# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Paul Duval' 'Charles L. Barnes' 'Shanmugaperumal Kannan' _publ_contact_author_name 'Paul Duval' _publ_contact_author_address ; Department of Chemistry University of Missouri 240 Chemistry Building Columbia Missouri 65211 UNITED STATES OF AMERICA ; _publ_contact_author_email DUVALP@MISSOURI.EDU _publ_requested_journal 'Chemical Communications' _publ_section_title ; Versatile New Uranyl(VI) Dihalide Complexes Supported by Tunable Organic Amide Ligands ; data_Kannan4 _database_code_depnum_ccdc_archive 'CCDC 283797' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H50 Br2 N2 O4 U' _chemical_formula_weight 828.51 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' Br Br -0.2901 2.4595 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2~1~/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.8340(11) _cell_length_b 14.0098(9) _cell_length_c 14.4084(9) _cell_angle_alpha 90.00 _cell_angle_beta 106.0300(10) _cell_angle_gamma 90.00 _cell_volume 3266.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 8286 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 27.1 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.685 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1608 _exptl_absorpt_coefficient_mu 7.444 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.17 _exptl_absorpt_correction_T_max 0.26 _exptl_absorpt_process_details ; Data were corrected for decay and absorption using the program SADABS based on the method of R.H. Blessing (Acta Cryst. A51, 33-38, 1995). ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 SMART CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 22823 _diffrn_reflns_av_R_equivalents 0.0314 _diffrn_reflns_av_sigmaI/netI 0.0380 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 27.14 _reflns_number_total 7182 _reflns_number_gt 4530 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _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^)+(0.0016P)^2^+15.9614P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7182 _refine_ls_number_parameters 313 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0776 _refine_ls_R_factor_gt 0.0396 _refine_ls_wR_factor_ref 0.0744 _refine_ls_wR_factor_gt 0.0662 _refine_ls_goodness_of_fit_ref 1.154 _refine_ls_restrained_S_all 1.154 _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 U1A U 0.5000 0.5000 0.0000 0.02566(8) Uani 1 2 d S . . Br1A Br 0.63332(5) 0.62821(7) 0.02797(6) 0.0653(3) Uani 1 1 d . . . O1A O 0.5688(3) 0.4108(3) 0.1297(3) 0.0471(13) Uani 1 1 d . . . N1A N 0.5790(3) 0.3003(4) 0.2459(4) 0.0423(15) Uani 1 1 d . . . C1A C 0.6106(4) 0.3721(5) 0.2085(4) 0.0327(15) Uani 