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#$Date: 2017-07-04 11:21:31 +0300 (Tue, 04 Jul 2017) $
#$Revision: 198368 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/34/59/4345904.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_4345904
loop_
_publ_author_name
'Pedrick, Elizabeth A.'
'Assefa, Mikiyas K.'
'Wakefield, Megan E.'
'Wu, Guang'
'Hayton, Trevor W.'
_publ_section_title
;
 Uranyl Coordination by the 14-Membered Macrocycle
 Dibenzotetramethyltetraaza[14]annulene.
;
_journal_issue                   11
_journal_name_full               'Inorganic chemistry'
_journal_page_first              6638
_journal_page_last               6644
_journal_paper_doi               10.1021/acs.inorgchem.7b00700
_journal_volume                  56
_journal_year                    2017
_chemical_formula_sum            'C44 H46 N8 O2 U'
_chemical_formula_weight         956.92
_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   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                91.799(15)
_cell_angle_beta                 94.571(15)
_cell_angle_gamma                90.844(15)
_cell_formula_units_Z            1
_cell_length_a                   8.538(7)
_cell_length_b                   9.684(7)
_cell_length_c                   11.786(9)
_cell_measurement_reflns_used    8057
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.9
_cell_measurement_theta_min      1.5
_cell_volume                     970.8(13)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1286
_diffrn_reflns_av_unetI/netI     0.1923
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_number            12025
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.304
_diffrn_reflns_theta_min         1.734
_exptl_absorpt_coefficient_mu    4.229
_exptl_absorpt_correction_T_max  0.745369
_exptl_absorpt_correction_T_min  0.487483
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   twinabs
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.637
_exptl_crystal_description       block
_exptl_crystal_F_000             474
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         3.938
_refine_diff_density_min         -3.120
_refine_diff_density_rms         0.263
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3860
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.1252
_refine_ls_R_factor_gt           0.0781
_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)+(0.1083P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1697
_refine_ls_wR_factor_ref         0.1853
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2960
_reflns_number_total             3860
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ic7b00700_si_001.cif
_cod_data_source_block           twin4_a
_cod_database_code               4345904
_shelx_shelxl_version_number     2014/7
_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.
;
_shelx_estimated_absorpt_t_min   0.364
_shelx_estimated_absorpt_t_max   0.485
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
_atom_site_refinement_flags_occupancy
C1 C 0.3041(13) 0.8054(11) 0.4734(9) 0.026(3) Uani 1 1 d . . .
C2 C 0.3361(13) 0.8261(11) 0.3623(10) 0.027(2) Uani 1 1 d . . .
H2 H 0.3546 0.7480 0.3147 0.032 Uiso 1 1 calc R U .
C3 C 0.3421(13) 0.9554(12) 0.3180(10) 0.030(3) Uani 1 1 d . . .
H3 H 0.3646 0.9657 0.2410 0.037 Uiso 1 1 calc R U .
C4 C 0.3160(13) 1.0681(12) 0.3843(10) 0.030(3) Uani 1 1 d . . .
H4 H 0.3147 1.1574 0.3531 0.036 Uiso 1 1 calc R U .
C5 C 0.2915(12) 1.0526(11) 0.4968(9) 0.024(2) Uani 1 1 d . . .
H5 H 0.2769 1.1322 0.5437 0.029 Uiso 1 1 calc R U .
C6 C 0.2877(12) 0.9230(12) 0.5434(10) 0.028(3) Uani 1 1 d . . .
C7 C 0.2051(13) 0.9642(12) 0.7421(10) 0.031(3) Uani 1 1 d . . .
C8 C 0.0850(14) 1.0687(13) 0.7097(12) 0.039(3) Uani 1 1 d . . .
H8A H 0.0087 1.0741 0.7675 0.059 Uiso 1 1 calc R U .
H8B H 0.0306 1.0417 0.6358 0.059 Uiso 1 1 calc R U .
H8C H 0.1365 1.1591 0.7044 0.059 Uiso 1 1 calc R U .
C9 C 0.2403(13) 0.9347(12) 0.8531(10) 0.031(3) Uani 1 1 d . . .
H9 H 0.1799 0.9785 0.9077 0.037 Uiso 1 1 calc R U .
C10 C 0.3597(14) 0.8441(13) 0.8947(10) 0.034(3) Uani 1 1 d . . .
C11 C 0.3822(15) 0.8241(15) 1.0199(10) 0.041(3) Uani 1 1 d . . .
