#------------------------------------------------------------------------------
#$Date: 2016-03-23 00:26:11 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179110 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/72/4307241.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_4307241
loop_
_publ_author_name
'Pierre Thuéry'
_publ_contact_author_address
;
      CEA/Saclay, SCM (CNRS URA 331)
      Bât. 125
      91191 Gif-sur-Yvette
      France
;
_publ_contact_author_email       pierre.thuery@cea.fr
_publ_contact_author_fax         '33 1 69 08 66 40'
_publ_contact_author_name        'P. Thuéry'
_publ_contact_author_phone       '33 1 69 08 63 29'
_publ_section_title
;
Uranyl Ion Complexation by Citric and Citramalic Acids in the Presence of
Diamines
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              2307
_journal_page_last               2315
_journal_paper_doi               10.1021/ic061772k
_journal_volume                  46
_journal_year                    2007
_chemical_absolute_configuration ad
_chemical_formula_sum            'C16 H24 N2 O14 U2'
_chemical_formula_weight         944.43
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.247(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.3086(4)
_cell_length_b                   10.3366(3)
_cell_length_c                   14.0153(7)
_cell_measurement_reflns_used    39066
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.68
_cell_measurement_theta_min      2.95
_cell_volume                     1184.47(9)
_computing_cell_refinement       'HKL2000 (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_data_reduction        'HKL2000 (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1999)'
_computing_publication_material
'SHELXTL (Sheldrick, 1999); PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(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'
_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  0.0514
_diffrn_reflns_av_sigmaI/netI    0.0239
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            39066
_diffrn_reflns_theta_full        25.68
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         2.95
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    13.726
_exptl_absorpt_correction_T_max  0.168
_exptl_absorpt_correction_T_min  0.107
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            'translucent dark yellow'
_exptl_crystal_density_diffrn    2.648
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             860
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         2.416
_refine_diff_density_min         -1.811
_refine_diff_density_rms         0.340
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.001(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         4483
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0442
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0670P)²+24.4370P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1157
_refine_ls_wR_factor_ref         0.1161
_reflns_number_gt                4412
_reflns_number_total             4483
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic061772ksi20060919_082125_3.cif
_cod_data_source_block           2
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4307241
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
U1 U 0.75497(5) 0.26252(5) 0.70106(3) 0.02393(15) Uani 1 1 d . . .
U2 U 1.20775(6) 0.22831(5) 0.82855(3) 0.02339(15) Uani 1 1 d . . .
O1 O 0.7084(14) 0.0953(8) 0.7179(8) 0.030(2) Uani 1 1 d . . .
O2 O 0.7895(13) 0.4300(12) 0.6814(8) 0.034(3) Uani 1 1 d . . .
O3 O 1.2093(12) 0.0545(11) 0.8508(9) 0.030(2) Uani 1 1 d . . .
O4 O 1.2192(14) 0.3935(9) 0.8058(9) 0.040(3) Uani 1 1 d . . .
O5 O 1.0210(11) 0.2088(11) 0.6770(7) 0.025(2) Uani 1 1 d . . .
O6 O 0.7707(11) 0.2201(12) 0.5374(7) 0.031(2) Uani 1 1 d . . .
O7 O 0.9106(12) 0.1999(11) 0.4195(7) 0.030(2) Uani 1 1 d . . .
O8 O 1.3594(13) 0.1784(12) 0.7076(8) 0.035(3) Uani 1 1 d . . .
O9 O 1.4809(12) 0.2907(11) 0.6052(7) 0.032(3) Uani 1 1 d . . .
O10 O 0.9337(10) 0.2519(11) 0.8533(6) 0.0227(19) Uani 1 1 d . . .
O11 O 1.1850(11) 0.2585(12) 0.9925(7) 0.029(2) Uani 1 1 d . . .
O12 O 1.0420(11) 0.2567(11) 1.1108(7) 0.031(2) Uani 1 1 d . . .
O13 O 0.6005(12) 0.3368(11) 0.8156(7) 0.027(2) Uani 1 1 d . . .
O14 O 0.4814(10) 0.2471(13) 0.9276(7) 0.031(2) Uani 1 1 d . . .
N1 N 0.6165(13) 0.2251(14) 0.3125(7) 0.025(2) Uani 1 1 d . . .
H1 H 0.7168 0.2219 0.3568 0.030 Uiso 1 1 d R . .
N2 N 0.3465(13) 0.2584(14) 0.2044(7) 0.025(2) Uani 1 1 d . . .
H2 H 0.2386 0.2831 0.1695 0.030 Uiso 1 1 d R . .
C1 C 1.0562(17) 0.1793(14) 0.5846(9) 0.024(3) Uani 1 1 d . . .
C2 C 0.9016(17) 0.2021(14) 0.5070(11) 0.021(3) Uani 1 1 d . . .
C3 C 1.1917(16) 0.2654(18) 0.5617(11) 0.033(3) Uani 1 1 d . . .
H3A H 1.1596 0.3551 0.5661 0.039 Uiso 1 1 calc R . .
H3B H 1.2060 0.2494 0.4955 0.039 Uiso 1 1 calc R . .