1 1 d . . . O2A O 0.4590(3) 0.5688(4) 0.0762(4) 0.0521(14) Uani 1 1 d . . . C2A C 0.6939(4) 0.4128(5) 0.2542(5) 0.0354(16) Uani 1 1 d . . . H2A H 0.7208 0.3746 0.3132 0.042 Uiso 1 1 calc R . . C3A C 0.6850(5) 0.5145(5) 0.2841(5) 0.057(2) Uani 1 1 d . . . H3A1 H 0.6606 0.5532 0.2266 0.086 Uiso 1 1 calc R . . H3A2 H 0.7395 0.5401 0.3178 0.086 Uiso 1 1 calc R . . H3A3 H 0.6490 0.5163 0.3272 0.086 Uiso 1 1 calc R . . C4A C 0.7477(5) 0.4073(7) 0.1847(6) 0.071(3) Uani 1 1 d . . . H4A1 H 0.7507 0.3409 0.1644 0.106 Uiso 1 1 calc R . . H4A2 H 0.8034 0.4304 0.2171 0.106 Uiso 1 1 calc R . . H4A3 H 0.7234 0.4470 0.1279 0.106 Uiso 1 1 calc R . . C5A C 0.6234(4) 0.2467(6) 0.3348(5) 0.0462(19) Uani 1 1 d . . . H5A H 0.5833 0.1970 0.3431 0.055 Uiso 1 1 calc R . . C6A C 0.6428(5) 0.3052(6) 0.4276(5) 0.057(2) Uani 1 1 d . . . H6A1 H 0.6913 0.3453 0.4317 0.086 Uiso 1 1 calc R . . H6A2 H 0.6541 0.2622 0.4833 0.086 Uiso 1 1 calc R . . H6A3 H 0.5953 0.3458 0.4274 0.086 Uiso 1 1 calc R . . C7A C 0.6971(5) 0.1905(6) 0.3202(5) 0.058(2) Uani 1 1 d . . . H7A1 H 0.6783 0.1547 0.2588 0.070 Uiso 1 1 calc R . . H7A2 H 0.7395 0.2367 0.3129 0.070 Uiso 1 1 calc R . . C8A C 0.7380(7) 0.1206(9) 0.3993(9) 0.118(4) Uani 1 1 d . . . H8A1 H 0.7464 0.1514 0.4624 0.177 Uiso 1 1 calc R . . H8A2 H 0.7915 0.1009 0.3912 0.177 Uiso 1 1 calc R . . H8A3 H 0.7025 0.0645 0.3955 0.177 Uiso 1 1 calc R . . C9A C 0.4932(5) 0.2646(7) 0.1958(6) 0.082(4) Uani 1 1 d . . . H9A H 0.4712 0.3059 0.1377 0.098 Uiso 1 1 calc R . . C10A C 0.4965(7) 0.1626(8) 0.1593(8) 0.134(6) Uani 1 1 d . . . H10A H 0.5315 0.1608 0.1151 0.201 Uiso 1 1 calc R . . H10B H 0.4405 0.1415 0.1252 0.201 Uiso 1 1 calc R . . H10C H 0.5195 0.1202 0.2142 0.201 Uiso 1 1 calc R . . C11A C 0.4374(6) 0.2772(10) 0.2591(10) 0.130(6) Uani 1 1 d . . . H11A H 0.4616 0.2437 0.3209 0.155 Uiso 1 1 calc R . . H11B H 0.3836 0.2468 0.2277 0.155 Uiso 1 1 calc R . . C12A C 0.4227(7) 0.3817(13) 0.2802(11) 0.157(7) Uani 1 1 d . . . H12A H 0.4758 0.4127 0.3101 0.235 Uiso 1 1 calc R . . H12B H 0.3876 0.3850 0.3243 0.235 Uiso 1 1 calc R . . H12C H 0.3952 0.4144 0.2197 0.235 Uiso 1 1 calc R . . U1B U 1.0000 0.5000 0.5000 0.02788(9) Uani 1 2 d S . . Br1B Br 0.89276(5) 0.34246(6) 0.45347(5) 0.04584(19) Uani 1 1 d . . . O1B O 1.0633(3) 0.4503(3) 0.3857(3) 0.0393(11) Uani 1 1 d . . . N1B N 1.0748(3) 0.3558(4) 0.2638(4) 0.0430(15) Uani 1 1 d . . . C1B C 1.1080(4) 0.4133(5) 0.3368(5) 0.0368(16) Uani 1 1 d . . . O2B O 0.9314(3) 0.5693(3) 0.4116(3) 0.0409(12) Uani 1 1 d . . . C2B C 1.1982(4) 0.4425(7) 0.3633(6) 0.058(2) Uani 1 1 d . . . H2B H 1.2259 0.4070 0.3206 0.070 Uiso 1 1 calc R . . C3B C 1.2411(5) 0.4185(9) 0.4658(6) 