# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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
_database_code_depnum_ccdc_archive 'CCDC 1586483'
_audit_update_record             
;
2017-11-20 deposited with the CCDC.
2017-11-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            'Uranyl 3,5-pyridinedicarboxylate'
_chemical_melting_point          N/a
_chemical_formula_moiety         'C11 H10 N2 O9 U'
_chemical_formula_sum            'C11 H10 N2 O9 U'
_chemical_formula_weight         552.24

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'
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      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                   6.5282(6)
_cell_length_b                   10.9208(11)
_cell_length_c                   10.9233(11)
_cell_angle_alpha                93.983(4)
_cell_angle_beta                 106.175(4)
_cell_angle_gamma                103.677(4)
_cell_volume                     719.04(12)
_cell_formula_units_Z            2
_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       Blcok
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.551
_exptl_crystal_F_000             508
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.035
_exptl_absorpt_coefficient_mu    11.339
_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  0.401
_exptl_absorpt_correction_T_max  0.672
_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            14771
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_av_R_equivalents  0.0601
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.551
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             2534
_reflns_number_gt                2340
_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)+(0.0166P)²+1.1123P] 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         2534
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0266
_refine_ls_R_factor_gt           0.0232
_refine_ls_wR_factor_ref         0.0517
_refine_ls_wR_factor_gt          0.0507
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_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 0.21392(3) 0.63996(2) 0.88626(2) 0.01373(8) Uani 1 1 d . . . . .
O2 O 0.0295(7) 0.4938(4) 0.8821(4) 0.0306(10) Uani 1 1 d . . . . .
O5 O 0.5616(6) 0.3738(3) 0.9064(3) 0.0202(8) Uani 1 1 d . . . . .
O1 O 0.4068(6) 0.7817(3) 0.8800(3) 0.0231(8) Uani 1 1 d . . . . .
O7 O 0.1008(6) 0.2882(4) 0.2277(3) 0.0268(9) Uani 1 1 d . . . . .
O4 O 0.4349(6) 0.5308(4) 0.8232(3) 0.0262(9) Uani 1 1 d . . . . .
O3 O 0.1170(6) 0.7691(3) 1.0337(3) 0.0212(8) Uani 1 1 d . . . . .
O6 O -0.0396(6) 0.3919(3) 0.3494(3) 0.0205(8) Uani 1 1 d . . . . .
O9 O 0.7193(7) 0.1206(4) 0.4185(4) 0.0420(12) Uani 1 1 d . . . . .
O8 O 0.9287(6) 0.1951(4) 0.6124(4) 0.0305(10) Uani 1 1 d . . . . .
C4 C 0.4920(8) 0.4282(5) 0.8131(5) 0.0158(11) Uani 1 1 d . . . . .
C11 C 0.1089(8) 0.3397(5) 0.3381(5) 0.0178(11) Uani 1 1 d . . . . .
N2 N -0.0195(7) 0.9051(4) 1.1305(4) 0.0207(10) Uani 1 1 d . . . . .
N1 N 0.7634(7) 0.1859(4) 0.5221(4) 0.0228(10) Uani 1 1 d . . . . .
C1 C -0.0429(8) 0.8004(5) 1.0565(5) 0.0184(11) Uani 1 1 d . . . . .
H1B H -0.1845 0.7466 1.0192 0.022 Uiso 1 1 calc R U . . .
C7 C 0.2955(8) 0.3344(5) 0.4528(5) 0.0165(11) Uani 1 1 d . . . . .
C5 C 0.4753(8) 0.3729(5) 0.6810(5) 0.0144(11) Uani 1 1 d . . . . .
C8 C 0.4457(8) 0.2698(5) 0.4339(5) 0.0158(11) Uani 1 1 d . . . . .
H8A H 0.4385 0.2368 0.3515 0.019 Uiso 1 1 calc R U . . .
C6 C 0.3124(8) 0.3892(5) 0.5742(5) 0.0146(11) Uani 1 1 d . . . . .
H6A H 0.2160 0.4366 0.5849 0.017 Uiso 1 1 calc R U . . .
C10 C 0.6237(8) 0.3051(5) 0.6649(5) 0.0155(11) Uani 1 1 d . . . . .
