# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_Compound_1
_database_code_depnum_ccdc_archive 'CCDC 1838828'
_audit_update_record             
;
2018-04-23 deposited with the CCDC.
2018-06-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H10 O6 U'
_exptl_crystal_recrystallization_method Hydrothermal
_chemical_melting_point          ?

_exptl_crystal_description       Plate
_exptl_crystal_colour            Yellow

_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         512.25

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'
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           12
_space_group_name_H-M_alt        'C 2/m'
_space_group_name_Hall           '-C 2y'
_chemical_absolute_configuration ?

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_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.
;

_cell_length_a                   7.632(6)
_cell_length_b                   17.468(9)
_cell_length_c                   5.313(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.791(7)
_cell_angle_gamma                90
_cell_volume                     704.7(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9180
_cell_measurement_theta_min      4.664
_cell_measurement_theta_max      54.360
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.414
_exptl_crystal_F_000             468
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_exptl_absorpt_coefficient_mu    11.540
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.4227
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   'TWINABS (Sheldrick, 2008)'

_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8871
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.332
_diffrn_reflns_theta_max         27.564
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             846
_reflns_number_gt                846
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 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       'APEX, Bruker-AXS'
_computing_cell_refinement       'SAINT, Bruker-AXS'
_computing_data_reduction        'SAINT, Bruker-AXS'
_computing_structure_solution    'SIR92 (Gualardi, 1994)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'WINGX (Farrugia, 2012)'
_computing_publication_material  'Crystal Maker (Palmer, 2009)'

_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)+(0.0142P)²+0.6711P] 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         846
_refine_ls_number_parameters     53
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0141
_refine_ls_R_factor_gt           0.0141
_refine_ls_wR_factor_ref         0.0322
_refine_ls_wR_factor_gt          0.0322
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_restrained_S_all      1.145
_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 0.0000 0.0000 0.0000 0.02759(7) Uani 1 4 d S T P . .
O1 O 0.2264(4) 0.0000 0.0922(7) 0.0479(8) Uani 1 2 d S T P . .
O2 O 0.0418(3) 0.09255(12) -0.2953(4) 0.0463(5) Uani 1 1 d . . . . .
C1 C 0.0000 0.1274(2) -0.5000 0.0297(8) Uani 1 2 d S T P . .
C2 C 0.0000 0.2117(2) -0.5000 0.0272(7) Uani 1 2 d S T P . .
C3 C 0.0780(4) 0.25143(17) -0.2920(6) 0.0392(7) Uani 1 1 d . . . . .
H3 H 0.1299 0.2250 -0.1520 0.047 Uiso 1 1 calc R U . . .
C5 C 0.0000 0.3697(3) -0.5000 0.0658(17) Uani 1 2 d S T P . .
H5 H 0.0000 0.4230 -0.5000 0.079 Uiso 1 2 calc R U P . .
C4 C 0.0783(5) 0.3308(2) -0.2938(8) 0.0570(10) Uani 1 1 d . . . . .
H4 H 0.1315 0.3577 -0.1555 0.068 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 O1 1.748(4) . ?
U1 O1 1.748(4) 5 ?
U1 O2 2.297(2) 6 ?
U1 O2 2.297(2) 2 ?
U1 O2 2.297(2) 5 ?
U1 O2 2.297(2) . ?
O2 C1 1.259(3) . ?
C1 O2 1.259(3) 2_554 ?
C1 C2 1.472(5) . ?
C2 C3 1.388(4) 2_554 ?
C2 C3 1.388(4) . ?
C3 C4 1.386(5) . ?
C3 H3 0.9300 . ?
C5 C4 1.374(5) . ?
C5 C4 1.374(5) 2_554 ?
C5 H5 0.9300 . ?
C4 H4 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 . 5 ?
O1 U1 O2 89.42(11) . 6 ?
O1 U1 O2 90.58(11) 5 6 ?
O1 U1 O2 90.58(11) . 2 ?
O1 U1 O2 89.42(11) 5 2 ?
O2 U1 O2 180.00(14) 6 2 ?
O1 U1 O2 90.58(11) . 5 ?
O1 U1 O2 89.42(11) 5 5 ?
O2 U1 O2 90.55(13) 6 5 ?
O2 U1 O2 89.45(13) 2 5 ?
O1 U1 O2 89.42(11) . . ?
O1 U1 O2 90.58(11) 5 . ?
O2 U1 O2 89.45(13) 6 . ?
O2 U1 O2 90.55(13) 2 . ?
O2 U1 O2 180.0 5 . ?
C1 O2 U1 152.81(19) . . ?
O2 C1 O2 122.2(4) . 2_554 ?
O2 C1 C2 118.90(18) . . ?
O2 C1 C2 118.90(18) 2_554 . ?
C3 C2 C3 119.9(4) 2_554 . ?
C3 C2 C1 120.03(19) 2_554 . ?
C3 C2 C1 120.04(19) . . ?
C2 C3 C4 119.7(3) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C4 C5 C4 120.6(4) . 2_554 ?
C4 C5 H5 119.7 . . ?
C4 C5 H5 119.7 2_554 . ?
C5 C4 C3 120.0(4) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?