0.096(4) Uani 1 1 d . . . H3B1 H 1.2171 0.4559 0.5088 0.145 Uiso 1 1 calc R . . H3B2 H 1.3001 0.4335 0.4792 0.145 Uiso 1 1 calc R . . H3B3 H 1.2344 0.3503 0.4768 0.145 Uiso 1 1 calc R . . C4B C 1.2043(6) 0.5501(7) 0.3448(7) 0.079(3) Uani 1 1 d . . . H4B1 H 1.2626 0.5690 0.3614 0.118 Uiso 1 1 calc R . . H4B2 H 1.1761 0.5859 0.3849 0.118 Uiso 1 1 calc R . . H4B3 H 1.1781 0.5639 0.2766 0.118 Uiso 1 1 calc R . . C5B C 0.9826(4) 0.3383(6) 0.2334(5) 0.051(2) Uani 1 1 d . . . H5B H 0.9590 0.3761 0.2784 0.061 Uiso 1 1 calc R . . C6B C 0.9629(6) 0.2348(6) 0.2466(7) 0.081(3) Uani 1 1 d . . . H6B1 H 0.9032 0.2275 0.2366 0.122 Uiso 1 1 calc R . . H6B2 H 0.9921 0.2143 0.3121 0.122 Uiso 1 1 calc R . . H6B3 H 0.9805 0.1955 0.1996 0.122 Uiso 1 1 calc R . . C7B C 0.9462(5) 0.3798(8) 0.1332(6) 0.072(3) Uani 1 1 d . . . H7B1 H 0.9752 0.3511 0.0889 0.086 Uiso 1 1 calc R . . H7B2 H 0.8874 0.3607 0.1104 0.086 Uiso 1 1 calc R . . C8B C 0.9512(7) 0.4862(8) 0.1264(8) 0.102(4) Uani 1 1 d . . . H8B1 H 0.9201 0.5158 0.1672 0.152 Uiso 1 1 calc R . . H8B2 H 0.9276 0.5061 0.0593 0.152 Uiso 1 1 calc R . . H8B3 H 1.0091 0.5063 0.1484 0.152 Uiso 1 1 calc R . . C9B C 1.1215(5) 0.3013(6) 0.2071(6) 0.057(2) Uani 1 1 d . . . H9B H 1.0786 0.2621 0.1610 0.068 Uiso 1 1 calc R . . C10B C 1.1818(5) 0.2272(7) 0.2688(7) 0.091(4) Uani 1 1 d . . . H10D H 1.2280 0.2605 0.3134 0.137 Uiso 1 1 calc R . . H10E H 1.2028 0.1856 0.2264 0.137 Uiso 1 1 calc R . . H10F H 1.1525 0.1887 0.3057 0.137 Uiso 1 1 calc R . . C11B C 1.1569(5) 0.3644(7) 0.1433(6) 0.073(3) Uani 1 1 d . . . H11C H 1.1181 0.4173 0.1174 0.087 Uiso 1 1 calc R . . H11D H 1.2098 0.3924 0.1817 0.087 Uiso 1 1 calc R . . C12B C 1.1712(9) 0.3067(11) 0.0610(9) 0.157(6) Uani 1 1 d . . . H12D H 1.2044 0.2503 0.0867 0.235 Uiso 1 1 calc R . . H12E H 1.2005 0.3459 0.0247 0.235 Uiso 1 1 calc R . . H12F H 1.1179 0.2866 0.0181 0.235 Uiso 1 1 calc R . . 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 U1A 0.02642(16) 0.02638(19) 0.02219(17) 0.00112(17) 0.00338(13) 0.00145(16) Br1A 0.0514(4) 0.0714(6) 0.0542(5) 0.0277(5) -0.0168(4) -0.0316(4) O1A 0.037(3) 0.046(3) 0.046(3) 0.024(2) -0.009(2) -0.010(2) N1A 0.035(3) 0.049(4) 0.033(3) 0.020(3) -0.007(2) -0.012(3) C1A 0.030(3) 0.034(4) 0.029(3) 0.007(3) 0.000(3) -0.001(3) O2A 0.062(3) 0.047(3) 0.049(3) -0.014(3) 0.019(3) 0.006(3) C2A 0.026(3) 0.047(5) 0.029(4) 0.013(3) 0.002(3) -0.003(3) C3A 0.074(5) 0.042(6) 0.041(4) 0.005(4) -0.011(4) -0.019(4) C4A 0.042(4) 0.105(8) 0.071(6) 0.041(6) 0.024(4) 0.017(5) C5A 0.048(4) 0.050(5) 0.035(4) 0.020(4) 0.001(3) -0.016(4) C6A 0.051(5) 0.077(6) 0.043(5) 0.013(4) 0.012(4) -0.007(4) C7A 0.084(6) 0.037(5) 0.044(5) 0.009(4) 