data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Cahill, Christopher' _publ_contact_author_email cahill@gwu.edu _publ_section_title ; Uranyl triazolate formation via an in situ Huisgen 1,3-dipolar cycloaddition reaction ; loop_ _publ_author_name K.Knope C.Cahill # Attachment '- Cahill_C20H16N6O18U3_CIF.txt' data_shelxl _database_code_depnum_ccdc_archive 'CCDC 778238' #TrackingRef '- Cahill_C20H16N6O18U3_CIF.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H16 N6 O18 U3' _chemical_formula_sum 'C20 H16 N6 O18 U3' _chemical_formula_weight 1342.48 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' 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.9037(11) _cell_length_b 6.1373(5) _cell_length_c 18.3478(16) _cell_angle_alpha 90.00 _cell_angle_beta 98.450(2) _cell_angle_gamma 90.00 _cell_volume 1437.3(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9847 _cell_measurement_theta_min 1.81 _cell_measurement_theta_max 30.33 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.102 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1196 _exptl_absorpt_coefficient_mu 16.955 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.448 _exptl_absorpt_correction_T_max 0.508 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker ApexII CCD' _diffrn_measurement_method 'omega and phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26513 _diffrn_reflns_av_R_equivalents 0.0456 _diffrn_reflns_av_sigmaI/netI 0.0311 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 30.33 _reflns_number_total 4090 _reflns_number_gt 3612 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART v5.05 (Bruker AXS)' _computing_cell_refinement 'APEX2 v2008.3-0 Software Suite (Bruker AXS)' _computing_data_reduction 'APEX2 v2008.3-0 Software Suite (Bruker AXS)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008 )' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELX-97 (Sheldrick, 2008)' _computing_publication_material 'WINGX (Farrugia, 1998)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0176P)^2^+3.2525P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4090 _refine_ls_number_parameters 226 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0280 _refine_ls_R_factor_gt 0.0215 _refine_ls_wR_factor_ref 0.0458 _refine_ls_wR_factor_gt 0.0438 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 _atom_site_disorder_assembly _atom_site_disorder_group U1 U 0.623256(10) 0.42442(2) 0.066482(7) 0.00833(4) Uani 1 1 d . . . U2 U 1.5000 0.5000 0.5000 0.00885(5) Uani 1 2 d S . . O3 O 0.6445(2) 0.0336(4) 0.07280(15) 0.0124(6) Uani 1 1 d . . . O4 O 0.4870(2) 0.2966(4) -0.01749(16) 0.0136(6) Uani 1 1 d D . . O1 O 0.5491(2) 0.3904(4) 0.13988(15) 0.0131(6) Uani 