#------------------------------------------------------------------------------
#$Date: 2016-03-22 21:15:57 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179016 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/14/4121480.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_4121480
loop_
_publ_author_name
'Ho, I-Ting'
'Zhang, Zhan'
'Ishida, Masatoshi'
'Lynch, Vincent M.'
'Cha, Won-Young'
'Sung, Young Mo'
'Kim, Dongho'
'Sessler, Jonathan L.'
_publ_section_title
;
 A Hybrid Macrocycle with a Pyridine Subunit Displays Aromatic Character
 upon Uranyl Cation Complexation.
;
_journal_issue                   11
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4281
_journal_page_last               4286
_journal_paper_doi               10.1021/ja412520g
_journal_volume                  136
_journal_year                    2014
_chemical_formula_sum            'C48 H0 N9 O4 S0'
_chemical_formula_weight         766.57
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_space_group_name_H-M   'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.766(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.1607(9)
_cell_length_b                   21.6697(14)
_cell_length_c                   16.7388(9)
_cell_measurement_temperature    100(2)
_cell_volume                     4918.1(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0561
_diffrn_reflns_av_sigmaI/netI    0.0321
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            45270
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         1.58
_exptl_absorpt_coefficient_mu    0.070
_exptl_crystal_density_diffrn    1.035
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1532
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.762
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         5620
_refine_ls_number_restraints     210
_refine_ls_restrained_S_all      0.760
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0550
_refine_ls_shift/su_max          0.178
_refine_ls_shift/su_mean         0.030
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1490P)²+12.2899P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1688
_refine_ls_wR_factor_ref         0.1778
_reflns_number_gt                5258
_reflns_number_total             5620
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja412520g_si_002.cif
_cod_data_source_block           shelxl
_cod_database_code               4121480
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.2500 0.83468(14) 0.0000 0.0394(8) Uani 1 2 d SU
H1 H 0.2500 0.8785 0.0000 0.047 Uiso 1 2 calc SR
C2 C 0.22124(18) 0.80335(10) 0.06115(14) 0.0342(5) Uani 1 1 d U
H2 H 0.2020 0.8251 0.1033 0.041 Uiso 1 1 calc R
C3 C 0.22124(14) 0.73860(9) 0.05922(13) 0.0255(4) Uani 1 1 d U
C4 C 0.19197(14) 0.69834(9) 0.11886(12) 0.0245(4) Uani 1 1 d U
C5 C 0.14055(15) 0.70619(9) 0.17817(13) 0.0276(4) Uani 1 1 d U
C6 C 0.13200(15) 0.64734(9) 0.21274(12) 0.0262(4) Uani 1 1 d U
C7 C 0.17934(14) 0.60473(9) 0.17461(12) 0.0235(4) Uani 1 1 d U
C8 C 0.19321(13) 0.53816(9) 0.18027(11) 0.0215(4) Uani 1 1 d U
C9 C 0.20433(14) 0.49462(9) 0.24350(12) 0.0226(4) Uani 1 1 d U
C10 C 0.21633(14) 0.43560(9) 0.20951(12) 0.0226(4) Uani 1 1 d U
C11 C 0.21369(14) 0.44511(9) 0.12619(12) 0.0216(4) Uani 1 1 d U
C12 C 0.23295(14) 0.40774(9) 0.06085(11) 0.0223(4) Uani 1 1 d U
C13 C 0.23905(16) 0.34744(9) 0.03931(13) 0.0283(4) Uani 1 1 d U
