.2598 0.1304 0.175 Uiso 1 1 calc R U . . .
H13C H 0.6779 0.2532 0.2811 0.175 Uiso 1 1 calc R 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 O8 1.726(18) . ?
U1 O7 1.798(14) . ?
U1 O2 2.318(12) 2_765 ?
U1 F1 2.336(12) 2_665 ?
U1 F1 2.342(11) . ?
U1 O1 2.345(14) . ?
U1 O4 2.373(14) 1_565 ?
U1 U1 3.9588(13) 2_665 ?
P1 O2 1.531(13) . ?
P1 O1 1.533(14) . ?
P1 O3 1.559(14) . ?
P1 C1 1.78(2) . ?
P2 O4 1.515(15) . ?
P2 O5 1.524(14) . ?
P2 O6 1.554(15) . ?
P2 C3 1.80(2) . ?
F1 U1 2.336(12) 2_665 ?
O2 U1 2.318(12) 2_765 ?
O3 H3 0.8200 . ?
O4 U1 2.373(14) 1_545 ?
O6 H6 0.8200 . ?
C1 C6 1.36(3) . ?
C1 C2 1.40(3) . ?
C2 C3 1.40(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.37(3) . ?
C4 C5 1.38(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.40(3) . ?
C5 H5 0.9300 . ?
C6 H6A 0.9300 . ?
N1 C7 1.30(5) . ?
N1 C11 1.35(5) . ?
N1 C12 1.59(7) . ?
C7 C8 1.24(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.28(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.39(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.38(6) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.38(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

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 179.2(7) . . ?
O8 U1 O2 86.6(6) . 2_765 ?
O7 U1 O2 92.6(6) . 2_765 ?
O8 U1 F1 90.5(6) . 2_665 ?
O7 U1 F1 90.1(6) . 2_665 ?
O2 U1 F1 144.7(4) 2_765 2_665 ?
O8 U1 F1 90.0(6) . . ?
O7 U1 F1 90.8(6) . . ?
O2 U1 F1 150.6(4) 2_765 . ?
F1 U1 F1 64.4(5) 2_665 . ?
O8 U1 O1 90.9(7) . . ?
O7 U1 O1 88.7(6) . . ?
O2 U1 O1 74.5(5) 2_765 . ?
F1 U1 O1 70.4(4) 2_665 . ?
F1 U1 O1 134.8(4) . . ?
O8 U1 O4 93.5(7) . 1_565 ?
O7 U1 O4 86.5(6) . 1_565 ?
O2 U1 O4 76.3(5) 2_765 1_565 ?
F1 U1 O4 139.0(4) 2_665 1_565 ?
F1 U1 O4 74.8(4) . 1_565 ?
O1 U1 O4 150.2(5) . 1_565 ?
O8 U1 U1 90.3(5) . 2_665 ?
O7 U1 U1 90.5(5) . 2_665 ?
O2 U1 U1 175.7(3) 2_765 2_665 ?
F1 U1 U1 32.2(3) 2_665 2_665 ?
F1 U1 U1 32.2(3) . 2_665 ?
O1 U1 U1 102.6(3) . 2_665 ?
O4 U1 U1 106.8(3) 1_565 2_665 ?
O2 P1 O1 113.0(8) . . ?
O2 P1 O3 108.7(8) . . ?
O1 P1 O3 108.2(8) . . ?
O2 P1 C1 111.1(8) . . ?
O1 P1 C1 107.7(9) . . ?
O3 P1 C1 108.0(9) . . ?
O4 P2 O5 114.7(8) . . ?
O4 P2 O6 110.0(8) . . ?
O5 P2 O6 111.0(8) . . ?
O4 P2 C3 108.6(8) . . ?
O5 P2 C3 107.4(9) . . ?
O6 P2 C3 104.6(9) . . ?
U1 F1 U1 115.6(5) 2_665 . ?
P1 O1 U1 147.5(8) . . ?
P1 O2 U1 147.0(8) . 2_765 ?
P1 O3 H3 109.5 . . ?
P2 O4 U1 133.4(8) . 1_545 ?
P2 O6 H6 109.5 . . ?
C6 C1 C2 120.3(19) . . ?
