# Electronic Supplementary Material (ESI) for ChemComm.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1579368'
_audit_update_record             
;
2017-12-12 deposited with the CCDC.
2017-12-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            'compound 1'
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H35 N3 O13 U'
_chemical_formula_sum            'C29 H35 N3 O13 U'
_chemical_formula_weight         871.63

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   11.217(2)
_cell_length_b                   10.2614(18)
_cell_length_c                   14.346(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.541(6)
_cell_angle_gamma                90
_cell_volume                     1637.0(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    168(2)
_cell_measurement_reflns_used    3986
_cell_measurement_theta_min      2.332
_cell_measurement_theta_max      24.995

_exptl_crystal_description       BULK
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.768
_exptl_crystal_F_000             852
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.030
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    5.026
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.886
_exptl_absorpt_correction_T_max  0.951
_exptl_absorpt_process_details   'SADABS, Bruker'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      168(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'BRUKER apex II'
_diffrn_measurement_method       '0.5 wide w/ exposures'
_diffrn_detector_area_resol_mean 0
_diffrn_reflns_number            26318
_diffrn_reflns_av_unetI/netI     0.1027
_diffrn_reflns_av_R_equivalents  0.0772
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.943
_diffrn_reflns_theta_max         27.776
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             7710
_reflns_number_gt                6092
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.896
_reflns_Friedel_fraction_max     0.991
_reflns_Friedel_fraction_full    0.999

_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0626P)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_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.053(17)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         7710
_refine_ls_number_parameters     432
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0772
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_ref         0.1207
_refine_ls_wR_factor_gt          0.1108
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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 -0.83068(3) 0.07498(10) 1.19987(3) 0.01772(14) Uani 1 1 d . . . . .
O1 O -1.0240(7) 0.579(2) 1.6852(5) 0.032(2) Uani 1 1 d . . . . .
O2 O -0.2850(8) 0.569(2) 0.9345(6) 0.035(2) Uani 1 1 d . . . . .
O3 O -0.2525(8) 0.4181(11) 1.3684(7) 0.029(2) Uani 1 1 d . . . . .
O4 O -0.7696(9) -0.0741(9) 1.2456(7) 0.031(2) Uani 1 1 d . . . . .
O5 O -0.4922(9) 0.4389(13) 1.6128(7) 0.038(3) Uani 1 1 d . . . . .
C1 C -0.5574(13) 0.2899(13) 1.3774(9) 0.017(3) Uani 1 1 d . . . . .
O6 O -0.7484(8) 0.1815(10) 1.3488(7) 0.027(2) Uani 1 1 d . . . . .
C2 C -0.775(4) -0.483(3) 1.249(3) 0.089(12) Uani 1 1 d . . . . .
H1 H -0.7054 -0.4820 1.2985 0.107 Uiso 1 1 calc R U . . .
H2 H -0.8432 -0.5242 1.2735 0.107 Uiso 1 1 calc R U . . .
H3 H -0.7545 -0.5323 1.1949 0.107 Uiso 1 1 calc R U . . .
C3 C -0.7967(12) 0.557(2) 1.6252(9) 0.024(4) Uani 1 1 d . . . . .
H4 H -0.8545 0.6129 1.5917 0.029 Uiso 1 1 calc R U . . .
O7 O -0.8926(9) 0.2242(11) 1.1557(8) 0.034(3) Uani 1 1 d . . . . .
C5 C -0.3061(13) 0.5496(17) 1.1291(10) 0.030(5) Uani 1 1 d . . . . .
H5 H -0.3563 0.6111 1.0934 0.036 Uiso 1 1 calc R U . . .
C6 C -0.6528(12) 0.2129(14) 1.3185(9) 0.020(3) Uani 1 1 d . . . . .
C7 C -0.9427(12) 0.5150(13) 1.7373(9) 0.020(3) Uani 1 1 d . . . . .
C8 C -0.2056(12) 0.5099(14) 0.9884(10) 0.023(3) Uani 1 1 d . . . . .
O8 O -0.6358(8) 0.1825(10) 1.2358(6) 0.027(2) Uani 1 1 d . . . . .
O9 O -0.1132(9) 0.4681(12) 0.9534(7) 0.034(3) Uani 1 1 d . . . . .
C9 C -0.7400(12) 0.4128(15) 1.7521(10) 0.027(3) Uani 1 1 d . . . . .
H6 H -0.7579 0.3688 1.8069 0.033 Uiso 1 1 calc R U . . .