H13 H 0.2305 0.3122 0.0703 0.034 Uiso 1 1 calc R
C14 C 0.09470(17) 0.76443(10) 0.19978(15) 0.0351(5) Uani 1 1 d U
H14A H 0.1335 0.8005 0.1909 0.042 Uiso 1 1 calc R
H14B H 0.0975 0.7634 0.2595 0.042 Uiso 1 1 calc R
C15 C -0.0121(2) 0.77219(15) 0.1474(2) 0.0621(9) Uani 1 1 d U
H15A H -0.0144 0.7793 0.0890 0.093 Uiso 1 1 calc R
H15B H -0.0413 0.8076 0.1680 0.093 Uiso 1 1 calc R
H15C H -0.0493 0.7348 0.1514 0.093 Uiso 1 1 calc R
C16 C 0.07340(16) 0.63269(11) 0.27252(14) 0.0319(5) Uani 1 1 d U
H16A H 0.0543 0.6718 0.2943 0.038 Uiso 1 1 calc R
H16B H 0.1156 0.6092 0.3204 0.038 Uiso 1 1 calc R
C17 C -0.01965(18) 0.59510(12) 0.23207(16) 0.0400(5) Uani 1 1 d U
H17A H -0.0639 0.6192 0.1871 0.060 Uiso 1 1 calc R
H17B H -0.0533 0.5852 0.2741 0.060 Uiso 1 1 calc R
H17C H -0.0014 0.5568 0.2091 0.060 Uiso 1 1 calc R
C18 C 0.20464(15) 0.50758(10) 0.33066(12) 0.0288(4) Uani 1 1 d U
C19 C 0.1195(2) 0.4863(2) 0.43173(18) 0.0736(11) Uani 1 1 d U
H19A H 0.1844 0.4797 0.4733 0.088 Uiso 1 1 calc R
H19B H 0.0973 0.5287 0.4387 0.088 Uiso 1 1 calc R
C20 C 0.0486(4) 0.44189(15) 0.4451(3) 0.0843(14) Uani 1 1 d U
H20A H -0.0162 0.4498 0.4055 0.126 Uiso 1 1 calc R
H20B H 0.0441 0.4459 0.5022 0.126 Uiso 1 1 calc R
H20C H 0.0700 0.4000 0.4366 0.126 Uiso 1 1 calc R
C21 C 0.23689(15) 0.37554(9) 0.25100(12) 0.0262(4) Uani 1 1 d U
C22 C 0.29242(18) 0.32312(11) 0.38101(14) 0.0358(5) Uani 1 1 d U
H22A H 0.2457 0.2908 0.3519 0.043 Uiso 1 1 calc R
H22B H 0.2846 0.3285 0.4375 0.043 Uiso 1 1 calc R
C23 C 0.39619(18) 0.30301(11) 0.38825(15) 0.0360(5) Uani 1 1 d U
H23A H 0.4010 0.2909 0.3332 0.054 Uiso 1 1 calc R
H23B H 0.4136 0.2678 0.4265 0.054 Uiso 1 1 calc R
H23C H 0.4417 0.3372 0.4098 0.054 Uiso 1 1 calc R
C24 C 0.95410(19) 0.41424(15) 0.20158(16) 0.0464(6) Uani 1 1 d U
H24A H 0.9250 0.4501 0.2212 0.070 Uiso 1 1 calc R
H24B H 1.0210 0.4075 0.2382 0.070 Uiso 1 1 calc R
H24C H 0.9137 0.3777 0.2025 0.070 Uiso 1 1 calc R
C25 C 0.99287(19) 0.35225(12) 0.0743(2) 0.0518(7) Uani 1 1 d U
H25A H 0.9428 0.3227 0.0799 0.078 Uiso 1 1 calc R
H25B H 1.0568 0.3414 0.1133 0.078 Uiso 1 1 calc R
H25C H 0.9978 0.3510 0.0171 0.078 Uiso 1 1 calc R
N1 N 0.2500 0.70766(10) 0.0000 0.0244(5) Uani 1 2 d SU
N2 N 0.21452(12) 0.63688(7) 0.11788(10) 0.0232(3) Uani 1 1 d U
H2A H 0.2469 0.6202 0.0856 0.028 Uiso 1 1 calc R
N3 N 0.19810(11) 0.50651(7) 0.11042(10) 0.0209(3) Uani 1 1 d U
H3 H 0.1919 0.5238 0.0616 0.025 Uiso 1 1 calc R
O1 O 0.2500 0.44461(8) 0.0000 0.0221(4) Uani 1 2 d SU
O2 O 0.26277(12) 0.53983(9) 0.37927(10) 0.0397(4) Uani 1 1 d U
O3 O 0.12850(11) 0.47855(9) 0.34786(9) 0.0388(4) Uani 1 1 d U
O4 O 0.22734(12) 0.32626(7) 0.21484(10) 0.0338(4) Uani 1 1 d U
O5 O 0.26952(12) 0.38098(7) 0.33506(9) 0.0311(3) Uani 1 1 d U
O6 O 0.85236(10) 0.43503(6) 0.04686(9) 0.0260(3) Uani 1 1 d U
S1 S 0.95877(4) 0.42783(2) 0.09702(3) 0.02626(16) Uani 1 1 d 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'
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 C2 121.2(3) . 2
C2 C1 H1 119.4 . .
C2 C1 H1 119.4 2 .
C1 C2 C3 118.1(2) . .
C1 C2 H2 120.9 . .
C3 C2 H2 120.9 . .
N1 C3 C2 120.9(2) . .
N1 C3 C4 113.95(17) . .
C2 C3 C4 125.10(19) . .
N2 C4 C5 107.29(17) . .
N2 C4 C3 117.09(17) . .
C5 C4 C3 135.57(18) . .
C4 C5 C6 107.62(17) . .
C4 C5 C14 128.2(2) . .
C6 C5 C14 124.04(19) . .
C7 C6 C5 107.36(17) . .
C7 C6 C16 126.32(19) . .
C5 C6 C16 126.01(18) . .