C6 C1 P1 118.4(16) . . ?
C2 C1 P1 121.3(15) . . ?
C3 C2 C1 119.3(18) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C4 C3 C2 119.3(19) . . ?
C4 C3 P2 120.0(16) . . ?
C2 C3 P2 120.7(15) . . ?
C3 C4 C5 122(2) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C4 C5 C6 119(2) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C1 C6 C5 120(2) . . ?
C1 C6 H6A 119.8 . . ?
C5 C6 H6A 119.8 . . ?
C7 N1 C11 119(4) . . ?
C7 N1 C12 119(4) . . ?
C11 N1 C12 121(4) . . ?
C8 C7 N1 126(4) . . ?
C8 C7 H7 116.9 . . ?
N1 C7 H7 116.9 . . ?
C7 C8 C9 120(4) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C8 C9 C10 120(4) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C11 C10 C9 118(4) . . ?
C11 C10 H10 121.0 . . ?
C9 C10 H10 121.0 . . ?
N1 C11 C10 117(4) . . ?
N1 C11 H11 121.7 . . ?
C10 C11 H11 121.7 . . ?
C13 C12 N1 88(4) . . ?
C13 C12 H12A 114.0 . . ?
N1 C12 H12A 114.0 . . ?
C13 C12 H12B 114.0 . . ?
N1 C12 H12B 114.0 . . ?
H12A C12 H12B 111.2 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 P1 O1 U1 -49.4(19) . . . . ?
O3 P1 O1 U1 -169.9(15) . . . . ?
C1 P1 O1 U1 73.7(18) . . . . ?
O1 P1 O2 U1 142.7(13) . . . 2_765 ?
O3 P1 O2 U1 -97.1(15) . . . 2_765 ?
C1 P1 O2 U1 21.6(17) . . . 2_765 ?
O5 P2 O4 U1 52.3(13) . . . 1_545 ?
O6 P2 O4 U1 -73.7(13) . . . 1_545 ?
C3 P2 O4 U1 172.4(10) . . . 1_545 ?
O2 P1 C1 C6 60.3(18) . . . . ?
O1 P1 C1 C6 -63.9(18) . . . . ?
O3 P1 C1 C6 179.4(15) . . . . ?
O2 P1 C1 C2 -121.2(16) . . . . ?
O1 P1 C1 C2 114.6(16) . . . . ?
O3 P1 C1 C2 -2.0(18) . . . . ?
C6 C1 C2 C3 4(3) . . . . ?
P1 C1 C2 C3 -174.0(14) . . . . ?
C1 C2 C3 C4 -4(3) . . . . ?
C1 C2 C3 P2 179.5(14) . . . . ?
O4 P2 C3 C4 176.0(16) . . . . ?
O5 P2 C3 C4 -59.4(18) . . . . ?
O6 P2 C3 C4 58.6(18) . . . . ?
O4 P2 C3 C2 -7.8(18) . . . . ?
O5 P2 C3 C2 116.8(16) . . . . ?
O6 P2 C3 C2 -125.2(16) . . . . ?
C2 C3 C4 C5 2(3) . . . . ?
P2 C3 C4 C5 178.2(18) . . . . ?
C3 C4 C5 C6 0(4) . . . . ?
C2 C1 C6 C5 -2(3) . . . . ?
P1 C1 C6 C5 176.3(17) . . . . ?
C4 C5 C6 C1 0(3) . . . . ?
C11 N1 C7 C8 -3(3) . . . . ?
C12 N1 C7 C8 170(3) . . . . ?
N1 C7 C8 C9 -3(3) . . . . ?
C7 C8 C9 C10 3(4) . . . . ?
C8 C9 C10 C11 2(5) . . . . ?
C7 N1 C11 C10 8(4) . . . . ?
C12 N1 C11 C10 -164(3) . . . . ?
C9 C10 C11 N1 -8(5) . . . . ?
C7 N1 C12 C13 122(4) . . . . ?
C11 N1 C12 C13 -65(5) . . . . ?

_refine_diff_density_max         5.654
_refine_diff_density_min         -7.156
_refine_diff_density_rms         0.461

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 'ionothermal reactions'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_IL-13pbp-1
_audit_block_doi                 10.5517/cc1jdxys
_database_code_depnum_ccdc_archive 'CCDC 1412606'
_audit_update_record             
;
2015-07-14 deposited with the CCDC.
