#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/75/2017564.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_2017564
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          '(C6 H8 N)2 [U (C4 H4 O5)2 O2]'
_chemical_formula_moiety         '2C6 H8 N + , C8 H8 O12 U 2-'
_chemical_formula_sum            'C20 H24 N2 O12 U'
_chemical_formula_weight         722.44
_chemical_name_systematic
;
bis(3-methylpyridinium) dioxidobis(oxydiacetato)uranate(VI)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 91.224(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.415(2)
_cell_length_b                   13.312(5)
_cell_length_c                   11.806(4)
_cell_measurement_reflns_used    7099
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      3.15
_cell_volume                     1165.1(7)
_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      295(2)
_diffrn_detector_area_resol_mean 105
_diffrn_measured_fraction_theta_full 0.920
_diffrn_measured_fraction_theta_max 0.920
_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  0.1037
_diffrn_reflns_av_sigmaI/netI    0.0649
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7099
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.15
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    7.034
_exptl_absorpt_correction_T_max  0.500
_exptl_absorpt_correction_T_min  0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2000)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.059
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             692
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         2.195
_refine_diff_density_min         -3.343
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         1885
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0497
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0872P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1235
_refine_ls_wR_factor_ref         0.1297
_reflns_number_gt                1544
_reflns_number_total             1885
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gg3221.cif
_cod_data_source_block           III
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2017564
_cod_database_fobs_code          2017564
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.3040(7) 0.1055(4) -0.1778(5) 0.0350(13) Uani d . 1 . .
C C2 0.4052(8) 0.1423(5) -0.0752(5) 0.0382(14) Uani d . 1 . .
H H2A 0.5286 0.1181 -0.0753 0.046 Uiso calc R 1 . .
H H2B 0.4072 0.2152 -0.0741 0.046 Uiso calc R 1 . .
C C3 0.3940(7) 0.1299(5) 0.1269(4) 0.0357(13) Uani d . 1 . .
H H3A 0.4141 0.2018 0.1316 0.043 Uiso calc R 1 . .
H H3B 0.5089 0.0959 0.1369 0.043 Uiso calc R 1 . .
C C4 0.2661(7) 0.0971(4) 0.2150(4) 0.0313(12) Uani d . 1 . .
O O1 -0.1292(6) 0.1104(3) -0.0077(3) 0.0449(10) Uani d . 1 . .
O O2 0.1649(6) 0.0525(5) -0.1586(3) 0.0546(14) Uani d . 1 . .
O O3 0.3562(6) 0.1286(4) -0.2724(3) 0.0507(12) Uani d . 1 . .
O O4 0.3135(6) 0.1045(3) 0.0216(3) 0.0474(11) Uani d . 1 . .
O O5 0.1239(5) 0.0552(4) 0.1814(3) 0.0489(12) Uani d . 1 . .
O O6 0.3048(5) 0.1155(3) 0.3162(3) 0.0417(10) Uani d . 1 . .
U U1 0.0000 0.0000 0.0000 0.0259(2) Uani d S 1 . .
C C5 -0.1428(8) 0.0746(5) 0.3917(5) 0.0372(13) Uani d . 1 . .
H H5 -0.1378 0.0447 0.3207 0.045 Uiso calc R 1 . .
C C6 -0.3006(8) 0.0792(5) 0.4459(5) 0.0420(14) Uani d . 1 . .
H H6 -0.4049 0.0527 0.4125 0.050 Uiso calc R 1 . .
C C7 -0.3058(8) 0.1237(5) 0.5515(5) 0.0402(14) Uani d . 1 . .
H H7 -0.4148 0.1269 0.5889 0.048 Uiso calc R 1 . .
C C8 -0.1529(9) 0.1636(5) 0.6025(5) 0.0355(13) Uani d . 1 . .
C C9 0.0049(11) 0.1569(6) 0.5431(7) 0.0424(17) Uani d . 1 . .
H H9 0.1115 0.1827 0.5741 0.051 Uiso calc R 1 . .
C C10 -0.1552(11) 0.2138(5) 0.7147(5) 0.0583(19) Uani d . 1 . .
H H10A -0.0521 0.1929 0.7592 0.087 Uiso calc R 1 . .
H H10B -0.2634 0.1957 0.7530 0.087 Uiso calc R 1 . .
H H10C -0.1517 0.2853 0.7045 0.087 Uiso calc R 1 . .
N N1 0.0051(8) 0.1127(4) 0.4394(5) 0.0355(13) Uani d . 1 . .
H H1 0.121(9) 0.101(5) 0.410(6) 0.047(19) Uiso 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
O3 C1 O2 . . 124.9(6) ?
O3 C1 C2 . . 119.5(5) ?
O2 C1 C2 . . 115.6(5) ?
O4 C2 C1 . . 107.0(4) ?