N2 C7 C6 107.23(17) . .
N2 C7 C8 118.42(16) . .
C6 C7 C8 134.28(18) . .
N3 C8 C9 106.63(16) . .
N3 C8 C7 118.57(16) . .
C9 C8 C7 134.79(17) . .
C8 C9 C10 107.69(16) . .
C8 C9 C18 125.91(18) . .
C10 C9 C18 126.39(17) . .
C11 C10 C9 107.02(16) . .
C11 C10 C21 123.22(17) . .
C9 C10 C21 129.54(18) . .
N3 C11 C10 107.05(16) . .
N3 C11 C12 117.07(16) . .
C10 C11 C12 135.51(17) . .
C13 C12 O1 108.89(16) . .
C13 C12 C11 140.78(18) . .
O1 C12 C11 110.33(16) . .
C12 C13 C13 106.79(11) . 2
C12 C13 H13 126.6 . .
C13 C13 H13 126.6 2 .
C5 C14 C15 112.24(19) . .
C5 C14 H14A 109.2 . .
C15 C14 H14A 109.2 . .
C5 C14 H14B 109.2 . .
C15 C14 H14B 109.2 . .
H14A C14 H14B 107.9 . .
C14 C15 H15A 109.5 . .
C14 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C14 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C6 C16 C17 112.77(18) . .
C6 C16 H16A 109.0 . .
C17 C16 H16A 109.0 . .
C6 C16 H16B 109.0 . .
C17 C16 H16B 109.0 . .
H16A C16 H16B 107.8 . .
C16 C17 H17A 109.5 . .
C16 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C16 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
O2 C18 O3 124.11(19) . .
O2 C18 C9 125.67(19) . .
O3 C18 C9 110.21(17) . .
C20 C19 O3 109.2(3) . .
C20 C19 H19A 109.8 . .
O3 C19 H19A 109.9 . .
C20 C19 H19B 109.8 . .
O3 C19 H19B 109.8 . .
H19A C19 H19B 108.3 . .
C19 C20 H20A 109.5 . .
C19 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
C19 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
O4 C21 O5 123.33(18) . .
O4 C21 C10 124.50(18) . .
O5 C21 C10 112.16(17) . .
O5 C22 C23 110.81(17) . .
O5 C22 H22A 109.5 . .
C23 C22 H22A 109.5 . .
O5 C22 H22B 109.5 . .
C23 C22 H22B 109.5 . .
H22A C22 H22B 108.1 . .
C22 C23 H23A 109.5 . .
C22 C23 H23B 109.5 . .
H23A C23 H23B 109.5 . .
C22 C23 H23C 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
S1 C24 H24A 109.5 . .
S1 C24 H24B 109.5 . .
H24A C24 H24B 109.5 . .
S1 C24 H24C 109.5 . .
H24A C24 H24C 109.5 . .
H24B C24 H24C 109.5 . .
S1 C25 H25A 109.5 . .
S1 C25 H25B 109.5 . .
H25A C25 H25B 109.5 . .
S1 C25 H25C 109.5 . .
H25A C25 H25C 109.5 . .
H25B C25 H25C 109.5 . .
C3 N1 C3 120.6(2) . 2
C4 N2 C7 110.50(16) . .
C4 N2 H2A 124.8 . .
C7 N2 H2A 124.8 . .
C11 N3 C8 111.57(16) . .
C11 N3 H3 124.2 . .
C8 N3 H3 124.2 . .
C12 O1 C12 108.6(2) . 2
C18 O3 C19 116.7(2) . .
C21 O5 C22 115.53(17) . .
O6 S1 C25 105.40(11) . .
O6 S1 C24 104.37(10) . .
C25 S1 C24 98.40(16) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.384(3) .
C1 C2 1.384(3) 2
C1 H1 0.9500 .
C2 C3 1.403(3) .
C2 H2 0.9500 .
C3 N1 1.353(2) .
C3 C4 1.473(3) .
C4 N2 1.371(2) .
C4 C5 1.401(3) .
C5 C6 1.420(3) .
C5 C14 1.510(3) .
C6 C7 1.399(3) .
C6 C16 1.506(3) .
C7 N2 1.382(2) .
C7 C8 1.455(3) .
C8 N3 1.374(2) .
C8 C9 1.392(3) .
C9 C10 1.430(3) .
C9 C18 1.485(3) .
C10 C11 1.400(3) .
C10 C21 1.464(3) .
C11 N3 1.362(2) .
C11 C12 1.449(3) .
C12 C13 1.365(3) .
C12 O1 1.370(2) .
C13 C13 1.437(4) 2
C13 H13 0.9500 .
C14 C15 1.523(4) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C16 C17 1.531(3) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
C18 O2 1.201(3) .
C18 O3 1.349(3) .