2015-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H11 O16 P4 U2, C8 H16 N2, C4 H6 N2'
_chemical_formula_sum            ' C24 H33 N4 O16 P4 U2'
_chemical_formula_weight         1232.48
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           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                   9.7669(5)
_cell_length_b                   19.1321(10)
_cell_length_c                   19.1390(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3576.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_meas      NONE
_exptl_crystal_density_method    NONE
_exptl_crystal_density_diffrn    2.291
_exptl_crystal_F_000             2304
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.040
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    9.298
_shelx_estimated_absorpt_T_min   0.342
_shelx_estimated_absorpt_T_max   0.427
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.696
_exptl_absorpt_correction_T_max  0.757
_exptl_absorpt_process_details   'SADABS, Bruker'
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker,Apex 2,CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            68075
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_av_R_equivalents  0.0746
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.505
_diffrn_reflns_theta_max         27.529
_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 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             8243
_reflns_number_gt                7038
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.795
_reflns_Friedel_fraction_max     0.999
_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
_computing_data_reduction        SMART
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014 (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)+(0.0174P)²+8.0267P] 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_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.193(10)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         8243
_refine_ls_number_parameters     457
_refine_ls_number_restraints     714
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0587
_refine_ls_wR_factor_gt          0.0551
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.034
_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 -0.01511(3) 0.23478(2) 1.24913(3) 0.01772(8) Uani 1 1 d . U . . .
U2 U 0.28929(3) 0.00314(2) 0.74185(2) 0.01515(8) Uani 1 1 d . U . . .
P1 P 0.0725(3) 0.10782(16) 1.11375(15) 0.0177(7) Uani 1 1 d . U . . .
P2 P 0.3766(3) 0.12444(16) 0.87158(15) 0.0170(7) Uani 1 1 d . U . . .
P3 P 0.4131(4) 0.12749(17) 0.61974(16) 0.0203(8) Uani 1 1 d . U . . .
P4 P 0.1117(4) 0.10901(17) 0.37779(16) 0.0191(7) Uani 1 1 d . U . . .
O1 O -0.0121(8) 0.0511(4) 1.0789(4) 0.0217(18) Uani 1 1 d . U . . .
O2 O 0.1919(9) 0.0773(4) 1.1544(4) 0.024(2) Uani 1 1 d . U . . .
O3 O -0.0151(9) 0.1555(4) 1.1595(4) 0.0205(18) Uani 1 1 d . U . . .
O4 O 0.4557(9) 0.1796(4) 0.8323(4) 0.022(2) Uani 1 1 d . U . . .
O5 O 0.4730(8) 0.0731(4) 0.9061(4) 0.0260(19) Uani 1 1 d . U . . .
H5 H 0.4440 0.0332 0.9006 0.039 Uiso 1 1 calc R U . . .
O6 O 0.2696(9) 0.0896(4) 0.8238(4) 0.0247(19) Uani 1 1 d . U . . .
O7 O 0.4818(11) 0.1814(4) 0.6656(4) 0.029(2) Uani 1 1 d . U . . .
O8 O 0.3016(10) 0.0861(4) 0.6557(4) 0.0248(19) Uani 1 1 d . U . . .
O9 O 0.5244(9) 0.0796(4) 0.5900(4) 0.031(2) Uani 1 1 d . U . . .
H9 H 0.5040 0.0387 0.5974 0.046 Uiso 1 1 calc R U . . .
O10 O 0.2188(10) 0.0772(4) 0.3303(4) 0.0252(19) Uani 1 1 d . U . . .
O11 O 0.0124(10) 0.1552(4) 0.3381(4) 0.026(2) Uani 1 1 d . U . . .
O12 O 0.0382(8) 0.0534(4) 0.4202(4) 0.029(2) Uani 1 1 d . U . . .
O13 O -0.1944(6) 0.2250(3) 1.2559(4) 0.0306(14) Uani 1 1 d . U . . .
O14 O 0.1651(6) 0.2428(3) 1.2432(5) 0.0291(15) Uani 1 1 d . U . . .