_refine_diff_density_max         0.647
_refine_diff_density_min         -0.712
_refine_diff_density_rms         0.092

_shelxl_version_number           2014-1

####################################################################### 
# 
# 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_Compound_3
_database_code_depnum_ccdc_archive 'CCDC 1838830'
_audit_update_record             
;
2018-04-23 deposited with the CCDC.
2018-06-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H8 Br2 O6 U'
_exptl_crystal_recrystallization_method Hydrothermal
_chemical_melting_point          ?

_exptl_crystal_description       Plate
_exptl_crystal_colour            Yellow

_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         670.05

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'
_chemical_absolute_configuration ?

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'

_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.
;

_cell_length_a                   5.1074(4)
_cell_length_b                   17.6516(15)
_cell_length_c                   9.0688(8)
_cell_angle_alpha                90
_cell_angle_beta                 94.061(9)
_cell_angle_gamma                90
_cell_volume                     815.53(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    10720
_cell_measurement_theta_min      5.060
_cell_measurement_theta_max      54.046
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.729
_exptl_crystal_F_000             604
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    14.876
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.5008
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2015)'

_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10491
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.308
_diffrn_reflns_theta_max         27.589
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1883
_reflns_number_gt                1495
_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       'APEX, Bruker-AXS'
_computing_cell_refinement       'SAINT, Bruker-AXS'
_computing_data_reduction        'SAINT, Bruker-AXS'
_computing_structure_solution    'SIR92 (Gualardi, 1994)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'WINGX (Farrugia, 2012)'
_computing_publication_material  'Crystal Maker (Palmer, 2009)'

