#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:33:07 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180267 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/53/7115360.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_7115360
loop_
_publ_author_name
'C. A. Hawkins'
'C. G. Bustillos'
'R. Copping'
'B. L. Scott'
'I. May'
'M. Nilsson'
_publ_section_title
;
 Challenging conventional f-element separation chemistry - reversing
 uranyl(VI)/lanthanide(III) solvent extraction selectivity
;
_journal_name_full               Chem.Commun.
_journal_page_first              8670
_journal_paper_doi               10.1039/C4cc03031A
_journal_volume                  50
_journal_year                    2014
_chemical_formula_sum            'C16 H32 N2 Na2 O20 S2 U'
_chemical_formula_weight         920.57
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                89.043(1)
_cell_angle_beta                 88.581(1)
_cell_angle_gamma                72.240(1)
_cell_formula_units_Z            2
_cell_length_a                   8.4220(11)
_cell_length_b                   9.3646(12)
_cell_length_c                   19.946(3)
_cell_measurement_reflns_used    9879
_cell_measurement_temperature    140(1)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.49
_cell_volume                     1497.6(4)
_computing_cell_refinement       'SAINT+, v. 7.66a (Bruker AXS, 2009)'
_computing_data_collection       'APEX II, v. 7.0 (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT+, v. 7.66a (Bruker AXS, 2009)'
_computing_molecular_graphics    'SHELXTL, v. 6.14, (Bruker AXS, 2000)'
_computing_publication_material  'SHELXTL, v. 6.14, (Bruker AXS, 2000)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      140(1)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.914
_diffrn_measurement_device_type  'Bruker D8 with APEXII CCD'
_diffrn_measurement_method       'ω scans'
_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  0.0139
_diffrn_reflns_av_sigmaI/netI    0.0162
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_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            16975
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.38
_diffrn_reflns_theta_min         2.04
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.674
_exptl_absorpt_correction_T_max  0.5039
_exptl_absorpt_correction_T_min  0.3966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v. 2.03 (Sheldrick, 2008)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    2.041
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.860
_refine_diff_density_min         -0.505
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.753
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     391
_refine_ls_number_reflns         6864
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.753
_refine_ls_R_factor_all          0.0170
_refine_ls_R_factor_gt           0.0166
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0244P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0570
_refine_ls_wR_factor_ref         0.0572
_reflns_number_gt                6724
_reflns_number_total             6864
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc03031a2.cif
_cod_data_source_block           apx1733
_cod_original_cell_volume        1497.6(3)
_cod_database_code               7115360
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
U1 U 0.744749(10) 0.761256(9) 0.561580(4) 0.00757(4) Uani 1 1 d .
Na1 Na 1.0000 1.0000 1.0000 0.0110(3) Uani 1 2 d S
Na2 Na 0.89229(13) 0.68375(11) 0.99706(5) 0.0110(2) Uani 1 1 d .
Na3 Na 0.5000 0.5000 1.0000 0.0119(3) Uani 1 2 d S
S1 S 0.64978(7) 0.99551(7) 0.90981(3) 0.00809(12) Uani 1 1 d .
S2 S 0.70429(8) 0.44353(7) 0.22091(3) 0.00930(12) Uani 1 1 d .
N1 N 0.8514(3) 0.5740(2) 0.65517(11) 0.0098(4) Uani 1 1 d .
N2 N 0.7240(3) 0.4981(2) 0.54030(11) 0.0095(4) Uani 1 1 d .
O1 O 0.5633(2) 0.8314(2) 0.61428(10) 0.0120(4) Uani 1 1 d .
O2 O 0.9249(2) 0.6958(2) 0.50949(10) 0.0120(4) Uani 1 1 d .
O3 O 0.8968(2) 0.8481(2) 0.63430(9) 0.0109(4) Uani 1 1 d .
O4 O 0.5671(2) 0.7665(2) 0.47633(9) 0.0117(4) Uani 1 1 d .
O5 O 0.4787(2) 1.0890(2) 0.89818(9) 0.0127(4) Uani 1 1 d .