O15 O 0.1081(5) 0.0009(3) 0.7343(3) 0.0286(15) Uani 1 1 d . U . . .
O16 O 0.4700(5) 0.0056(3) 0.7483(3) 0.0251(12) Uani 1 1 d . U . . .
N1 N 0.9519(14) 0.8839(7) 0.6464(7) 0.069(3) Uani 1 1 d . U . . .
N2 N 0.8905(16) 0.9691(9) 0.5687(8) 0.111(5) Uani 1 1 d . U . . .
H2A H 0.8918 1.0021 0.5382 0.134 Uiso 1 1 calc R U . . .
N3 N 0.9179(15) 0.1341(7) 0.7298(9) 0.094(4) Uani 1 1 d . U . . .
N4 N 0.8543(16) 0.0891(9) 0.8362(9) 0.098(4) Uani 1 1 d . U . . .
C1 C 0.1474(11) 0.1609(5) 1.0459(5) 0.019(2) Uani 1 1 d . U . . .
C2 C 0.2168(12) 0.1285(6) 0.9911(5) 0.019(2) Uani 1 1 d . U . . .
H2 H 0.2193 0.0799 0.9887 0.023 Uiso 1 1 calc R U . . .
C3 C 0.2830(12) 0.1682(5) 0.9395(5) 0.019(2) Uani 1 1 d . U . . .
C4 C 0.2758(13) 0.2395(6) 0.9437(6) 0.037(3) Uani 1 1 d . U . . .
H4 H 0.3184 0.2665 0.9096 0.045 Uiso 1 1 calc R U . . .
C5 C 0.2061(15) 0.2729(6) 0.9980(5) 0.046(3) Uani 1 1 d . U . . .
H5A H 0.2015 0.3214 0.9998 0.055 Uiso 1 1 calc R U . . .
C6 C 0.1437(12) 0.2324(6) 1.0495(6) 0.034(3) Uani 1 1 d . U . . .
H6 H 0.0992 0.2542 1.0866 0.041 Uiso 1 1 calc R U . . .
C7 C 0.3343(11) 0.1702(5) 0.5462(5) 0.021(2) Uani 1 1 d . U . . .
C8 C 0.2623(10) 0.1319(7) 0.4982(4) 0.024(3) Uani 1 1 d . U . . .
H8 H 0.2541 0.0839 0.5047 0.028 Uiso 1 1 calc R U . . .
C9 C 0.2015(12) 0.1622(6) 0.4408(5) 0.022(2) Uani 1 1 d . U . . .
C10 C 0.2152(12) 0.2356(6) 0.4324(6) 0.033(3) Uani 1 1 d . U . . .
H10 H 0.1761 0.2576 0.3939 0.039 Uiso 1 1 calc R U . . .
C11 C 0.2851(14) 0.2738(6) 0.4802(6) 0.042(3) Uani 1 1 d . U . . .
H11 H 0.2933 0.3219 0.4741 0.050 Uiso 1 1 calc R U . . .
C12 C 0.3444(12) 0.2427(5) 0.5378(6) 0.030(3) Uani 1 1 d . U . . .
H12 H 0.3906 0.2696 0.5707 0.036 Uiso 1 1 calc R U . . .
C13 C 0.952(2) 0.1218(9) 0.7981(11) 0.094(5) Uani 1 1 d . U . . .
H13 H 1.0359 0.1348 0.8168 0.113 Uiso 1 1 calc R U . . .
C14 C 0.788(2) 0.1082(9) 0.7198(11) 0.102(5) Uani 1 1 d . U . . .
H14 H 0.7361 0.1081 0.6790 0.122 Uiso 1 1 calc R U . . .
C15 C 0.753(2) 0.0829(10) 0.7833(11) 0.106(5) Uani 1 1 d . U . . .
H15 H 0.6685 0.0625 0.7918 0.128 Uiso 1 1 calc R U . . .
C16 C 0.995(2) 0.1640(12) 0.6744(12) 0.149(9) Uani 1 1 d . U . . .
H16A H 1.0880 0.1706 0.6892 0.223 Uiso 1 1 calc R U . . .
H16B H 0.9561 0.2083 0.6617 0.223 Uiso 1 1 calc R U . . .