_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)+(0.0220P)²+1.3273P] 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         1883
_refine_ls_number_parameters     106
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0223
_refine_ls_wR_factor_ref         0.0512
_refine_ls_wR_factor_gt          0.0478
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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 0.0000 0.0000 0.0000 0.02802(8) Uani 1 2 d S . P . .
Br1 Br -0.22350(12) 0.40770(3) -0.06783(7) 0.05761(16) Uani 1 1 d . . . . .
O3 O -0.2771(6) 0.10357(16) 0.0006(4) 0.0433(8) Uani 1 1 d . . . . .
C4 C -0.4120(10) 0.3356(2) 0.0363(5) 0.0387(11) Uani 1 1 d . . . . .
O1 O 0.0593(7) 0.02207(18) -0.1820(4) 0.0466(9) Uani 1 1 d . . . . .
C6 C -0.7490(10) 0.3071(3) 0.1968(6) 0.0465(12) Uani 1 1 d . . . . .
H6 H -0.8727 0.3233 0.2604 0.056 Uiso 1 1 calc R U . . .
C2 C -0.5246(8) 0.2066(2) 0.0817(5) 0.0311(9) Uani 1 1 d . . . . .
C7 C -0.7162(9) 0.2302(3) 0.1725(5) 0.0409(11) Uani 1 1 d . . . . .
H7 H -0.8212 0.1950 0.2166 0.049 Uiso 1 1 calc R U . . .
C3 C -0.3722(9) 0.2594(2) 0.0126(5) 0.0344(10) Uani 1 1 d . . . . .
H3 H -0.2447 0.2435 -0.0489 0.041 Uiso 1 1 calc R U . . .
C5 C -0.6010(10) 0.3596(3) 0.1280(5) 0.0435(12) Uani 1 1 d . . . . .
H5 H -0.6276 0.4110 0.1429 0.052 Uiso 1 1 calc R U . . .
C1 C -0.4864(8) 0.1244(2) 0.0534(5) 0.0346(10) Uani 1 1 d . . . . .
O2 O 0.3344(6) 0.07871(17) 0.0827(4) 0.0468(9) 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 O1 1.743(3) . ?
U1 O1 1.743(3) 3 ?
U1 O2 2.286(3) . ?
U1 O2 2.286(3) 3 ?
U1 O3 2.312(3) 3 ?
U1 O3 2.312(3) . ?
Br1 C4 1.888(5) . ?
O3 C1 1.257(5) . ?
C4 C3 1.380(6) . ?
C4 C5 1.384(7) . ?
C6 C5 1.373(7) . ?
C6 C7 1.387(6) . ?
C6 H6 0.9300 . ?
C2 C3 1.392(6) . ?
C2 C7 1.387(6) . ?
C2 C1 1.489(6) . ?
C7 H7 0.9300 . ?
C3 H3 0.9300 . ?
C5 H5 0.9300 . ?
C1 O2 1.262(5) 1_455 ?
O2 C1 1.262(5) 1_655 ?

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 . 3 ?
O1 U1 O2 89.95(15) . . ?
O1 U1 O2 90.06(15) 3 . ?
O1 U1 O2 90.05(15) . 3 ?
O1 U1 O2 89.94(15) 3 3 ?
O2 U1 O2 180.0 . 3 ?
O1 U1 O3 91.55(14) . 3 ?
O1 U1 O3 88.45(14) 3 3 ?
O2 U1 O3 92.19(11) . 3 ?
O2 U1 O3 87.81(11) 3 3 ?
O1 U1 O3 88.45(14) . . ?
O1 U1 O3 91.55(14) 3 . ?
O2 U1 O3 87.81(11) . . ?
O2 U1 O3 92.19(11) 3 . ?
O3 U1 O3 180.0 3 . ?
C1 O3 U1 140.3(3) . . ?
C3 C4 C5 120.5(4) . . ?
C3 C4 Br1 119.6(4) . . ?
C5 C4 Br1 119.8(3) . . ?
C5 C6 C7 120.7(5) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C3 C2 C7 120.4(4) . . ?
C3 C2 C1 119.4(4) . . ?
C7 C2 C1 120.2(4) . . ?
C6 C7 C2 119.2(5) . . ?
C6 C7 H7 120.4 . . ?
C2 C7 H7 120.4 . . ?
C4 C3 C2 119.3(4) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C6 C5 C4 119.8(4) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
O3 C1 O2 122.9(4) . 1_455 ?
O3 C1 C2 118.4(4) . . ?
O2 C1 C2 118.7(4) 1_455 . ?
C1 O2 U1 148.8(3) 1_655 . ?

_refine_diff_density_max         2.014
_refine_diff_density_min         -0.486
_refine_diff_density_rms         0.118

_shelxl_version_number           2014-1

####################################################################### 
# 
# 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_Compound_4
_database_code_depnum_ccdc_archive 'CCDC 1838831'
_audit_update_record             
;
2018-04-23 deposited with the CCDC.
2018-06-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H8 I2 O6 U'
_exptl_crystal_recrystallization_method Hydrothermal
_chemical_melting_point          ?

_exptl_crystal_description       Plate
_exptl_crystal_colour            Yellow

_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         764.03

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'
_chemical_absolute_configuration ?

