# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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_umt_ob7
_database_code_depnum_ccdc_archive 'CCDC 1897633'
loop_
_audit_author_name
_audit_author_address
'Dan Decato'
;University of Montana
United States of America
;
_audit_update_record             
;
2019-02-17 deposited with the CCDC.	2019-03-08 downloaded from the CCDC.
;
_audit_creation_date             2018-07-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H20 N8 O18 U2, H2 O'
_chemical_formula_sum            'C16 H22 N8 O19 U2'
_chemical_formula_weight         1106.47
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
U U -9.6767 9.6646 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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 1 2/c 1'
_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                   14.7408(7)
_cell_length_b                   9.3327(5)
_cell_length_c                   20.6545(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.134(2)
_cell_angle_gamma                90
_cell_volume                     2834.1(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9884
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.514
_cell_measurement_theta_min      3.194
_shelx_estimated_absorpt_T_max   0.500
_shelx_estimated_absorpt_T_min   0.339
_exptl_absorpt_coefficient_mu    11.513
_exptl_absorpt_correction_T_max  0.0949
_exptl_absorpt_correction_T_min  0.0593
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.0788 before and 0.0467 after correction. The Ratio of minimum to maximum transmission is 0.6249. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.593
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             2040
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0102
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            76494
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.528
_diffrn_reflns_theta_min         3.194
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker Photon-100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Duo'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'TRIUMPH graphite'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2915
_reflns_number_total             3268
_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_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX3 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.927
_refine_diff_density_min         -0.968
_refine_diff_density_rms         0.106
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3268
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0243
_refine_ls_R_factor_gt           0.0199
_refine_ls_restrained_S_all      1.154
_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)+(0.0135P)²+16.0367P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0409
_refine_ls_wR_factor_ref         0.0423
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2C,H2D)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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 0.63377(2) 0.49409(2) 0.78034(2) 0.01921(4) Uani 1 1 d . . . . .
O1 O 0.52244(16) 0.5388(3) 0.68920(12) 0.0252(5) Uani 1 1 d . . . . .
O2 O 0.60925(17) 0.3114(3) 0.76840(12) 0.0259(5) Uani 1 1 d . . . . .
O3 O 0.65606(17) 0.6781(3) 0.79270(13) 0.0264(5) Uani 1 1 d . . . . .
O4 O 0.70365(16) 0.5111(3) 0.67429(12) 0.0307(6) Uani 1 1 d . . . . .
O5 O 0.79858(16) 0.4739(3) 0.75673(12) 0.0236(5) Uani 1 1 d . . . . .
O6 O 0.84892(17) 0.4977(3) 0.66072(13) 0.0309(6) Uani 1 1 d . . . . .
O7 O 0.74667(17) 0.4113(3) 0.86919(12) 0.0280(6) Uani 1 1 d . . . . .
O8 O 0.61779(16) 0.4817(3) 0.90060(12) 0.0274(5) Uani 1 1 d . . . . .
O9 O 0.72071(18) 0.3995(3) 0.97197(13) 0.0344(6) Uani 1 1 d . . . . .
N1 N 0.5300(2) 0.6679(4) 0.65483(16) 0.0268(7) Uani 1 1 d . . . . .
H1 H 0.525(3) 0.760(5) 0.670(2) 0.034(12) Uiso 1 1 d . . . . .
N2 N 0.5696(2) 0.5460(4) 0.56471(17) 0.0297(7) Uani 1 1 d . . . . .
H2A H 0.595(3) 0.548(5) 0.528(2) 0.029(11) Uiso 1 1 d . . . . .
H2B H 0.568(3) 0.465(5) 0.584(2) 0.039(13) Uiso 1 1 d . . . . .
N3 N 0.78655(19) 0.4943(3) 0.69566(15) 0.0236(6) Uani 1 1 d . . . . .
N4 N 0.6963(2) 0.4295(3) 0.91615(15) 0.0254(6) Uani 1 1 d . . . . .
C1 C 0.5538(2) 0.6662(4) 0.59462(18) 0.0283(8) Uani 1 1 d . . . . .
C2 C 0.5587(3) 0.8073(4) 0.56024(19) 0.0309(8) Uani 1 1 d . . . . .
H2C H 0.6219 0.8244 0.5489 0.037 Uiso 1 1 calc R . . . .