O6 O 0.7477(2) 1.0808(2) 0.94074(9) 0.0113(4) Uani 1 1 d .
O7 O 0.6585(2) 0.85721(19) 0.94617(9) 0.0109(4) Uani 1 1 d .
O8 O 0.8013(2) 0.5230(2) 0.18092(9) 0.0133(4) Uani 1 1 d .
O9 O 0.5411(2) 0.4646(2) 0.19152(9) 0.0144(4) Uani 1 1 d .
O10 O 0.7957(2) 0.2873(2) 0.23221(9) 0.0135(4) Uani 1 1 d .
O11 O 0.7153(2) 1.0059(2) 0.51581(9) 0.0135(4) Uani 1 1 d .
O12 O 0.9201(2) 1.2204(2) 1.06887(10) 0.0147(4) Uani 1 1 d .
O13 O 0.8637(2) 0.8811(2) 1.07624(10) 0.0131(4) Uani 1 1 d .
O14 O 0.9446(2) 0.4898(2) 0.92051(9) 0.0122(4) Uani 1 1 d .
O15 O 0.3135(2) 0.6203(2) 1.09430(10) 0.0133(4) Uani 1 1 d .
O16 O 0.5785(2) 0.2926(2) 1.07499(10) 0.0138(4) Uani 1 1 d .
O17 O 0.3308(2) 0.3780(2) 0.94634(10) 0.0127(4) Uani 1 1 d .
O18 O 0.8818(3) 1.0002(3) 0.40392(11) 0.0276(5) Uani 1 1 d .
O19 O 0.9063(3) 0.7844(2) 0.20995(10) 0.0186(4) Uani 1 1 d .
O20 O 0.7055(3) 0.0449(2) 0.28287(11) 0.0222(5) Uani 1 1 d .
C1 C 0.8499(3) 0.8753(3) 0.69752(13) 0.0105(5) Uani 1 1 d .
C2 C 0.8379(3) 1.0160(3) 0.72471(13) 0.0125(5) Uani 1 1 d .
H2 H 0.8670 1.0873 0.6983 0.015 Uiso 1 1 calc R
C3 C 0.7837(3) 1.0494(3) 0.79010(14) 0.0131(5) Uani 1 1 d .
H3 H 0.7759 1.1429 0.8075 0.016 Uiso 1 1 calc R
C4 C 0.7404(3) 0.9427(3) 0.83019(12) 0.0090(5) Uani 1 1 d .
C5 C 0.7594(3) 0.8013(3) 0.80551(13) 0.0096(5) Uani 1 1 d .
H5 H 0.7364 0.7290 0.8333 0.012 Uiso 1 1 calc R
C6 C 0.8130(3) 0.7658(3) 0.73925(13) 0.0095(5) Uani 1 1 d .
C7 C 0.8441(3) 0.6126(3) 0.71660(13) 0.0102(5) Uani 1 1 d .
H7 H 0.8597 0.5375 0.7491 0.012 Uiso 1 1 calc R
C8 C 0.8970(3) 0.4145(3) 0.63898(13) 0.0110(5) Uani 1 1 d .
H8A H 0.9089 0.3549 0.6799 0.013 Uiso 1 1 calc R
H8B H 1.0024 0.3842 0.6143 0.013 Uiso 1 1 calc R
C9 C 0.7594(3) 0.3899(3) 0.59662(13) 0.0114(5) Uani 1 1 d .
H9A H 0.7942 0.2885 0.5795 0.014 Uiso 1 1 calc R
H9B H 0.6593 0.4031 0.6240 0.014 Uiso 1 1 calc R
C10 C 0.7154(3) 0.4451(3) 0.48171(13) 0.0097(5) Uani 1 1 d .
H10 H 0.7350 0.3422 0.4785 0.012 Uiso 1 1 calc R
C11 C 0.6030(3) 0.6904(3) 0.41995(13) 0.0100(5) Uani 1 1 d .
C12 C 0.5609(3) 0.7672(3) 0.35800(13) 0.0113(5) Uani 1 1 d .