H11A H 0.4420 0.7400 1.0343 0.061 Uiso 1 1 calc R U .
H11B H 0.2794 0.8154 1.0508 0.061 Uiso 1 1 calc R U .
H11C H 0.4399 0.9038 1.0567 0.061 Uiso 1 1 calc R U .
C12 C 0.5823(12) 0.7066(12) 0.8455(10) 0.028(3) Uani 1 1 d . . .
C13 C 0.7080(14) 0.7599(14) 0.9218(10) 0.035(3) Uani 1 1 d . . .
H13 H 0.6944 0.8411 0.9670 0.042 Uiso 1 1 calc R U .
C14 C 0.8499(14) 0.6925(14) 0.9294(11) 0.039(3) Uani 1 1 d . . .
H14 H 0.9331 0.7280 0.9809 0.047 Uiso 1 1 calc R U .
C15 C 0.8733(13) 0.5780(14) 0.8656(11) 0.039(3) Uani 1 1 d . . .
H15 H 0.9709 0.5320 0.8730 0.047 Uiso 1 1 calc R U .
C16 C 0.7521(13) 0.5283(13) 0.7889(11) 0.035(3) Uani 1 1 d . . .
H16 H 0.7703 0.4508 0.7405 0.042 Uiso 1 1 calc R U .
C17 C 0.6059(12) 0.5880(12) 0.7809(9) 0.025(3) Uani 1 1 d . . .
C18 C 0.3395(13) 0.5213(11) 0.7336(10) 0.028(3) Uani 1 1 d . . .
C19 C 0.2026(12) 0.5415(11) 0.6667(10) 0.027(3) Uani 1 1 d . . .
H19 H 0.1127 0.4888 0.6827 0.032 Uiso 1 1 calc R U .
C20 C 0.1847(12) 0.6326(11) 0.5774(9) 0.023(2) Uani 1 1 d . . .
C21 C 0.3221(14) 0.4731(15) 0.8529(11) 0.043(3) Uani 1 1 d . . .
H21A H 0.4262 0.4554 0.8903 0.065 Uiso 1 1 calc R U .
H21B H 0.2582 0.3880 0.8492 0.065 Uiso 1 1 calc R U .
H21C H 0.2708 0.5448 0.8965 0.065 Uiso 1 1 calc R U .
C22 C 0.0234(13) 0.6922(12) 0.5530(10) 0.031(3) Uani 1 1 d . . .
H22A H 0.0138 0.7760 0.6005 0.046 Uiso 1 1 calc R U .
H22B H -0.0568 0.6242 0.5702 0.046 Uiso 1 1 calc R U .
H22C H 0.0084 0.7150 0.4725 0.046 Uiso 1 1 calc R U .
N1 N 0.3078(11) 0.6683(10) 0.5199(8) 0.028(2) Uani 1 1 d . . .
N2 N 0.4832(10) 0.5403(9) 0.6997(8) 0.025(2) Uani 1 1 d . . .
N3 N 0.2855(10) 0.9014(10) 0.6605(8) 0.027(2) Uani 1 1 d . . .
N4 N 0.4464(11) 0.7818(10) 0.8238(8) 0.030(2) Uani 1 1 d . . .
H4A H 0.4144 0.7883 0.7513 0.036 Uiso 1 1 calc R U .
O1 O 0.3550(8) 0.3696(7) 0.4949(6) 0.0235(16) Uiso 1 1 d . . .
U1 U 0.5000 0.5000 0.5000 0.0254(2) Uani 1 2 d S . P
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
C2 C1 C6 117.3(10) . .
C2 C1 N1 121.2(10) . .
C6 C1 N1 121.0(9) . .
C3 C2 C1 122.4(11) . .
C3 C2 H2 118.8 . .
C1 C2 H2 118.8 . .
C4 C3 C2 119.8(11) . .
C4 C3 H3 120.1 . .
C2 C3 H3 120.1 . .
C3 C4 C5 119.6(11) . .
C3 C4 H4 120.2 . .
C5 C4 H4 120.2 . .
C4 C5 C6 121.3(11) . .
C4 C5 H5 119.3 . .
C6 C5 H5 119.3 . .
C5 C6 C1 119.4(10) . .
C5 C6 N3 123.8(11) . .
C1 C6 N3 116.5(9) . .
N3 C7 C9 119.4(10) . .
N3 C7 C8 119.8(10) . .
C9 C7 C8 120.8(10) . .
C7 C8 H8A 109.5 . .
