# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_nonirradiated_sample
_database_code_depnum_ccdc_archive 'CCDC 1937185'
loop_
_audit_author_name
_audit_author_address
'Jian Xie'
;Soochow University
China
;
_audit_update_record             
;
2019-08-21 deposited with the CCDC.	2019-09-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        nonirradiated_sample
_chemical_name_common            'Uranyl oxalate'
_chemical_melting_point          N/a
_chemical_formula_moiety         'C3 O8 U, C12 H9 N2'
_chemical_formula_sum            'C15 H9 N2 O8 U '
_chemical_formula_weight         583.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
U U -9.6767 9.6646 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   7.1196(4)
_cell_length_b                   11.8468(7)
_cell_length_c                   18.6262(11)
_cell_angle_alpha                90
_cell_angle_beta                 98.714(2)
_cell_angle_gamma                90
_cell_volume                     1552.88(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1850
_cell_measurement_theta_min      3.04
_cell_measurement_theta_max      24.99

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.495
_exptl_crystal_F_000             1076.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    10.504
_shelx_estimated_absorpt_T_min   0.110
_shelx_estimated_absorpt_T_max   0.350
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.379
_exptl_absorpt_correction_T_max  0.730
_exptl_absorpt_process_details   SHELTXPREP

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       '0.5 wide w/ exposures'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32021
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.367
_diffrn_reflns_theta_max         27.600
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3603
_reflns_number_gt                3104
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0151P)²+1.8517P] 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         3576
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0201
_refine_ls_wR_factor_ref         0.0400
_refine_ls_wR_factor_gt          0.0382
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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 0.53736(2) 1.03500(2) 0.17053(2) 0.02090(5) Uani 1 1 d . . . . .
O8 O 0.2862(3) 1.0286(2) 0.16336(13) 0.0336(6) Uani 1 1 d . . . . .
O7 O 0.7877(4) 1.0398(2) 0.17597(14) 0.0380(6) Uani 1 1 d . . . . .
O6 O 0.5288(4) 0.84097(18) 0.21052(11) 0.0317(6) Uani 1 1 d . . . . .
O5 O 0.4909(4) 1.12269(18) 0.05022(12) 0.0329(6) Uani 1 1 d . . . . .
O3 O 0.5417(4) 0.90278(19) 0.07020(11) 0.0313(5) Uani 1 1 d . . . . .
