# Electronic Supplementary Material (ESI) for Energy & Environmental Science.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1419942'
_audit_update_record             
;
2015-08-21 deposited with the CCDC.
2015-11-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        'Uranyl Benzamidoxime'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H22 N4 O6 U'
_chemical_formula_weight         604.40

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                   10.4376(8)
_cell_length_b                   5.7148(4)
_cell_length_c                   15.9916(11)
_cell_angle_alpha                90
_cell_angle_beta                 102.543(2)
_cell_angle_gamma                90
_cell_volume                     931.11(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.156
_exptl_crystal_F_000             572
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    8.758
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'INCOATEC ImuS micro-focus source'
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100 CMOS'
_diffrn_measurement_method       'omega and phi scan'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            11878
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_av_R_equivalents  0.0685
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.610
_diffrn_reflns_theta_max         27.155
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2068
_reflns_number_gt                1407
_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       'APEX2 v.2014.9-0 (Bruker AXS Inc., 2014)'
_computing_cell_refinement       'SAINT V 8.27 (Bruker AXS Inc., 2012)'
_computing_data_reduction        'SAINT V 8.27 (Bruker AXS Inc., 2012)'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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+2.7468P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2068
_refine_ls_number_parameters     129
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0288
_refine_ls_wR_factor_ref         0.0550
_refine_ls_wR_factor_gt          0.0485
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.003
_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 0.0000 1.0000 1.0000 0.00681(8) Uani 1 2 d S . P . .
C0AA C 0.2677(5) 0.9561(9) 0.8232(3) 0.0078(15) Uani 1 1 d . . . . .
N4 N 0.1342(4) 1.1450(8) 0.9051(3) 0.0105(10) Uani 1 1 d . . . . .
N5 N 0.0965(4) 1.2346(9) 0.7600(3) 0.0126(10) Uani 1 1 d . . . . .
H5A H 0.0498 1.1318 0.7252 0.015 Uiso 1 1 d R U . . .
H5B H 0.0437 1.3388 0.7752 0.015 Uiso 1 1 d R U . . .
C1AA C 0.2509(5) 0.7932(10) 0.7568(3) 0.0116(12) Uani 1 1 d . . . . .
H1AA H 0.1722 0.7922 0.7138 0.014 Uiso 1 1 calc R U . . .
C2AA C 0.1623(5) 1.1232(10) 0.8306(3) 0.0089(11) Uani 1 1 d . . . . .
C8 C 0.4654(6) 0.6370(11) 0.8143(4) 0.0155(13) Uani 1 1 d . . . . .
H8 H 0.5325 0.5265 0.8118 0.019 Uiso 1 1 calc R U . . .
C9 C 0.3862(5) 0.9605(11) 0.8836(3) 0.0124(15) Uani 1 1 d . . . . .
H9 H 0.3997 1.0727 0.9285 0.015 Uiso 1 1 calc R U . . .
C10 C 0.4831(6) 0.8037(11) 0.8784(3) 0.0158(13) Uani 1 1 d . . . . .
H10 H 0.5638 0.8094 0.9195 0.019 Uiso 1 1 calc R U . . .
C11 C 0.3489(6) 0.6338(11) 0.7540(4) 0.0161(13) Uani 1 1 d . . . . .
H11 H 0.3360 0.5197 0.7098 0.019 Uiso 1 1 calc R U . . .
O2 O 0.1191(3) 1.1215(7) 1.0872(2) 0.0088(8) Uani 1 1 d . . . . .
O4 O 0.0298(3) 1.3028(6) 0.9065(2) 0.0089(8) Uani 1 1 d . . . . .
C6 C 0.2638(5) 0.6163(11) 1.0277(4) 0.0167(13) Uani 1 1 d . . . . .
H6A H 0.3171 0.5486 0.9903 0.025 Uiso 1 1 calc R U . . .
H6B H 0.2539 0.5018 1.0714 0.025 Uiso 1 1 calc R U . . .
H6C H 0.3071 0.7570 1.0555 0.025 Uiso 1 1 calc R U . . .
O7 O 0.1375(4) 0.6768(7) 0.9778(2) 0.0102(8) Uani 1 1 d D . . . .
H7 H 0.097(5) 0.557(6) 0.951(3) 0.015 Uiso 1 1 d 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 O2 1.794(4) 3_577 ?
U1 O2 1.794(4) . ?
U1 O4 2.352(4) 3_577 ?
U1 O4 2.352(4) . ?
U1 O7 2.412(4) . ?
U1 O7 2.412(4) 3_577 ?
U1 N4 2.424(4) . ?
U1 N4 2.424(4) 3_577 ?
C0AA C1AA 1.394(7) . ?
C0AA C9 1.395(7) . ?
C0AA C2AA 1.481(7) . ?
N4 C2AA 1.294(6) . ?
N4 O4 1.418(5) . ?
N5 C2AA 1.346(7) . ?
C1AA C11 1.379(8) . ?
C8 C11 1.378(8) . ?
C8 C10 1.383(8) . ?
C9 C10 1.367(8) . ?
C6 O7 1.427(6) . ?

