#------------------------------------------------------------------------------
#$Date: 2017-03-04 04:02:43 +0200 (Sat, 04 Mar 2017) $
#$Revision: 192966 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/34/54/4345414.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4345414
loop_
_publ_author_name
'Thuéry, Pierre'
'Harrowfield, Jack'
_publ_section_title
;
 Coordination Polymers and Cage-Containing Frameworks in Uranyl Ion
 Complexes with rac- and (1R,2R)-trans-1,2-Cyclohexanedicarboxylates:
 Consequences of Chirality.
;
_journal_issue                   3
_journal_name_full               'Inorganic chemistry'
_journal_page_first              1455
_journal_page_last               1469
_journal_paper_doi               10.1021/acs.inorgchem.6b02537
_journal_volume                  56
_journal_year                    2017
_chemical_formula_sum            'C13 H19 N O7 U'
_chemical_formula_weight         539.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 112.903(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6986(7)
_cell_length_b                   11.8302(5)
_cell_length_c                   13.1803(7)
_cell_measurement_reflns_used    57746
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.68
_cell_measurement_theta_min      2.56
_cell_volume                     1680.31(16)
_computing_cell_refinement       'HKL2000 (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction        'HKL2000 (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008); PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
'Nonius Kappa-CCD area-detector diffractometer'
_diffrn_measurement_method
'two φ and five ω scans with 2° steps (379 frames)'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            57746
_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         25.680
_diffrn_reflns_theta_min         2.557
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    9.691
_exptl_absorpt_correction_T_max  0.748
_exptl_absorpt_correction_T_min  0.443
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            'translucent light yellow'
_exptl_crystal_density_diffrn    2.132
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.906
_refine_diff_density_min         -1.196
_refine_diff_density_rms         0.147
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3189
_refine_ls_number_restraints     96
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0234
_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)+(0.0337P)²+0.4111P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0560
_refine_ls_wR_factor_ref         0.0579
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2783
_reflns_number_total             3189
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ic6b02537_si_002.cif
_cod_data_source_block           4
_cod_database_code               4345414
_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.
;
_shelxl_version_number           2014-3
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'
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
U1 U 0.45922(2) 0.60274(2) 0.29788(2) 0.02575(8) Uani 1 1 d . . .
O1 O 0.5546(3) 0.7190(3) 0.3604(2) 0.0438(8) Uani 1 1 d . . .
O2 O 0.3616(3) 0.4886(2) 0.2320(2) 0.0418(8) Uani 1 1 d . . .
O3 O 0.3721(3) 0.7127(2) 0.1284(2) 0.0302(6) Uani 1 1 d . . .
O4 O 0.2738(3) 0.7264(2) 0.2395(2) 0.0366(7) Uani 1 1 d . . .
O5 O 0.4038(4) 0.9114(3) -0.0552(3) 0.0553(11) Uani 1 1 d . . .
O6 O 0.3784(3) 0.9798(2) 0.0898(2) 0.0328(7) Uani 1 1 d . . .
O7 O 0.5787(3) 0.5649(3) 0.1918(2) 0.0415(8) Uani 1 1 d . . .
C1 C 0.1864(4) 0.8248(3) 0.0660(3) 0.0279(9) Uani 1 1 d . . .
H1 H 0.1774 0.8963 0.1027 0.033 Uiso 1 1 calc R U .
C2 C 0.2229(4) 0.8555(4) -0.0309(3) 0.0276(9) Uani 1 1 d . . .
H2 H 0.2344 0.7833 -0.0653 0.033 Uiso 1 1 calc R U .
C3 C 0.1210(4) 0.9227(4) -0.1189(4) 0.0373(10) Uani 1 1 d . . .
H3A H 0.1099 0.9961 -0.0878 0.045 Uiso 1 1 calc R U .
H3B H 0.1460 0.9383 -0.1812 0.045 Uiso 1 1 calc R U .