O2 O 0.5736(4) 1.01205(18) 0.29649(12) 0.0315(6) Uani 1 1 d . . . . .
O1 O 0.5668(4) 0.9017(2) 0.39403(11) 0.0358(6) Uani 1 1 d . . . . .
C9 C 0.8284(5) 0.0438(3) 0.56493(18) 0.0270(7) Uani 1 1 d . . . . .
C8 C 0.5142(5) 0.9363(2) 0.00548(16) 0.0235(7) Uani 1 1 d . . . . .
C7 C 0.8899(5) 0.0322(3) 0.63990(19) 0.0318(8) Uani 1 1 d . . . . .
C6 C 0.5569(5) 0.9184(3) 0.32908(16) 0.0238(7) Uani 1 1 d . . . . .
C5 C 0.5186(5) 0.8182(3) 0.27563(17) 0.0244(7) Uani 1 1 d . . . . .
C4 C 0.9537(5) 0.2343(3) 0.5665(2) 0.0355(9) Uani 1 1 d . . . . .
C3 C 1.0118(5) 0.2225(3) 0.6432(2) 0.0420(10) Uani 1 1 d . . . . .
H3A H 1.0717 0.2826 0.6694 0.050 Uiso 1 1 calc R U . . .
N1 N 0.7951(4) 0.1479(3) 0.45507(16) 0.0377(7) Uani 1 1 d . . . . .
C1 C 0.8586(5) 0.1455(3) 0.52687(19) 0.0291(8) Uani 1 1 d . . . . .
C11 C 0.9816(5) 0.1264(4) 0.6781(2) 0.0420(10) Uani 1 1 d . . . . .
H11A H 1.0211 0.1212 0.7280 0.050 Uiso 1 1 calc R U . . .
N2 N 0.7349(4) -0.0430(2) 0.52748(16) 0.0301(6) Uani 1 1 d . . . . .
H2A H 0.6982 -0.0351 0.4816 0.036 Uiso 1 1 calc R U . . .
C12 C 0.8536(6) -0.0707(4) 0.6716(2) 0.0418(10) Uani 1 1 d . . . . .
H12A H 0.8961 -0.0821 0.7208 0.050 Uiso 1 1 calc R U . . .
C13 C 0.9880(6) 0.3313(3) 0.5268(3) 0.0496(11) Uani 1 1 d . . . . .
H13A H 1.0520 0.3928 0.5500 0.060 Uiso 1 1 calc R U . . .
C14 C 0.9265(6) 0.3342(4) 0.4540(3) 0.0564(12) Uani 1 1 d . . . . .
H14A H 0.9502 0.3970 0.4269 0.068 Uiso 1 1 calc R U . . .
C15 C 0.7569(6) -0.1548(3) 0.6318(2) 0.0440(10) Uani 1 1 d . . . . .
H15A H 0.7309 -0.2222 0.6539 0.053 Uiso 1 1 calc R U . . .
C16 C 0.8275(6) 0.2417(4) 0.4205(2) 0.0476(10) Uani 1 1 d . . . . .
H16A H 0.7818 0.2465 0.3711 0.057 Uiso 1 1 calc R U . . .
C17 C 0.6980(5) -0.1390(3) 0.5586(2) 0.0357(9) Uani 1 1 d . . . . .
H17A H 0.6323 -0.1960 0.5311 0.043 Uiso 1 1 calc R U . . .
O4 O 0.4795(4) 0.72375(19) 0.29791(13) 0.0416(7) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
U1 O7 1.771(3) . ?
U1 O8 1.775(2) . ?
U1 O4 2.320(2) 2_655 ?
U1 O2 2.337(2) . ?
U1 O6 2.420(2) . ?
U1 O3 2.442(2) . ?
U1 O5 2.447(2) . ?
O6 C5 1.255(4) . ?
O5 C8 1.247(4) 3_675 ?
O3 C8 1.256(4) . ?
O2 C6 1.278(4) . ?
O1 C6 1.217(4) . ?
C9 N2 1.359(4) . ?
C9 C7 1.406(5) . ?
C9 C1 1.430(5) . ?
C8 O5 1.247(4) 3_675 ?
C8 C8 1.532(6) 3_675 ?
C7 C12 1.396(5) . ?
C7 C11 1.428(5) . ?
C6 C5 1.547(4) . ?
C5 O4 1.239(4) . ?
C4 C1 1.400(5) . ?
C4 C13 1.409(5) . ?
C4 C3 1.432(5) . ?
C3 C11 1.345(6) . ?
N1 C16 1.323(5) . ?
N1 C1 1.346(4) . ?
N2 C17 1.321(4) . ?
C12 C15 1.365(6) . ?
C13 C14 1.360(6) . ?
C14 C16 1.398(6) . ?
C15 C17 1.376(5) . ?
O4 U1 2.320(2) 2_645 ?

