#------------------------------------------------------------------------------
#$Date: 2019-11-07 22:26:13 +0200 (Thu, 07 Nov 2019) $
#$Revision: 223784 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/04/96/7049652.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_7049652
loop_
_publ_author_name
'Thuéry, Pierre'
'Atoini, Youssef'
'Harrowfield, Jack'
_publ_section_title
;
 The sulfonate group as a ligand: a fine balance between hydrogen bonding
 and metal ion coordination in uranyl ion complexes.
;
_journal_issue                   24
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              8756
_journal_page_last               8772
_journal_paper_doi               10.1039/c9dt01024f
_journal_volume                  48
_journal_year                    2019
_chemical_formula_sum            'C28 H42 N6 Ni O14 S2 U'
_chemical_formula_weight         1047.53
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2019-01-23 deposited with the CCDC.    2019-04-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.972(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.4686(3)
_cell_length_b                   9.9123(4)
_cell_length_c                   21.7475(8)
_cell_measurement_reflns_used    48315
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.68
_cell_measurement_theta_min      2.78
_cell_volume                     1821.17(12)
_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 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
'Nonius Kappa-CCD area-detector diffractometer'
_diffrn_measurement_method
'two φ and three ω scans with 2° steps (392 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  0.0247
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_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       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            48315
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.679
_diffrn_reflns_theta_min         2.784
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.146
_exptl_absorpt_correction_T_max  0.512
_exptl_absorpt_correction_T_min  0.428
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            'translucent light orange'
_exptl_crystal_density_diffrn    1.910
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         1.292
_refine_diff_density_min         -1.352
_refine_diff_density_rms         0.138
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3452
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0267
_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)+(0.0475P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0689
_refine_ls_wR_factor_ref         0.0720
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2865
_reflns_number_total             3452
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9dt01024f1.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7049652--7049661.cif.'
_cod_database_code               7049652
_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
_atom_site_refinement_flags_occupancy
U1 U 0.5000 0.5000 0.5000 0.02100(9) Uani 1 2 d S . P
Ni1 Ni 0.0000 0.5000 1.0000 0.02628(17) Uani 1 2 d S . P
S1 S 0.35397(10) 0.46614(10) 0.90062(4) 0.02699(18) Uani 1 1 d . . .
O1 O 0.6987(2) 0.5481(2) 0.51801(9) 0.0279(4) Uani 1 1 d . . .
O2 O 0.5147(2) 0.3952(2) 0.60337(9) 0.0286(5) Uani 1 1 d . . .
O3 O 0.4017(2) 0.5941(2) 0.59737(9) 0.0275(5) Uani 1 1 d . . .
O4 O 0.2515(3) 0.5730(2) 0.91615(10) 0.0420(6) Uani 1 1 d . . .
O5 O 0.2938(3) 0.3339(2) 0.91480(11) 0.0527(7) Uani 1 1 d . . .
O6 O 0.5137(4) 0.4820(4) 0.92615(16) 0.0938(18) Uani 1 1 d . U .
O7 O 0.4388(3) 0.7406(2) 0.49666(9) 0.0298(5) Uani 1 1 d . . .
H7A H 0.4198 0.7937 0.4646 0.036 Uiso 1 1 d R U .
H7B H 0.4981 0.7785 0.5281 0.036 Uiso 1 1 d R U .
N1 N -0.0488(3) 0.6925(3) 0.99759(12) 0.0316(6) Uani 1 1 d . . .
H1 H -0.1458 0.6897 1.0172 0.038 Uiso 1 1 d R U .
N2 N -0.1389(3) 0.4641(3) 0.92725(14) 0.0321(6) Uani 1 1 d . . .
H2 H -0.2356 0.4715 0.9373 0.039 Uiso 1 1 d R U .
N3 N 0.0605(4) 0.8526(3) 0.77354(16) 0.0512(8) Uani 1 1 d . . .
C1 C 0.4441(4) 0.4909(2) 0.62828(18) 0.0232(8) Uani 1 1 d . . .
C2 C 0.4106(4) 0.4799(3) 0.69487(16) 0.0227(7) Uani 1 1 d . . .
C3 C 0.4823(3) 0.3783(3) 0.73107(13) 0.0265(6) Uani 1 1 d . . .
H3 H 0.5460 0.3127 0.7128 0.032 Uiso 1 1 calc R U .
C4 C 0.4615(3) 0.3722(3) 0.79330(13) 0.0262(6) Uani 1 1 d . . .
H4 H 0.5104 0.3027 0.8179 0.031 Uiso 1 1 calc R U .
C5 C 0.3681(4) 0.4689(3) 0.81967(15) 0.0230(6) Uani 1 1 d . . .
C6 C 0.2911(3) 0.5671(3) 0.78374(13) 0.0236(6) Uani 1 1 d . . .
H6 H 0.2237 0.6301 0.8018 0.028 Uiso 1 1 calc R U .