O4 C2 H2A . . 110.3 ?
C1 C2 H2A . . 110.3 ?
O4 C2 H2B . . 110.3 ?
C1 C2 H2B . . 110.3 ?
H2A C2 H2B . . 108.6 ?
O4 C3 C4 . . 106.4(4) ?
O4 C3 H3A . . 110.5 ?
C4 C3 H3A . . 110.5 ?
O4 C3 H3B . . 110.5 ?
C4 C3 H3B . . 110.5 ?
H3A C3 H3B . . 108.6 ?
O6 C4 O5 . . 124.5(5) ?
O6 C4 C3 . . 118.4(5) ?
O5 C4 C3 . . 117.1(5) ?
C1 O2 U1 . . 137.7(4) ?
C3 O4 C2 . . 114.8(4) ?
C3 O4 U1 . . 123.5(3) ?
C2 O4 U1 . . 121.6(3) ?
C4 O5 U1 . . 135.7(3) ?
O1 U1 O1 . 3 180.0 ?
O1 U1 O2 . . 90.1(2) ?
O1 U1 O2 3 . 89.9(2) ?
O1 U1 O2 . 3 89.9(2) ?
O1 U1 O2 3 3 90.1(2) ?
O2 U1 O2 . 3 180.0 ?
O1 U1 O5 . 3 90.67(18) ?
O1 U1 O5 3 3 89.33(18) ?
O2 U1 O5 . 3 65.35(14) ?
O2 U1 O5 3 3 114.66(14) ?
O1 U1 O5 . . 89.33(18) ?
O1 U1 O5 3 . 90.67(18) ?
O2 U1 O5 . . 114.65(14) ?
O2 U1 O5 3 . 65.35(14) ?
O5 U1 O5 3 . 180.0 ?
O1 U1 O4 . 3 87.64(17) ?
O1 U1 O4 3 3 92.35(17) ?
O2 U1 O4 . 3 122.21(13) ?
O2 U1 O4 3 3 57.79(13) ?
O5 U1 O4 3 3 56.95(12) ?
O5 U1 O4 . 3 123.05(12) ?
O1 U1 O4 . . 92.36(17) ?
O1 U1 O4 3 . 87.64(17) ?
O2 U1 O4 . . 57.79(13) ?
O2 U1 O4 3 . 122.21(13) ?
O5 U1 O4 3 . 123.05(12) ?
O5 U1 O4 . . 56.95(12) ?
O4 U1 O4 3 . 180.0 ?
N1 C5 C6 . . 120.1(6) ?
N1 C5 H5 . . 119.9 ?
C6 C5 H5 . . 119.9 ?
C5 C6 C7 . . 119.3(6) ?
C5 C6 H6 . . 120.3 ?
C7 C6 H6 . . 120.3 ?
C8 C7 C6 . . 121.4(5) ?
C8 C7 H7 . . 119.3 ?
C6 C7 H7 . . 119.3 ?
C7 C8 C9 . . 116.8(6) ?
C7 C8 C10 . . 122.5(6) ?
C9 C8 C10 . . 120.6(6) ?
N1 C9 C8 . . 120.2(8) ?
N1 C9 H9 . . 119.9 ?
C8 C9 H9 . . 119.9 ?
C8 C10 H10A . . 109.5 ?
C8 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C8 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C5 N1 C9 . . 122.2(7) ?
C5 N1 H1 . . 122(4) ?
C9 N1 H1 . . 115(4) ?
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 O3 . 1.229(7) ?
C1 O2 . 1.274(7) ?
C1 C2 . 1.494(8) ?
C2 O4 . 1.435(7) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 O4 . 1.408(6) ?
C3 C4 . 1.487(7) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 O6 . 1.247(6) ?
C4 O5 . 1.250(6) ?
O1 U1 . 1.756(4) ?
O2 U1 . 2.364(4) ?
O4 U1 . 2.716(4) ?
O5 U1 . 2.426(4) ?
U1 O1 3 1.756(4) ?
U1 O2 3 2.364(4) ?
U1 O5 3 2.426(4) ?
U1 O4 3 2.716(4) ?
C5 N1 . 1.322(8) ?
C5 C6 . 1.346(8) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.382(8) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.379(9) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.380(10) ?
C8 C10 . 1.484(8) ?
C9 N1 . 1.359(12) ?
C9 H9 . 0.9300 ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
N1 H1 . 0.95(7) ?
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 O6 1_555 0.94(7) 1.79(7) 2.682(7) 157(6)
C3 H3A O3 4_566 0.97 2.57 3.441(8) 150.0
C5 H5 O2 3_555 0.93 2.32 3.233(8) 168.7
C6 H6 O6 1_455 0.93 2.55 3.309(7) 138.6
C7 H7 O3 1_456 0.93 2.38 3.291(7) 164.9