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
O7 U1 O8 178.81(11) . . ?
O7 U1 O4 92.57(11) . 2_655 ?
O8 U1 O4 88.27(11) . 2_655 ?
O7 U1 O2 89.38(10) . . ?
O8 U1 O2 91.57(10) . . ?
O4 U1 O2 81.94(8) 2_655 . ?
O7 U1 O6 94.87(10) . . ?
O8 U1 O6 84.87(10) . . ?
O4 U1 O6 146.40(8) 2_655 . ?
O2 U1 O6 65.45(7) . . ?
O7 U1 O3 86.28(10) . . ?
O8 U1 O3 92.55(10) . . ?
O4 U1 O3 145.01(8) 2_655 . ?
O2 U1 O3 132.95(7) . . ?
O6 U1 O3 68.29(7) . . ?
O7 U1 O5 91.95(10) . . ?
O8 U1 O5 87.38(10) . . ?
O4 U1 O5 79.50(8) 2_655 . ?
O2 U1 O5 161.44(7) . . ?
O6 U1 O5 132.77(7) . . ?
O3 U1 O5 65.61(7) . . ?
C5 O6 U1 120.64(19) . . ?
C8 O5 U1 120.45(18) 3_675 . ?
C8 O3 U1 120.88(19) . . ?
C6 O2 U1 125.0(2) . . ?
N2 C9 C7 119.4(3) . . ?
N2 C9 C1 118.8(3) . . ?
C7 C9 C1 121.8(3) . . ?
O5 C8 O3 127.0(3) 3_675 . ?
O5 C8 C8 117.1(3) 3_675 3_675 ?
O3 C8 C8 116.0(3) . 3_675 ?
C12 C7 C9 117.2(3) . . ?
C12 C7 C11 124.8(3) . . ?
C9 C7 C11 118.0(3) . . ?
O1 C6 O2 128.2(3) . . ?
O1 C6 C5 119.5(3) . . ?
O2 C6 C5 112.4(3) . . ?
O4 C5 O6 124.5(3) . . ?
O4 C5 C6 120.3(3) . . ?
O6 C5 C6 115.2(3) . . ?
C1 C4 C13 116.4(4) . . ?
C1 C4 C3 119.7(3) . . ?
C13 C4 C3 123.9(4) . . ?
C11 C3 C4 121.5(4) . . ?
C16 N1 C1 116.4(3) . . ?
N1 C1 C4 124.8(3) . . ?
N1 C1 C9 117.2(3) . . ?
C4 C1 C9 117.9(3) . . ?
C3 C11 C7 121.0(4) . . ?
C17 N2 C9 122.7(3) . . ?
C15 C12 C7 121.2(3) . . ?
C14 C13 C4 119.2(4) . . ?
C13 C14 C16 119.4(4) . . ?
C12 C15 C17 119.5(4) . . ?
N1 C16 C14 123.6(4) . . ?
N2 C17 C15 120.1(3) . . ?
C5 O4 U1 167.9(3) . 2_645 ?

_refine_diff_density_max         0.871
_refine_diff_density_min         -0.723
_refine_diff_density_rms         0.108

_shelxl_version_number           2014-3


_chemical_properties_physical    Photo-sensitive
_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_irradiated_sample
_database_code_depnum_ccdc_archive 'CCDC 1937186'
loop_
_audit_author_name
_audit_author_address
'Jian Xie'
;Soochow University
China
;
_audit_update_record             
;
2019-08-21 deposited with the CCDC.	2019-09-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        irradiated_sample
_chemical_name_common            'Uranyl oxalate'
_chemical_melting_point          N/a
_chemical_formula_moiety         'C3 O8 U, C12 H9 N2'
_chemical_formula_sum            'C15 H9 N2 O8 U'
_chemical_formula_weight         583.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
U U -9.6767 9.6646 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   7.219(2)
_cell_length_b                   11.787(3)
_cell_length_c                   18.586(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.556(7)
_cell_angle_gamma                90
_cell_volume                     1563.9(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1850
_cell_measurement_theta_min      3.04
_cell_measurement_theta_max      24.99

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.447
_exptl_crystal_F_000             1076
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    10.430
_shelx_estimated_absorpt_T_min   0.110
_shelx_estimated_absorpt_T_max   0.350
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.382
_exptl_absorpt_correction_T_max  0.731
_exptl_absorpt_process_details   SHELTXPREP