C4 C -0.0011(5) 0.8585(5) -0.1606(4) 0.0489(12) Uani 1 1 d . . .
H4A H -0.0662 0.9057 -0.2149 0.059 Uiso 1 1 calc R U .
H4B H 0.0079 0.7888 -0.1983 0.059 Uiso 1 1 calc R U .
C5 C -0.0406(4) 0.8275(5) -0.0674(4) 0.0496(13) Uani 1 1 d . . .
H5A H -0.1167 0.7808 -0.0967 0.060 Uiso 1 1 calc R U .
H5B H -0.0603 0.8973 -0.0360 0.060 Uiso 1 1 calc R U .
C6 C 0.0611(4) 0.7623(4) 0.0232(4) 0.0376(10) Uani 1 1 d . . .
H6A H 0.0716 0.6875 -0.0057 0.045 Uiso 1 1 calc R U .
H6B H 0.0350 0.7496 0.0852 0.045 Uiso 1 1 calc R U .
C7 C 0.2829(4) 0.7523(3) 0.1495(3) 0.0282(9) Uani 1 1 d . . .
C8 C 0.3435(4) 0.9203(3) 0.0056(3) 0.0274(9) Uani 1 1 d . . .
N1A N 0.7093(5) 0.5717(4) 0.1034(4) 0.0357(11) Uani 0.809(6) 1 d . U P
N1B N 0.695(2) 0.6530(18) 0.1189(16) 0.033(3) Uani 0.191(6) 1 d . U P
C9A C 0.6416(7) 0.6224(5) 0.1503(5) 0.0313(14) Uani 0.809(6) 1 d . U P
C9B C 0.643(3) 0.573(2) 0.138(2) 0.031(4) Uani 0.191(6) 1 d . U P
C10 C 0.6528(5) 0.7510(4) 0.1417(4) 0.0496(12) Uani 1 1 d . U .
H10A H 0.6734 0.7861 0.2123 0.060 Uiso 0.809(6) 1 d R U P
H10B H 0.5763 0.7824 0.0907 0.060 Uiso 0.809(6) 1 d R U P
H10C H 0.6068 0.7373 0.1870 0.074 Uiso 0.191(6) 1 d R U P
H10D H 0.7215 0.8001 0.1799 0.074 Uiso 0.191(6) 1 d R U P
H10E H 0.5996 0.7861 0.0741 0.074 Uiso 0.191(6) 1 d R U P
C11A C 0.7532(5) 0.7658(5) 0.1014(5) 0.0421(14) Uani 0.809(6) 1 d . U P
H11A H 0.8290 0.7871 0.1608 0.051 Uiso 0.809(6) 1 d R U P
H11B H 0.7318 0.8233 0.0457 0.051 Uiso 0.809(6) 1 d R U P
C11B C 0.778(3) 0.502(2) 0.0562(19) 0.042(4) Uani 0.191(6) 1 d . U P
H11C H 0.8609 0.4808 0.1021 0.050 Uiso 0.191(6) 1 d R U P
H11D H 0.7608 0.4738 -0.0165 0.050 Uiso 0.191(6) 1 d R U P
C12 C 0.7680(5) 0.6465(4) 0.0521(4) 0.0425(11) Uani 1 1 d . U .
H12A H 0.7264 0.6451 -0.0267 0.051 Uiso 0.809(6) 1 d R U P
H12B H 0.8538 0.6271 0.0723 0.051 Uiso 0.809(6) 1 d R U P
H12C H 0.8477 0.6821 0.0858 0.051 Uiso 0.191(6) 1 d R U P
H12D H 0.7248 0.6746 -0.0213 0.051 Uiso 0.191(6) 1 d R U P
C13 C 0.7105(6) 0.4527(4) 0.0901(4) 0.0567(14) Uani 1 1 d . U .
