# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_c2byc
_database_code_depnum_ccdc_archive 'CCDC 1035178'
_audit_update_record             
;
2015-03-06 deposited with the CCDC.
2015-04-02 downloaded from the CCDC.
;
_audit_creation_date             2015-03-03
_audit_creation_method           
;
 ?
;
_shelxl_version_number           2013-3

_chemical_formula_moiety         'C12 H10 N4 O12 U'
_chemical_formula_sum            'C12 H10 N4 O12 U'
_chemical_formula_weight         640.27
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0070 0.0040 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0120 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
U U -10.8300 4.1630 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   14.539(3)
_cell_length_b                   9.1699(18)
_cell_length_c                   13.700(3)
_cell_angle_alpha                90
_cell_angle_beta                 116.31(3)
_cell_angle_gamma                90
_cell_volume                     1637.3(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.648
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.597
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0113
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12644
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.950
_diffrn_reflns_theta_max         28.278
_diffrn_reflns_theta_min         2.787
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  '3-BM1 Australian Synchrotron'
_diffrn_measurement_method       'Phi Scan'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.7293
_diffrn_source                   'Synchrotron BM'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1648
_reflns_number_total             1864
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       'BLU-ICE (McPhillips et al., 2002)'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_structure_solution    
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_diff_density_max         0.566
_refine_diff_density_min         -1.485
_refine_diff_density_rms         0.148
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1864
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0223
_refine_ls_R_factor_gt           0.0200
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0380P)²+5.2230P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0552
_refine_ls_wR_factor_ref         0.0573
_refine_special_details          
;
 ?
;
_Refinement_description          
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 -0.2500 0.2500 0.0000 0.00939(8) Uani 1 2 d S T P . .
O1 O -0.14751(13) 0.16957(19) -0.01676(14) 0.0104(3) Uani 1 1 d . . . . .
O2 O -0.4477(2) 0.24641(17) -0.3350(2) 0.0153(5) Uani 1 1 d . . . . .
O3 O -0.33703(16) 0.3607(2) -0.19069(17) 0.0147(4) Uani 1 1 d . . . . .
O4 O -0.36009(16) 0.1301(2) -0.18257(16) 0.0135(4) Uani 1 1 d . . . . .
O5 O -0.23704(13) 0.67189(19) -0.11961(14) 0.0126(4) Uani 1 1 d . . . . .
O6 O -0.18340(14) 0.47355(19) -0.01411(14) 0.0137(4) Uani 1 1 d . . . . .
N1 N -0.3839(3) 0.2450(2) -0.2401(3) 0.0123(6) Uani 1 1 d . . . . .
N2 N 0.0840(2) 0.8274(3) 0.1957(2) 0.0117(5) Uani 1 1 d . . . . .
C1 C -0.17580(18) 0.6056(3) -0.03879(18) 0.0072(4) Uani 1 1 d . . . . .
C2 C -0.0812(2) 0.6846(3) 0.0424(2) 0.0098(5) Uani 1 1 d . . . . .
C3 C -0.0775(2) 0.8372(3) 0.0440(2) 0.0116(5) Uani 1 1 d . . . . .
H3 H -0.1311 0.8911 -0.0078 0.014 Uiso 1 1 calc R . . . .
C4 C 0.0066(2) 0.9067(3) 0.1231(2) 0.0132(5) Uani 1 1 d . . . . .
H4 H 0.0095 1.0080 0.1261 0.016 Uiso 1 1 calc R . . . .
C5 C 0.0849(2) 0.6809(4) 0.1941(2) 0.0144(6) Uani 1 1 d . . . . .
H5 H 0.1416 0.6301 0.2441 0.017 Uiso 1 1 calc R . . . .
C6 C 0.0016(2) 0.6062(3) 0.1182(2) 0.0128(5) Uani 1 1 d . . . . .
H6 H 0.0007 0.5048 0.1177 0.015 Uiso 1 1 calc R . . . .
H2 H 0.126(3) 0.863(4) 0.237(3) 0.012(9) Uiso 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 O1 1.7665(17) . ?
U1 O1 1.7665(17) 7_455 ?
U1 O3 2.555(2) . ?
U1 O3 2.555(2) 7_455 ?
U1 O4 2.545(2) . ?
U1 O4 2.545(2) 7_455 ?
U1 O6 2.3115(17) . ?
U1 O6 2.3115(17) 7_455 ?
U1 N1 2.989(3) 7_455 ?
U1 N1 2.989(3) . ?
O2 N1 1.218(4) . ?
O3 N1 1.280(3) . ?
O4 N1 1.268(3) . ?
O5 C1 1.231(3) . ?
O6 C1 1.275(3) . ?
N2 C4 1.339(4) . ?
N2 C5 1.343(5) . ?