H2D H 0.5418 0.8852 0.5896 0.037 Uiso 1 1 calc R . . . .
C3 C 0.4950(2) 0.8105(4) 0.49844(19) 0.0241(7) Uani 1 1 d . . . . .
C4 C 0.4012(2) 0.8015(4) 0.50273(18) 0.0296(8) Uani 1 1 d . . . . .
H4 H 0.3770 0.7973 0.5441 0.036 Uiso 1 1 calc R . . . .
C5 C 0.3431(2) 0.7986(4) 0.44659(19) 0.0295(8) Uani 1 1 d . . . . .
H5 H 0.2792 0.7919 0.4497 0.035 Uiso 1 1 calc R . . . .
C6 C 0.3780(3) 0.8055(4) 0.38610(18) 0.0272(8) Uani 1 1 d . . . . .
H6 H 0.3383 0.8016 0.3478 0.033 Uiso 1 1 calc R . . . .
C7 C 0.4712(3) 0.8180(4) 0.38156(18) 0.0285(8) Uani 1 1 d . . . . .
H7 H 0.4952 0.8248 0.3402 0.034 Uiso 1 1 calc R . . . .
C8 C 0.5294(2) 0.8206(4) 0.43790(19) 0.0276(8) Uani 1 1 d . . . . .
H8 H 0.5932 0.8293 0.4347 0.033 Uiso 1 1 calc R . . . .
O10 O 0.5000 0.8788(5) 0.7500 0.0447(12) Uani 1 2 d S T P . .
H10 H 0.459(4) 0.929(6) 0.739(3) 0.070(19) 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 U1 4.0513(3) 2_656 ?
U1 O1 2.442(2) . ?
U1 O1 2.466(2) 2_656 ?
U1 O2 1.757(3) . ?
U1 O3 1.764(3) . ?
U1 O4 2.492(3) . ?
U1 O5 2.519(2) . ?
U1 O7 2.509(2) . ?
U1 O8 2.515(3) . ?
U1 N3 2.949(3) . ?
U1 N4 2.951(3) . ?
O1 U1 2.466(2) 2_656 ?
O1 N1 1.408(4) . ?
O4 N3 1.279(4) . ?
O5 N3 1.275(4) . ?
O6 N3 1.209(4) . ?
O7 N4 1.275(4) . ?
O8 N4 1.275(4) . ?
O9 N4 1.216(4) . ?
N1 H1 0.91(5) . ?
N1 C1 1.316(5) . ?
N2 H2A 0.87(5) . ?
N2 H2B 0.85(5) . ?
N2 C1 1.310(5) . ?
C1 C2 1.500(5) . ?
C2 H2C 0.9900 . ?
C2 H2D 0.9900 . ?
C2 C3 1.529(5) . ?
C3 C4 1.394(5) . ?
C3 C8 1.386(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.392(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.387(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.388(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.396(5) . ?
C8 H8 0.9500 . ?
O10 H10 0.79(5) . ?

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 U1 34.19(6) 2_656 2_656 ?
O1 U1 U1 34.56(6) . 2_656 ?
O1 U1 O1 65.15(10) . 2_656 ?
O1 U1 O4 131.78(8) 2_656 . ?
O1 U1 O4 66.99(8) . . ?
O1 U1 O5 117.86(8) . . ?
O1 U1 O5 173.38(8) 2_656 . ?
O1 U1 O7 171.81(9) . . ?
O1 U1 O7 116.61(8) 2_656 . ?
O1 U1 O8 131.57(8) . . ?
O1 U1 O8 66.43(8) 2_656 . ?
O1 U1 N3 156.65(8) 2_656 . ?
O1 U1 N3 92.42(8) . . ?
O1 U1 N4 156.05(8) . . ?
O1 U1 N4 91.46(8) 2_656 . ?
O2 U1 U1 76.74(8) . 2_656 ?
O2 U1 O1 90.77(10) . 2_656 ?
O2 U1 O1 86.41(10) . . ?
O2 U1 O3 178.82(11) . . ?
O2 U1 O4 91.85(10) . . ?
O2 U1 O5 95.27(10) . . ?
O2 U1 O7 85.57(11) . . ?
O2 U1 O8 93.50(10) . . ?
O2 U1 N3 94.34(10) . . ?