C10 C -0.6873(12) 0.5401(13) 1.5935(10) 0.029(4) Uani 1 1 d . . . . .
H7 H -0.6690 0.5858 1.5396 0.034 Uiso 1 1 calc R U . . .
O10 O -0.9658(9) 0.4755(11) 1.8162(7) 0.029(2) Uani 1 1 d . . . . .
C11 C -0.4507(12) 0.3217(14) 1.3422(9) 0.021(3) Uani 1 1 d . . . . .
H8 H -0.4380 0.2956 1.2807 0.025 Uiso 1 1 calc R U . . .
C12 C -0.8244(12) 0.4942(14) 1.7037(9) 0.023(3) Uani 1 1 d . . . . .
C13 C 0.050(2) 0.368(2) 1.4507(15) 0.045(7) Uani 1 1 d . . . . .
H9 H 0.1281 0.3498 1.4294 0.054 Uiso 1 1 calc R U . . .
H10 H -0.0142 0.3545 1.3986 0.054 Uiso 1 1 calc R U . . .
H11 H 0.0486 0.4584 1.4724 0.054 Uiso 1 1 calc R U . . .
N2 N 0.0330(11) 0.2806(13) 1.5276(9) 0.029(3) Uani 1 1 d . . . . .
C14 C -0.2198(12) 0.4821(14) 1.0874(10) 0.023(3) Uani 1 1 d . . . . .
C15 C -0.1447(13) 0.3934(15) 1.1402(9) 0.027(3) Uani 1 1 d . . . . .
H12 H -0.0831 0.3499 1.1129 0.032 Uiso 1 1 calc R U . . .
C16 C -0.3788(12) 0.4332(14) 1.4869(9) 0.021(3) Uani 1 1 d . . . . .
H13 H -0.3180 0.4831 1.5230 0.025 Uiso 1 1 calc R U . . .
C17 C 0.1244(16) 0.1835(18) 1.5563(13) 0.048(5) Uani 1 1 d . . . . .
H14 H 0.1910 0.1936 1.5190 0.058 Uiso 1 1 calc R U . . .
H15 H 0.1544 0.1949 1.6231 0.058 Uiso 1 1 calc R U . . .
H16 H 0.0897 0.0962 1.5462 0.058 Uiso 1 1 calc R U . . .
C18 C -0.3193(14) 0.5274(14) 1.2229(10) 0.029(4) Uani 1 1 d . . . . .
H17 H -0.3781 0.5743 1.2512 0.035 Uiso 1 1 calc R U . . .
C19 C -0.4040(18) 0.143(2) 1.1033(14) 0.059(6) Uani 1 1 d . . . . .
H18 H -0.3470 0.0728 1.0962 0.071 Uiso 1 1 calc R U . . .
H19 H -0.3675 0.2053 1.1507 0.071 Uiso 1 1 calc R U . . .
H20 H -0.4773 0.1070 1.1234 0.071 Uiso 1 1 calc R U . . .
C20 C -0.6054(11) 0.4572(16) 1.6403(10) 0.024(3) Uani 1 1 d . . . . .
C21 C -0.2483(11) 0.4390(14) 1.2739(9) 0.022(3) Uani 1 1 d . . . . .
C22 C -0.3649(11) 0.3915(13) 1.3982(9) 0.019(3) Uani 1 1 d . . . . .
C23 C -0.1608(13) 0.3692(15) 1.2332(10) 0.027(3) Uani 1 1 d . . . . .
H21 H -0.1128 0.3058 1.2689 0.032 Uiso 1 1 calc R U . . .
C24 C -0.6283(13) 0.3947(16) 1.7209(11) 0.034(4) Uani 1 1 d . . . . .
H22 H -0.5692 0.3402 1.7548 0.041 Uiso 1 1 calc R U . . .
C25 C -0.3807(17) 0.166(2) 0.9388(14) 0.053(5) Uani 1 1 d . . . . .
H23 H -0.3267 0.0946 0.9484 0.064 Uiso 1 1 calc R U . . .
C26 C -0.4844(13) 0.4006(14) 1.5227(9) 0.023(3) Uani 1 1 d . . . . .
C27 C -0.5727(13) 0.3267(15) 1.4692(9) 0.022(3) Uani 1 1 d . . . . .
H24 H -0.6431 0.3013 1.4949 0.027 Uiso 1 1 calc R U . . .
O11 O -0.3993(12) 0.2134(14) 0.8627(10) 0.060(4) Uani 1 1 d . . . . .