1 1 d . . . O5 O 0.7072(2) 0.7288(4) 0.12947(15) 0.0139(6) Uani 1 1 d . . . O2 O 0.7091(2) 0.4574(5) -0.00071(15) 0.0147(6) Uani 1 1 d . . . N2 N 0.8682(2) 0.3741(5) 0.19374(17) 0.0100(6) Uani 1 1 d . . . N3 N 0.9304(2) 0.2049(5) 0.22189(16) 0.0088(6) Uani 1 1 d . . . C2 C 0.7939(3) 0.0621(6) 0.1602(2) 0.0092(7) Uani 1 1 d . . . C3 C 0.8870(3) 0.0098(6) 0.2027(2) 0.0098(7) Uani 1 1 d . . . H3 H 0.9139 -0.1280 0.2153 0.012 Uiso 1 1 calc R . . C1 C 0.7106(3) -0.0715(6) 0.1182(2) 0.0089(7) Uani 1 1 d . . . C5 C 1.1134(3) 0.1119(6) 0.2658(2) 0.0120(8) Uani 1 1 d . . . H5 H 1.1072 -0.0116 0.2361 0.014 Uiso 1 1 calc R . . C4 C 1.0289(3) 0.2537(6) 0.2659(2) 0.0097(7) Uani 1 1 d . . . O9 O 1.5344(2) 0.6864(5) 0.43330(15) 0.0144(6) Uani 1 1 d . . . O6 O 1.3971(2) 0.2881(5) 0.40031(15) 0.0151(6) Uani 1 1 d . . . O7 O 1.3149(2) 0.5448(5) 0.45221(16) 0.0157(6) Uani 1 1 d . . . O8 O 1.5904(2) 0.1838(5) 0.45165(16) 0.0151(6) Uani 1 1 d D . . C9 C 1.0368(3) 0.4410(6) 0.3085(2) 0.0110(7) Uani 1 1 d . . . H9 H 0.9800 0.5350 0.3071 0.013 Uiso 1 1 calc R . . C10 C 1.3136(3) 0.3944(6) 0.4045(2) 0.0127(8) Uani 1 1 d . . . C7 C 1.2152(3) 0.3449(7) 0.3543(2) 0.0114(7) Uani 1 1 d . . . C8 C 1.1305(3) 0.4863(6) 0.3532(2) 0.0119(7) Uani 1 1 d . . . H8 H 1.1368 0.6108 0.3824 0.014 Uiso 1 1 calc R . . C6 C 1.2065(3) 0.1590(7) 0.3106(2) 0.0131(7) Uani 1 1 d . . . H6 H 1.2635 0.0657 0.3116 0.016 Uiso 1 1 calc R . . N1 N 0.7851(2) 0.2822(5) 0.15543(17) 0.0100(6) Uani 1 1 d . . . H8C H 1.643(3) 0.135(9) 0.474(3) 0.039(17) Uiso 1 1 d D . . H8D H 1.555(4) 0.082(7) 0.438(4) 0.06(2) Uiso 1 1 d D . . H4C H 0.457(4) 0.182(5) -0.025(3) 0.025(14) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 U1 0.00814(7) 0.00566(7) 0.01000(7) 0.00032(5) -0.00265(5) -0.00067(5) U2 0.00619(9) 0.01142(10) 0.00836(9) -0.00219(7) -0.00085(7) -0.00047(7) O3 0.0122(13) 0.0028(13) 0.0191(15) -0.0004(10) -0.0075(11) -0.0024(10) O4 0.0146(14) 0.0045(13) 0.0191(14) -0.0008(11) -0.0062(11) -0.0017(11) O1 0.0143(13) 0.0118(15) 0.0131(13) 0.0004(10) 0.0014(11) -0.0010(11) O5 0.0146(14) 0.0057(13) 0.0191(14) 0.0009(11) -0.0053(11) -0.0015(10) O2 0.0139(14) 0.0154(15) 0.0141(14) 0.0004(11) -0.0002(11) -0.0020(11) N2 0.0104(15) 0.0069(16) 0.0114(15) 0.0000(12) -0.0030(12) 0.0019(12) N3 0.0075(14) 0.0074(15) 0.0103(15) -0.0007(12) -0.0026(12) 0.0013(11) C2 0.0094(17) 0.0081(17) 0.0090(17) 0.0000(14) -0.0022(14) -0.0012(14) C3 0.0128(18) 0.0045(17) 0.0120(18) -0.0009(14) 0.0015(14) -0.0004(14) C1 0.0093(17) 0.0079(17) 0.0087(17) -0.0026(13) -0.0014(13) 0.0018(14) C5 0.0141(18) 0.009(2) 0.0129(18) -0.0040(14) 0.0008(15) 0.0020(14) C4 0.0052(16) 0.0118(19) 0.0110(17) 0.0012(14) -0.0023(13) -0.0045(14) O9 