H12 H 0.5117 0.8707 0.3575 0.014 Uiso 1 1 calc R
C13 C 0.5921(3) 0.6906(3) 0.29880(13) 0.0113(5) Uani 1 1 d .
H13 H 0.5638 0.7421 0.2584 0.014 Uiso 1 1 calc R
C14 C 0.6667(3) 0.5342(3) 0.29888(13) 0.0100(5) Uani 1 1 d .
C15 C 0.7075(3) 0.4561(3) 0.35849(13) 0.0102(5) Uani 1 1 d .
H15 H 0.7547 0.3525 0.3581 0.012 Uiso 1 1 calc R
C16 C 0.6777(3) 0.5336(3) 0.42026(13) 0.0097(5) Uani 1 1 d .
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'
S S 0.1246 0.1234 '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'
Na Na 0.0362 0.0249 '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
O2 U1 O1 178.74(7) . .
O2 U1 O3 89.05(8) . .
O1 U1 O3 90.16(8) . .
O2 U1 O4 93.40(8) . .
O1 U1 O4 86.97(8) . .
O3 U1 O4 158.33(7) . .
O2 U1 O11 87.09(8) . .
O1 U1 O11 91.79(8) . .
O3 U1 O11 78.78(6) . .
O4 U1 O11 79.84(6) . .
O2 U1 N1 95.42(8) . .
O1 U1 N1 85.22(8) . .
O3 U1 N1 69.15(7) . .
O4 U1 N1 131.84(7) . .
O11 U1 N1 147.76(7) . .
O2 U1 N2 82.22(8) . .
O1 U1 N2 99.04(8) . .
O3 U1 N2 132.39(7) . .
O4 U1 N2 69.22(7) . .
O11 U1 N2 146.45(7) . .
N1 U1 N2 65.30(7) . .
O13 Na1 O13 180.00(7) 2_777 .
O13 Na1 O6 92.60(7) 2_777 .
O13 Na1 O6 87.40(7) . .
O13 Na1 O6 87.40(7) 2_777 2_777
O13 Na1 O6 92.60(7) . 2_777
O6 Na1 O6 180.00(5) . 2_777
O13 Na1 O12 89.68(7) 2_777 2_777
O13 Na1 O12 90.32(7) . 2_777
O6 Na1 O12 87.97(7) . 2_777
O6 Na1 O12 92.03(6) 2_777 2_777
O13 Na1 O12 90.32(7) 2_777 .
O13 Na1 O12 89.68(7) . .
O6 Na1 O12 92.03(6) . .
O6 Na1 O12 87.97(7) 2_777 .
O12 Na1 O12 179.999(1) 2_777 .
O13 Na1 Na2 134.22(5) 2_777 .
O13 Na1 Na2 45.77(5) . .
O6 Na1 Na2 78.70(5) . .
O6 Na1 Na2 101.30(5) 2_777 .
O12 Na1 Na2 45.65(5) 2_777 .
O12 Na1 Na2 134.35(5) . .
O13 Na1 Na2 45.78(5) 2_777 2_777
O13 Na1 Na2 134.23(5) . 2_777
O6 Na1 Na2 101.30(5) . 2_777
O6 Na1 Na2 78.70(5) 2_777 2_777
O12 Na1 Na2 134.35(5) 2_777 2_777
O12 Na1 Na2 45.65(5) . 2_777
Na2 Na1 Na2 180.000(1) . 2_777
O14 Na2 O7 99.45(7) . .
O14 Na2 O17 94.91(7) . 2_667
O7 Na2 O17 79.16(7) . 2_667
O14 Na2 O12 87.31(7) . 2_777
O7 Na2 O12 91.01(7) . 2_777
O17 Na2 O12 170.15(8) 2_667 2_777
O14 Na2 O13 175.06(8) . .
O7 Na2 O13 84.12(7) . .
O17 Na2 O13 89.10(7) 2_667 .
O12 Na2 O13 89.22(7) 2_777 .
