#------------------------------------------------------------------------------
#$Date: 2015-09-06 00:34:46 +0300 (Sun, 06 Sep 2015) $
#$Revision: 154600 $
#$URL: svn://www.crystallography.net/cod/cif/4/34/34/4343409.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_4343409
loop_
_publ_author_name
'Thuéry, Pierre'
'Harrowfield, Jack'
_publ_section_title
;
 Uranyl Ion Complexes with 1,1'-Biphenyl-2,2',6,6'-tetracarboxylic Acid:
 Structural and Spectroscopic Studies of One- to Three-Dimensional
 Assemblies.
;
_journal_issue                   13
_journal_name_full               'Inorganic chemistry'
_journal_page_first              6296
_journal_page_last               6305
_journal_paper_doi               10.1021/acs.inorgchem.5b00596
_journal_volume                  54
_journal_year                    2015
_chemical_formula_sum            'C18 H17 N O16 U2'
_chemical_formula_weight         979.39
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     heavy
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                72.739(2)
_cell_angle_beta                 73.394(3)
_cell_angle_gamma                67.672(3)
_cell_formula_units_Z            2
_cell_length_a                   9.0667(3)
_cell_length_b                   10.4968(5)
_cell_length_c                   13.9008(7)
_cell_measurement_reflns_used    67336
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.51
_cell_measurement_theta_min      2.61
_cell_volume                     1146.01(9)
_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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
'Nonius Kappa-CCD area-detector diffractometer'
_diffrn_measurement_method
'2 φ and 13 ω scans with 2° steps (755 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  0.0394
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_laue_measured_fraction_full 0.998
_diffrn_reflns_laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            67336
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.507
_diffrn_reflns_theta_min         2.611
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    14.198
_exptl_absorpt_correction_T_max  0.210
_exptl_absorpt_correction_T_min  0.151
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            'translucent light yellow'
_exptl_crystal_density_diffrn    2.838
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.721
_refine_diff_density_min         -3.095
_refine_diff_density_rms         0.243
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         6979
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0333
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0304P)²+7.7432P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.0926
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6114
_reflns_number_total             6979
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ic5b00596_si_002.cif
_cod_data_source_block           2
_cod_depositor_comments
'Adding full bibliography for 4343408--4343413.cif.'
_cod_database_code               4343409
_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, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
U1 U 0.40548(3) 0.27086(2) 1.04268(2) 0.02070(6) Uani 1 1 d . .
U2 U 1.14131(3) 0.21958(2) 0.50192(2) 0.03334(7) Uani 1 1 d . .
O1 O 0.2811(5) 0.3024(4) 0.9560(3) 0.0253(8) Uani 1 1 d . .
O2 O 0.5355(6) 0.2407(4) 1.1260(3) 0.0304(9) Uani 1 1 d . .
O3 O 0.9937(7) 0.2885(6) 0.4237(4) 0.0445(12) Uani 1 1 d . .
O4 O 1.2846(7) 0.1503(5) 0.5825(4) 0.0406(11) Uani 1 1 d . .
O5 O 0.5608(5) 0.4002(4) 0.9176(3) 0.0231(8) Uani 1 1 d . .
O6 O 0.7323(5) 0.4963(4) 0.9317(3) 0.0271(8) Uani 1 1 d . .
O7 O 0.9782(7) 0.0911(5) 0.6173(4) 0.0389(11) Uani 1 1 d . .
O8 O 1.0045(9) -0.1084(6) 0.7338(5) 0.0606(18) Uani 1 1 d . .
O9 O 0.5999(5) 0.0962(4) 0.9561(3) 0.0218(7) Uani 1 1 d . .
O10 O 0.6246(6) -0.0479(4) 0.8588(3) 0.0317(10) Uani 1 1 d . .
O11 O 0.9740(6) 0.3783(5) 0.6103(4) 0.0347(10) Uani 1 1 d . .