C7 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C7 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C7 C9 C10 125.7(10) . .
C7 C9 H9 117.1 . .
C10 C9 H9 117.1 . .
N4 C10 C9 119.7(11) . .
N4 C10 C11 121.8(11) . .
C9 C10 C11 118.4(10) . .
C10 C11 H11A 109.5 . .
C10 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C10 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C17 C12 N4 119.8(10) . .
C17 C12 C13 118.8(10) . .
N4 C12 C13 120.8(11) . .
C14 C13 C12 119.5(12) . .
C14 C13 H13 120.3 . .
C12 C13 H13 120.3 . .
C15 C14 C13 121.7(13) . .
C15 C14 H14 119.1 . .
C13 C14 H14 119.1 . .
C14 C15 C16 118.8(11) . .
C14 C15 H15 120.6 . .
C16 C15 H15 120.6 . .
C17 C16 C15 122.0(11) . .
C17 C16 H16 119.0 . .
C15 C16 H16 119.0 . .
C16 C17 C12 119.1(11) . .
C16 C17 N2 122.1(10) . .
C12 C17 N2 118.5(9) . .
N2 C18 C19 124.4(10) . .
N2 C18 C21 119.0(10) . .
C19 C18 C21 116.6(10) . .
C18 C19 C20 125.6(10) . .
C18 C19 H19 117.2 . .
C20 C19 H19 117.2 . .
N1 C20 C19 120.6(9) . .
N1 C20 C22 122.5(9) . .
C19 C20 C22 116.8(9) . .
C18 C21 H21A 109.5 . .
C18 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C18 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
C20 C22 H22A 109.5 . .
C20 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
C20 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
C20 N1 C1 116.0(9) . .
C20 N1 U1 116.6(7) . .
C1 N1 U1 127.3(6) . .
C18 N2 C17 118.9(9) . .
C18 N2 U1 114.0(7) . .
C17 N2 U1 127.0(6) . .
C7 N3 C6 131.7(9) . .
C10 N4 C12 129.5(10) . .
C10 N4 H4A 115.2 . .
C12 N4 H4A 115.2 . .
O1 U1 O1 180.0 2_666 .
O1 U1 N1 89.8(3) 2_666 .
O1 U1 N1 90.2(3) . .
O1 U1 N1 90.2(3) 2_666 2_666
O1 U1 N1 89.8(3) . 2_666
N1 U1 N1 180.0(3) . 2_666
O1 U1 N2 91.7(3) 2_666 2_666
O1 U1 N2 88.3(3) . 2_666
N1 U1 N2 106.8(3) . 2_666
N1 U1 N2 73.2(3) 2_666 2_666
O1 U1 N2 88.3(3) 2_666 .
O1 U1 N2 91.7(3) . .
N1 U1 N2 73.2(3) . .
N1 U1 N2 106.8(3) 2_666 .
N2 U1 N2 180.0(4) 2_666 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.378(15) .
C1 C6 1.401(15) .
C1 N1 1.452(14) .
C2 C3 1.374(16) .
C2 H2 0.9500 .
C3 C4 1.355(16) .
C3 H3 0.9500 .
C4 C5 1.371(15) .
C4 H4 0.9500 .
C5 C6 1.387(15) .
C5 H5 0.9500 .
C6 N3 1.403(15) .
C7 N3 1.359(14) .
C7 C9 1.360(16) .
C7 C8 1.488(14) .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 C10 1.423(15) .
C9 H9 0.9500 .
C10 N4 1.300(15) .
C10 C11 1.491(16) .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C12 C17 1.384(16) .
C12 N4 1.390(13) .
C12 C13 1.423(17) .
C13 C14 1.383(16) .
C13 H13 0.9500 .
C14 C15 1.346(18) .
C14 H14 0.9500 .
C15 C16 1.389(18) .
C15 H15 0.9500 .
C16 C17 1.381(14) .
C16 H16 0.9500 .
C17 N2 1.423(15) .
C18 N2 1.333(14) .
C18 C19 1.377(15) .
C18 C21 1.513(16) .
C19 C20 1.395(15) .
C19 H19 0.9500 .
C20 N1 1.342(14) .
C20 C22 1.511(14) .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
N1 U1 2.350(9) .
N2 U1 2.389(9) .
N4 H4A 0.8800 .
O1 U1 1.752(7) .
U1 O1 1.752(7) 2_666
U1 N1 2.350(9) 2_666
U1 N2 2.389(9) 2_666