O14 Na2 O14 89.75(7) . 2_767
O7 Na2 O14 159.51(8) . 2_767
O17 Na2 O14 81.86(7) 2_667 2_767
O12 Na2 O14 107.78(8) 2_777 2_767
O13 Na2 O14 87.96(7) . 2_767
O14 Na2 Na1 132.72(6) . .
O7 Na2 Na1 78.70(5) . .
O17 Na2 Na1 129.96(6) 2_667 .
O12 Na2 Na1 45.89(5) 2_777 .
O13 Na2 Na1 44.42(5) . .
O14 Na2 Na1 108.33(5) 2_767 .
O14 Na2 Na2 46.13(5) . 2_767
O7 Na2 Na2 142.06(7) . 2_767
O17 Na2 Na2 87.54(6) 2_667 2_767
O12 Na2 Na2 100.82(6) 2_777 2_767
O13 Na2 Na2 131.43(7) . 2_767
O14 Na2 Na2 43.63(5) 2_767 2_767
Na1 Na2 Na2 134.01(5) . 2_767
O14 Na2 Na3 69.75(5) . .
O7 Na2 Na3 71.37(5) . .
O17 Na2 Na3 28.58(5) 2_667 .
O12 Na2 Na3 147.54(6) 2_777 .
O13 Na2 Na3 114.82(6) . .
O14 Na2 Na3 95.17(5) 2_767 .
Na1 Na2 Na3 145.84(3) . .
Na2 Na2 Na3 79.99(4) 2_767 .
O17 Na3 O17 179.999(1) . 2_667
O17 Na3 O16 87.68(7) . .
O17 Na3 O16 92.32(7) 2_667 .
O17 Na3 O16 92.32(7) . 2_667
O17 Na3 O16 87.68(7) 2_667 2_667
O16 Na3 O16 180.00(12) . 2_667
O17 Na3 O15 100.70(6) . .
O17 Na3 O15 79.30(6) 2_667 .
O16 Na3 O15 83.30(6) . .
O16 Na3 O15 96.70(6) 2_667 .
O17 Na3 O15 79.30(6) . 2_667
O17 Na3 O15 100.70(6) 2_667 2_667
O16 Na3 O15 96.70(6) . 2_667
O16 Na3 O15 83.30(6) 2_667 2_667
O15 Na3 O15 180.0 . 2_667
O17 Na3 Na2 28.82(5) . 2_667
O17 Na3 Na2 151.18(5) 2_667 2_667
O16 Na3 Na2 74.17(5) . 2_667
O16 Na3 Na2 105.82(5) 2_667 2_667
O15 Na3 Na2 73.99(5) . 2_667
O15 Na3 Na2 106.01(5) 2_667 2_667
O17 Na3 Na2 151.18(5) . .
O17 Na3 Na2 28.82(5) 2_667 .
O16 Na3 Na2 105.83(5) . .
O16 Na3 Na2 74.18(5) 2_667 .
O15 Na3 Na2 106.01(5) . .
O15 Na3 Na2 73.99(5) 2_667 .
Na2 Na3 Na2 180.0 2_667 .
O7 S1 O5 112.91(11) . .
O7 S1 O6 112.68(11) . .
O5 S1 O6 111.50(11) . .
O7 S1 C4 106.54(11) . .
O5 S1 C4 106.10(12) . .
O6 S1 C4 106.54(12) . .
O10 S2 O9 112.87(11) . .
O10 S2 O8 112.50(11) . .
O9 S2 O8 110.79(11) . .
O10 S2 C14 108.35(12) . .
O9 S2 C14 106.61(12) . .
O8 S2 C14 105.22(12) . .
C7 N1 C8 119.1(2) . .
C7 N1 U1 122.42(17) . .
C8 N1 U1 117.73(15) . .
C10 N2 C9 116.8(2) . .
C10 N2 U1 124.38(17) . .
C9 N2 U1 117.57(15) . .
C1 O3 U1 121.85(15) . .
C11 O4 U1 126.75(16) . .
