# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_eh1011 _database_code_depnum_ccdc_archive 'CCDC 907974' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'bis pyridinium tetrachlorodioxouranate pyridine solvate' _chemical_melting_point ? _chemical_formula_moiety 'Cl4 O2 U, 2(C5 H5 N), 2(C5H6 N)' _chemical_formula_sum 'C20 H22 Cl4 N4 O2 U' _chemical_formula_weight 730.25 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' Cl Cl 0.1484 0.1585 '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' U U -9.6767 9.6646 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.4466(17) _cell_length_b 9.1058(18) _cell_length_c 9.865(2) _cell_angle_alpha 111.85(3) _cell_angle_beta 91.90(3) _cell_angle_gamma 115.10(3) _cell_volume 621.0(2) _cell_formula_units_Z 1 _cell_measurement_temperature 108(2) _cell_measurement_reflns_used 2317 _cell_measurement_theta_min 2.2839 _cell_measurement_theta_max 31.1529 _exptl_crystal_description platelet _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.953 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 346 _exptl_absorpt_coefficient_mu 6.988 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.4796 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'face indexed' _exptl_special_details ; ? ; _diffrn_ambient_temperature 108(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector CCD _diffrn_measurement_device ; Saturn724 (2x2 bin mode) ; _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6237 _diffrn_reflns_av_R_equivalents 0.0434 _diffrn_reflns_av_sigmaI/netI 0.0525 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.71 _diffrn_reflns_theta_max 31.36 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_measurement_details ; scan: Number of images: 300 Slice: -110.0000 - 40.0000 Image width: 0.5000 Exp time: 20.0000 Rotation axis: Omega Omega: 0.0000 Kappa: 0.0000 Phi: 0.0000 XTD: 44.7245 2theta: -19.7193 scan: Number of images: 244 Slice: -55.0000 - 67.0000 Image width: 0.5000 Exp time: 20.0000 Rotation axis: Omega Omega: 0.0000 Kappa: 50.0000 Phi: 0.0000 XTD: 44.7245 2theta: -19.7193 scan: Number of images: 170 Slice: -55.0000 - 30.0000 Image width: 0.5000 Exp time: 20.0000 Rotation axis: Omega Omega: 0.0000 Kappa: 50.0000 Phi: 90.0000 XTD: 44.7245 2theta: -19.7193 scan: Number of images: 60 Slice: -50.0000 - -20.0000 Image width: 0.5000 Exp time: 20.0000 Rotation axis: Omega Omega: 0.0000 Kappa: 0.0000 Phi: 90.0000 XTD: 44.7245 2theta: -19.7193 ; _diffrn_measurement_device_details ; AFC12 (Right): Kappa 3 circle ; _reflns_number_total 3306 _reflns_number_gt 3298 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^ > 2\s(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. ; _iucr_refine_instructions_details ; TITL eh1011 in P-1 CELL 0.71073 8.4466 9.1058 9.8650 111.850 91.900 115.100 ZERR 1.00 0.0017 0.0018 0.0020 0.030 