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'

_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.
;

_cell_length_a                   5.0806(4)
_cell_length_b                   17.9621(12)
_cell_length_c                   9.3867(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.553(8)
_cell_angle_gamma                90
_cell_volume                     854.97(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8379
_cell_measurement_theta_min      4.535
_cell_measurement_theta_max      54.639
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.968
_exptl_crystal_F_000             676
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_absorpt_coefficient_mu    13.128
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.3050
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2015)'

_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8183
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.268
_diffrn_reflns_theta_max         27.363
_diffrn_reflns_theta_full        25.500
_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             1944
_reflns_number_gt                1772
_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       'APEX, Bruker-AXS'
_computing_cell_refinement       'SAINT, Bruker-AXS'
_computing_data_reduction        'SAINT, Bruker-AXS'
_computing_structure_solution    'SIR92 (Gualardi, 1994)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'WINGX (Farrugia, 2012)'
_computing_publication_material  'Crystal Maker (Palmer, 2009)'

_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)+(0.0313P)²+0.6561P] 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         1944
_refine_ls_number_parameters     106
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0263
_refine_ls_R_factor_gt           0.0233
_refine_ls_wR_factor_ref         0.0570
_refine_ls_wR_factor_gt          0.0558
_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 0.0000 0.5000 0.5000 0.02210(8) Uani 1 2 d S . P . .
I1 I -0.21575(7) 0.08996(2) 0.43741(4) 0.04562(11) Uani 1 1 d . . . . .
O2 O -0.2797(6) 0.39829(17) 0.5033(4) 0.0388(8) Uani 1 1 d . . . . .
O1 O 0.0694(7) 0.47568(19) 0.3241(4) 0.0399(8) Uani 1 1 d . . . . .
O3 O 0.3334(6) 0.42379(17) 0.5869(4) 0.0386(8) Uani 1 1 d . . . . .
C7 C -0.7126(9) 0.2760(3) 0.6835(5) 0.0334(10) Uani 1 1 d . . . . .
H7 H -0.8161 0.3114 0.7258 0.040 Uiso 1 1 calc R U . . .
C1 C -0.4887(8) 0.3787(2) 0.5589(5) 0.0281(9) Uani 1 1 d . . . . .
C3 C -0.3746(8) 0.2456(2) 0.5239(5) 0.0284(9) Uani 1 1 d . . . . .
H3 H -0.2488 0.2605 0.4620 0.034 Uiso 1 1 calc R U . . .
C2 C -0.5252(8) 0.2981(2) 0.5908(4) 0.0252(8) Uani 1 1 d . . . . .
C5 C -0.5963(10) 0.1482(3) 0.6468(5) 0.0369(10) Uani 1 1 d . . . . .
H5 H -0.6184 0.0979 0.6668 0.044 Uiso 1 1 calc R U . . .
C6 C -0.7452(10) 0.2019(3) 0.7126(5) 0.0407(11) Uani 1 1 d . . . . .
H6 H -0.8676 0.1873 0.7768 0.049 Uiso 1 1 calc R U . . .
C4 C -0.4146(9) 0.1707(2) 0.5508(5) 0.0302(9) 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 O1 1.764(3) 3_566 ?
U1 O1 1.764(3) . ?
U1 O3 2.288(3) . ?
U1 O3 2.288(3) 3_566 ?
U1 O2 2.316(3) . ?
U1 O2 2.316(3) 3_566 ?
I1 C4 2.095(4) . ?
O2 C1 1.262(5) . ?
O3 C1 1.253(5) 1_655 ?
C7 C6 1.372(6) . ?
C7 C2 1.386(6) . ?
C7 H7 0.9300 . ?
C1 O3 1.253(5) 1_455 ?
C1 C2 1.493(5) . ?
C3 C4 1.386(6) . ?
C3 C2 1.389(6) . ?
C3 H3 0.9300 . ?
C5 C4 1.390(6) . ?
C5 C6 1.394(7) . ?
C5 H5 0.9300 . ?
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(2) 3_566 . ?
O1 U1 O3 90.06(15) 3_566 . ?
O1 U1 O3 89.94(15) . . ?
O1 U1 O3 89.94(15) 3_566 3_566 ?
O1 U1 O3 90.06(15) . 3_566 ?
O3 U1 O3 180.0 . 3_566 ?
O1 U1 O2 91.41(15) 3_566 . ?
O1 U1 O2 88.59(15) . . ?
O3 U1 O2 87.98(11) . . ?
O3 U1 O2 92.02(12) 3_566 . ?
O1 U1 O2 88.59(15) 3_566 3_566 ?
O1 U1 O2 91.41(15) . 3_566 ?
O3 U1 O2 92.02(12) . 3_566 ?
O3 U1 O2 87.98(11) 3_566 3_566 ?
O2 U1 O2 180.0 . 3_566 ?
C1 O2 U1 139.3(3) . . ?
C1 O3 U1 147.1(3) 1_655 . ?
C6 C7 C2 119.9(4) . . ?
C6 C7 H7 120.0 . . ?
C2 C7 H7 120.0 . . ?
O3 C1 O2 122.9(4) 1_455 . ?
O3 C1 C2 119.0(4) 1_455 . ?
O2 C1 C2 118.1(4) . . ?
C4 C3 C2 119.1(4) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C7 C2 C3 120.6(4) . . ?
C7 C2 C1 120.1(4) . . ?
C3 C2 C1 119.3(4) . . ?
C4 C5 C6 119.1(4) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C7 C6 C5 120.5(4) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C3 C4 C5 120.8(4) . . ?
C3 C4 I1 119.9(3) . . ?
C5 C4 I1 119.2(3) . . ?