0.001(4) 0.004(4) C8A 0.099(9) 0.111(10) 0.148(12) 0.041(9) 0.039(8) 0.012(8) C9A 0.055(5) 0.100(8) 0.063(6) 0.054(6) -0.028(4) -0.042(5) C10A 0.154(11) 0.074(8) 0.109(9) 0.031(7) -0.072(8) -0.073(8) C11A 0.047(6) 0.153(13) 0.170(13) 0.105(12) -0.001(7) -0.029(8) C12A 0.071(8) 0.23(2) 0.170(15) 0.073(15) 0.033(9) 0.005(11) U1B 0.02638(16) 0.0336(2) 0.02208(17) -0.00092(18) 0.00412(13) 0.00124(17) Br1B 0.0476(4) 0.0466(4) 0.0437(4) -0.0088(4) 0.0133(3) -0.0155(4) O1B 0.039(3) 0.050(3) 0.032(3) -0.014(2) 0.014(2) -0.005(2) N1B 0.037(3) 0.058(4) 0.032(3) -0.014(3) 0.008(3) 0.010(3) C1B 0.033(3) 0.047(5) 0.032(4) -0.009(3) 0.010(3) 0.005(3) O2B 0.036(3) 0.048(3) 0.034(3) 0.010(2) 0.001(2) 0.005(2) C2B 0.032(4) 0.091(7) 0.050(5) -0.024(5) 0.007(4) -0.001(4) C3B 0.053(6) 0.171(12) 0.054(6) -0.024(7) -0.003(5) -0.002(7) C4B 0.070(6) 0.080(8) 0.100(8) -0.021(6) 0.045(6) -0.019(6) C5B 0.036(4) 0.070(6) 0.045(4) -0.023(4) 0.010(3) -0.002(4) C6B 0.089(7) 0.068(7) 0.103(8) -0.041(6) 0.055(6) -0.028(6) C7B 0.044(5) 0.115(9) 0.047(5) -0.026(6) -0.005(4) 0.016(5) C8B 0.100(8) 0.102(10) 0.101(9) 0.016(8) 0.025(7) 0.037(7) C9B 0.046(4) 0.068(6) 0.055(5) -0.026(4) 0.012(4) 0.014(4) C10B 0.065(6) 0.090(8) 0.098(8) -0.045(6) -0.010(5) 0.048(6) C11B 0.052(5) 0.110(8) 0.061(6) -0.026(6) 0.025(4) -0.004(5) C12B 0.176(14) 0.203(17) 0.124(11) -0.048(11) 0.098(11) -0.010(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 U1A O2A 1.741(5) 3_665 ? U1A O2A 1.741(5) . ? U1A O1A 2.281(4) . ? U1A O1A 2.281(4) 3_665 ? U1A Br1A 2.8153(7) . ? U1A Br1A 2.8153(7) 3_665 ? O1A C1A 1.279(7) . ? N1A C1A 1.320(8) . ? N1A C5A 1.496(8) . ? N1A C9A 1.510(9) . ? C1A C2A 1.489(8) . ? C2A C3A 1.507(10) . ? C2A C4A 1.526(9) . ? C5A C6A 1.525(10) . ? C5A C7A 1.532(11) . ? C7A C8A 1.515(12) . ? C9A C11A 1.489(16) . ? C9A C10A 1.529(15) . ? C11A C12A 1.530(19) . ? U1B O2B 1.757(4) 3_766 ? U1B O2B 1.757(4) . ? U1B O1B 2.303(4) . ? U1B O1B 2.303(4) 3_766 ? U1B Br1B 2.8127(7) . ? U1B Br1B 2.8127(7) 3_766 ? O1B C1B 1.274(7) . ? N1B C1B 1.320(8) . ? N1B C9B 1.491(8) . ? N1B C5B 1.512(8) . ? C1B C2B 1.516(9) . ? C2B C3B 1.493(11) . ? C2B C4B 1.540(12) . ? C5B C6B 1.511(11) . ? C5B C7B 1.519(11) . ? C7B C8B 1.497(13) . ? C9B C11B 1.511(12) . ? C9B C10B 1.549(11) . ? C11B C12B 1.508(13) . ? 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 O2A U1A O2A 180.0(3) 3_665 . ? O2A U1A O1A 90.8(2) 3_665 . ? O2A U1A O1A 89.2(2) . . ? O2A U1A O1A 89.2(2) 3_665 3_665 ? O2A U1A O1A 90.8(2) . 3_665 ? O1A U1A O1A 180.0(2) . 3_665 ? O2A U1A Br1A 90.26(17) 3_665 . ? O2A U1A Br1A 89.74(17) . . ? O1A U1A Br1A 91.59(11) . . ? O1A U1A Br1A 88.41(11) 3_665 . ? O2A U1A Br1A 89.74(17) 3_665 3_665 ? O2A U1A Br1A 90.26(17) . 