0.030 0.030 LATT 1 SFAC C H CL N U O UNIT 20 22 4 4 1 2 MERG 2 FMAP 2 PLAN 20 SIZE 0.05 0.20 0.30 ACTA 50.00 BOND CONF L.S. 12 TEMP -165.00 WGHT 0.064900 0.868400 EXTI 0.011733 FVAR 4.75246 MOLE 1 U1 5 0.500000 1.000000 0.500000 10.50000 0.02584 0.02414 = 0.02329 0.01244 0.00577 0.00774 CL1 3 0.629189 1.024866 0.760856 11.00000 0.03376 0.03521 = 0.02531 0.01607 0.00347 0.01219 CL2 3 0.640509 0.790009 0.355285 11.00000 0.03539 0.03427 = 0.03138 0.01511 0.01092 0.01865 O1 6 0.299704 0.807192 0.476238 11.00000 0.02731 0.02918 = 0.02984 0.01464 0.00592 0.00757 MOLE 2 N1 4 0.897584 0.703120 0.883269 11.00000 0.03890 0.03810 = 0.03096 0.01814 0.01271 0.02163 C1 1 1.055281 0.841963 0.906620 11.00000 0.03535 0.04477 = 0.03174 0.01990 0.00876 0.01939 AFIX 43 H1 2 1.142836 0.890755 0.995583 11.00000 -1.20000 AFIX 0 C2 1 1.096950 0.918073 0.806895 11.00000 0.03229 0.04095 = 0.03362 0.01920 0.01004 0.01135 AFIX 43 H2 2 1.212373 1.015162 0.825319 11.00000 -1.20000 AFIX 0 C3 1 0.968620 0.851162 0.680095 11.00000 0.05002 0.04379 = 0.03347 0.02425 0.01750 0.02610 AFIX 43 H3 2 0.993371 0.902552 0.610336 11.00000 -1.20000 AFIX 0 C4 1 0.804675 0.709329 0.656066 11.00000 0.04582 0.04811 = 0.03418 0.02031 0.00790 0.02591 AFIX 43 H4 2 0.713412 0.661989 0.570051 11.00000 -1.20000 AFIX 0 C5 1 0.773543 0.635570 0.759095 11.00000 0.03309 0.03706 = 0.03525 0.01857 0.01070 0.01342 AFIX 43 H5 2 0.661276 0.534605 0.740792 11.00000 -1.20000 AFIX 0 MOLE 3 N2 4 0.182314 0.449917 0.927477 11.00000 0.03752 0.03355 = 0.03363 0.01865 0.01405 0.01946 C6 1 0.067327 0.385396 0.798226 11.00000 0.03039 0.03198 = 0.03634 0.01710 0.01083 0.01192 AFIX 43 H6 2 -0.046047 0.282866 0.772664 11.00000 -1.20000 AFIX 0 C7 1 0.111938 0.466404 0.701835 11.00000 0.03212 0.03749 = 0.03046 0.01497 0.01021 0.01502 AFIX 43 H7 2 0.030205 0.421298 0.610316 11.00000 -1.20000 AFIX 0 C8 1 0.277771 0.614322 0.741152 11.00000 0.03633 0.03283 = 0.03582 0.02063 0.01360 0.01531 AFIX 43 H8 2 0.311317 0.671462 0.675852 11.00000 -1.20000 AFIX 0 C9 1 0.394752 0.679560 0.874129 11.00000 0.03659 0.02966 = 0.03239 0.01548 0.00614 0.00899 AFIX 43 H9 2 0.508945 0.781725 0.901821 11.00000 -1.20000 AFIX 0 C10 1 0.343193 0.593929 0.966457 11.00000 0.03762 0.03333 = 0.02690 0.01419 0.00901 0.01533 AFIX 43 H10 2 0.422612 0.637477 1.058834 11.00000 -1.20000 AFIX 0 H2N 2 0.140427 0.378844 0.979980 11.00000 0.03692 HKLF 4 REM eh1011 in P-1 REM R1 = 0.0415 for 3298 Fo > 4sig(Fo) and 0.0418 for all 3306 data REM 147 parameters refined using 0 restraints END WGHT 0.0648 0.8668 REM Highest difference peak 1.432, deepest hole -4.142, 1-sigma level 0.205 Q1 1 0.3729 0.8932 0.4629 11.00000 0.05 1.43 Q2 1 0.5782 1.0273 0.3923 11.00000 0.05 1.34 Q3 1 0.3599 0.9730 0.6413 11.00000 0.05 0.89 Q4 1 0.7794 1.0387 0.6110 11.00000 0.05 0.84 Q5 1 0.3787 0.8216 0.6740 11.00000 0.05 