N2 H2 0.71(3) . ?
C1 C2 1.516(4) . ?
C2 C3 1.400(5) . ?
C2 C6 1.392(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.379(4) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C5 C6 1.380(4) . ?
C6 H6 0.9300 . ?

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
O1 U1 O1 180.0 . 7_455 ?
O1 U1 O3 95.56(8) 7_455 7_455 ?
O1 U1 O3 84.44(8) 7_455 . ?
O1 U1 O3 84.44(8) . 7_455 ?
O1 U1 O3 95.56(8) . . ?
O1 U1 O4 83.75(8) . . ?
O1 U1 O4 96.24(8) . 7_455 ?
O1 U1 O4 96.25(8) 7_455 . ?
O1 U1 O4 83.76(8) 7_455 7_455 ?
O1 U1 O6 92.83(8) . 7_455 ?
O1 U1 O6 92.83(8) 7_455 . ?
O1 U1 O6 87.17(8) 7_455 7_455 ?
O1 U1 O6 87.17(8) . . ?
O1 U1 N1 88.51(8) 7_455 . ?
O1 U1 N1 91.49(8) 7_455 7_455 ?
O1 U1 N1 88.51(8) . 7_455 ?
O1 U1 N1 91.49(8) . . ?
O3 U1 O3 180.0 7_455 . ?
O3 U1 N1 25.17(6) . . ?
O3 U1 N1 25.17(6) 7_455 7_455 ?
O3 U1 N1 154.83(6) . 7_455 ?
O3 U1 N1 154.83(6) 7_455 . ?
O4 U1 O3 130.10(8) . 7_455 ?
O4 U1 O3 49.90(8) 7_455 7_455 ?
O4 U1 O3 49.90(8) . . ?
O4 U1 O3 130.10(8) 7_455 . ?
O4 U1 O4 180.00(7) . 7_455 ?
O4 U1 N1 24.87(6) . . ?
O4 U1 N1 155.13(6) 7_455 . ?
O4 U1 N1 24.87(6) 7_455 7_455 ?
O4 U1 N1 155.13(6) . 7_455 ?
O6 U1 O3 113.70(6) 7_455 . ?
O6 U1 O3 66.30(6) 7_455 7_455 ?
O6 U1 O3 113.70(7) . 7_455 ?
O6 U1 O3 66.30(6) . . ?
O6 U1 O4 113.90(6) . . ?
O6 U1 O4 66.10(6) . 7_455 ?
O6 U1 O4 66.10(6) 7_455 . ?
O6 U1 O4 113.90(6) 7_455 7_455 ?
O6 U1 O6 180.0 7_455 . ?
O6 U1 N1 90.81(6) . . ?
O6 U1 N1 89.19(6) . 7_455 ?
O6 U1 N1 89.19(6) 7_455 . ?
O6 U1 N1 90.81(6) 7_455 7_455 ?
N1 U1 N1 180.0 . 7_455 ?
N1 O3 U1 96.75(17) . . ?
N1 O4 U1 97.55(17) . . ?
C1 O6 U1 162.38(17) . . ?
O2 N1 U1 172.5(2) . . ?
O2 N1 O3 122.1(2) . . ?
O2 N1 O4 122.8(2) . . ?
O3 N1 U1 58.08(16) . . ?
O4 N1 U1 57.58(15) . . ?
O4 N1 O3 115.2(3) . . ?
C4 N2 C5 122.9(2) . . ?
C4 N2 H2 120(3) . . ?
C5 N2 H2 118(3) . . ?
O5 C1 O6 126.5(2) . . ?
O5 C1 C2 118.9(2) . . ?
O6 C1 C2 114.6(2) . . ?
C3 C2 C1 120.3(2) . . ?
C6 C2 C1 120.3(3) . . ?
C6 C2 C3 119.4(2) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 C2 119.2(2) . . ?
C4 C3 H3 120.4 . . ?
N2 C4 C3 119.6(3) . . ?
N2 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
N2 C5 H5 120.1 . . ?
N2 C5 C6 119.8(3) . . ?
C6 C5 H5 120.1 . . ?
C2 C6 H6 120.5 . . ?
C5 C6 C2 119.1(3) . . ?
C5 C6 H6 120.5 . . ?

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
U1 O3 N1 O2 171.2(3) . . . . ?
U1 O3 N1 O4 -7.8(3) . . . . ?
U1 O4 N1 O2 -171.1(3) . . . . ?
U1 O4 N1 O3 7.9(3) . . . . ?
U1 O6 C1 O5 -27.4(7) . . . . ?
U1 O6 C1 C2 152.1(5) . . . . ?
O5 C1 C2 C3 18.5(3) . . . . ?
O5 C1 C2 C6 -163.5(3) . . . . ?
O6 C1 C2 C3 -161.0(2) . . . . ?