S1 O6 Na1 130.95(11) . .
S1 O7 Na2 128.75(11) . .
Na2 O12 Na1 88.46(7) 2_777 .
Na1 O13 Na2 89.81(7) . .
Na2 O14 Na2 90.25(7) . 2_767
Na3 O17 Na2 122.60(9) . 2_667
O3 C1 C2 119.5(2) . .
O3 C1 C6 121.6(2) . .
C2 C1 C6 118.8(2) . .
C3 C2 C1 120.8(2) . .
C2 C3 C4 120.0(2) . .
C5 C4 C3 120.1(2) . .
C5 C4 S1 121.02(19) . .
C3 C4 S1 118.79(19) . .
C4 C5 C6 120.7(2) . .
C5 C6 C1 119.5(2) . .
C5 C6 C7 119.1(2) . .
C1 C6 C7 121.2(2) . .
N1 C7 C6 124.6(2) . .
N1 C8 C9 108.2(2) . .
N2 C9 C8 109.6(2) . .
N2 C10 C16 125.2(2) . .
O4 C11 C16 121.3(2) . .
O4 C11 C12 119.3(2) . .
C16 C11 C12 119.3(2) . .
C13 C12 C11 120.6(2) . .
C12 C13 C14 120.2(2) . .
C15 C14 C13 120.5(2) . .
C15 C14 S2 121.8(2) . .
C13 C14 S2 117.69(19) . .
C14 C15 C16 120.1(2) . .
C11 C16 C15 119.2(2) . .
C11 C16 C10 122.8(2) . .
C15 C16 C10 117.8(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
U1 O2 1.7703(19) .
U1 O1 1.7898(19) .
U1 O3 2.2740(18) .
U1 O4 2.2829(18) .
U1 O11 2.3957(18) .
U1 N1 2.526(2) .
U1 N2 2.566(2) .
Na1 O13 2.3469(19) 2_777
Na1 O13 2.3469(19) .
Na1 O6 2.3663(18) .
Na1 O6 2.3664(18) 2_777
Na1 O12 2.408(2) 2_777
Na1 O12 2.409(2) .
Na1 Na2 3.3533(11) .
Na1 Na2 3.3534(11) 2_777
Na2 O14 2.323(2) .
Na2 O7 2.375(2) .
Na2 O17 2.382(2) 2_667
Na2 O12 2.399(2) 2_777
Na2 O13 2.403(2) .
Na2 O14 2.427(2) 2_767
Na2 Na2 3.367(2) 2_767
Na2 Na3 4.1635(11) .
Na3 O17 2.3643(19) .
Na3 O17 2.3643(19) 2_667
Na3 O16 2.3699(19) .
Na3 O16 2.3699(19) 2_667
Na3 O15 2.4739(19) .
Na3 O15 2.4739(19) 2_667
Na3 Na2 4.1635(11) 2_667
S1 O7 1.4569(18) .
S1 O5 1.4613(18) .
S1 O6 1.4633(18) .
S1 C4 1.756(2) .
S2 O10 1.4470(19) .
S2 O9 1.4634(19) .
S2 O8 1.4750(19) .
S2 C14 1.760(3) .
N1 C7 1.278(3) .
N1 C8 1.464(3) .
N2 C10 1.289(3) .
N2 C9 1.474(3) .
O3 C1 1.318(3) .
O4 C11 1.320(3) .
O12 Na2 2.399(2) 2_777
O14 Na2 2.427(2) 2_767
O17 Na2 2.382(2) 2_667
C1 C2 1.407(4) .
C1 C6 1.412(3) .
C2 C3 1.380(4) .
C3 C4 1.397(3) .
C4 C5 1.382(3) .
C5 C6 1.398(3) .
C6 C7 1.456(3) .
C8 C9 1.526(4) .
C10 C16 1.454(3) .
C11 C16 1.410(4) .
C11 C12 1.417(4) .
C12 C13 1.370(4) .
C13 C14 1.406(4) .
C14 C15 1.380(4) .
C15 C16 1.418(3) .