C4 C 1.3539(15) 0.2438(16) 0.6291(9) 0.022(3) Uani 1 1 d . . .
C5 C 1.090(2) 0.0350(16) 0.5772(12) 0.036(4) Uani 1 1 d . . .
H5A H 1.1868 0.0127 0.6226 0.054 Uiso 1 1 calc R . .
H5B H 1.1059 0.0149 0.5127 0.054 Uiso 1 1 calc R . .
H5C H 0.9988 -0.0134 0.5918 0.054 Uiso 1 1 calc R . .
C6 C 0.8992(16) 0.2225(15) 0.9459(9) 0.025(3) Uani 1 1 d . . .
C7 C 1.0523(16) 0.2478(16) 1.0228(9) 0.025(3) Uani 1 1 d . . .
C8 C 0.7591(15) 0.3119(14) 0.9710(9) 0.021(3) Uani 1 1 d . . .
H8A H 0.7413 0.2924 1.0360 0.025 Uiso 1 1 calc R . .
H8B H 0.7927 0.4016 0.9697 0.025 Uiso 1 1 calc R . .
C9 C 0.6013(19) 0.2930(15) 0.9002(11) 0.028(4) Uani 1 1 d . . .
C10 C 0.8529(17) 0.0826(15) 0.9565(11) 0.030(3) Uani 1 1 d . . .
H10A H 0.7454 0.0674 0.9199 0.045 Uiso 1 1 calc R . .
H10B H 0.8537 0.0636 1.0236 0.045 Uiso 1 1 calc R . .
H10C H 0.9301 0.0277 0.9326 0.045 Uiso 1 1 calc R . .
C11 C 0.6395(19) 0.3083(18) 0.2287(14) 0.043(4) Uani 1 1 d . . .
H11A H 0.6959 0.2603 0.1851 0.051 Uiso 1 1 calc R . .
H11B H 0.7046 0.3837 0.2516 0.051 Uiso 1 1 calc R . .
C12 C 0.4681(19) 0.3507(15) 0.1751(12) 0.034(4) Uani 1 1 d . . .
H12A H 0.4447 0.4384 0.1931 0.041 Uiso 1 1 calc R . .
H12B H 0.4635 0.3476 0.1055 0.041 Uiso 1 1 calc R . .
C13 C 0.547(2) 0.1005(18) 0.2779(17) 0.053(5) Uani 1 1 d . . .
H13A H 0.5071 0.0551 0.3297 0.063 Uiso 1 1 calc R . .
H13B H 0.6291 0.0473 0.2558 0.063 Uiso 1 1 calc R . .
C14 C 0.404(2) 0.1274(16) 0.1930(13) 0.039(4) Uani 1 1 d . . .
H14A H 0.4409 0.1189 0.1315 0.046 Uiso 1 1 calc R . .
H14B H 0.3159 0.0661 0.1944 0.046 Uiso 1 1 calc R . .
C15 C 0.500(2) 0.296(2) 0.3668(13) 0.051(5) Uani 1 1 d . . .
H15A H 0.5014 0.2568 0.4297 0.062 Uiso 1 1 calc R . .
H15B H 0.5324 0.3860 0.3764 0.062 Uiso 1 1 calc R . .
C16 C 0.3299(19) 0.287(2) 0.3060(11) 0.044(4) Uani 1 1 d . . .
H16A H 0.2682 0.2191 0.3307 0.052 Uiso 1 1 calc R . .
H16B H 0.2721 0.3682 0.3088 0.052 Uiso 1 1 calc R . .
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'
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
O2 U1 O1 176.8(5) . . ?
O2 U1 O13 84.9(5) . . ?
O1 U1 O13 93.9(5) . . ?
O2 U1 O5 91.5(5) . . ?
O1 U1 O5 91.2(5) . . ?
O13 U1 O5 144.3(3) . . ?
O2 U1 O6 89.6(5) . . ?
O1 U1 O6 89.9(5) . . ?
O13 U1 O6 148.6(3) . . ?
O5 U1 O6 66.6(3) . . ?
O2 U1 O10 95.2(4) . . ?
O1 U1 O10 87.3(4) . . ?
O13 U1 O10 74.5(3) . . ?
O5 U1 O10 70.5(3) . . ?
O6 U1 O10 136.9(3) . . ?
O2 U1 O9 87.7(4) . 1_455 ?
O1 U1 O9 89.1(5) . 1_455 ?
O13 U1 O9 76.6(3) . 1_455 ?
O5 U1 O9 138.9(3) . 1_455 ?
O6 U1 O9 72.3(3) . 1_455 ?
O10 U1 O9 150.5(3) . 1_455 ?
O4 U2 O3 176.3(6) . . ?
O4 U2 O8 91.7(5) . . ?
O3 U2 O8 85.3(5) . . ?
O4 U2 O11 93.8(5) . . ?
O3 U2 O11 87.9(5) . . ?
O8 U2 O11 151.7(3) . . ?
O4 U2 O10 90.7(5) . . ?
O3 U2 O10 93.1(4) . . ?
O8 U2 O10 141.3(3) . . ?
O11 U2 O10 66.4(3) . . ?