C19 C20 1.454(5) .
C19 O3 1.455(3) .
C19 H19A 0.9900 .
C19 H19B 0.9900 .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
C21 O4 1.216(3) .
C21 O5 1.354(2) .
C22 O5 1.458(2) .
C22 C23 1.504(3) .
C22 H22A 0.9900 .
C22 H22B 0.9900 .
C23 H23A 0.9800 .
C23 H23B 0.9800 .
C23 H23C 0.9800 .
C24 S1 1.795(3) .
C24 H24A 0.9800 .
C24 H24B 0.9800 .
C24 H24C 0.9800 .
C25 S1 1.779(3) .
C25 H25A 0.9800 .
C25 H25B 0.9800 .
C25 H25C 0.9800 .
N1 C3 1.353(2) 2
N2 H2A 0.8800 .
N3 H3 0.8800 .
O1 C12 1.370(2) 2
O6 S1 1.5066(14) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C2 C1 C2 C3 -0.48(14) 2 .
C1 C2 C3 N1 1.0(3) . .
C1 C2 C3 C4 -179.40(17) . .
N1 C3 C4 N2 12.1(2) . .
C2 C3 C4 N2 -167.5(2) . .
N1 C3 C4 C5 -164.8(2) . .
C2 C3 C4 C5 15.6(4) . .
N2 C4 C5 C6 -0.4(2) . .
C3 C4 C5 C6 176.7(2) . .
N2 C4 C5 C14 -176.5(2) . .
C3 C4 C5 C14 0.6(4) . .
C4 C5 C6 C7 0.7(2) . .
C14 C5 C6 C7 176.91(19) . .
C4 C5 C6 C16 -173.38(19) . .
C14 C5 C6 C16 2.9(3) . .
C5 C6 C7 N2 -0.7(2) . .
C16 C6 C7 N2 173.37(19) . .
C5 C6 C7 C8 -177.4(2) . .
C16 C6 C7 C8 -3.4(4) . .
N2 C7 C8 N3 -28.7(3) . .
C6 C7 C8 N3 147.8(2) . .
N2 C7 C8 C9 150.8(2) . .
C6 C7 C8 C9 -32.7(4) . .
N3 C8 C9 C10 0.1(2) . .
C7 C8 C9 C10 -179.4(2) . .
N3 C8 C9 C18 179.55(18) . .
C7 C8 C9 C18 0.0(3) . .
C8 C9 C10 C11 0.9(2) . .
C18 C9 C10 C11 -178.50(18) . .
C8 C9 C10 C21 175.61(19) . .
C18 C9 C10 C21 -3.8(3) . .
C9 C10 C11 N3 -1.6(2) . .
C21 C10 C11 N3 -176.71(17) . .
C9 C10 C11 C12 170.8(2) . .
C21 C10 C11 C12 -4.3(4) . .
N3 C11 C12 C13 -167.9(3) . .
C10 C11 C12 C13 20.2(4) . .
N3 C11 C12 O1 11.4(2) . .
C10 C11 C12 O1 -160.5(2) . .
O1 C12 C13 C13 -0.1(3) . 2
C11 C12 C13 C13 179.2(2) . 2
C4 C5 C14 C15 90.3(3) . .
C6 C5 C14 C15 -85.1(3) . .
C7 C6 C16 C17 -64.7(3) . .
C5 C6 C16 C17 108.3(2) . .
C8 C9 C18 O2 -61.3(3) . .
C10 C9 C18 O2 118.0(3) . .
C8 C9 C18 O3 117.7(2) . .
C10 C9 C18 O3 -63.0(3) . .
C11 C10 C21 O4 -20.9(3) . .
C9 C10 C21 O4 165.2(2) . .
C11 C10 C21 O5 158.21(18) . .
C9 C10 C21 O5 -15.7(3) . .
C2 C3 N1 C3 -0.51(15) . 2
C4 C3 N1 C3 179.85(19) . 2
C5 C4 N2 C7 0.0(2) . .
C3 C4 N2 C7 -177.69(17) . .
C6 C7 N2 C4 0.4(2) . .
C8 C7 N2 C4 177.79(17) . .
C10 C11 N3 C8 1.8(2) . .
C12 C11 N3 C8 -172.29(16) . .
C9 C8 N3 C11 -1.2(2) . .
C7 C8 N3 C11 178.44(16) . .
C13 C12 O1 C12 0.04(11) . 2
C11 C12 O1 C12 -179.51(19) . 2
O2 C18 O3 C19 -1.7(4) . .
C9 C18 O3 C19 179.3(2) . .
C20 C19 O3 C18 -167.5(3) . .
O4 C21 O5 C22 -0.5(3) . .
C10 C21 O5 C22 -179.55(16) . .
C23 C22 O5 C21 85.8(2) . .