3_665 ? O1A U1A Br1A 88.41(11) . 3_665 ? O1A U1A Br1A 91.59(11) 3_665 3_665 ? Br1A U1A Br1A 180.0 . 3_665 ? C1A O1A U1A 171.9(5) . . ? C1A N1A C5A 124.7(5) . . ? C1A N1A C9A 119.8(5) . . ? C5A N1A C9A 115.4(5) . . ? O1A C1A N1A 120.0(5) . . ? O1A C1A C2A 116.7(6) . . ? N1A C1A C2A 123.3(5) . . ? C1A C2A C3A 109.4(6) . . ? C1A C2A C4A 110.3(6) . . ? C3A C2A C4A 111.1(6) . . ? N1A C5A C6A 114.6(6) . . ? N1A C5A C7A 111.9(6) . . ? C6A C5A C7A 114.3(6) . . ? C8A C7A C5A 116.4(7) . . ? C11A C9A N1A 110.5(8) . . ? C11A C9A C10A 114.2(9) . . ? N1A C9A C10A 110.7(8) . . ? C9A C11A C12A 113.5(10) . . ? O2B U1B O2B 180.000(1) 3_766 . ? O2B U1B O1B 90.55(19) 3_766 . ? O2B U1B O1B 89.45(19) . . ? O2B U1B O1B 89.45(19) 3_766 3_766 ? O2B U1B O1B 90.55(19) . 3_766 ? O1B U1B O1B 180.000(1) . 3_766 ? O2B U1B Br1B 89.40(15) 3_766 . ? O2B U1B Br1B 90.60(15) . . ? O1B U1B Br1B 89.18(11) . . ? O1B U1B Br1B 90.82(11) 3_766 . ? O2B U1B Br1B 90.60(15) 3_766 3_766 ? O2B U1B Br1B 89.40(15) . 3_766 ? O1B U1B Br1B 90.82(11) . 3_766 ? O1B U1B Br1B 89.18(11) 3_766 3_766 ? Br1B U1B Br1B 180.00(2) . 3_766 ? C1B O1B U1B 168.2(4) . . ? C1B N1B C9B 125.3(6) . . ? C1B N1B C5B 120.3(5) . . ? C9B N1B C5B 114.4(6) . . ? O1B C1B N1B 120.3(6) . . ? O1B C1B C2B 117.0(6) . . ? N1B C1B C2B 122.6(6) . . ? C3B C2B C1B 111.5(7) . . ? C3B C2B C4B 110.7(8) . . ? C1B C2B C4B 109.3(7) . . ? C6B C5B N1B 111.3(7) . . ? C6B C5B C7B 116.2(7) . . ? N1B C5B C7B 109.0(6) . . ? C8B C7B C5B 115.3(8) . . ? N1B C9B C11B 112.9(7) . . ? N1B C9B C10B 112.9(7) . . ? C11B C9B C10B 115.8(7) . . ? C12B C11B C9B 109.9(9) . . ? 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 O2A U1A O1A C1A 132(3) 3_665 . . . ? O2A U1A O1A C1A -48(3) . . . . ? O1A U1A O1A C1A -130(100) 3_665 . . . ? Br1A U1A O1A C1A 42(3) . . . . ? Br1A U1A O1A C1A -138(3) 3_665 . . . ? U1A O1A C1A N1A 134(3) . . . . ? U1A O1A C1A C2A -45(3) . . . . ? C5A N1A C1A O1A 177.0(7) . . . . ? C9A N1A C1A O1A -0.4(11) . . . . ? C5A N1A C1A C2A -3.8(11) . . . . ? C9A N1A C1A C2A 178.8(8) . . . . ? O1A C1A C2A C3A 63.9(8) . . . . ? N1A C1A C2A C3A -115.3(7) . . . . ? O1A C1A C2A C4A -58.6(8) . . . . ? N1A C1A C2A C4A 122.2(7) . . . . ? C1A N1A C5A C6A 66.3(9) . . . . ? C9A N1A C5A C6A -116.2(8) . . . . ? C1A N1A C5A C7A -66.0(9) . . . . ? C9A N1A C5A C7A 111.5(8) . . . . ? N1A C5A C7A C8A -170.1(8) . . . . ? C6A C5A C7A C8A 57.5(10) . . . . ? C1A N1A C9A C11A -117.9(9) . . . . ? C5A N1A C9A C11A 64.5(11) . . . . ? C1A N1A C9A C10A 114.7(8) . . . . ? C5A N1A C9A C10A -63.0(10) . . . . ? N1A C9A C11A C12A 64.8(12) . . . . ? C10A C9A C11A C12A -169.7(10) . . . . ? O2B U1B O1B C1B -1(2) 3_766 . . . ? O2B U1B O1B C1B 179(2) . . . . ? O1B U1B O1B C1B -100(100) 3_766 . . . ? Br1B U1B O1B C1B -90(2) . . . . ? Br1B U1B O1B C1B 90(2) 3_766 . . . ? U1B O1B C1B N1B 118(2) . . . . ? U1B O1B C1B C2B -65(2) . . . . ? C9B N1B C1B O1B -174.1(7) . . . . ? C5B N1B C1B O1B 3.9(10) . . . . ? C9B N1B C1B C2B 9.2(12) . . . . ? C5B N1B C1B C2B -172.8(7) . . . . ? O1B C1B C2B C3B 59.3(10) . . . . ? N1B C1B C2B C3B -123.9(9) . . . . ? O1B C1B C2B C4B -63.4(9) . . . . ? N1B C1B C2B C4B 113.4(8) . . . . ? C1B N1B C5B C6B -116.6(8) . . . . ? C9B N1B C5B C6B 61.5(8) . . . . ? C1B N1B C5B C7B 113.9(8) . . . . ? C9B N1B C5B C7B -68.0(9) . . . . ? C6B C5B C7B C8B 167.7(8) . . . . ? N1B C5B C7B C8B -65.6(9) . . . . ? C1B N1B C9B C11B -70.7(9) . . . . ? C5B N1B C9B C11B 111.2(8) . . . . ? C1B N1B C9B C10B 63.1(10) . . . . ? C5B N1B C9B C10B -114.9(8) . . . . ? N1B C9B C11B C12B -156.7(8) . . . . ? C10B C9B C11B C12B 70.9(11) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.14 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.024 _refine_diff_density_min -0.968 _refine_diff_density_rms 0.121 data_Kannan9 _database_code_depnum_ccdc_archive 'CCDC 283798' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H42 Cl2 N2 O4 U' _chemical_formula_weight 683.49 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' Cl Cl 0.1484 0.1585 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2~1~/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.5267(4) _cell_length_b 11.3761(5) _cell_length_c 13.8153(6) _cell_angle_alpha 90.00 _cell_angle_beta 96.7450(10) _cell_angle_gamma 90.00 _cell_volume 1330.82(10) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5860 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 27.1 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.706 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 668 _exptl_absorpt_coefficient_mu 6.324 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.19 _exptl_absorpt_correction_T_max 0.30 _exptl_absorpt_process_details ; Data were corrected for decay and absorption using the program SADABS based on the method of R.H. Blessing (Acta Cryst. A51, 33-38, 1995). ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 SMART CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 9261 _diffrn_reflns_av_R_equivalents 0.0185 _diffrn_reflns_av_sigmaI/netI 0.0187 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 27.11 _reflns_number_total 2905 _reflns_number_gt 2380 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _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^)+(0.0254P)^2^+0.7524P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2905 _refine_ls_number_parameters 139 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0247 _refine_ls_R_factor_gt 0.0177 _refine_ls_wR_factor_ref 0.0494 _refine_ls_wR_factor_gt 0.0454 _refine_ls_goodness_of_fit_ref 1.128 _refine_ls_restrained_S_all 1.128 _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 0.0000 0.5000 0.0000 0.01761(6) Uani 1 2 d S . . Cl1 Cl 0.08297(11) 0.27623(7) -0.00683(6) 0.03908(18) Uani 1 1 d . . . O1 O -0.0945(2) 0.46528(19) 0.14778(13) 0.0237(4) Uani 1 1 d . . . N1 N -0.2406(3) 0.4577(2) 0.27191(15) 0.0188(4) Uani 1 1 d . . . C1 C -0.1003(3) 0.4580(2) 0.23904(18) 0.0191(5) Uani 1 1 d . . . O2 O 0.1887(2) 0.5376(2) 0.05925(14) 0.0272(4) Uani 1 1 d . . . C2 C 0.0527(3) 0.4513(3) 0.30569(19) 0.0236(6) Uani 1 1 d . . . H2 H 0.0297 0.4222 0.3708 0.028 Uiso 1 1 calc R . . C3 C 0.1241(4) 0.5754(3) 0.3183(3) 0.0402(8) Uani 1 1 d . . . H3A H 0.1385 0.6079 0.2542 0.060 Uiso 1 1 calc R . . H3B H 0.2265 0.5713 0.3586 0.060 Uiso 1 1 calc R . . H3C H 0.0526 0.6262 0.3501 0.060 Uiso 1 1 calc R . . C4 C 0.1677(3) 0.3664(3) 0.2657(2) 0.0311(7) Uani 1 1 d . . . H4A H 0.1150 0.2910 0.2506 0.047 Uiso 1 1 calc R . . H4B H 0.2593 0.3545 0.3145 0.047 Uiso 1 1 calc R . . H4C H 0.2026 0.3993 0.2063 0.047 Uiso 1 1 calc R . . C5 C -0.2617(3) 0.4558(3) 0.37739(19) 0.0241(6) Uani 1 1 d . . . H5 H -0.1546 0.4634 0.4150 0.029 Uiso 1 1 calc R . . C6 C -0.3600(4) 0.5609(3) 0.4042(2) 0.0370(8) Uani 1 1 d . . . H6A H -0.3176 0.6332 0.3788 0.055 Uiso 1 1 calc R . . H6B H -0.3555 0.5663 0.4753 0.055 Uiso 1 1 calc R . . H6C H -0.4699 0.5504 0.3757 0.055 Uiso 1 1 calc R . . C7 C -0.3304(4) 0.3392(3) 0.4053(2) 0.0351(7) Uani 1 1 d . . . H7A H -0.4357 0.3289 0.3694 0.053 Uiso 1 1 calc R . . H7B H -0.3385 0.3384 0.4755 0.053 Uiso 1 1 calc R . . H7C H -0.2615 0.2750 0.3890 0.053 Uiso 1 1 calc R . . C8 C -0.3895(3) 0.4590(3) 0.2034(2) 0.0232(5) Uani 1 1 d . . . H8 H -0.4775 0.4532 0.2450 0.028 Uiso 1 1 calc R . . C9 C -0.4143(4) 0.5756(3) 0.1481(2) 0.0340(7) Uani 1 1 d . . . H9A H -0.4033 0.6410 0.1946 0.051 Uiso 1 1 calc R . . H9B H -0.5203 0.5770 0.1119 0.051 Uiso 1 1 calc R . . H9C H -0.3353 0.5834 0.1024 0.051 Uiso 1 1 calc R . . C10 C -0.4061(4) 0.3521(3) 0.1362(2) 0.0318(7) Uani 1 1 d . . . H10A H -0.3279 0.3567 0.0897 0.048 Uiso 1 1 calc R . . H10B H -0.5126 0.3506 0.1006 0.048 Uiso 1 1 calc R . . H10C H -0.3887 0.2803 0.1752 0.048 Uiso 1 1 calc R . . 