_refine_diff_density_max         1.021
_refine_diff_density_min         -1.732
_refine_diff_density_rms         0.179

_shelxl_version_number           2014-1

####################################################################### 
# 
# 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_Compound_2
_database_code_depnum_ccdc_archive 'CCDC 1838829'
_audit_update_record             
;
2018-04-23 deposited with the CCDC.
2018-06-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H20 Cl4 O14 U2'
_exptl_crystal_recrystallization_method Hydrothermal
_chemical_melting_point          ?

_exptl_crystal_description       Plate
_exptl_crystal_colour            Yellow

_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         1198.30

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'
_chemical_absolute_configuration ?

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'

_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.
;

_cell_length_a                   18.391(8)
_cell_length_b                   8.604(5)
_cell_length_c                   10.512(7)
_cell_angle_alpha                90
_cell_angle_beta                 90.911(6)
_cell_angle_gamma                90
_cell_volume                     1663.2(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    42676
_cell_measurement_theta_min      5.227
_cell_measurement_theta_max      54.374
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.393
_exptl_crystal_F_000             1104
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    10.113
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.5114
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   'TWINABS (Sheldrick, 2008)'

_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36470
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.215
_diffrn_reflns_theta_max         27.606
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3862
_reflns_number_gt                3140
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 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       'APEX, Bruker-AXS'
_computing_cell_refinement       'SAINT, Bruker-AXS'
_computing_data_reduction        'SAINT, Bruker-AXS'
_computing_structure_solution    'SIR92 (Gualardi, 1994)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'WINGX (Farrugia, 2012)'
_computing_publication_material  'Crystal Maker (Palmer, 2009)'