O1W O 0.1829(13) 0.4016(16) 0.9927(11) 0.067(4) Uani 1 1 d . . . . .
C28 C -0.912(2) -0.344(2) 1.1450(18) 0.073(7) Uani 1 1 d . . . . .
H25 H -0.9298 -0.2524 1.1282 0.087 Uiso 1 1 calc R U . . .
H26 H -0.8936 -0.3912 1.0894 0.087 Uiso 1 1 calc R U . . .
H27 H -0.9823 -0.3832 1.1680 0.087 Uiso 1 1 calc DR U . . .
N1 N -0.8062(19) -0.350(2) 1.2206(16) 0.048(5) Uani 1 1 d D . . . .
N3 N -0.4341(13) 0.2105(17) 1.0133(11) 0.050(4) Uani 1 1 d . . . . .
C29 C -0.512(3) 0.310(3) 1.012(3) 0.093(11) Uani 1 1 d . . . . .
H28 H -0.5361 0.3212 1.0751 0.111 Uiso 1 1 calc R U . . .
H29 H -0.4734 0.3906 0.9943 0.111 Uiso 1 1 calc R U . . .
H30 H -0.5832 0.2923 0.9669 0.111 Uiso 1 1 calc R U . . .
O12 O -0.0937(15) 0.2094(17) 1.6278(12) 0.085(5) Uani 1 1 d . . . . .
C30 C -0.068(2) 0.292(3) 1.5654(18) 0.045(7) Uani 1 1 d . . . . .
H31 H -0.1226 0.3605 1.5463 0.054 Uiso 1 1 calc R U . . .
H33 H -0.735(14) -0.325(13) 1.204(10) 0.02(4) Uiso 1 1 d . . . . .
H3W H 0.115(13) 0.426(13) 0.947(9) 0.02(4) Uiso 1 1 d . . . . .
H34 H -0.850(4) -0.32(3) 1.263(13) 0.20(18) Uiso 1 1 d D . . . .
H2W H 0.149(11) 0.309(13) 0.985(8) 0.00(3) 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 O7 1.765(11) . ?
U1 O4 1.767(10) . ?
U1 O8 2.442(9) . ?
U1 O2 2.462(8) 2_447 ?
U1 O9 2.464(10) 2_447 ?
U1 O1 2.466(8) 2_348 ?
U1 O6 2.469(10) . ?
U1 O10 2.483(10) 2_348 ?
U1 C6 2.826(14) . ?
U1 C8 2.863(13) 2_447 ?
U1 C7 2.873(13) 2_348 ?
O1 C7 1.282(19) . ?
O1 U1 2.466(7) 2_358 ?
O2 C8 1.259(18) . ?
O2 U1 2.462(8) 2_457 ?
O3 C21 1.379(16) . ?
O3 C22 1.410(15) . ?
O5 C26 1.366(16) . ?
O5 C20 1.391(16) . ?
C1 C11 1.398(19) . ?
C1 C27 1.401(18) . ?
C1 C6 1.499(19) . ?
O6 C6 1.252(15) . ?
C2 N1 1.46(3) . ?
C3 C12 1.37(2) . ?
C3 C10 1.374(18) . ?
C5 C14 1.39(2) . ?
C5 C18 1.392(19) . ?
C6 O8 1.265(14) . ?
C7 O10 1.261(16) . ?
C7 C12 1.486(18) . ?
C7 U1 2.873(13) 2_358 ?
C8 O9 1.284(16) . ?
C8 C14 1.477(19) . ?
C8 U1 2.863(13) 2_457 ?
O9 U1 2.464(10) 2_457 ?
C9 C12 1.380(19) . ?
C9 C24 1.397(19) . ?
C10 C20 1.36(2) . ?
O10 U1 2.483(10) 2_358 ?
C11 C22 1.372(19) . ?
C13 N2 1.45(3) . ?
N2 C30 1.33(2) . ?
N2 C17 1.45(2) . ?
C14 C15 1.39(2) . ?
C15 C23 1.393(18) . ?
C16 C22 1.371(17) . ?
C16 C26 1.392(19) . ?
C18 C21 1.36(2) . ?
C19 N3 1.46(3) . ?
C20 C24 1.38(2) . ?
C21 C23 1.403(19) . ?
C25 O11 1.19(2) . ?
C25 N3 1.37(2) . ?
C26 C27 1.40(2) . ?
C28 N1 1.50(3) . ?