H16C H 0.9931 0.1333 0.6348 0.223 Uiso 1 1 calc R U . . .
C17 C 0.863(2) 0.0554(12) 0.9026(11) 0.119(6) Uani 1 1 d . U . . .
H17A H 0.7715 0.0487 0.9206 0.143 Uiso 1 1 calc R U . . .
H17B H 0.9112 0.0862 0.9346 0.143 Uiso 1 1 calc R U . . .
C18 C 0.932(2) -0.0112(12) 0.9021(11) 0.128(6) Uani 1 1 d . U . . .
H18A H 1.0185 -0.0062 0.8776 0.154 Uiso 1 1 calc R U . . .
H18B H 0.9524 -0.0244 0.9499 0.154 Uiso 1 1 calc R U . . .
C19 C 0.859(3) -0.0633(13) 0.8716(13) 0.147(8) Uani 1 1 d . U . . .
H19A H 0.8448 -0.0520 0.8227 0.176 Uiso 1 1 calc R U . . .
H19B H 0.7698 -0.0662 0.8937 0.176 Uiso 1 1 calc R U . . .
C20 C 0.930(3) -0.1345(11) 0.8769(11) 0.125(7) Uani 1 1 d . U . . .
H20A H 0.9401 -0.1472 0.9252 0.187 Uiso 1 1 calc R U . . .
H20B H 1.0192 -0.1317 0.8556 0.187 Uiso 1 1 calc R U . . .
H20C H 0.8766 -0.1692 0.8533 0.187 Uiso 1 1 calc R U . . .
C21 C 0.9954(17) 0.9276(8) 0.5937(8) 0.074(4) Uani 1 1 d . U . . .
H21 H 1.0847 0.9290 0.5770 0.088 Uiso 1 1 calc R U . . .
C22 C 0.7847(16) 0.9426(8) 0.6065(8) 0.070(4) Uani 1 1 d . U . . .
H22 H 0.6939 0.9559 0.6006 0.084 Uiso 1 1 calc R U . . .
C23 C 0.8267(17) 0.8953(9) 0.6528(9) 0.078(4) Uani 1 1 d . U . . .
H23 H 0.7703 0.8736 0.6854 0.093 Uiso 1 1 calc R U . . .
C24 C 1.0314(19) 0.8316(10) 0.6855(10) 0.114(7) Uani 1 1 d . U . . .
H24A H 0.9768 0.7904 0.6923 0.172 Uiso 1 1 calc R U . . .
H24B H 1.0571 0.8505 0.7301 0.172 Uiso 1 1 calc R U . . .
H24C H 1.1124 0.8197 0.6596 0.172 Uiso 1 1 calc R 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 O13 1.766(6) . ?
U1 O14 1.771(6) . ?
U1 O4 2.279(7) 4_457 ?
U1 O7 2.288(7) 4_457 ?
U1 O3 2.289(7) . ?
U1 O11 2.299(8) 1_556 ?
U2 O16 1.770(5) . ?
U2 O15 1.776(5) . ?
U2 O2 2.281(8) 2_554 ?
U2 O10 2.288(8) 2 ?
U2 O6 2.288(8) . ?
U2 O8 2.292(7) . ?
P1 O2 1.518(9) . ?
P1 O1 1.519(8) . ?
P1 O3 1.528(8) . ?
P1 C1 1.803(10) . ?
P2 O4 1.508(8) . ?
P2 O5 1.512(8) . ?
P2 O6 1.540(8) . ?
P2 C3 1.796(10) . ?
P3 O7 1.512(8) . ?
P3 O8 1.512(9) . ?
P3 O9 1.531(8) . ?
P3 C7 1.801(11) . ?
P4 O10 1.514(9) . ?
P4 O11 1.517(9) . ?
P4 O12 1.518(8) . ?
P4 C9 1.806(11) . ?
O2 U2 2.281(8) 2 ?
O4 U1 2.279(7) 4_557 ?
O5 H5 0.8200 . ?
O7 U1 2.288(7) 4_557 ?
O9 H9 0.8200 . ?
O10 U2 2.288(7) 2_554 ?
O11 U1 2.299(8) 1_554 ?