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       '0.5 wide w/ exposures'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29012
_diffrn_reflns_av_unetI/netI     0.1209
_diffrn_reflns_av_R_equivalents  0.1697
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.336
_diffrn_reflns_theta_max         27.502
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3589
_reflns_number_gt                2022
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0474P)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_number_reflns         3572
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1423
_refine_ls_R_factor_gt           0.0599
_refine_ls_wR_factor_ref         0.1119
_refine_ls_wR_factor_gt          0.0928
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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 0.53835(6) 1.03492(3) 0.17057(2) 0.03714(17) Uani 1 1 d . . . . .
O8 O 0.2989(11) 1.0295(6) 0.1636(4) 0.054(2) Uani 1 1 d . . . . .
O7 O 0.7829(11) 1.0392(6) 0.1751(4) 0.053(2) Uani 1 1 d . . . . .
O6 O 0.5296(11) 0.8414(6) 0.2111(3) 0.047(2) Uani 1 1 d . . . . .
O5 O 0.4956(11) 1.1231(6) 0.0506(3) 0.049(2) Uani 1 1 d . . . . .
O3 O 0.5372(11) 0.9015(6) 0.0699(3) 0.049(2) Uani 1 1 d . . . . .
O2 O 0.5741(12) 1.0119(6) 0.2967(4) 0.054(2) Uani 1 1 d . . . . .
O1 O 0.5672(13) 0.9014(7) 0.3943(4) 0.068(3) Uani 1 1 d . . . . .
C9 C 0.8276(15) 0.0464(10) 0.5648(6) 0.042(3) Uani 1 1 d . . . . .
C8 C 0.5122(14) 0.9358(8) 0.0047(5) 0.031(3) Uani 1 1 d . . . . .
C7 C 0.8906(16) 0.0349(11) 0.6387(6) 0.048(3) Uani 1 1 d . . . . .
C6 C 0.5545(17) 0.9179(10) 0.3287(6) 0.048(3) Uani 1 1 d . . . . .
C5 C 0.5183(16) 0.8188(10) 0.2764(5) 0.041(3) Uani 1 1 d . . . . .
C4 C 0.9565(16) 0.2361(10) 0.5647(8) 0.056(3) Uani 1 1 d . . . . .
C3 C 1.0149(17) 0.2221(13) 0.6421(8) 0.072(4) Uani 1 1 d . . . . .
H3A H 1.0760 0.2814 0.6688 0.086 Uiso 1 1 calc R U . . .
N1 N 0.7965(14) 0.1499(9) 0.4539(5) 0.059(3) Uani 1 1 d . . . . .
C1 C 0.8632(15) 0.1453(10) 0.5256(7) 0.048(3) Uani 1 1 d . . . . .
C11 C 0.9827(19) 0.1247(14) 0.6764(7) 0.072(4) Uani 1 1 d . . . . .
H11A H 1.0229 0.1179 0.7261 0.087 Uiso 1 1 calc R U . . .
N2 N 0.7377(13) -0.0430(8) 0.5285(5) 0.053(3) Uani 1 1 d . . . . .
H2A H 0.7046 -0.0366 0.4823 0.064 Uiso 1 1 calc R U . . .
C12 C 0.8525(19) -0.0651(12) 0.6709(7) 0.063(4) Uani 1 1 d . . . . .
H12A H 0.8915 -0.0746 0.7206 0.076 Uiso 1 1 calc R U . . .
C13 C 0.9939(19) 0.3289(12) 0.5229(9) 0.072(4) Uani 1 1 d . . . . .
H13A H 1.0643 0.3888 0.5451 0.086 Uiso 1 1 calc R U . . .
C14 C 0.931(2) 0.3342(12) 0.4520(9) 0.077(4) Uani 1 1 d . . . . .
H14A H 0.9545 0.3985 0.4257 0.092 Uiso 1 1 calc R U . . .
C15 C 0.758(2) -0.1522(13) 0.6320(7) 0.077(4) Uani 1 1 d . . . . .
H15A H 0.7348 -0.2197 0.6549 0.092 Uiso 1 1 calc R U . . .
C16 C 0.829(2) 0.2419(13) 0.4160(8) 0.082(5) Uani 1 1 d . . . . .
H16A H 0.7851 0.2458 0.3664 0.098 Uiso 1 1 calc R U . . .
C17 C 0.6983(17) -0.1381(10) 0.5594(6) 0.053(3) Uani 1 1 d . . . . .
H17A H 0.6309 -0.1949 0.5324 0.063 Uiso 1 1 calc R U . . .
O4 O 0.4774(12) 0.7227(6) 0.3003(4) 0.061(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
U1 O8 1.715(8) . ?
U1 O7 1.756(8) . ?
U1 O4 2.286(8) 2_655 ?
U1 O2 2.335(7) . ?
U1 O6 2.406(7) . ?
U1 O5 2.438(6) . ?
U1 O3 2.442(7) . ?
O6 C5 1.257(11) . ?
O5 C8 1.235(10) 3_675 ?
O3 C8 1.265(10) . ?
O2 C6 1.276(13) . ?
O1 C6 1.224(12) . ?
C9 N2 1.362(13) . ?
C9 C7 1.389(15) . ?
C9 C1 1.418(15) . ?
C8 O5 1.235(10) 3_675 ?
C8 C8 1.530(18) 3_675 ?
C7 C12 1.369(16) . ?
C7 C11 1.384(17) . ?
C6 C5 1.519(15) . ?
C5 O4 1.267(12) . ?
C4 C13 1.392(17) . ?
C4 C1 1.407(15) . ?
C4 C3 1.448(17) . ?
C3 C11 1.350(18) . ?
N1 C1 1.349(14) . ?
N1 C16 1.333(15) . ?
N2 C17 1.310(13) . ?
C12 C15 1.377(17) . ?
C13 C14 1.329(19) . ?
C14 C16 1.425(19) . ?
C15 C17 1.363(16) . ?
O4 U1 2.286(8) 2_645 ?