H13A H 0.6669 0.4170 0.1299 0.085 Uiso 0.809(6) 1 d R U P
H13B H 0.6711 0.4339 0.0134 0.085 Uiso 0.809(6) 1 d R U P
H13C H 0.7949 0.4269 0.1183 0.085 Uiso 0.809(6) 1 d R U P
H13D H 0.6481 0.4106 0.0329 0.068 Uiso 0.191(6) 1 d R U P
H13E H 0.7549 0.4025 0.1496 0.068 Uiso 0.191(6) 1 d R U P
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
O1 U1 O2 178.40(13) . .
O1 U1 O5 89.88(14) . 4_576
O2 U1 O5 91.07(14) . 4_576
O1 U1 O7 90.66(14) . .
O2 U1 O7 88.98(13) . .
O5 U1 O7 156.35(12) 4_576 .
O1 U1 O6 88.80(13) . 2_645
O2 U1 O6 92.62(13) . 2_645
O5 U1 O6 81.34(10) 4_576 2_645
O7 U1 O6 75.04(9) . 2_645
O1 U1 O3 88.55(12) . .
O2 U1 O3 89.85(12) . .
O5 U1 O3 131.54(10) 4_576 .
O7 U1 O3 72.11(10) . .
O6 U1 O3 147.00(9) 2_645 .
O1 U1 O4 90.18(13) . .
O2 U1 O4 88.74(13) . .
O5 U1 O4 78.64(10) 4_576 .
O7 U1 O4 125.00(9) . .
O6 U1 O4 159.95(9) 2_645 .
O3 U1 O4 52.94(8) . .
C7 O3 U1 94.7(2) . .
C7 O4 U1 93.0(2) . .
C8 O5 U1 164.2(3) . 4_575
C8 O6 U1 143.5(3) . 2_655
C9B O7 C9A 28.1(13) . .
C9B O7 U1 164.5(14) . .
C9A O7 U1 136.5(4) . .
C7 C1 C2 111.8(3) . .
C7 C1 C6 109.3(3) . .
C2 C1 C6 110.0(3) . .
C7 C1 H1 108.6 . .
C2 C1 H1 108.6 . .
C6 C1 H1 108.6 . .
C8 C2 C3 109.6(3) . .
C8 C2 C1 112.4(3) . .
C3 C2 C1 111.5(4) . .
C8 C2 H2 107.7 . .
C3 C2 H2 107.7 . .
C1 C2 H2 107.7 . .
C4 C3 C2 111.2(4) . .
C4 C3 H3A 109.4 . .
C2 C3 H3A 109.4 . .
C4 C3 H3B 109.4 . .
C2 C3 H3B 109.4 . .
H3A C3 H3B 108.0 . .
C5 C4 C3 111.6(4) . .
C5 C4 H4A 109.3 . .
C3 C4 H4A 109.3 . .
C5 C4 H4B 109.3 . .
C3 C4 H4B 109.3 . .
H4A C4 H4B 108.0 . .
C4 C5 C6 111.4(4) . .
C4 C5 H5A 109.3 . .
C6 C5 H5A 109.3 . .
C4 C5 H5B 109.3 . .
C6 C5 H5B 109.3 . .
H5A C5 H5B 108.0 . .
C5 C6 C1 112.7(4) . .
C5 C6 H6A 109.1 . .
C1 C6 H6A 109.1 . .
C5 C6 H6B 109.1 . .
C1 C6 H6B 109.1 . .
H6A C6 H6B 107.8 . .
O4 C7 O3 119.4(4) . .
O4 C7 C1 120.8(4) . .
O3 C7 C1 119.8(3) . .
O6 C8 O5 123.0(4) . .
O6 C8 C2 121.0(4) . .
O5 C8 C2 116.0(4) . .
C9A N1A C13 122.9(6) . .
C9A N1A C12 115.0(5) . .
C13 N1A C12 121.5(5) . .
C9B N1B C10 112(2) . .
C9B N1B C12 124(2) . .
C10 N1B C12 122.6(16) . .
O7 C9A N1A 120.7(6) . .
O7 C9A C10 129.9(6) . .
N1A C9A C10 109.3(6) . .