0.0149(14) 0.0138(15) 0.0144(14) -0.0015(11) 0.0020(11) -0.0022(11) O6 0.0083(13) 0.0194(16) 0.0157(14) -0.0047(11) -0.0044(11) 0.0011(11) O7 0.0092(13) 0.0203(16) 0.0159(14) -0.0059(11) -0.0043(11) -0.0005(11) O8 0.0100(14) 0.0165(17) 0.0174(15) -0.0061(12) -0.0025(12) 0.0022(12) C9 0.0089(17) 0.0111(19) 0.0121(18) -0.0035(14) -0.0017(14) 0.0014(14) C10 0.0098(17) 0.015(2) 0.0132(18) -0.0001(15) 0.0011(14) -0.0018(14) C7 0.0078(16) 0.0162(19) 0.0098(17) -0.0001(15) -0.0001(13) -0.0033(15) C8 0.0136(18) 0.0072(18) 0.0135(18) -0.0017(14) -0.0023(15) -0.0010(14) C6 0.0090(17) 0.0127(19) 0.0165(19) -0.0024(16) -0.0021(14) 0.0016(15) N1 0.0093(15) 0.0068(15) 0.0126(15) -0.0018(12) -0.0023(12) -0.0008(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag U1 O1 1.775(3) . ? U1 O2 1.786(3) . ? U1 O4 2.299(3) . ? U1 O4 2.322(3) 3_665 ? U1 O5 2.373(3) . ? U1 O3 2.415(3) . ? U1 N1 2.605(3) . ? U1 U1 3.8275(4) 3_665 ? U2 O9 1.779(3) 3_866 ? U2 O9 1.779(3) . ? U2 O7 2.436(3) 3_866 ? U2 O7 2.436(3) . ? U2 O6 2.467(3) 3_866 ? U2 O6 2.467(3) . ? U2 O8 2.493(3) . ? U2 O8 2.493(3) 3_866 ? U2 C10 2.834(4) 3_866 ? U2 C10 2.834(4) . ? O3 C1 1.276(4) . ? O4 U1 2.322(3) 3_665 ? O4 H4C 0.803(19) . ? O5 C1 1.245(5) 1_565 ? N2 N1 1.319(4) . ? N2 N3 1.367(4) . ? N3 C3 1.347(5) . ? N3 C4 1.434(5) . ? C2 N1 1.358(5) . ? C2 C3 1.370(5) . ? C2 C1 1.477(5) . ? C3 H3 0.9300 . ? C1 O5 1.245(5) 1_545 ? C5 C6 1.383(5) . ? C5 C4 1.395(5) . ? C5 H5 0.9300 . ? C4 C9 1.385(5) . ? O6 C10 1.272(5) . ? O7 C10 1.270(5) . ? O8 H8C 0.80(2) . ? O8 H8D 0.79(2) . ? C9 C8 1.386(5) . ? C9 H9 0.9300 . ? C10 C7 1.487(5) . ? C7 C6 1.390(5) . ? C7 C8 1.394(5) . ? C8 H8 0.9300 . ? C6 H6 0.9300 . ? 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 _geom_angle_publ_flag O1 U1 O2 174.37(12) . . ? O1 U1 O4 91.36(11) . . ? O2 U1 O4 93.84(12) . . ? O1 U1 O4 90.70(11) . 3_665 ? O2 U1 O4 93.23(12) . 3_665 ? O4 U1 O4 68.13(11) . 3_665 ? O1 U1 O5 88.94(11) . . ? O2 U1 O5 87.81(11) . . ? O4 U1 O5 147.63(10) . . ? O4 U1 O5 79.50(10) 3_665 . ? O1 U1 O3 85.23(11) . . ? O2 U1 O3 93.92(11) . . ? O4 U1 O3 76.31(9) . . ? O4 U1 O3 144.09(9) 3_665 . ? O5 U1 O3 135.90(9) . . ? O1 U1 N1 87.57(11) . . ? O2 U1 N1 87.06(11) . . ? O4 U1 N1 140.30(10) . . ? O4 U1 N1 151.54(10) 3_665 . ? O5 U1 N1 72.06(10) . . ? O3 U1 N1 64.05(9) . . ? O1 U1 U1 91.24(9) . 3_665 ? O2 U1 U1 94.27(9) . 3_665 ? O4 U1 U1 34.25(7) . 3_665 ? O4 U1 U1 33.87(7) 3_665 3_665 ? O5 U1 U1 113.37(7) . 3_665 ? O3 U1 U1 110.43(6) . 3_665 ? N1 U1 U1 174.43(7) . 3_665 ? O9 U2 O9 180.0 3_866 . ? O9 U2 O7 90.61(11) 3_866 3_866 ? O9 U2 O7 89.39(11) . 3_866 ? O9 U2 O7 89.39(11) 3_866 . ? O9 U2 O7 90.61(11) . . ? O7 U2 O7 180.00(13) 3_866 . ? O9 U2 O6 89.45(11) 3_866 3_866 ? O9 U2 O6 90.55(11) . 