N1 C23 1.25(2) . ?
N1 C21 1.377(19) . ?
N1 C24 1.47(2) . ?
N2 C22 1.359(19) . ?
N2 C21 1.38(2) . ?
N2 H2A 0.8600 . ?
N3 C13 1.37(2) . ?
N3 C14 1.38(2) . ?
N3 C16 1.42(2) . ?
N4 C13 1.35(2) . ?
N4 C15 1.42(2) . ?
N4 C17 1.43(2) . ?
C1 C6 1.371(15) . ?
C1 C2 1.396(13) . ?
C2 C3 1.405(13) . ?
C2 H2 0.9300 . ?
C3 C4 1.369(15) . ?
C4 C5 1.397(15) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(15) . ?
C5 H5A 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.369(14) . ?
C7 C12 1.399(15) . ?
C8 C9 1.376(14) . ?
C8 H8 0.9300 . ?
C9 C10 1.420(15) . ?
C10 C11 1.356(14) . ?
C10 H10 0.9300 . ?
C11 C12 1.381(13) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.35(2) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.44(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.36(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.53(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21 0.9300 . ?
C22 C23 1.33(2) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

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
O13 U1 O14 178.8(3) . . ?
O13 U1 O4 90.1(3) . 4_457 ?
O14 U1 O4 91.0(3) . 4_457 ?
O13 U1 O7 90.5(3) . 4_457 ?
O14 U1 O7 89.9(4) . 4_457 ?
O4 U1 O7 89.0(2) 4_457 4_457 ?
O13 U1 O3 89.1(3) . . ?
O14 U1 O3 90.6(3) . . ?
O4 U1 O3 87.9(3) 4_457 . ?
O7 U1 O3 176.9(3) 4_457 . ?
O13 U1 O11 89.5(3) . 1_556 ?
O14 U1 O11 89.4(3) . 1_556 ?
O4 U1 O11 175.4(3) 4_457 1_556 ?
O7 U1 O11 86.4(3) 4_457 1_556 ?
O3 U1 O11 96.69(19) . 1_556 ?
O16 U2 O15 179.3(3) . . ?
O16 U2 O2 89.4(3) . 2_554 ?
O15 U2 O2 90.3(3) . 2_554 ?
O16 U2 O10 90.0(3) . 2 ?
O15 U2 O10 90.6(3) . 2 ?
O2 U2 O10 95.3(2) 2_554 2 ?
O16 U2 O6 90.9(3) . . ?
O15 U2 O6 89.4(3) . . ?
O2 U2 O6 176.1(3) 2_554 . ?
O10 U2 O6 88.6(2) 2 . ?
O16 U2 O8 88.8(3) . . ?
O15 U2 O8 90.6(3) . . ?
O2 U2 O8 86.3(2) 2_554 . ?
O10 U2 O8 178.0(3) 2 . ?
O6 U2 O8 89.8(2) . . ?
O2 P1 O1 111.6(5) . . ?
O2 P1 O3 111.5(5) . . ?
O1 P1 O3 112.0(5) . . ?
O2 P1 C1 105.9(5) . . ?
O1 P1 C1 107.8(5) . . ?
O3 P1 C1 107.7(5) . . ?
O4 P2 O5 110.7(5) . . ?
O4 P2 O6 110.8(5) . . ?
O5 P2 O6 113.6(5) . . ?
O4 P2 C3 107.1(5) . . ?
O5 P2 C3 107.7(5) . . ?
O6 P2 C3 106.6(5) . . ?
O7 P3 O8 114.4(5) . . ?
O7 P3 O9 108.0(6) . . ?
O8 P3 O9 111.5(5) . . ?
O7 P3 C7 109.5(5) . . ?
O8 P3 C7 106.6(5) . . ?
O9 P3 C7 106.5(5) . . ?
O10 P4 O11 112.1(5) . . ?
O10 P4 O12 111.4(5) . . ?
O11 P4 O12 112.0(5) . . ?
O10 P4 C9 107.0(5) . . ?
O11 P4 C9 108.5(5) . . ?
O12 P4 C9 105.5(5) . . ?
P1 O2 U2 134.2(5) . 2 ?
P1 O3 U1 145.6(6) . . ?