O6 C1 C2 C6 17.0(4) . . . . ?
N2 C5 C6 C2 1.7(4) . . . . ?
C1 C2 C3 C4 175.7(3) . . . . ?
C1 C2 C6 C5 -177.2(3) . . . . ?
C2 C3 C4 N2 1.3(4) . . . . ?
C3 C2 C6 C5 0.8(4) . . . . ?
C4 N2 C5 C6 -2.9(3) . . . . ?
C5 N2 C4 C3 1.4(4) . . . . ?
C6 C2 C3 C4 -2.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_pbca
_database_code_depnum_ccdc_archive 'CCDC 1035179'
_audit_update_record             
;
2015-03-06 deposited with the CCDC.
2015-04-02 downloaded from the CCDC.
;
_audit_creation_date             2015-03-03
_audit_creation_method           
;
 ?
;
_shelxl_version_number           2013-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C6 H5 N O5 U'
_chemical_formula_sum            'C6 H5 N O5 U'
_chemical_formula_weight         409.14
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0040 0.0020 '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 0.0070 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0120 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
U U -12.0990 4.4900 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.191(2)
_cell_length_b                   8.6030(17)
_cell_length_c                   18.665(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1636.4(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   0.914
_shelx_estimated_absorpt_T_min   0.839
_exptl_absorpt_coefficient_mu    9.108
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    3.321
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.015
_exptl_crystal_size_min          0.01
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1003
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_Laue_measured_fraction_full 0.885
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17201
_diffrn_reflns_point_group_measured_fraction_full 0.885
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_min         2.239
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.885
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  '3-BM1 Australian Synchrotron'
_diffrn_measurement_method       'Phi Scan'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.7293
_diffrn_source                   'Synchrotron BM'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1200
_reflns_number_total             1321
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       'BLU-ICE (McPhillips et al., 2002)'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_structure_solution    
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_diff_density_max         3.437
_refine_diff_density_min         -1.107
_refine_diff_density_rms         0.304
_refine_ls_extinction_coef       0.00174(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     81
_refine_ls_number_reflns         1321
_refine_ls_number_restraints     40
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0305
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0430P)²+8.9320P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0756
_refine_ls_wR_factor_ref         0.0772
_refine_special_details          
;
 ?
;
_Refinement_description          
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 C1, C2, C3, C4, C5, C6
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6: within 1.7A with sigma of 0.04
and sigma for terminal atoms of 0.08
Uanis(C1) = Uanis(C2) = Uanis(C3) = Uanis(C4) = Uanis(C5) = Uanis(C6)
Uanis(O1) = Uanis(O2) = Uanis(O3)
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4), C5(H5), C6(H6)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.78604(2) 0.13314(3) 0.56657(2) 0.00544(19) Uani 1 1 d . . . . .
O1 O 0.6176(4) 0.0968(5) 0.5880(2) 0.0116(6) Uani 1 1 d . . . . .
O2 O 0.9549(4) 0.1643(5) 0.5459(2) 0.0116(6) Uani 1 1 d . . . . .
O3 O 0.7915(4) -0.1213(5) 0.5265(3) 0.0116(6) Uani 1 1 d . . . . .
H3 H 0.857(11) -0.129(8) 0.499(5) 0.03(3) Uiso 1 1 d . . . . .
O4 O 0.8085(4) 0.3024(5) 0.6653(2) 0.0123(10) Uani 1 1 d . . . . .
O5 O 0.6541(4) 0.4860(5) 0.6730(2) 0.0127(10) Uani 1 1 d . . . . .
N1 N 0.7607(7) 0.3701(5) 0.9295(3) 0.0097(14) Uani 1 1 d . . . . .
C1 C 0.7315(6) 0.3901(7) 0.7003(4) 0.0113(6) Uani 1 1 d . U . . .
C2 C 0.7374(7) 0.3812(6) 0.7804(4) 0.0113(6) Uani 1 1 d . U . . .
C3 C 0.6365(6) 0.4293(7) 0.8241(3) 0.0113(6) Uani 1 1 d . U . . .
H3A H 0.5591 0.4668 0.8041 0.014 Uiso 1 1 calc R . . . .
C4 C 0.6503(6) 0.4219(8) 0.8975(3) 0.0113(6) Uani 1 1 d . U . . .
H4 H 0.5807 0.4540 0.9261 0.014 Uiso 1 1 calc R . . . .
C5 C 0.8590(6) 0.3206(7) 0.8867(3) 0.0113(6) Uani 1 1 d . U . . .
H5 H 0.9354 0.2837 0.9079 0.014 Uiso 1 1 calc R . . . .
C6 C 0.8515(6) 0.3222(7) 0.8132(3) 0.0113(6) Uani 1 1 d . U . . .