3_866 ? O7 U2 O6 53.15(9) 3_866 3_866 ? O7 U2 O6 126.85(9) . 3_866 ? O9 U2 O6 90.55(11) 3_866 . ? O9 U2 O6 89.45(11) . . ? O7 U2 O6 126.85(9) 3_866 . ? O7 U2 O6 53.15(9) . . ? O6 U2 O6 179.999(1) 3_866 . ? O9 U2 O8 85.49(11) 3_866 . ? O9 U2 O8 94.51(11) . . ? O7 U2 O8 63.59(9) 3_866 . ? O7 U2 O8 116.41(9) . . ? O6 U2 O8 116.44(9) 3_866 . ? O6 U2 O8 63.56(9) . . ? O9 U2 O8 94.51(11) 3_866 3_866 ? O9 U2 O8 85.49(11) . 3_866 ? O7 U2 O8 116.42(9) 3_866 3_866 ? O7 U2 O8 63.58(9) . 3_866 ? O6 U2 O8 63.56(9) 3_866 3_866 ? O6 U2 O8 116.44(9) . 3_866 ? O8 U2 O8 179.999(1) . 3_866 ? O9 U2 C10 89.82(12) 3_866 3_866 ? O9 U2 C10 90.17(12) . 3_866 ? O7 U2 C10 26.53(10) 3_866 3_866 ? O7 U2 C10 153.47(10) . 3_866 ? O6 U2 C10 26.62(10) 3_866 3_866 ? O6 U2 C10 153.37(10) . 3_866 ? O8 U2 C10 89.94(11) . 3_866 ? O8 U2 C10 90.06(11) 3_866 3_866 ? O9 U2 C10 90.18(12) 3_866 . ? O9 U2 C10 89.82(12) . . ? O7 U2 C10 153.47(10) 3_866 . ? O7 U2 C10 26.53(10) . . ? O6 U2 C10 153.38(10) 3_866 . ? O6 U2 C10 26.62(10) . . ? O8 U2 C10 90.05(11) . . ? O8 U2 C10 89.94(11) 3_866 . ? C10 U2 C10 180.0 3_866 . ? C1 O3 U1 126.4(2) . . ? U1 O4 U1 111.87(11) . 3_665 ? U1 O4 H4C 136(4) . . ? U1 O4 H4C 109(4) 3_665 . ? C1 O5 U1 135.9(3) 1_565 . ? N1 N2 N3 105.2(3) . . ? C3 N3 N2 112.2(3) . . ? C3 N3 C4 129.3(3) . . ? N2 N3 C4 118.5(3) . . ? N1 C2 C3 109.1(3) . . ? N1 C2 C1 118.1(3) . . ? C3 C2 C1 132.7(4) . . ? N3 C3 C2 103.7(3) . . ? N3 C3 H3 128.2 . . ? C2 C3 H3 128.2 . . ? O5 C1 O3 124.8(4) 1_545 . ? O5 C1 C2 120.0(3) 1_545 . ? O3 C1 C2 115.2(3) . . ? C6 C5 C4 118.6(3) . . ? C6 C5 H5 120.7 . . ? C4 C5 H5 120.7 . . ? C9 C4 C5 121.8(3) . . ? C9 C4 N3 118.5(3) . . ? C5 C4 N3 119.8(3) . . ? C10 O6 U2 93.0(2) . . ? C10 O7 U2 94.5(2) . . ? U2 O8 H8C 121(4) . . ? U2 O8 H8D 116(5) . . ? H8C O8 H8D 106(6) . . ? C4 C9 C8 119.1(4) . . ? C4 C9 H9 120.5 . . ? C8 C9 H9 120.5 . . ? O7 C10 O6 119.3(4) . . ? O7 C10 C7 119.9(3) . . ? O6 C10 C7 120.8(3) . . ? O7 C10 U2 59.0(2) . . ? O6 C10 U2 60.4(2) . . ? C7 C10 U2 178.6(3) . . ? C6 C7 C8 120.4(3) . . ? C6 C7 C10 121.0(3) . . ? C8 C7 C10 118.6(4) . . ? C9 C8 C7 119.8(4) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C5 C6 C7 120.3(4) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? N2 N1 C2 109.7(3) . . ? N2 N1 U1 134.8(2) . . ? C2 N1 U1 115.2(2) . . ? 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 O8 H8C O2 0.80(2) 2.19(3) 2.958(4) 162(5) 2_745 O8 H8D O9 0.79(2) 2.45(4) 3.143(4) 149(6) 1_545 O4 H4C O3 0.803(19) 1.98(3) 2.740(4) 159(5) 3_655 _diffrn_measured_fraction_theta_max 0.945 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.245 _refine_diff_density_min -1.196 _refine_diff_density_rms 0.200