P2 O4 U1 155.2(6) . 4_557 ?
P2 O5 H5 109.5 . . ?
P2 O6 U2 131.5(5) . . ?
P3 O7 U1 153.9(7) . 4_557 ?
P3 O8 U2 136.7(6) . . ?
P3 O9 H9 109.5 . . ?
P4 O10 U2 133.7(6) . 2_554 ?
P4 O11 U1 146.3(6) . 1_554 ?
C23 N1 C21 105.5(15) . . ?
C23 N1 C24 125.9(17) . . ?
C21 N1 C24 128.5(16) . . ?
C22 N2 C21 99.5(15) . . ?
C22 N2 H2A 130.3 . . ?
C21 N2 H2A 130.3 . . ?
C13 N3 C14 107.1(18) . . ?
C13 N3 C16 131(2) . . ?
C14 N3 C16 122.0(19) . . ?
C13 N4 C15 98.2(18) . . ?
C13 N4 C17 130.2(19) . . ?
C15 N4 C17 129.8(19) . . ?
C6 C1 C2 119.6(10) . . ?
C6 C1 P1 121.1(8) . . ?
C2 C1 P1 119.2(8) . . ?
C1 C2 C3 120.8(10) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C4 C3 C2 118.3(10) . . ?
C4 C3 P2 122.3(8) . . ?
C2 C3 P2 119.4(8) . . ?
C3 C4 C5 121.7(10) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C6 C5 C4 119.1(12) . . ?
C6 C5 H5A 120.5 . . ?
C4 C5 H5A 120.5 . . ?
C1 C6 C5 120.5(11) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C8 C7 C12 119.4(10) . . ?
C8 C7 P3 120.0(9) . . ?
C12 C7 P3 120.6(8) . . ?
C7 C8 C9 122.1(13) . . ?
C7 C8 H8 118.9 . . ?
C9 C8 H8 118.9 . . ?
C8 C9 C10 117.8(10) . . ?
C8 C9 P4 120.4(9) . . ?
C10 C9 P4 121.8(8) . . ?
C11 C10 C9 120.3(10) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 121.2(11) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C11 C12 C7 119.3(10) . . ?
C11 C12 H12 120.4 . . ?
C7 C12 H12 120.4 . . ?
N4 C13 N3 115(2) . . ?
N4 C13 H13 122.5 . . ?
N3 C13 H13 122.5 . . ?
C15 C14 N3 103.5(18) . . ?
C15 C14 H14 128.2 . . ?
N3 C14 H14 128.2 . . ?
C14 C15 N4 116.0(19) . . ?
C14 C15 H15 122.0 . . ?
N4 C15 H15 122.0 . . ?
N3 C16 H16A 109.5 . . ?
N3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N4 C17 C18 115.1(18) . . ?
N4 C17 H17A 108.5 . . ?
C18 C17 H17A 108.5 . . ?
N4 C17 H17B 108.5 . . ?
C18 C17 H17B 108.5 . . ?
H17A C17 H17B 107.5 . . ?
C19 C18 C17 114(2) . . ?
C19 C18 H18A 108.7 . . ?
C17 C18 H18A 108.7 . . ?
C19 C18 H18B 108.7 . . ?
C17 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
C18 C19 C20 113(2) . . ?
C18 C19 H19A 109.1 . . ?
C20 C19 H19A 109.1 . . ?
C18 C19 H19B 109.1 . . ?
C20 C19 H19B 109.1 . . ?
H19A C19 H19B 107.8 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N1 C21 N2 112.0(15) . . ?
N1 C21 H21 124.0 . . ?
N2 C21 H21 124.0 . . ?
C23 C22 N2 112.0(16) . . ?
C23 C22 H22 124.0 . . ?
N2 C22 H22 124.0 . . ?
N1 C23 C22 110.8(17) . . ?
N1 C23 H23 124.6 . . ?
C22 C23 H23 124.6 . . ?
N1 C24 H24A 109.5 . . ?
N1 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N1 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

_refine_diff_density_max         0.690
_refine_diff_density_min         -0.931
_refine_diff_density_rms         0.157

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 'ionothermal reactions'
_exptl_crystal_preparation       Luminescent