N3 C29 1.35(4) . ?
O12 C30 1.29(3) . ?

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 O4 179.2(5) . . ?
O7 U1 O8 89.0(4) . . ?
O4 U1 O8 91.1(4) . . ?
O7 U1 O2 87.8(6) . 2_447 ?
O4 U1 O2 93.0(6) . 2_447 ?
O8 U1 O2 68.0(4) . 2_447 ?
O7 U1 O9 91.3(5) . 2_447 ?
O4 U1 O9 89.3(4) . 2_447 ?
O8 U1 O9 120.4(3) . 2_447 ?
O2 U1 O9 52.4(4) 2_447 2_447 ?
O7 U1 O1 87.8(6) . 2_348 ?
O4 U1 O1 91.4(6) . 2_348 ?
O8 U1 O1 120.2(4) . 2_348 ?
O2 U1 O1 170.6(3) 2_447 2_348 ?
O9 U1 O1 119.3(4) 2_447 2_348 ?
O7 U1 O6 90.7(4) . . ?
O4 U1 O6 88.8(4) . . ?
O8 U1 O6 52.8(3) . . ?
O2 U1 O6 120.8(4) 2_447 . ?
O9 U1 O6 172.9(3) 2_447 . ?
O1 U1 O6 67.6(4) 2_348 . ?
O7 U1 O10 90.5(4) . 2_348 ?
O4 U1 O10 89.2(4) . 2_348 ?
O8 U1 O10 172.5(3) . 2_348 ?
O2 U1 O10 119.4(4) 2_447 2_348 ?
O9 U1 O10 67.0(3) 2_447 2_348 ?
O1 U1 O10 52.3(4) 2_348 2_348 ?
O6 U1 O10 119.8(3) . 2_348 ?
O7 U1 C6 89.7(4) . . ?
O4 U1 C6 90.1(4) . . ?
O8 U1 C6 26.5(3) . . ?
O2 U1 C6 94.6(4) 2_447 . ?
O9 U1 C6 146.9(3) 2_447 . ?
O1 U1 C6 93.8(4) 2_348 . ?
O6 U1 C6 26.3(3) . . ?
O10 U1 C6 146.0(3) 2_348 . ?
O7 U1 C8 87.8(5) . 2_447 ?
O4 U1 C8 93.0(5) . 2_447 ?
O8 U1 C8 94.0(3) . 2_447 ?
O2 U1 C8 26.0(4) 2_447 2_447 ?
O9 U1 C8 26.6(3) 2_447 2_447 ?
O1 U1 C8 145.4(4) 2_348 2_447 ?
O6 U1 C8 146.8(3) . 2_447 ?
O10 U1 C8 93.4(3) 2_348 2_447 ?
C6 U1 C8 120.5(4) . 2_447 ?
O7 U1 C7 88.6(4) . 2_348 ?
O4 U1 C7 90.8(4) . 2_348 ?
O8 U1 C7 146.6(3) . 2_348 ?
O2 U1 C7 145.1(4) 2_447 2_348 ?
O9 U1 C7 93.0(4) 2_447 2_348 ?
O1 U1 C7 26.4(4) 2_348 2_348 ?
O6 U1 C7 93.9(3) . 2_348 ?
O10 U1 C7 25.9(3) 2_348 2_348 ?
C6 U1 C7 120.2(4) . 2_348 ?
C8 U1 C7 119.2(4) 2_447 2_348 ?
C7 O1 U1 94.8(8) . 2_358 ?
C8 O2 U1 95.1(8) . 2_457 ?
C21 O3 C22 118.4(10) . . ?
C26 O5 C20 118.8(11) . . ?
C11 C1 C27 119.6(13) . . ?
C11 C1 C6 120.0(11) . . ?
C27 C1 C6 120.4(12) . . ?
C6 O6 U1 93.0(8) . . ?
C12 C3 C10 121.7(15) . . ?
C14 C5 C18 120.2(14) . . ?
O6 C6 O8 120.3(13) . . ?
O6 C6 C1 121.3(11) . . ?
O8 C6 C1 118.4(12) . . ?
O6 C6 U1 60.7(7) . . ?
O8 C6 U1 59.5(7) . . ?
C1 C6 U1 177.3(9) . . ?
O10 C7 O1 118.3(11) . . ?
O10 C7 C12 122.9(12) . . ?
O1 C7 C12 118.8(11) . . ?
O10 C7 U1 59.5(7) . 2_358 ?