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 O2 180.0(2) 3_577 . ?
O2 U1 O4 92.55(15) 3_577 3_577 ?
O2 U1 O4 87.45(15) . 3_577 ?
O2 U1 O4 87.45(15) 3_577 . ?
O2 U1 O4 92.55(15) . . ?
O4 U1 O4 180.0 3_577 . ?
O2 U1 O7 85.61(15) 3_577 . ?
O2 U1 O7 94.39(15) . . ?
O4 U1 O7 72.25(12) 3_577 . ?
O4 U1 O7 107.75(13) . . ?
O2 U1 O7 94.39(15) 3_577 3_577 ?
O2 U1 O7 85.61(15) . 3_577 ?
O4 U1 O7 107.75(13) 3_577 3_577 ?
O4 U1 O7 72.25(12) . 3_577 ?
O7 U1 O7 180.0 . 3_577 ?
O2 U1 N4 92.47(15) 3_577 . ?
O2 U1 N4 87.53(16) . . ?
O4 U1 N4 145.49(13) 3_577 . ?
O4 U1 N4 34.51(13) . . ?
O7 U1 N4 74.13(14) . . ?
O7 U1 N4 105.87(14) 3_577 . ?
O2 U1 N4 87.53(16) 3_577 3_577 ?
O2 U1 N4 92.47(15) . 3_577 ?
O4 U1 N4 34.51(13) 3_577 3_577 ?
O4 U1 N4 145.49(13) . 3_577 ?
O7 U1 N4 105.87(14) . 3_577 ?
O7 U1 N4 74.13(14) 3_577 3_577 ?
N4 U1 N4 180.0(2) . 3_577 ?
C1AA C0AA C9 119.0(5) . . ?
C1AA C0AA C2AA 121.2(5) . . ?
C9 C0AA C2AA 119.7(5) . . ?
C2AA N4 O4 113.8(4) . . ?
C2AA N4 U1 145.2(4) . . ?
O4 N4 U1 70.0(2) . . ?
C11 C1AA C0AA 119.7(5) . . ?
N4 C2AA N5 123.4(5) . . ?
N4 C2AA C0AA 117.1(5) . . ?
N5 C2AA C0AA 119.4(5) . . ?
C11 C8 C10 118.9(5) . . ?
C10 C9 C0AA 120.2(5) . . ?
C9 C10 C8 121.0(5) . . ?
C8 C11 C1AA 121.1(5) . . ?
N4 O4 U1 75.5(2) . . ?
C6 O7 U1 127.6(3) . . ?

_refine_diff_density_max         1.316
_refine_diff_density_min         -0.867
_refine_diff_density_rms         0.175

_shelxl_version_number           2013-4