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 178.4(3) . . ?
O8 U1 O4 88.2(3) . 2_655 ?
O7 U1 O4 92.6(3) . 2_655 ?
O8 U1 O2 91.8(3) . . ?
O7 U1 O2 89.7(3) . . ?
O4 U1 O2 82.9(3) 2_655 . ?
O8 U1 O6 85.1(3) . . ?
O7 U1 O6 94.9(3) . . ?
O4 U1 O6 147.1(2) 2_655 . ?
O2 U1 O6 65.1(2) . . ?
O8 U1 O5 87.5(3) . . ?
O7 U1 O5 91.3(3) . . ?
O4 U1 O5 78.5(2) 2_655 . ?
O2 U1 O5 161.4(2) . . ?
O6 U1 O5 133.2(2) . . ?
O8 U1 O3 91.7(3) . . ?
O7 U1 O3 86.8(3) . . ?
O4 U1 O3 144.1(2) 2_655 . ?
O2 U1 O3 132.9(2) . . ?
O6 U1 O3 68.4(2) . . ?
O5 U1 O3 65.7(2) . . ?
C5 O6 U1 120.8(7) . . ?
C8 O5 U1 120.4(6) 3_675 . ?
C8 O3 U1 120.8(6) . . ?
C6 O2 U1 124.5(7) . . ?
N2 C9 C7 118.4(11) . . ?
N2 C9 C1 119.5(10) . . ?
C7 C9 C1 122.0(11) . . ?
O5 C8 O3 126.9(9) 3_675 . ?
O5 C8 C8 118.1(10) 3_675 3_675 ?
O3 C8 C8 115.0(10) . 3_675 ?
C12 C7 C9 117.4(11) . . ?
C12 C7 C11 123.4(12) . . ?
C9 C7 C11 119.2(12) . . ?
O1 C6 O2 127.3(11) . . ?
O1 C6 C5 119.7(11) . . ?
O2 C6 C5 112.9(10) . . ?
O6 C5 O4 125.5(10) . . ?
O6 C5 C6 115.2(10) . . ?
O4 C5 C6 119.3(9) . . ?
C13 C4 C1 115.3(13) . . ?
C13 C4 C3 126.4(13) . . ?
C1 C4 C3 118.2(13) . . ?
C11 C3 C4 121.4(13) . . ?
C1 N1 C16 119.3(12) . . ?
N1 C1 C9 118.3(10) . . ?
N1 C1 C4 123.5(12) . . ?
C9 C1 C4 118.0(12) . . ?
C3 C11 C7 121.0(12) . . ?
C17 N2 C9 124.3(10) . . ?
C7 C12 C15 121.8(12) . . ?
C14 C13 C4 121.6(14) . . ?
C13 C14 C16 120.4(14) . . ?
C17 C15 C12 119.2(13) . . ?
N1 C16 C14 119.5(14) . . ?
N2 C17 C15 118.7(12) . . ?
C5 O4 U1 166.1(8) . 2_645 ?

_refine_diff_density_max         1.801
_refine_diff_density_min         -1.054
_refine_diff_density_rms         0.231

_shelxl_version_number           2014-3


_chemical_properties_physical    Photo-sensitive
_exptl_crystal_preparation       Luminescent