0.76 Q6 1 0.6533 0.7560 0.4641 11.00000 0.05 0.73 Q7 1 0.3338 0.7650 0.4373 11.00000 0.05 0.72 Q8 1 0.5000 0.5000 0.5000 10.50000 0.05 0.71 Q9 1 0.5411 0.9465 0.7387 11.00000 0.05 0.71 Q10 1 0.6709 0.9410 0.5882 11.00000 0.05 0.69 Q11 1 0.1559 0.6984 0.4117 11.00000 0.05 0.68 Q12 1 0.5134 1.1220 0.4672 11.00000 0.05 0.67 Q13 1 0.3596 0.6176 0.9185 11.00000 0.05 0.66 Q14 1 0.8822 0.7996 0.6693 11.00000 0.05 0.66 Q15 1 0.5054 0.9029 0.3138 11.00000 0.05 0.66 Q16 1 1.0829 0.7230 0.7859 11.00000 0.05 0.64 Q17 1 0.6415 1.0198 0.6567 11.00000 0.05 0.63 Q18 1 0.7705 0.7856 0.5333 11.00000 0.05 0.63 Q19 1 0.6127 0.8443 0.4282 11.00000 0.05 0.62 Q20 1 0.4753 0.9603 0.6749 11.00000 0.05 0.62 ; _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^)+(0.0649P)^2^+0.8684P] 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 SHELXL _refine_ls_extinction_coef 0.0117(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3306 _refine_ls_number_parameters 147 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0418 _refine_ls_R_factor_gt 0.0415 _refine_ls_wR_factor_ref 0.1062 _refine_ls_wR_factor_gt 0.1060 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _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 0.5000 1.0000 0.5000 0.02521(12) Uani 1 2 d S . . Cl1 Cl 0.6292(2) 1.02487(18) 0.76086(15) 0.0320(3) Uani 1 1 d . . . Cl2 Cl 0.6405(2) 0.79001(18) 0.35528(15) 0.0323(3) Uani 1 1 d . . . O1 O 0.2997(6) 0.8072(5) 0.4762(5) 0.0303(8) Uani 1 1 d . . . N1 N 0.8976(8) 0.7031(7) 0.8833(6) 0.0333(10) Uani 1 1 d . . . C1 C 1.0553(9) 0.8420(9) 0.9066(7) 0.0358(12) Uani 1 1 d . . . H1 H 1.1428 0.8908 0.9956 0.043 Uiso 1 1 calc R . . C2 C 1.0970(9) 0.9181(9) 0.8069(7) 0.0368(13) Uani 1 1 d . . . H2 H 1.2124 1.0152 0.8253 0.044 Uiso 1 1 calc R . . C3 C 0.9686(10) 0.8512(9) 0.6801(7) 0.0380(14) Uani 1 1 d . . . H3 H 0.9934 0.9026 0.6103 0.046 Uiso 1 1 calc R . . C4 C 0.8047(10) 0.7093(9) 0.6561(7) 0.0403(14) Uani 1 1 d . . . H4 H 0.7134 0.6620 0.5701 0.048 Uiso 1 1 calc R . . C5 C 0.7735(9) 0.6356(8) 0.7591(7) 0.0352(12) Uani 1 1 d . . . H5 H 0.6613 0.5346 0.7408 0.042 Uiso 1 1 calc R . . N2 N 0.1823(8) 0.4499(7) 0.9275(6) 0.0322(10) Uani 1 1 d . . . C6 C 0.0673(8) 0.3854(8) 0.7982(7) 0.0331(12) Uani 1 1 d . . . H6 H -0.0460 0.2829 0.7727 0.040 Uiso 1 1 calc R . . C7 C 0.1119(9) 0.4664(8) 0.7018(7) 0.0336(12) Uani 1 1 d . . . H7 H 0.0302 0.4213 0.6103 0.040 Uiso 1 1 calc R . . C8 C 0.2778(9) 0.6143(8) 0.7412(7) 0.0332(12) Uani 1 1 d . . . H8 H 0.3113 0.6715 0.6759 0.040 Uiso 1 1 calc R . . C9 C 0.3948(9) 0.6796(7) 0.8741(7) 0.0348(12) Uani 1 1 d . . . H9 H 0.5089 0.7817 0.9018 0.042 Uiso 1 1 calc R . . C10 C 0.3432(9) 0.5939(8) 0.9665(6) 0.0327(12) Uani 1 1 d . . . H10 H 0.4226 0.6375 1.0588 0.039 Uiso 1 1 calc R . . H2N H 0.140(11) 0.379(10) 0.980(9) 0.04(2) Uiso 1 1 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 