C7 C 0.3128(3) 0.5732(3) 0.72143(13) 0.0238(6) Uani 1 1 d . . .
H7 H 0.2611 0.6411 0.6967 0.029 Uiso 1 1 calc R U .
C8 C -0.0625(4) 0.7636(4) 0.93765(18) 0.0429(10) Uani 1 1 d . . .
H8A H 0.0407 0.7608 0.9189 0.051 Uiso 1 1 calc R U .
H8B H -0.0896 0.8594 0.9444 0.051 Uiso 1 1 calc R U .
C9 C -0.1875(4) 0.7007(4) 0.89399(17) 0.0484(10) Uani 1 1 d . . .
H9A H -0.2891 0.6989 0.9139 0.058 Uiso 1 1 calc R U .
H9B H -0.2024 0.7576 0.8566 0.058 Uiso 1 1 calc R U .
C10 C -0.1471(4) 0.5599(4) 0.87519(16) 0.0432(9) Uani 1 1 d . . .
H10A H -0.2279 0.5283 0.8434 0.052 Uiso 1 1 calc R U .
H10B H -0.0437 0.5611 0.8565 0.052 Uiso 1 1 calc R U .
C11 C -0.1033(4) 0.3270(4) 0.90518(18) 0.0497(10) Uani 1 1 d . . .
H11A H -0.0102 0.3297 0.8801 0.060 Uiso 1 1 calc R U .
H11B H -0.1946 0.2917 0.8792 0.060 Uiso 1 1 calc R U .
C12 C -0.0703(4) 0.2380(4) 0.9597(2) 0.0495(11) Uani 1 1 d . . .
H12A H -0.0283 0.1500 0.9467 0.059 Uiso 1 1 calc R U .
H12B H -0.1687 0.2215 0.9806 0.059 Uiso 1 1 calc R U .
C13 C 0.1060(4) 0.9550(5) 0.79009(17) 0.0378(8) Uani 1 1 d . . .
C14 C 0.1643(5) 1.0879(4) 0.8096(2) 0.0544(11) Uani 1 1 d . . .
H14A H 0.2632 1.1070 0.7904 0.082 Uiso 1 1 calc R U .
H14B H 0.1835 1.0894 0.8545 0.082 Uiso 1 1 calc R U .
H14C H 0.0852 1.1564 0.7969 0.082 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'
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'
Ni Ni 0.3393 1.1124 '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
O1 U1 O1 180.0 3_666 .
O1 U1 O7 93.44(9) 3_666 .
O1 U1 O7 86.56(9) . .
O1 U1 O7 86.56(9) 3_666 3_666
O1 U1 O7 93.44(9) . 3_666
O7 U1 O7 180.0 . 3_666
O1 U1 O2 94.33(8) 3_666 .
O1 U1 O2 85.67(8) . .
O7 U1 O2 115.78(6) . .
O7 U1 O2 64.22(6) 3_666 .
O1 U1 O2 85.67(8) 3_666 3_666
O1 U1 O2 94.33(8) . 3_666
O7 U1 O2 64.22(6) . 3_666
O7 U1 O2 115.78(6) 3_666 3_666
O2 U1 O2 180.0 . 3_666
O1 U1 O3 94.55(8) 3_666 3_666
O1 U1 O3 85.45(8) . 3_666
O7 U1 O3 114.86(7) . 3_666
O7 U1 O3 65.14(7) 3_666 3_666
O2 U1 O3 127.80(7) . 3_666
O2 U1 O3 52.20(7) 3_666 3_666
O1 U1 O3 85.46(8) 3_666 .
O1 U1 O3 94.55(8) . .
O7 U1 O3 65.14(7) . .
O7 U1 O3 114.86(7) 3_666 .
O2 U1 O3 52.20(7) . .
O2 U1 O3 127.80(7) 3_666 .
O3 U1 O3 180.0 3_666 .
N2 Ni1 N2 180.0 3_567 .
N2 Ni1 N1 87.58(12) 3_567 .
N2 Ni1 N1 92.42(12) . .
N2 Ni1 N1 92.42(12) 3_567 3_567
N2 Ni1 N1 87.58(12) . 3_567
N1 Ni1 N1 180.0 . 3_567
O4 S1 O6 113.6(2) . .
O4 S1 O5 113.18(15) . .
O6 S1 O5 110.7(2) . .
O4 S1 C5 107.93(15) . .
O6 S1 C5 104.82(18) . .
O5 S1 C5 105.94(15) . .
C1 O2 U1 94.54(19) . .
C1 O3 U1 92.8(2) . .
U1 O7 H7A 129.4 . .
U1 O7 H7B 106.2 . .
H7A O7 H7B 114.5 . .
C8 N1 C12 109.7(3) . 3_567
C8 N1 Ni1 119.5(2) . .
C12 N1 Ni1 107.6(2) 3_567 .
C8 N1 H1 113.0 . .