O12 O 0.7731(7) 0.5763(5) 0.5739(4) 0.0437(12) Uani 1 1 d . .
O13 O 0.1711(7) 0.2886(5) 1.1866(4) 0.0522(16) Uani 1 1 d . .
H13A H 0.0982 0.2433 1.2158 0.063 Uiso 1 1 d R U
H13B H 0.1054 0.3736 1.2038 0.063 Uiso 1 1 d R U
O14 O 1.3748(9) 0.1749(7) 0.3581(5) 0.0659(19) Uani 1 1 d . .
H14A H 1.3437 0.2319 0.2981 0.079 Uiso 1 1 d R U
H14B H 1.4522 0.2085 0.3613 0.079 Uiso 1 1 d R U
O15 O 1.2218(7) -0.0138(6) 0.4576(4) 0.0458(13) Uani 1 1 d . .
H15A H 1.1382 -0.0281 0.4475 0.055 Uiso 1 1 d R U
H15B H 1.2730 -0.1078 0.4990 0.055 Uiso 1 1 d R U
O16 O -0.0803(10) 0.5179(7) 1.2365(6) 0.079(2) Uani 1 1 d . .
N1 N 0.3584(14) 0.7748(11) 0.6168(9) 0.094(3) Uani 1 1 d D U
C1 C 0.8502(7) 0.2116(5) 0.8065(4) 0.0217(10) Uani 1 1 d . .
C2 C 0.8466(7) 0.2785(5) 0.8816(4) 0.0223(10) Uani 1 1 d . .
C3 C 0.9741(8) 0.2288(6) 0.9331(5) 0.0278(12) Uani 1 1 d . .
H3 H 0.9721 0.2761 0.9823 0.033 Uiso 1 1 calc R U
C4 C 1.1054(8) 0.1096(7) 0.9132(5) 0.0324(13) Uani 1 1 d . .
H4 H 1.1929 0.0763 0.9485 0.039 Uiso 1 1 calc R U
C5 C 1.1084(8) 0.0402(6) 0.8425(5) 0.0324(13) Uani 1 1 d . .
H5 H 1.1957 -0.0431 0.8309 0.039 Uiso 1 1 calc R U
C6 C 0.9831(7) 0.0925(6) 0.7881(4) 0.0247(11) Uani 1 1 d . .
C7 C 0.7033(7) 0.4002(5) 0.9115(4) 0.0211(10) Uani 1 1 d . .
C8 C 0.9897(8) 0.0166(6) 0.7095(5) 0.0326(13) Uani 1 1 d . .
C9 C 0.7164(7) 0.2600(5) 0.7487(4) 0.0220(10) Uani 1 1 d . .
C10 C 0.6050(7) 0.1866(6) 0.7773(4) 0.0237(10) Uani 1 1 d . .
C11 C 0.4851(9) 0.2208(7) 0.7216(5) 0.0327(13) Uani 1 1 d . .
H11 H 0.4158 0.1650 0.7395 0.039 Uiso 1 1 calc R U
C12 C 0.4665(10) 0.3358(9) 0.6399(6) 0.0450(19) Uani 1 1 d . .
H12 H 0.3819 0.3622 0.6032 0.054 Uiso 1 1 calc R U
C13 C 0.5732(11) 0.4116(8) 0.6127(5) 0.0453(19) Uani 1 1 d . .
H13 H 0.5589 0.4922 0.5580 0.054 Uiso 1 1 calc R U
C14 C 0.6999(8) 0.3738(7) 0.6626(5) 0.0307(12) Uani 1 1 d . .
C15 C 0.6103(7) 0.0699(5) 0.8707(4) 0.0212(10) Uani 1 1 d . .
C16 C 0.8246(9) 0.4488(7) 0.6141(5) 0.0326(13) Uani 1 1 d . .