H10A H 0.7318 0.2929 0.7355 0.019 Uiso 1 1 calc R U . . .
C9 C 0.6061(8) 0.2562(5) 0.5409(5) 0.0159(11) Uani 1 1 d . . . . .
C3 C -0.2054(9) 0.9382(6) 1.1608(6) 0.0305(14) Uani 1 1 d . . . . .
H3A H -0.1535 1.0185 1.2163 0.046 Uiso 1 1 calc R U . . .
H3B H -0.3126 0.9444 1.0826 0.046 Uiso 1 1 calc R U . . .
H3C H -0.2723 0.8734 1.2035 0.046 Uiso 1 1 calc R U . . .
C2 C 0.1981(10) 0.9931(6) 1.1902(6) 0.0333(15) Uani 1 1 d . . . . .
H2B H 0.1845 1.0644 1.2409 0.050 Uiso 1 1 calc R U . . .
H2C H 0.2925 0.9503 1.2446 0.050 Uiso 1 1 calc R U . . .
H2D H 0.2610 1.0225 1.1244 0.050 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 O2 1.746(4) . ?
U1 O1 1.768(4) . ?
U1 O4 2.287(3) . ?
U1 O5 2.367(3) 2_667 ?
U1 O3 2.378(3) . ?
U1 O7 2.421(3) 2_566 ?
U1 O6 2.470(3) 2_566 ?
U1 C11 2.813(5) 2_566 ?
O5 C4 1.246(6) . ?
O5 U1 2.367(3) 2_667 ?
O7 C11 1.277(6) . ?
O7 U1 2.421(3) 2_566 ?
O4 C4 1.269(6) . ?
O3 C1 1.254(6) . ?
O6 C11 1.264(6) . ?
O6 U1 2.470(3) 2_566 ?
O9 N1 1.218(6) . ?
O8 N1 1.220(6) . ?
C4 C5 1.489(7) . ?
C11 C7 1.500(7) . ?
C11 U1 2.813(5) 2_566 ?
N2 C1 1.306(7) . ?
N2 C2 1.455(7) . ?
N2 C3 1.458(7) . ?
N1 C9 1.467(6) . ?
C1 H1B 0.9300 . ?
C7 C6 1.380(7) . ?
C7 C8 1.386(7) . ?
C5 C6 1.397(7) . ?
C5 C10 1.391(7) . ?
C8 C9 1.379(7) . ?
C8 H8A 0.9300 . ?
C6 H6A 0.9300 . ?
C10 C9 1.385(7) . ?
C10 H10A 0.9300 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C2 H2D 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
O2 U1 O1 175.20(16) . . ?
O2 U1 O4 88.45(17) . . ?
O1 U1 O4 87.41(16) . . ?
O2 U1 O5 91.22(16) . 2_667 ?
O1 U1 O5 90.60(15) . 2_667 ?
O4 U1 O5 82.06(12) . 2_667 ?
O2 U1 O3 99.46(16) . . ?
O1 U1 O3 85.30(15) . . ?
O4 U1 O3 155.04(13) . . ?
O5 U1 O3 74.19(12) 2_667 . ?
O2 U1 O7 88.00(17) . 2_566 ?
O1 U1 O7 93.14(15) . 2_566 ?
O4 U1 O7 134.03(12) . 2_566 ?
O5 U1 O7 143.82(12) 2_667 2_566 ?
O3 U1 O7 70.30(11) . 2_566 ?
O2 U1 O6 85.37(15) . 2_566 ?
O1 U1 O6 91.56(15) . 2_566 ?
O4 U1 O6 80.51(12) . 2_566 ?
O5 U1 O6 162.32(11) 2_667 2_566 ?
O3 U1 O6 123.48(11) . 2_566 ?
O7 U1 O6 53.52(11) 2_566 2_566 ?
O2 U1 C11 84.82(17) . 2_566 ?
O1 U1 C11 94.08(16) . 2_566 ?
O4 U1 C11 107.15(14) . 2_566 ?
O5 U1 C11 169.82(13) 2_667 2_566 ?
O3 U1 C11 97.18(13) . 2_566 ?
O7 U1 C11 26.92(13) 2_566 2_566 ?
O6 U1 C11 26.68(13) 2_566 2_566 ?
C4 O5 U1 155.7(3) . 2_667 ?
C11 O7 U1 93.9(3) . 2_566 ?
C4 O4 U1 149.1(4) . . ?
C1 O3 U1 143.4(3) . . ?
C11 O6 U1 92.0(3) . 2_566 ?
O5 C4 O4 123.8(5) . . ?
O5 C4 C5 119.5(4) . . ?
O4 C4 C5 116.7(4) . . ?
O6 C11 O7 120.2(4) . . ?
O6 C11 C7 121.4(5) . . ?
O7 C11 C7 118.4(4) . . ?
O6 C11 U1 61.3(3) . 2_566 ?
O7 C11 U1 59.1(2) . 2_566 ?
C7 C11 U1 175.2(4) . 2_566 ?
C1 N2 C2 120.7(4) . . ?
C1 N2 C3 122.5(5) . . ?
C2 N2 C3 116.8(4) . . ?
O9 N1 O8 124.1(4) . . ?
O9 N1 C9 118.1(4) . . ?
O8 N1 C9 117.8(4) . . ?
O3 C1 N2 122.9(5) . . ?
O3 C1 H1B 118.6 . . ?
N2 C1 H1B 118.6 . . ?
C6 C7 C8 121.2(5) . . ?
C6 C7 C11 120.7(5) . . ?
C8 C7 C11 118.1(5) . . ?
C6 C5 C10 120.3(5) . . ?
C6 C5 C4 120.3(4) . . ?
C10 C5 C4 119.4(4) . . ?
C9 C8 C7 117.9(5) . . ?
C9 C8 H8A 121.0 . . ?
C7 C8 H8A 121.0 . . ?
C7 C6 C5 119.6(4) . . ?
C7 C6 H6A 120.2 . . ?
C5 C6 H6A 120.2 . . ?
C9 C10 C5 118.1(5) . . ?
C9 C10 H10A 120.9 . . ?
C5 C10 H10A 120.9 . . ?
C8 C9 C10 122.8(5) . . ?
C8 C9 N1 118.4(4) . . ?
C10 C9 N1 118.8(4) . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N2 C2 H2B 109.5 . . ?
N2 C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N2 C2 H2D 109.5 . . ?
H2B C2 H2D 109.5 . . ?
H2C C2 H2D 109.5 . . ?

_refine_diff_density_max         2.365
_refine_diff_density_min         -0.887
_refine_diff_density_rms         0.154

_shelxl_version_number           2014-3