O4 U2 O5 88.2(5) . . ?
O3 U2 O5 93.0(5) . . ?
O8 U2 O5 71.8(3) . . ?
O11 U2 O5 136.1(3) . . ?
O10 U2 O5 69.7(3) . . ?
O4 U2 O14 87.2(5) . 1_655 ?
O3 U2 O14 90.2(5) . 1_655 ?
O8 U2 O14 82.2(3) . 1_655 ?
O11 U2 O14 70.4(3) . 1_655 ?
O10 U2 O14 136.5(3) . 1_655 ?
O5 U2 O14 153.4(3) . 1_655 ?
C1 O5 U1 122.3(7) . . ?
C1 O5 U2 128.5(7) . . ?
U1 O5 U2 109.1(4) . . ?
C2 O6 U1 124.1(9) . . ?
C4 O8 U2 124.2(9) . . ?
C4 O9 U1 123.4(9) . 1_655 ?
C6 O10 U1 129.7(7) . . ?
C6 O10 U2 117.9(7) . . ?
U1 O10 U2 109.6(3) . . ?
C7 O11 U2 123.0(8) . . ?
C9 O13 U1 127.4(9) . . ?
C9 O14 U2 125.2(9) . 1_455 ?
C13 N1 C11 110.2(14) . . ?
C13 N1 C15 110.0(15) . . ?
C11 N1 C15 107.2(14) . . ?
C14 N2 C16 112.3(13) . . ?
C14 N2 C12 108.2(12) . . ?
C16 N2 C12 108.5(13) . . ?
O5 C1 C3 110.5(12) . . ?
O5 C1 C5 110.2(12) . . ?
C3 C1 C5 114.0(13) . . ?
O5 C1 C2 109.3(11) . . ?
C3 C1 C2 108.5(11) . . ?
C5 C1 C2 104.0(11) . . ?
O7 C2 O6 123.2(13) . . ?
O7 C2 C1 120.2(12) . . ?
O6 C2 C1 116.6(13) . . ?
C1 C3 C4 113.1(13) . . ?
O9 C4 O8 121.8(12) . . ?
O9 C4 C3 118.0(12) . . ?
O8 C4 C3 120.2(12) . . ?
O10 C6 C10 113.1(12) . . ?
O10 C6 C7 109.3(10) . . ?
C10 C6 C7 106.7(12) . . ?
O10 C6 C8 111.0(11) . . ?
C10 C6 C8 109.2(11) . . ?
C7 C6 C8 107.2(11) . . ?
O11 C7 O12 122.9(12) . . ?
O11 C7 C6 116.5(11) . . ?
O12 C7 C6 120.6(12) . . ?
C9 C8 C6 111.6(11) . . ?
O14 C9 O13 124.2(14) . . ?
O14 C9 C8 120.3(13) . . ?
O13 C9 C8 115.3(14) . . ?
N1 C11 C12 108.0(13) . . ?
N2 C12 C11 107.1(12) . . ?
N1 C13 C14 107.5(13) . . ?
N2 C14 C13 107.8(13) . . ?
C16 C15 N1 107.6(14) . . ?
N2 C16 C15 108.3(13) . . ?
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 O2 1.784(13) . ?
U1 O1 1.796(7) . ?
U1 O13 2.355(9) . ?
U1 O5 2.361(9) . ?
U1 O6 2.362(9) . ?
U1 O10 2.375(8) . ?
U1 O9 2.447(9) 1_455 ?
U1 U2 3.8831(7) . ?
U1 U2 5.1846(7) 1_455 ?
U2 O4 1.743(9) . ?
U2 O3 1.823(12) . ?
U2 O8 2.343(11) . ?
U2 O11 2.360(10) . ?
U2 O10 2.376(8) . ?
U2 O5 2.406(9) . ?
U2 O14 2.452(9) 1_655 ?
O5 C1 1.411(15) . ?
O6 C2 1.250(17) . ?
O7 C2 1.242(18) . ?
O8 C4 1.284(18) . ?
O9 C4 1.259(17) . ?
O9 U1 2.447(9) 1_655 ?
O10 C6 1.412(15) . ?
O11 C7 1.255(17) . ?
O12 C7 1.256(16) . ?
O13 C9 1.268(19) . ?
O14 C9 1.23(2) . ?
O14 U2 2.452(9) 1_455 ?
N1 C13 1.46(2) . ?
N1 C11 1.50(2) . ?
N1 C15 1.52(2) . ?
N2 C14 1.45(2) . ?
N2 C16 1.485(18) . ?
N2 C12 1.50(2) . ?
C1 C3 1.51(2) . ?
C1 C5 1.52(2) . ?
C1 C2 1.546(18) . ?
C3 C4 1.518(17) . ?
C6 C10 1.51(2) . ?
C6 C7 1.536(18) . ?
C6 C8 1.574(18) . ?
C8 C9 1.509(18) . ?
C11 C12 1.55(2) . ?
C13 C14 1.55(2) . ?
C15 C16 1.52(2) . ?
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 O7 0.95 1.71 2.643(14) 169.0 .
N2 H2 O12 0.98 1.72 2.635(13) 155.6 1_454