C17 C 0.3252(19) 0.7076(15) 0.6938(10) 0.104(3) Uani 1 1 d D U
C18 C 0.2778(17) 0.6164(13) 0.7978(9) 0.090(3) Uani 1 1 d D U
H18A H 0.2212 0.6757 0.8486 0.135 Uiso 1 1 calc R U
H18B H 0.3759 0.5446 0.8197 0.135 Uiso 1 1 calc R U
H18C H 0.2058 0.5703 0.7920 0.135 Uiso 1 1 calc R U
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 178.0(2) . .
O1 U1 O5 90.40(17) . .
O2 U1 O5 87.72(18) . .
O1 U1 O9 87.48(17) . .
O2 U1 O9 91.49(18) . .
O5 U1 O9 78.36(13) . .
O1 U1 O6 89.19(17) . 2_667
O2 U1 O6 91.03(18) . 2_667
O5 U1 O6 77.00(14) . 2_667
O9 U1 O6 155.11(14) . 2_667
O1 U1 O10 97.11(18) . 2_657
O2 U1 O10 84.21(18) . 2_657
O5 U1 O10 149.97(15) . 2_657
O9 U1 O10 73.01(14) . 2_657
O6 U1 O10 131.88(15) 2_667 2_657
O1 U1 O13 91.1(2) . .
O2 U1 O13 90.8(2) . .
O5 U1 O13 143.65(15) . .
O9 U1 O13 137.99(14) . .
O6 U1 O13 66.71(15) 2_667 .
O10 U1 O13 65.52(15) 2_657 .
O4 U2 O3 178.6(2) . .
O4 U2 O7 91.0(2) . .
O3 U2 O7 87.7(2) . .
O4 U2 O11 89.4(2) . .
O3 U2 O11 89.8(2) . .
O7 U2 O11 78.42(16) . .
O4 U2 O12 91.2(2) . 2_766
O3 U2 O12 89.7(2) . 2_766
O7 U2 O12 155.17(18) . 2_766
O11 U2 O12 76.88(18) . 2_766
O4 U2 O14 86.7(3) . .
O3 U2 O14 94.6(3) . .
O7 U2 O14 135.9(2) . .
O11 U2 O14 145.5(2) . .
O12 U2 O14 69.0(2) 2_766 .
O4 U2 O15 90.6(2) . .
O3 U2 O15 89.5(2) . .
O7 U2 O15 70.76(18) . .
O11 U2 O15 149.18(17) . .
O12 U2 O15 133.92(19) 2_766 .
O14 U2 O15 65.2(2) . .
C7 O5 U1 130.2(3) . .
C7 O6 U1 138.9(4) . 2_667
C8 O7 U2 130.4(5) . .
C15 O9 U1 131.1(4) . .
C15 O10 U1 140.6(4) . 2_657
C16 O11 U2 127.7(4) . .
C16 O12 U2 141.9(5) . 2_766
U1 O13 H13A 136.0 . .
U1 O13 H13B 122.1 . .
H13A O13 H13B 96.3 . .
U2 O14 H14A 109.1 . .
U2 O14 H14B 110.8 . .
H14A O14 H14B 100.5 . .
U2 O15 H15A 111.4 . .
U2 O15 H15B 127.2 . .
H15A O15 H15B 100.1 . .
C6 C1 C2 118.1(5) . .
C6 C1 C9 119.1(5) . .
C2 C1 C9 122.8(5) . .
C3 C2 C1 120.3(5) . .
C3 C2 C7 118.0(5) . .
C1 C2 C7 121.6(5) . .
C2 C3 C4 120.3(6) . .
C2 C3 H3 119.8 . .
C4 C3 H3 119.8 . .
C5 C4 C3 120.1(6) . .
C5 C4 H4 119.9 . .
C3 C4 H4 119.9 . .
C4 C5 C6 119.8(6) . .
C4 C5 H5 120.1 . .
C6 C5 H5 120.1 . .
C5 C6 C1 121.3(6) . .
C5 C6 C8 119.1(5) . .
C1 C6 C8 119.6(6) . .
O6 C7 O5 123.6(5) . .
O6 C7 C2 117.0(5) . .