O1 C7 U1 58.8(6) . 2_358 ?
C12 C7 U1 175.9(10) . 2_358 ?
O2 C8 O9 117.7(12) . . ?
O2 C8 C14 121.9(12) . . ?
O9 C8 C14 120.4(12) . . ?
O2 C8 U1 58.9(6) . 2_457 ?
O9 C8 U1 59.1(7) . 2_457 ?
C14 C8 U1 176.9(10) . 2_457 ?
C6 O8 U1 93.9(8) . . ?
C8 O9 U1 94.3(8) . 2_457 ?
C12 C9 C24 120.3(13) . . ?
C20 C10 C3 119.2(14) . . ?
C7 O10 U1 94.6(8) . 2_358 ?
C22 C11 C1 118.6(12) . . ?
C3 C12 C9 118.9(13) . . ?
C3 C12 C7 120.7(13) . . ?
C9 C12 C7 120.5(12) . . ?
C30 N2 C17 123.7(18) . . ?
C30 N2 C13 118(2) . . ?
C17 N2 C13 118.6(16) . . ?
C5 C14 C15 119.9(13) . . ?
C5 C14 C8 119.1(13) . . ?
C15 C14 C8 120.9(13) . . ?
C23 C15 C14 119.5(14) . . ?
C22 C16 C26 118.3(13) . . ?
C21 C18 C5 120.1(14) . . ?
C10 C20 C24 121.2(13) . . ?
C10 C20 O5 121.7(13) . . ?
C24 C20 O5 116.9(13) . . ?
C18 C21 O3 122.8(13) . . ?
C18 C21 C23 120.7(13) . . ?
O3 C21 C23 116.5(12) . . ?
C16 C22 C11 123.4(12) . . ?
C16 C22 O3 115.9(12) . . ?
C11 C22 O3 120.7(11) . . ?
C15 C23 C21 119.6(14) . . ?
C20 C24 C9 118.8(13) . . ?
O11 C25 N3 123(2) . . ?
O5 C26 C16 116.4(12) . . ?
O5 C26 C27 123.2(13) . . ?
C16 C26 C27 120.3(12) . . ?
C26 C27 C1 119.8(13) . . ?
C2 N1 C28 112(2) . . ?
C29 N3 C25 127(2) . . ?
C29 N3 C19 116(2) . . ?
C25 N3 C19 117.2(17) . . ?
O12 C30 N2 121(2) . . ?

_refine_diff_density_max         1.639
_refine_diff_density_min         -1.218
_refine_diff_density_rms         0.228

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1579369'
_audit_update_record             
;
2017-12-12 deposited with the CCDC.
2017-12-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            'compound 2'
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H25.80 N O13.40 U'
_chemical_formula_sum            'C23 H25.80 N O13.40 U'
_chemical_formula_weight         768.67

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'
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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   11.4098(16)
_cell_length_b                   9.3291(13)
_cell_length_c                   14.383(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.391(4)
_cell_angle_gamma                90
_cell_volume                     1521.5(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    168(2)
_cell_measurement_reflns_used    3986
_cell_measurement_theta_min      2.332
_cell_measurement_theta_max      24.995

_exptl_crystal_description       BULK
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.678
_exptl_crystal_F_000             740
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.030
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    5.394
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.879
_exptl_absorpt_correction_T_max  0.947
_exptl_absorpt_process_details   'SADABS, Bruker'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      168(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'BRUKER apex II'
_diffrn_measurement_method       '0.5 wide w/ exposures'
_diffrn_detector_area_resol_mean 0
_diffrn_reflns_number            34868
_diffrn_reflns_av_unetI/netI     0.0536
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.075
_diffrn_reflns_theta_max         27.562
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7031
_reflns_number_gt                5915
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.886
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.999

_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

_refine_special_details          
'Refined as a 2-component inversion twin.,SQUEEZE'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1009P)²+1.6323P] 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_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.03(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         7031
_refine_ls_number_parameters     290
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0533
_refine_ls_wR_factor_ref         0.1554
_refine_ls_wR_factor_gt          0.1480
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.106
_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 0.83361(3) 0.66226(17) 0.80681(3) 0.03079(18) Uani 1 1 d . . . . .
O1 O 0.6328(8) 0.5677(12) 0.7691(7) 0.032(2) Uani 1 1 d . . . . .
O2 O 0.2824(7) 0.163(3) 1.0594(6) 0.044(2) Uani 1 1 d . . . . .
