#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/75/2017562.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2017562
loop_
_publ_author_name
'Lennartson, Anders'
'Håkansson, Mikael'
_publ_section_title
;
 Hydrogen-bonded network structures in dipyridinium,
 bis(2-methylpyridinium), bis(3-methylpyridinium) and
 bis(4-methylpyridinium) dioxidobis(oxydiacetato)uranate(VI)
;
_journal_coeditor_code           GG3221
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              m69
_journal_page_last               m74
_journal_paper_doi               10.1107/S0108270109053839
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          '(C5 H6 N)2 [U (C4 H4 O5)2 O2]'
_chemical_formula_moiety         '2C5 H6 N + , C8 H8 O12 U 2-'
_chemical_formula_sum            'C18 H20 N2 O12 U'
_chemical_formula_weight         694.39
_chemical_name_systematic
;
dipyridinium dioxidobis(oxydiacetato)uranate(VI)
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 110.946(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.675(2)
_cell_length_b                   23.025(5)
_cell_length_c                   7.500(2)
_cell_measurement_reflns_used    5883
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      3.04
_cell_volume                     1076.5(5)
_computing_cell_refinement       'CrystalClear (Rigaku, 2000)'
_computing_data_collection       'CrystalClear (Rigaku, 2000)'
_computing_data_reduction        'CrystalClear (Rigaku, 2000)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and PLUTON (Spek, 2009)
;
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1993)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 105
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device_type  'Rigaku R-AXIS IIC image-plate'
_diffrn_measurement_method       φ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_sigmaI/netI    0.0272
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5883
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         3.04
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    7.608
_exptl_absorpt_correction_T_max  0.470
_exptl_absorpt_correction_T_min  0.240
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2000)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.142
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             660
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.811
_refine_diff_density_min         -0.958
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         1853
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0176
_refine_ls_R_factor_gt           0.0156
_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)+(0.0169P)²+0.7202P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0371
_refine_ls_wR_factor_ref         0.0377
_reflns_number_gt                1763
_reflns_number_total             1853
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gg3221.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               2017562
_cod_database_fobs_code          2017562
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.2005(5) 0.14723(12) 0.6860(4) 0.0098(6) Uani d . 1 . .
C C2 0.1218(5) 0.19806(12) 0.7705(4) 0.0099(6) Uani d . 1 . .
H H2A -0.0305 0.1941 0.7456 0.012 Uiso calc R 1 . .
H H2B 0.1969 0.1994 0.9076 0.012 Uiso calc R 1 . .
C C3 0.6803(4) 0.15744(12) 0.2908(4) 0.0098(6) Uani d . 1 . .
C C4 0.6827(5) 0.19771(12) 0.1312(4) 0.0123(6) Uani d . 1 . .
H H4A 0.8299 0.2064 0.1458 0.015 Uiso calc R 1 . .
H H4B 0.6156 0.1784 0.0092 0.015 Uiso calc R 1 . .
C C5 0.7778(5) -0.01458(13) 0.5828(4) 0.0138(6) Uani d . 1 . .
H H5 0.8045 -0.0311 0.4803 0.017 Uiso calc R 1 . .
C C6 0.7802(5) -0.04867(13) 0.7335(4) 0.0163(6) Uani d . 1 . .
H H6 0.8081 -0.0883 0.7343 0.020 Uiso calc R 1 . .
C C7 0.7402(5) -0.02294(14) 0.8853(4) 0.0172(7) Uani d . 1 . .
H H7 0.7416 -0.0453 0.9891 0.021 Uiso calc R 1 . .
C C8 0.6982(5) 0.03611(14) 0.8813(4) 0.0153(6) Uani d . 1 . .
H H8 0.6709 0.0538 0.9819 0.018 Uiso calc R 1 . .
C C9 0.6976(5) 0.06821(13) 0.7265(4) 0.0130(6) Uani d . 1 . .
H H9 0.6697 0.1079 0.7215 0.016 Uiso calc R 1 . .
O O1 0.2058(5) 0.2500 0.2704(4) 0.0135(6) Uani d S 1 . .
O O2 0.6224(5) 0.2500 0.7273(4) 0.0122(6) Uani d S 1 . .
O O3 0.2918(3) 0.16052(9) 0.5665(3) 0.0152(5) Uani d . 1 . .
O O4 0.1753(3) 0.09789(9) 0.7362(3) 0.0146(4) Uani d . 1 . .
O O5 0.1617(5) 0.2500 0.6843(4) 0.0108(6) Uani d S 1 . .
O O6 0.6254(3) 0.17793(9) 0.4239(3) 0.0132(4) Uani d . 1 . .
O O7 0.7398(4) 0.10647(9) 0.2845(3) 0.0153(5) Uani d . 1 . .
O O8 0.5726(5) 0.2500 0.1329(4) 0.0133(6) Uani d S 1 . .
U U1 0.41668(2) 0.2500 0.497706(19) 0.00626(7) Uani d S 1 . .