O2 U1 N4 88.98(10) . . ?
O3 U1 U1 102.23(8) . 2_656 ?
O3 U1 O1 93.04(10) . . ?
O3 U1 O1 88.05(10) . 2_656 ?
O3 U1 O4 88.90(11) . . ?
O3 U1 O5 85.91(10) . . ?
O3 U1 O7 95.01(10) . . ?
O3 U1 O8 86.08(10) . . ?
O3 U1 N3 86.72(10) . . ?
O3 U1 N4 91.10(10) . . ?
O4 U1 U1 100.54(5) . 2_656 ?
O4 U1 O5 50.88(8) . . ?
O4 U1 O7 111.60(8) . . ?
O4 U1 O8 160.97(8) . . ?
O4 U1 N3 25.44(8) . . ?
O4 U1 N4 136.72(8) . . ?
O5 U1 U1 150.58(5) . 2_656 ?
O5 U1 N3 25.44(8) . . ?
O5 U1 N4 85.95(8) . . ?
O7 U1 U1 143.70(6) . 2_656 ?
O7 U1 O5 61.35(8) . . ?
O7 U1 O8 50.78(8) . . ?
O7 U1 N3 86.53(8) . . ?
O7 U1 N4 25.38(8) . . ?
O8 U1 U1 98.46(5) . 2_656 ?
O8 U1 O5 110.37(8) . . ?
O8 U1 N3 135.70(8) . . ?
O8 U1 N4 25.40(8) . . ?
N3 U1 U1 125.76(6) . 2_656 ?
N3 U1 N4 111.37(8) . . ?
N4 U1 U1 121.63(6) . 2_656 ?
U1 O1 U1 111.26(10) . 2_656 ?
N1 O1 U1 112.54(19) . 2_656 ?
N1 O1 U1 117.48(18) . . ?
N3 O4 U1 97.70(19) . . ?
N3 O5 U1 96.49(18) . . ?
N4 O7 U1 97.09(19) . . ?
N4 O8 U1 96.80(19) . . ?
O1 N1 H1 128(3) . . ?
C1 N1 O1 120.2(3) . . ?
C1 N1 H1 111(3) . . ?
H2A N2 H2B 117(4) . . ?
C1 N2 H2A 119(3) . . ?
C1 N2 H2B 122(3) . . ?
O4 N3 U1 56.85(16) . . ?
O5 N3 U1 58.07(15) . . ?
O5 N3 O4 114.9(3) . . ?
O6 N3 U1 178.5(2) . . ?
O6 N3 O4 122.7(3) . . ?
O6 N3 O5 122.4(3) . . ?
O7 N4 U1 57.53(16) . . ?
O7 N4 O8 115.3(3) . . ?
O8 N4 U1 57.80(16) . . ?
O9 N4 U1 178.2(3) . . ?
O9 N4 O7 122.8(3) . . ?
O9 N4 O8 121.9(3) . . ?
N1 C1 C2 117.5(4) . . ?
N2 C1 N1 121.6(4) . . ?
N2 C1 C2 120.8(4) . . ?
C1 C2 H2C 109.4 . . ?
C1 C2 H2D 109.4 . . ?
C1 C2 C3 111.4(3) . . ?
H2C C2 H2D 108.0 . . ?
C3 C2 H2C 109.4 . . ?
C3 C2 H2D 109.4 . . ?
C4 C3 C2 119.8(3) . . ?
C8 C3 C2 120.8(3) . . ?
C8 C3 C4 119.4(3) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.1(4) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.2(3) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 H6 120.1 . . ?
C5 C6 C7 119.9(3) . . ?
C7 C6 H6 120.1 . . ?
C6 C7 H7 120.1 . . ?
C6 C7 C8 119.8(3) . . ?
C8 C7 H7 120.1 . . ?
C3 C8 C7 120.5(3) . . ?
C3 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O10 0.91(5) 2.05(4) 2.839(5) 143(4) .
N2 H2A O9 0.87(5) 2.31(5) 3.083(4) 148(4) 6_565
O10 H10 O5 0.79(5) 2.45(6) 3.112(3) 143(6) 3_455
O10 H10 O6 0.79(5) 2.30(6) 3.000(3) 149(6) 3_455

_olex2_submission_special_instructions 'No special instructions were received'