O3 O 1.0273(8) 0.169(3) 0.3114(6) 0.044(3) Uani 1 1 d . . . . .
O4 O 0.5038(10) 0.3170(13) 0.3844(8) 0.039(3) Uani 1 1 d . . . . .
C1 C 0.9446(13) 0.2143(18) 0.2576(10) 0.040(4) Uani 1 1 d . . . . .
C2 C 0.5775(13) 0.4297(14) 0.5311(9) 0.026(3) Uani 1 1 d . . . . .
H1 H 0.6474 0.4606 0.5069 0.031 Uiso 1 1 calc R U . . .
C3 C 0.2508(12) 0.2879(16) 0.7198(9) 0.030(3) Uani 1 1 d . . . . .
C4 C 0.1993(13) 0.2156(18) 1.0025(10) 0.043(4) Uani 1 1 d . . . . .
C5 C 0.7015(13) 0.2156(17) 0.4126(11) 0.034(3) Uani 1 1 d . . . . .
H2 H 0.6876 0.1800 0.4723 0.041 Uiso 1 1 calc R U . . .
O5 O 0.9613(11) 0.2430(18) 0.1747(8) 0.063(4) Uani 1 1 d . . . . .
O6 O 0.2600(9) 0.3115(13) 0.6260(7) 0.039(2) Uani 1 1 d . . . . .
C6 C 0.3153(12) 0.181(3) 0.8699(10) 0.040(5) Uani 1 1 d . . . . .
H3 H 0.3689 0.1219 0.9075 0.048 Uiso 1 1 calc R U . . .
O7 O 0.7879(12) 0.8384(14) 0.7770(11) 0.052(3) Uani 1 1 d . . . . .
C7 C 0.8063(12) 0.1935(14) 0.3798(9) 0.029(4) Uani 1 1 d . . . . .
H4 H 0.8674 0.1460 0.4183 0.035 Uiso 1 1 calc R U . . .
O8 O 0.7440(9) 0.5779(12) 0.6541(7) 0.037(2) Uani 1 1 d . . . . .
C8 C 0.4916(13) 0.3499(15) 0.4753(9) 0.028(3) Uani 1 1 d . . . . .
C9 C 0.3879(12) 0.3099(16) 0.5083(10) 0.031(3) Uani 1 1 d . . . . .
H5 H 0.3302 0.2568 0.4699 0.038 Uiso 1 1 calc R U . . .
C10 C 0.3686(11) 0.3488(16) 0.5999(9) 0.028(3) Uani 1 1 d . . . . .
C11 C 0.6474(12) 0.5389(18) 0.6831(9) 0.030(3) Uani 1 1 d . . . . .
C12 C 0.8271(11) 0.2383(19) 0.2917(10) 0.032(3) Uani 1 1 d . . . . .
C13 C 0.5572(13) 0.4627(15) 0.6239(9) 0.024(3) Uani 1 1 d . . . . .
C14 C 0.6294(14) 0.3318(18) 0.2702(12) 0.041(4) Uani 1 1 d . . . . .
H6 H 0.5665 0.3737 0.2305 0.050 Uiso 1 1 calc R U . . .
C15 C 0.1541(13) 0.347(2) 0.7556(12) 0.047(4) Uani 1 1 d . . . . .
H7 H 0.1008 0.4059 0.7174 0.057 Uiso 1 1 calc R U . . .
O9 O 0.1018(11) 0.2423(19) 1.0323(9) 0.073(5) Uani 1 1 d . . . . .
C16 C 0.3319(14) 0.2090(17) 0.7761(12) 0.039(4) Uani 1 1 d . . . . .
H8 H 0.3998 0.1727 0.7514 0.047 Uiso 1 1 calc R U . . .
C17 C 0.1356(14) 0.319(2) 0.8460(11) 0.053(5) Uani 1 1 d . . . . .
H9 H 0.0649 0.3525 0.8678 0.063 Uiso 1 1 calc R U . . .
C18 C 0.4522(12) 0.4269(16) 0.6575(9) 0.029(3) Uani 1 1 d . . . . .
H10 H 0.4371 0.4549 0.7185 0.035 Uiso 1 1 calc R U . . .
C19 C 0.2171(14) 0.2443(19) 0.9077(11) 0.041(4) Uani 1 1 d . . . . .
O10 O 0.8795(10) 0.4843(15) 0.8382(9) 0.050(3) Uani 1 1 d . . . . .