O5 C7 C2 119.4(5) . .
O8 C8 O7 123.1(6) . .
O8 C8 C6 120.1(6) . .
O7 C8 C6 116.7(5) . .
C10 C9 C14 117.6(5) . .
C10 C9 C1 119.1(5) . .
C14 C9 C1 123.2(5) . .
C11 C10 C9 121.5(5) . .
C11 C10 C15 118.1(5) . .
C9 C10 C15 120.4(5) . .
C12 C11 C10 120.1(6) . .
C12 C11 H11 119.9 . .
C10 C11 H11 119.9 . .
C13 C12 C11 118.7(6) . .
C13 C12 H12 120.6 . .
C11 C12 H12 120.6 . .
C14 C13 C12 122.1(6) . .
C14 C13 H13 119.0 . .
C12 C13 H13 119.0 . .
C13 C14 C9 119.7(6) . .
C13 C14 C16 116.7(6) . .
C9 C14 C16 123.3(6) . .
O10 C15 O9 124.3(5) . .
O10 C15 C10 117.3(5) . .
O9 C15 C10 118.5(5) . .
O12 C16 O11 123.9(6) . .
O12 C16 C14 116.8(6) . .
O11 C16 C14 119.1(5) . .
N1 C17 C18 179.1(18) . .
C17 C18 H18A 109.5 . .
C17 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C17 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
U1 O1 1.758(4) .
U1 O2 1.764(4) .
U1 O5 2.345(4) .
U1 O9 2.357(4) .
U1 O6 2.368(4) 2_667
U1 O10 2.407(4) 2_657
U1 O13 2.458(5) .
U2 O4 1.761(5) .
U2 O3 1.768(6) .
U2 O7 2.335(5) .
U2 O11 2.369(5) .
U2 O12 2.400(5) 2_766
U2 O14 2.466(6) .
U2 O15 2.489(5) .
O5 C7 1.271(7) .
O6 C7 1.255(6) .
O6 U1 2.368(4) 2_667
O7 C8 1.299(8) .
O8 C8 1.217(8) .
O9 C15 1.268(7) .
O10 C15 1.249(6) .
O10 U1 2.407(4) 2_657
O11 C16 1.267(8) .
O12 C16 1.246(8) .
O12 U2 2.400(5) 2_766
O13 H13A 0.8936 .
O13 H13B 0.9213 .
O14 H14A 0.9192 .
O14 H14B 0.9136 .
O15 H15A 0.8811 .
O15 H15B 0.9947 .
N1 C17 1.124(8) .
C1 C6 1.396(8) .
C1 C2 1.408(8) .
C1 C9 1.491(8) .
C2 C3 1.383(8) .
C2 C7 1.497(7) .
C3 C4 1.394(9) .
C3 H3 0.9500 .
C4 C5 1.375(10) .
C4 H4 0.9500 .
C5 C6 1.391(9) .
C5 H5 0.9500 .
C6 C8 1.508(8) .
C9 C10 1.397(7) .
C9 C14 1.414(8) .
C10 C11 1.390(8) .
C10 C15 1.495(7) .
C11 C12 1.384(9) .
C11 H11 0.9500 .
C12 C13 1.382(10) .
C12 H12 0.9500 .
C13 C14 1.380(10) .
C13 H13 0.9500 .
C14 C16 1.508(9) .
C17 C18 1.526(9) .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
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
O13 H13A O8 0.89 1.85 2.716(8) 164.3 2_657
O13 H13B O16 0.92 1.84 2.718(8) 159.5 .
O14 H14A O13 0.92 2.31 3.111(11) 145.4 1_654
O14 H14A O2 0.92 2.52 3.125(7) 123.5 1_654
O14 H14B N1 0.91 1.91 2.795(15) 164.1 2_766
O15 H15A O7 0.88 1.95 2.780(8) 157.2 2_756
O15 H15B N1 0.99 1.90 2.814(12) 151.9 1_645