0.02584(18) 0.02414(14) 0.02329(14) 0.01244(10) 0.00577(10) 0.00774(10) Cl1 0.0338(7) 0.0352(6) 0.0253(5) 0.0161(5) 0.0035(5) 0.0122(5) Cl2 0.0354(7) 0.0343(6) 0.0314(6) 0.0151(5) 0.0109(5) 0.0186(5) O1 0.027(2) 0.0292(17) 0.0298(18) 0.0146(14) 0.0059(15) 0.0076(15) N1 0.039(3) 0.038(2) 0.031(2) 0.0181(19) 0.013(2) 0.022(2) C1 0.035(3) 0.045(3) 0.032(3) 0.020(2) 0.009(2) 0.019(3) C2 0.032(3) 0.041(3) 0.034(3) 0.019(2) 0.010(2) 0.011(2) C3 0.050(4) 0.044(3) 0.033(3) 0.024(2) 0.017(3) 0.026(3) C4 0.046(4) 0.048(3) 0.034(3) 0.020(3) 0.008(3) 0.026(3) C5 0.033(3) 0.037(3) 0.035(3) 0.019(2) 0.011(2) 0.013(2) N2 0.038(3) 0.034(2) 0.034(2) 0.0187(19) 0.014(2) 0.019(2) C6 0.030(3) 0.032(2) 0.036(3) 0.017(2) 0.011(2) 0.012(2) C7 0.032(3) 0.037(3) 0.030(3) 0.015(2) 0.010(2) 0.015(2) C8 0.036(3) 0.033(2) 0.036(3) 0.021(2) 0.014(2) 0.015(2) C9 0.037(3) 0.030(2) 0.032(3) 0.015(2) 0.006(2) 0.009(2) C10 0.038(3) 0.033(2) 0.027(2) 0.014(2) 0.009(2) 0.015(2) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.774(4) . ? U1 O1 1.774(4) 2_676 ? U1 Cl1 2.6523(15) . ? U1 Cl1 2.6523(15) 2_676 ? U1 Cl2 2.6662(16) 2_676 ? U1 Cl2 2.6662(16) . ? N1 C1 1.327(8) . ? N1 C5 1.336(9) . ? C1 C2 1.377(8) . ? C2 C3 1.376(10) . ? C3 C4 1.369(10) . ? C4 C5 1.389(9) . ? N2 C6 1.338(8) . ? N2 C10 1.339(8) . ? C6 C7 1.379(8) . ? C7 C8 1.379(8) . ? C8 C9 1.373(9) . ? C9 C10 1.376(8) . ? 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 O1 180.000(1) . 2_676 ? O1 U1 Cl1 90.21(14) . . ? O1 U1 Cl1 89.79(14) 2_676 . ? O1 U1 Cl1 89.79(14) . 2_676 ? O1 U1 Cl1 90.21(14) 2_676 2_676 ? Cl1 U1 Cl1 180.0 . 2_676 ? O1 U1 Cl2 90.30(14) . 2_676 ? O1 U1 Cl2 89.70(14) 2_676 2_676 ? Cl1 U1 Cl2 88.88(5) . 2_676 ? Cl1 U1 Cl2 91.12(5) 2_676 2_676 ? O1 U1 Cl2 89.70(14) . . ? O1 U1 Cl2 90.30(14) 2_676 . ? Cl1 U1 Cl2 91.12(5) . . ? Cl1 U1 Cl2 88.88(5) 2_676 . ? Cl2 U1 Cl2 180.0 2_676 . ? C1 N1 C5 118.8(5) . . ? N1 C1 C2 122.5(6) . . ? C3 C2 C1 118.9(6) . . ? C4 C3 C2 118.9(6) . . ? C3 C4 C5 119.1(6) . . ? N1 C5 C4 121.6(6) . . ? C6 N2 C10 121.1(5) . . ? N2 C6 C7 120.6(6) . . ? C6 C7 C8 118.6(6) . . ? C9 C8 C7 120.4(5) . . ? C8 C9 C10 118.7(6) . . ? N2 C10 C9 120.7(6) . . ? 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_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C1 C2 -0.7(10) . . . . ? N1 C1 C2 C3 1.9(10) . . . . ? C1 C2 C3 C4 -1.0(10) . . . . ? C2 C3 C4 C5 -0.9(10) . . . . ? C1 N1 C5 C4 -1.3(10) . . . . ? C3 C4 C5 N1 2.1(10) . . . . ? C10 N2 C6 C7 -0.1(9) . . . . ? N2 C6 C7 C8 0.4(9) . . . . ? C6 C7 C8 C9 -0.5(9) . . . . ? C7 C8 C9 C10 0.3(10) . . . . ? C6 N2 C10 C9 -0.1(9) . . . . ? C8 C9 C10 N2 0.0(9) . . . . ? _diffrn_measured_fraction_theta_max 0.806 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.957 _refine_diff_density_max 1.432 _refine_diff_density_min -4.142 _refine_diff_density_rms 0.205