_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)+(0.0325P)²] 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         3862
_refine_ls_number_parameters     225
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0246
_refine_ls_wR_factor_ref         0.0580
_refine_ls_wR_factor_gt          0.0555
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.004
_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 0.92459(2) 0.94758(2) 0.28355(2) 0.02652(6) Uani 1 1 d . . . . .
Cl2 Cl 1.37281(7) 0.8194(2) 0.47249(14) 0.0680(4) Uani 1 1 d . . . . .
Cl1 Cl 0.51268(7) 1.0325(2) 0.24835(17) 0.0780(5) Uani 1 1 d . . . . .
O4 O 0.83602(15) 0.8460(4) 0.1286(3) 0.0407(7) Uani 1 1 d . . . . .
C10 C 1.2306(2) 0.8819(5) 0.4301(4) 0.0351(10) Uani 1 1 d . . . . .
H10 H 1.2245 0.8622 0.5163 0.042 Uiso 1 1 calc R U . . .
O5 O 1.04683(15) 0.9829(4) 0.3369(3) 0.0378(7) Uani 1 1 d . . . . .
O3 O 0.79517(16) 0.9592(4) 0.2999(3) 0.0435(8) Uani 1 1 d . . . . .
OW1 O 0.98986(17) 0.8495(4) 0.0955(3) 0.0392(7) Uani 1 1 d D . . . .
O6 O 0.90888(15) 1.0821(3) 0.4733(3) 0.0373(7) Uani 1 1 d . . . . .
O2 O 0.92633(16) 0.7690(3) 0.3654(3) 0.0394(7) Uani 1 1 d . . . . .
O1 O 0.92436(16) 1.1289(3) 0.2057(3) 0.0400(7) Uani 1 1 d . . . . .
C13 C 1.2498(3) 0.9400(6) 0.1726(5) 0.0498(13) Uani 1 1 d . . . . .
H13 H 1.2564 0.9592 0.0865 0.060 Uiso 1 1 calc R U . . .
C11 C 1.2980(2) 0.8680(6) 0.3755(5) 0.0411(11) Uani 1 1 d . . . . .
C8 C 1.0987(2) 0.9425(5) 0.4089(4) 0.0307(9) Uani 1 1 d . . . . .
C9 C 1.1724(2) 0.9258(5) 0.3538(4) 0.0307(9) Uani 1 1 d . . . . .
C7 C 0.6903(3) 0.7769(6) 0.0463(4) 0.0448(12) Uani 1 1 d . . . . .
H7 H 0.7269 0.7242 0.0042 0.054 Uiso 1 1 calc R U . . .
C2 C 0.7068(2) 0.8719(5) 0.1489(4) 0.0313(9) Uani 1 1 d . . . . .
C3 C 0.6525(2) 0.9500(6) 0.2118(4) 0.0407(11) Uani 1 1 d . . . . .
H3 H 0.6637 1.0134 0.2810 0.049 Uiso 1 1 calc R U . . .
C12 C 1.3085(3) 0.8957(7) 0.2500(5) 0.0517(13) Uani 1 1 d . . . . .
H12 H 1.3546 0.8853 0.2158 0.062 Uiso 1 1 calc R U . . .
C5 C 0.5633(3) 0.8388(7) 0.0682(5) 0.0545(14) Uani 1 1 d . . . . .
H5 H 0.5152 0.8278 0.0411 0.065 Uiso 1 1 calc R U . . .
C1 C 0.7831(2) 0.8916(5) 0.1934(4) 0.0344(10) Uani 1 1 d . . . . .
C14 C 1.1825(3) 0.9548(5) 0.2243(5) 0.0414(11) Uani 1 1 d . . . . .
H14 H 1.1432 0.9844 0.1731 0.050 Uiso 1 1 calc R U . . .
C6 C 0.6183(3) 0.7612(7) 0.0071(5) 0.0584(15) Uani 1 1 d . . . . .
H6 H 0.6069 0.6973 -0.0617 0.070 Uiso 1 1 calc R U . . .
C4 C 0.5808(2) 0.9323(6) 0.1698(5) 0.0453(12) Uani 1 1 d . . . . .
HW1 H 1.0366(17) 0.806(7) 0.093(6) 0.10(2) Uiso 1 1 d D . . . .
HW2 H 0.962(3) 0.835(7) 0.018(3) 0.079(19) Uiso 1 1 d 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 1.762(3) . ?
U1 O2 1.761(3) . ?
U1 O6 2.328(3) . ?
U1 O5 2.328(3) . ?
U1 O3 2.391(3) . ?
U1 O4 2.446(3) . ?
U1 OW1 2.477(3) . ?