C20 C 0.7349(15) 0.313(2) 0.2372(12) 0.055(5) Uani 1 1 d . . . . .
H11 H 0.7473 0.3497 0.1775 0.067 Uiso 1 1 calc R U . . .
C21 C 0.6110(12) 0.2938(15) 0.3559(10) 0.029(3) 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 1.763(14) . ?
U1 O10 1.784(13) . ?
U1 O5 2.444(12) 2_756 ?
U1 O8 2.447(10) . ?
U1 O3 2.452(8) 2_756 ?
U1 O2 2.453(8) 2_657 ?
U1 O1 2.458(10) . ?
U1 O9 2.465(12) 2_657 ?
U1 C1 2.832(15) 2_756 ?
U1 C4 2.853(14) 2_657 ?
U1 C11 2.857(14) . ?
O1 C11 1.294(15) . ?
O2 C4 1.28(2) . ?
O2 U1 2.453(8) 2_647 ?
O3 C1 1.229(19) . ?
O3 U1 2.452(8) 2_746 ?
O4 C21 1.350(18) . ?
O4 C8 1.365(17) . ?
C1 O5 1.257(18) . ?
C1 C12 1.495(18) . ?
C1 U1 2.832(14) 2_746 ?
C2 C8 1.41(2) . ?
C2 C13 1.414(18) . ?
C3 C16 1.37(2) . ?
C3 O6 1.382(16) . ?
C3 C15 1.38(2) . ?
C4 O9 1.261(18) . ?
C4 C19 1.43(2) . ?
C4 U1 2.854(14) 2_647 ?
C5 C7 1.35(2) . ?
C5 C21 1.44(2) . ?
O5 U1 2.444(12) 2_746 ?
O6 C10 1.379(16) . ?
C6 C16 1.41(2) . ?
C6 C19 1.43(2) . ?
C7 C12 1.379(18) . ?
O8 C11 1.273(16) . ?
C8 C9 1.374(19) . ?
C9 C10 1.407(19) . ?
C10 C18 1.40(2) . ?
C11 C13 1.448(19) . ?
C12 C20 1.42(2) . ?
C13 C18 1.382(19) . ?
C14 C21 1.32(2) . ?
C14 C20 1.35(2) . ?
C15 C17 1.36(2) . ?
O9 U1 2.465(12) 2_647 ?
C17 C19 1.40(2) . ?

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 O10 179.4(6) . . ?
O7 U1 O5 89.6(6) . 2_756 ?
O10 U1 O5 90.5(6) . 2_756 ?
O7 U1 O8 89.9(6) . . ?
O10 U1 O8 90.6(5) . . ?
O5 U1 O8 119.8(3) 2_756 . ?
O7 U1 O3 90.3(8) . 2_756 ?
O10 U1 O3 90.2(8) . 2_756 ?
O5 U1 O3 51.9(4) 2_756 2_756 ?
O8 U1 O3 67.9(4) . 2_756 ?
O7 U1 O2 91.0(8) . 2_657 ?
O10 U1 O2 88.4(8) . 2_657 ?
O5 U1 O2 120.5(4) 2_756 2_657 ?
O8 U1 O2 119.8(4) . 2_657 ?
O3 U1 O2 172.2(3) 2_756 2_657 ?
O7 U1 O1 92.1(5) . . ?
O10 U1 O1 87.8(5) . . ?
O5 U1 O1 172.7(3) 2_756 . ?
O8 U1 O1 53.2(3) . . ?
O3 U1 O1 121.0(4) 2_756 . ?
O2 U1 O1 66.6(4) 2_657 . ?
O7 U1 O9 89.7(7) . 2_657 ?
O10 U1 O9 89.7(6) . 2_657 ?
O5 U1 O9 67.8(4) 2_756 2_657 ?
O8 U1 O9 172.4(3) . 2_657 ?
O3 U1 O9 119.7(4) 2_756 2_657 ?
O2 U1 O9 52.7(4) 2_657 2_657 ?
O1 U1 O9 119.3(3) . 2_657 ?
O7 U1 C1 90.7(5) . 2_756 ?
O10 U1 C1 89.7(5) . 2_756 ?
O5 U1 C1 26.3(4) 2_756 2_756 ?
O8 U1 C1 93.5(4) . 2_756 ?
O3 U1 C1 25.6(4) 2_756 2_756 ?
O2 U1 C1 146.7(4) 2_657 2_756 ?
O1 U1 C1 146.5(4) . 2_756 ?