H6 H 0.9207 0.2850 0.7856 0.014 Uiso 1 1 calc R . . . .


_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 O1 1.790(5) . ?
U1 O2 1.784(5) . ?
U1 O3 2.314(4) . ?
U1 O3 2.376(4) 7_765 ?
U1 O4 2.360(4) . ?
U1 O5 2.434(4) 7_755 ?
U1 N1 2.571(5) 8_565 ?
O3 U1 2.376(4) 7_755 ?
O3 H3 0.85(11) . ?
O4 C1 1.270(8) . ?
O5 U1 2.434(4) 7_765 ?
O5 C1 1.250(8) . ?
N1 U1 2.571(5) 8_566 ?
N1 C4 1.349(10) . ?
N1 C5 1.351(9) . ?
C1 C2 1.497(10) . ?
C2 C3 1.376(10) . ?
C2 C6 1.410(10) . ?
C3 H3A 0.9300 . ?
C3 C4 1.380(8) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C5 C6 1.374(9) . ?
C6 H6 0.9300 . ?

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
O1 U1 O3 85.99(18) . . ?
O1 U1 O3 84.63(18) . 7_765 ?
O1 U1 O4 91.52(18) . . ?
O1 U1 O5 88.15(18) . 7_755 ?
O1 U1 N1 97.1(2) . 8_565 ?
O2 U1 O1 178.5(2) . . ?
O2 U1 O3 92.80(18) . . ?
O2 U1 O3 96.83(18) . 7_765 ?
O2 U1 O4 89.02(18) . . ?
O2 U1 O5 90.75(18) . 7_755 ?
O2 U1 N1 83.3(2) . 8_565 ?
O3 U1 O3 138.3(2) . 7_765 ?
O3 U1 O4 146.51(16) . . ?
O3 U1 O5 76.46(16) . 7_755 ?
O3 U1 O5 143.41(16) 7_765 7_755 ?
O3 U1 N1 70.31(16) 7_765 8_565 ?
O3 U1 N1 70.76(16) . 8_565 ?
O4 U1 O3 74.31(16) . 7_765 ?
O4 U1 O5 70.08(15) . 7_755 ?
O4 U1 N1 142.50(15) . 8_565 ?
O5 U1 N1 146.28(15) 7_755 8_565 ?
U1 O3 U1 137.0(2) . 7_755 ?
U1 O3 H3 107(5) . . ?
U1 O3 H3 112(5) 7_755 . ?
C1 O4 U1 135.1(4) . . ?
C1 O5 U1 121.2(4) . 7_765 ?
C4 N1 U1 121.8(5) . 8_566 ?
C4 N1 C5 117.4(5) . . ?
C5 N1 U1 120.7(5) . 8_566 ?
O4 C1 C2 117.3(6) . . ?
O5 C1 O4 124.9(6) . . ?
O5 C1 C2 117.7(6) . . ?
C3 C2 C1 123.1(6) . . ?
C3 C2 C6 117.8(7) . . ?
C6 C2 C1 119.0(6) . . ?
C2 C3 H3A 120.0 . . ?
C2 C3 C4 120.0(6) . . ?
C4 C3 H3A 120.0 . . ?
N1 C4 C3 122.7(6) . . ?
N1 C4 H4 118.7 . . ?
C3 C4 H4 118.7 . . ?
N1 C5 H5 118.4 . . ?
N1 C5 C6 123.1(6) . . ?
C6 C5 H5 118.4 . . ?
C2 C6 H6 120.5 . . ?
C5 C6 C2 118.9(6) . . ?
C5 C6 H6 120.5 . . ?

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
U1 O4 C1 O5 -49.2(9) . . . . ?
U1 O4 C1 C2 132.9(5) . . . . ?
U1 O5 C1 O4 -36.7(8) 7_765 . . . ?
U1 O5 C1 C2 141.2(5) 7_765 . . . ?
U1 N1 C4 C3 177.8(5) 8_566 . . . ?
U1 N1 C5 C6 -178.9(5) 8_566 . . . ?
O4 C1 C2 C3 -159.1(6) . . . . ?
O4 C1 C2 C6 21.5(9) . . . . ?
O5 C1 C2 C3 22.9(9) . . . . ?
O5 C1 C2 C6 -156.5(6) . . . . ?
N1 C5 C6 C2 1.4(10) . . . . ?
C1 C2 C3 C4 -178.1(6) . . . . ?
C1 C2 C6 C5 177.1(6) . . . . ?
C2 C3 C4 N1 0.7(10) . . . . ?
C3 C2 C6 C5 -2.3(9) . . . . ?
C4 N1 C5 C6 0.6(9) . . . . ?
C5 N1 C4 C3 -1.6(9) . . . . ?
C6 C2 C3 C4 1.3(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