C12 N1 H1 107.5 3_567 .
Ni1 N1 H1 98.5 . .
C10 N2 C11 110.0(3) . .
C10 N2 Ni1 120.1(2) . .
C11 N2 Ni1 107.9(2) . .
C10 N2 H2 98.4 . .
C11 N2 H2 112.2 . .
Ni1 N2 H2 108.0 . .
O3 C1 O2 120.4(3) . .
O3 C1 C2 120.5(3) . .
O2 C1 C2 119.1(3) . .
C3 C2 C7 119.6(3) . .
C3 C2 C1 119.7(3) . .
C7 C2 C1 120.7(3) . .
C4 C3 C2 120.4(3) . .
C4 C3 H3 119.8 . .
C2 C3 H3 119.8 . .
C3 C4 C5 119.3(3) . .
C3 C4 H4 120.3 . .
C5 C4 H4 120.3 . .
C6 C5 C4 120.7(3) . .
C6 C5 S1 120.7(2) . .
C4 C5 S1 118.5(2) . .
C7 C6 C5 119.7(3) . .
C7 C6 H6 120.1 . .
C5 C6 H6 120.1 . .
C6 C7 C2 120.1(3) . .
C6 C7 H7 120.0 . .
C2 C7 H7 120.0 . .
N1 C8 C9 111.5(3) . .
N1 C8 H8A 109.3 . .
C9 C8 H8A 109.3 . .
N1 C8 H8B 109.3 . .
C9 C8 H8B 109.3 . .
H8A C8 H8B 108.0 . .
C10 C9 C8 113.2(3) . .
C10 C9 H9A 108.9 . .
C8 C9 H9A 108.9 . .
C10 C9 H9B 108.9 . .
C8 C9 H9B 108.9 . .
H9A C9 H9B 107.8 . .
N2 C10 C9 112.9(3) . .
N2 C10 H10A 109.0 . .
C9 C10 H10A 109.0 . .
N2 C10 H10B 109.0 . .
C9 C10 H10B 109.0 . .
H10A C10 H10B 107.8 . .
N2 C11 C12 108.5(3) . .
N2 C11 H11A 110.0 . .
C12 C11 H11A 110.0 . .
N2 C11 H11B 110.0 . .
C12 C11 H11B 110.0 . .
H11A C11 H11B 108.4 . .
C11 C12 N1 107.7(3) . 3_567
C11 C12 H12A 110.2 . .
N1 C12 H12A 110.2 3_567 .
C11 C12 H12B 110.2 . .
N1 C12 H12B 110.2 3_567 .
H12A C12 H12B 108.5 . .
N3 C13 C14 178.4(4) . .
C13 C14 H14A 109.5 . .
C13 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C13 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 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 1.766(2) 3_666
U1 O1 1.766(2) .
U1 O7 2.441(2) .
U1 O7 2.441(2) 3_666
U1 O2 2.4717(19) .
U1 O2 2.4717(19) 3_666
U1 O3 2.5082(19) 3_666
U1 O3 2.5083(19) .
Ni1 N2 1.938(3) 3_567
Ni1 N2 1.938(3) .
Ni1 N1 1.952(3) .
Ni1 N1 1.952(3) 3_567
S1 O4 1.424(2) .
S1 O6 1.435(3) .
S1 O5 1.447(3) .
S1 C5 1.773(3) .
O2 C1 1.263(4) .
O3 C1 1.262(4) .
O7 H7A 0.8798 .
O7 H7B 0.9011 .
N1 C8 1.480(4) .
N1 C12 1.492(5) 3_567
N1 H1 0.9521 .
N2 C10 1.476(5) .
N2 C11 1.479(5) .
N2 H2 0.8651 .
N3 C13 1.135(5) .
C1 C2 1.499(5) .
C2 C3 1.391(4) .
C2 C7 1.393(4) .
C3 C4 1.378(4) .
C3 H3 0.9500 .
C4 C5 1.392(4) .
C4 H4 0.9500 .
C5 C6 1.383(4) .
C6 C7 1.381(4) .
C6 H6 0.9500 .
C7 H7 0.9500 .
C8 C9 1.508(6) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 C10 1.500(6) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 C12 1.489(6) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 N1 1.492(5) 3_567
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 C14 1.459(6) .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 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
O7 H7A O4 0.88 2.16 2.934(3) 146.0 4_575
O7 H7A O6 0.88 2.52 3.232(4) 138.1 4_575
O7 H7B O5 0.90 2.16 3.014(4) 159.0 2_656
O7 H7B O6 0.90 2.26 2.935(4) 131.9 2_656
N1 H1 O5 0.95 2.02 2.924(3) 158.6 3_567
N2 H2 O6 0.87 2.12 2.945(4) 158.6 1_455
C8 H8A O4 0.99 2.58 3.322(4) 131.4 .
C12 H12B O7 0.99 2.38 3.324(5) 159.0 2_546