N1B C9B O7 131(3) . .
N1B C9B C13 102(2) . .
O7 C9B C13 125(2) . .
C11A C10 C9A 104.3(5) . .
C11A C10 H10A 111.3 . .
C9A C10 H10A 110.7 . .
C11A C10 H10B 110.9 . .
C9A C10 H10B 110.7 . .
H10A C10 H10B 109.0 . .
N1B C10 H10C 109.7 . .
N1B C10 H10D 109.6 . .
H10C C10 H10D 109.5 . .
N1B C10 H10E 109.1 . .
H10C C10 H10E 109.5 . .
H10D C10 H10E 109.5 . .
C10 C11A C12 105.6(4) . .
C10 C11A H11A 110.4 . .
C12 C11A H11A 110.7 . .
C10 C11A H11B 110.6 . .
C12 C11A H11B 110.7 . .
H11A C11A H11B 108.8 . .
C13 C11B C12 117.1(17) . .
C13 C11B H11C 106.8 . .
C12 C11B H11C 108.6 . .
C13 C11B H11D 107.1 . .
C12 C11B H11D 109.3 . .
H11C C11B H11D 107.4 . .
N1A C12 C11A 101.9(4) . .
N1B C12 C11B 94.6(12) . .
N1A C12 H12A 111.3 . .
C11A C12 H12A 111.5 . .
N1A C12 H12B 111.2 . .
C11A C12 H12B 111.5 . .
H12A C12 H12B 109.3 . .
N1B C12 H12C 113.1 . .
C11B C12 H12C 112.6 . .
N1B C12 H12D 113.0 . .
C11B C12 H12D 112.4 . .
H12C C12 H12D 110.4 . .
C11B C13 C9B 100.4(15) . .
N1A C13 H13A 109.7 . .
N1A C13 H13B 109.6 . .
H13A C13 H13B 109.5 . .
H13B C13 H13C 109.5 . .
C11B C13 H13D 111.7 . .
C9B C13 H13D 111.9 . .
C11B C13 H13E 112.5 . .
C9B C13 H13E 111.3 . .
H13D C13 H13E 108.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
U1 O1 1.761(3) .
U1 O2 1.763(3) .
U1 O5 2.274(3) 4_576
U1 O7 2.372(3) .
U1 O6 2.393(3) 2_645
U1 O3 2.439(2) .
U1 O4 2.477(3) .
O3 C7 1.271(5) .
O4 C7 1.268(4) .
O5 C8 1.262(5) .
O5 U1 2.274(3) 4_575
O6 C8 1.242(5) .
O6 U1 2.392(3) 2_655
O7 C9B 1.22(3) .
O7 C9A 1.272(8) .
C1 C7 1.502(6) .
C1 C2 1.539(5) .
C1 C6 1.540(6) .
C1 H1 1.0000 .
C2 C8 1.510(6) .
C2 C3 1.524(6) .
C2 H2 1.0000 .
C3 C4 1.519(7) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C4 C5 1.516(6) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 C6 1.526(6) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
N1A C9A 1.323(9) .
N1A C13 1.419(6) .
N1A C12 1.440(7) .
N1B C9B 1.20(4) .
N1B C10 1.34(2) .
N1B C12 1.45(2) .
C9A C10 1.536(7) .
C10 C11A 1.476(7) .
C10 H10A 0.9599 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
C10 H10D 0.9600 .
C10 H10E 0.9601 .
C11A C12 1.592(8) .
C11A H11A 0.9601 .
C11A H11B 0.9599 .
C11B C12 1.71(2) .
C11B H11C 0.9600 .
C11B H11D 0.9600 .
C12 H12A 0.9599 .
C12 H12B 0.9598 .
C12 H12C 0.9600 .
C12 H12D 0.9600 .
C13 H13A 0.9598 .
C13 H13B 0.9602 .
C13 H13C 0.9600 .
C13 H13D 0.9600 .
C13 H13E 0.9599 .