U1 C1 2.798(4) . ?
Cl2 C11 1.750(5) . ?
Cl1 C4 1.740(5) . ?
O4 C1 1.260(5) . ?
C10 C11 1.379(6) . ?
C10 C9 1.379(6) . ?
C10 H10 0.9300 . ?
O5 C8 1.258(5) . ?
O3 C1 1.278(5) . ?
OW1 HW1 0.94(2) . ?
OW1 HW2 0.964(19) . ?
O6 C8 1.265(5) 3_776 ?
C13 C14 1.365(7) . ?
C13 C12 1.395(7) . ?
C13 H13 0.9300 . ?
C11 C12 1.358(7) . ?
C8 O6 1.265(5) 3_776 ?
C8 C9 1.490(6) . ?
C9 C14 1.400(6) . ?
C7 C2 1.384(6) . ?
C7 C6 1.387(6) . ?
C7 H7 0.9300 . ?
C2 C3 1.381(6) . ?
C2 C1 1.480(6) . ?
C3 C4 1.393(6) . ?
C3 H3 0.9300 . ?
C12 H12 0.9300 . ?
C5 C4 1.371(7) . ?
C5 C6 1.379(7) . ?
C5 H5 0.9300 . ?
C14 H14 0.9300 . ?
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 O2 178.19(14) . . ?
O1 U1 O6 87.62(13) . . ?
O2 U1 O6 90.94(13) . . ?
O1 U1 O5 89.51(13) . . ?
O2 U1 O5 89.20(13) . . ?
O6 U1 O5 82.03(11) . . ?
O1 U1 O3 90.09(13) . . ?
O2 U1 O3 90.67(13) . . ?
O6 U1 O3 77.31(10) . . ?
O5 U1 O3 159.33(11) . . ?
O1 U1 O4 90.61(13) . . ?
O2 U1 O4 91.17(13) . . ?
O6 U1 O4 131.11(10) . . ?
O5 U1 O4 146.84(10) . . ?
O3 U1 O4 53.83(10) . . ?
O1 U1 OW1 85.91(13) . . ?
O2 U1 OW1 95.02(13) . . ?
O6 U1 OW1 157.13(11) . . ?
O5 U1 OW1 76.02(11) . . ?
O3 U1 OW1 124.55(10) . . ?
O4 U1 OW1 70.92(10) . . ?
O1 U1 C1 89.99(14) . . ?
O2 U1 C1 91.44(13) . . ?
O6 U1 C1 104.38(12) . . ?
O5 U1 C1 173.55(12) . . ?
O3 U1 C1 27.10(12) . . ?
O4 U1 C1 26.74(11) . . ?
OW1 U1 C1 97.53(12) . . ?
C1 O4 U1 92.4(3) . . ?
C11 C10 C9 118.4(4) . . ?
C11 C10 H10 120.8 . . ?
C9 C10 H10 120.8 . . ?
C8 O5 U1 146.1(3) . . ?
C1 O3 U1 94.5(3) . . ?
U1 OW1 HW1 128(4) . . ?
U1 OW1 HW2 117(3) . . ?
HW1 OW1 HW2 114(5) . . ?
C8 O6 U1 140.5(3) 3_776 . ?
C14 C13 C12 119.4(5) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C12 C11 C10 122.2(4) . . ?
C12 C11 Cl2 119.0(4) . . ?
C10 C11 Cl2 118.8(4) . . ?
O5 C8 O6 122.7(4) . 3_776 ?
O5 C8 C9 118.6(4) . . ?
O6 C8 C9 118.7(4) 3_776 . ?
C10 C9 C14 120.1(4) . . ?
C10 C9 C8 120.1(4) . . ?
C14 C9 C8 119.8(4) . . ?
C2 C7 C6 119.1(5) . . ?
C2 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
C3 C2 C7 120.6(4) . . ?
C3 C2 C1 118.8(4) . . ?
C7 C2 C1 120.6(4) . . ?
C2 C3 C4 119.0(5) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C11 C12 C13 119.6(4) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C4 C5 C6 118.8(4) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
O4 C1 O3 119.3(4) . . ?
O4 C1 C2 122.0(4) . . ?
O3 C1 C2 118.7(4) . . ?
O4 C1 U1 60.9(2) . . ?
O3 C1 U1 58.4(2) . . ?
C2 C1 U1 176.3(3) . . ?
C13 C14 C9 120.4(4) . . ?
C13 C14 H14 119.8 . . ?
C9 C14 H14 119.8 . . ?
C5 C6 C7 121.2(5) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C5 C4 C3 121.3(5) . . ?
C5 C4 Cl1 119.9(4) . . ?
C3 C4 Cl1 118.8(4) . . ?

_refine_diff_density_max         0.931
_refine_diff_density_min         -0.510
_refine_diff_density_rms         0.128

_shelxl_version_number           2014-1