O9 U1 C1 94.0(4) 2_657 2_756 ?
O7 U1 C4 90.2(6) . 2_657 ?
O10 U1 C4 89.1(5) . 2_657 ?
O5 U1 C4 93.9(4) 2_756 2_657 ?
O8 U1 C4 146.3(4) . 2_657 ?
O3 U1 C4 145.8(4) 2_756 2_657 ?
O2 U1 C4 26.6(4) 2_657 2_657 ?
O1 U1 C4 93.2(4) . 2_657 ?
O9 U1 C4 26.1(4) 2_657 2_657 ?
C1 U1 C4 120.2(4) 2_756 2_657 ?
O7 U1 C11 92.6(6) . . ?
O10 U1 C11 87.7(5) . . ?
O5 U1 C11 145.9(4) 2_756 . ?
O8 U1 C11 26.4(3) . . ?
O3 U1 C11 94.1(4) 2_756 . ?
O2 U1 C11 93.5(4) 2_657 . ?
O1 U1 C11 26.9(3) . . ?
O9 U1 C11 146.2(4) 2_657 . ?
C1 U1 C11 119.7(4) 2_756 . ?
C4 U1 C11 120.0(4) 2_657 . ?
C11 O1 U1 94.0(8) . . ?
C4 O2 U1 94.4(8) . 2_647 ?
C1 O3 U1 94.7(8) . 2_746 ?
C21 O4 C8 121.3(12) . . ?
O3 C1 O5 119.0(13) . . ?
O3 C1 C12 119.9(13) . . ?
O5 C1 C12 121.1(13) . . ?
O3 C1 U1 59.6(7) . 2_746 ?
O5 C1 U1 59.4(8) . 2_746 ?
C12 C1 U1 178.7(12) . 2_746 ?
C8 C2 C13 118.5(12) . . ?
C16 C3 O6 122.7(13) . . ?
C16 C3 C15 120.4(13) . . ?
O6 C3 C15 116.8(13) . . ?
O9 C4 O2 118.5(13) . . ?
O9 C4 C19 120.8(14) . . ?
O2 C4 C19 120.7(13) . . ?
O9 C4 U1 59.5(8) . 2_647 ?
O2 C4 U1 59.0(7) . 2_647 ?
C19 C4 U1 179.0(13) . 2_647 ?
C7 C5 C21 119.1(13) . . ?
C1 O5 U1 94.3(9) . 2_746 ?
C10 O6 C3 118.4(11) . . ?
C16 C6 C19 119.1(15) . . ?
C5 C7 C12 121.6(13) . . ?
C11 O8 U1 95.1(8) . . ?
O4 C8 C9 116.9(13) . . ?
O4 C8 C2 121.7(13) . . ?
C9 C8 C2 121.2(12) . . ?
C8 C9 C10 118.9(13) . . ?
O6 C10 C18 123.0(12) . . ?
O6 C10 C9 115.4(13) . . ?
C18 C10 C9 121.5(12) . . ?
O8 C11 O1 117.5(13) . . ?
O8 C11 C13 122.1(11) . . ?
O1 C11 C13 120.4(12) . . ?
O8 C11 U1 58.6(7) . . ?
O1 C11 U1 59.1(7) . . ?
C13 C11 U1 174.3(11) . . ?
C7 C12 C20 117.5(12) . . ?
C7 C12 C1 120.6(13) . . ?
C20 C12 C1 121.8(13) . . ?
C18 C13 C2 121.1(13) . . ?
C18 C13 C11 120.0(11) . . ?
C2 C13 C11 118.9(12) . . ?
C21 C14 C20 122.1(15) . . ?
C17 C15 C3 119.7(14) . . ?
C4 O9 U1 94.4(9) . 2_647 ?
C3 C16 C6 120.7(14) . . ?
C15 C17 C19 122.4(14) . . ?
C13 C18 C10 118.7(12) . . ?
C17 C19 C4 123.1(14) . . ?
C17 C19 C6 117.3(14) . . ?
C4 C19 C6 119.3(14) . . ?
C14 C20 C12 120.2(14) . . ?
C14 C21 O4 118.9(14) . . ?
C14 C21 C5 119.1(13) . . ?
O4 C21 C5 121.7(13) . . ?

_refine_diff_density_max         3.003
_refine_diff_density_min         -0.763
_refine_diff_density_rms         0.249

_shelxl_version_number           2014-3


# SQUEEZE RESULTS
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.029 -0.061 0.545 659 120 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          As