N N1 0.7374(4) 0.04215(11) 0.5828(3) 0.0118(5) Uani d D 1 . .
H H1 0.740(7) 0.0628(15) 0.486(4) 0.030(10) Uiso d D 1 . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O4 C1 O3 . . 125.8(3) ?
O4 C1 C2 . . 118.8(2) ?
O3 C1 C2 . . 115.5(2) ?
O5 C2 C1 . . 108.0(2) ?
O5 C2 H2A . . 110.1 ?
C1 C2 H2A . . 110.1 ?
O5 C2 H2B . . 110.1 ?
C1 C2 H2B . . 110.1 ?
H2A C2 H2B . . 108.4 ?
O7 C3 O6 . . 124.4(3) ?
O7 C3 C4 . . 116.9(2) ?
O6 C3 C4 . . 118.7(2) ?
O8 C4 C3 . . 111.2(2) ?
O8 C4 H4A . . 109.4 ?
C3 C4 H4A . . 109.4 ?
O8 C4 H4B . . 109.4 ?
C3 C4 H4B . . 109.4 ?
H4A C4 H4B . . 108.0 ?
N1 C5 C6 . . 120.2(3) ?
N1 C5 H5 . . 119.9 ?
C6 C5 H5 . . 119.9 ?
C5 C6 C7 . . 118.8(3) ?
C5 C6 H6 . . 120.6 ?
C7 C6 H6 . . 120.6 ?
C8 C7 C6 . . 119.8(3) ?
C8 C7 H7 . . 120.1 ?
C6 C7 H7 . . 120.1 ?
C9 C8 C7 . . 119.0(3) ?
C9 C8 H8 . . 120.5 ?
C7 C8 H8 . . 120.5 ?
N1 C9 C8 . . 119.8(3) ?
N1 C9 H9 . . 120.1 ?
C8 C9 H9 . . 120.1 ?
C1 O3 U1 . . 130.90(18) ?
C2 O5 C2 . 4_565 113.6(3) ?
C2 O5 U1 . . 121.01(15) ?
C2 O5 U1 4_565 . 121.01(15) ?
C3 O6 U1 . . 143.76(19) ?
C4 O8 C4 . 4_565 116.9(3) ?
O2 U1 O1 . . 178.59(12) ?
O2 U1 O3 . . 89.95(7) ?
O1 U1 O3 . . 89.38(7) ?
O2 U1 O3 . 4_565 89.95(7) ?
O1 U1 O3 . 4_565 89.38(7) ?
O3 U1 O3 . 4_565 122.68(10) ?
O2 U1 O6 . . 84.87(9) ?
O1 U1 O6 . . 96.12(8) ?
O3 U1 O6 . . 73.72(7) ?
O3 U1 O6 4_565 . 162.87(7) ?
O2 U1 O6 . 4_565 84.87(9) ?
O1 U1 O6 . 4_565 96.12(8) ?
O3 U1 O6 . 4_565 162.87(7) ?
O3 U1 O6 4_565 4_565 73.72(7) ?
O6 U1 O6 . 4_565 89.54(10) ?
O2 U1 O5 . . 84.54(12) ?
O1 U1 O5 . . 94.06(11) ?
O3 U1 O5 . . 61.48(5) ?
O3 U1 O5 4_565 . 61.48(5) ?
O6 U1 O5 . . 133.84(5) ?
O6 U1 O5 4_565 . 133.84(5) ?
C5 N1 C9 . . 122.4(3) ?
C5 N1 H1 . . 118(3) ?
C9 N1 H1 . . 120(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O4 . 1.227(4) ?
C1 O3 . 1.288(4) ?
C1 C2 . 1.512(4) ?
C2 O5 . 1.429(3) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 O7 . 1.245(4) ?
C3 O6 . 1.271(4) ?
C3 C4 . 1.519(4) ?
C4 O8 . 1.413(3) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 N1 . 1.334(4) ?
C5 C6 . 1.372(4) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.391(4) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.386(5) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.375(4) ?
C8 H8 . 0.9300 ?
C9 N1 . 1.340(4) ?
C9 H9 . 0.9300 ?
O1 U1 . 1.781(3) ?
O2 U1 . 1.777(3) ?
O3 U1 . 2.348(2) ?
O5 C2 4_565 1.429(3) ?
O5 U1 . 2.561(3) ?
O6 U1 . 2.357(2) ?
O8 C4 4_565 1.413(3) ?
U1 O3 4_565 2.348(2) ?
U1 O6 4_565 2.357(2) ?
N1 H1 . 0.875(19) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1 O7 1_555 0.87(3) 1.82(3) 2.688(3) 179(6)
C2 H2A O2 1_455 0.97 2.61 3.446(5) 144
C4 H4A O1 1_655 0.97 2.55 3.482(5) 161
C5 H5 O4 3_656 0.93 2.28 3.168(4) 161
C7 H7 O4 3_657 0.93 2.28 3.195(4) 167
C8 H8 O7 1_556 0.93 2.47 3.354(4) 159