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 0.01472(8) 0.02376(8) 0.01427(8) -0.00052(5) 0.00132(5) -0.00253(5) Cl1 0.0534(5) 0.0279(4) 0.0358(4) -0.0036(3) 0.0051(3) 0.0075(4) O1 0.0179(10) 0.0364(10) 0.0166(9) 0.0035(8) 0.0018(8) 0.0009(8) N1 0.0160(11) 0.0229(10) 0.0175(10) 0.0006(9) 0.0023(8) 0.0000(9) C1 0.0204(14) 0.0186(11) 0.0193(12) -0.0001(10) 0.0059(10) -0.0001(11) O2 0.0193(10) 0.0400(10) 0.0215(9) 0.0009(9) -0.0002(8) -0.0083(9) C2 0.0166(13) 0.0353(15) 0.0189(12) 0.0047(12) 0.0019(10) 0.0039(12) C3 0.0284(17) 0.0424(19) 0.0465(19) -0.0115(15) -0.0093(15) -0.0048(14) C4 0.0190(15) 0.0393(17) 0.0345(16) 0.0028(13) 0.0012(12) 0.0094(12) C5 0.0174(14) 0.0369(15) 0.0184(13) -0.0022(12) 0.0043(11) -0.0011(12) C6 0.0364(19) 0.039(2) 0.0389(17) -0.0149(15) 0.0171(14) -0.0048(15) C7 0.0374(18) 0.0395(18) 0.0296(15) 0.0109(13) 0.0086(13) 0.0009(14) C8 0.0158(13) 0.0281(13) 0.0250(14) 0.0018(12) -0.0006(11) -0.0013(11) C9 0.0235(15) 0.0372(18) 0.0394(17) 0.0129(14) -0.0047(13) 0.0032(13) C10 0.0283(16) 0.0358(17) 0.0306(15) -0.0091(13) 0.0003(13) -0.0081(13) _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 O2 1.770(2) 3_565 ? U1 O2 1.770(2) . ? U1 O1 2.3151(18) 3_565 ? U1 O1 2.3151(18) . ? U1 Cl1 2.6468(8) . ? U1 Cl1 2.6468(8) 3_565 ? O1 C1 1.270(3) . ? N1 C1 1.329(3) . ? N1 C5 1.489(3) . ? N1 C8 1.492(3) . ? C1 C2 1.508(4) . ? C2 C4 1.525(4) . ? C2 C3 1.539(5) . ? C5 C7 1.518(4) . ? C5 C6 1.530(4) . ? C8 C10 1.526(4) . ? C8 C9 1.533(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 _geom_angle_publ_flag O2 U1 O2 180.00(12) 3_565 . ? O2 U1 O1 91.43(8) 3_565 3_565 ? O2 U1 O1 88.57(8) . 3_565 ? O2 U1 O1 88.57(8) 3_565 . ? O2 U1 O1 91.43(8) . . ? O1 U1 O1 180.00(10) 3_565 . ? O2 U1 Cl1 89.06(8) 3_565 . ? O2 U1 Cl1 90.94(8) . . ? O1 U1 Cl1 90.60(5) 3_565 . ? O1 U1 Cl1 89.40(5) . . ? O2 U1 Cl1 90.93(8) 3_565 3_565 ? O2 U1 Cl1 89.07(8) . 3_565 ? O1 U1 Cl1 89.40(5) 3_565 3_565 ? O1 U1 Cl1 90.60(5) . 3_565 ? Cl1 U1 Cl1 180.00(3) . 3_565 ? C1 O1 U1 160.83(18) . . ? C1 N1 C5 123.5(2) . . ? C1 N1 C8 121.1(2) . . ? C5 N1 C8 115.4(2) . . ? O1 C1 N1 118.7(2) . . ? O1 C1 C2 118.5(2) . . ? N1 C1 C2 122.7(2) . . ? C1 C2 C4 111.0(2) . . ? C1 C2 C3 108.9(3) . . ? C4 C2 C3 111.1(2) . . ? N1 C5 C7 110.8(2) . . ? N1 C5 C6 111.0(2) . . ? C7 C5 C6 112.5(3) . . ? N1 C8 C10 112.9(2) . . ? N1 C8 C9 112.5(2) . . ? C10 C8 C9 112.9(3) . . ? 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 O2 U1 O1 C1 -176.7(6) 3_565 . . . ? O2 U1 O1 C1 3.3(6) . . . . ? O1 U1 O1 C1 10(100) 3_565 . . . ? Cl1 U1 O1 C1 94.3(6) . . . . ? Cl1 U1 O1 C1 -85.7(6) 3_565 . . . ? U1 O1 C1 N1 158.7(4) . . . . ? U1 O1 C1 C2 -20.7(7) . . . . ? C5 N1 C1 O1 -176.7(3) . . . . ? C8 N1 C1 O1 3.4(4) . . . . ? C5 N1 C1 C2 2.7(4) . . . . ? C8 N1 C1 C2 -177.2(3) . . . . ? O1 C1 C2 C4 -43.9(4) . . . . ? N1 C1 C2 C4 136.7(3) . . . . ? O1 C1 C2 C3 78.7(3) . . . . ? N1 C1 C2 C3 -100.7(3) . . . . ? C1 N1 C5 C7 -111.3(3) . . . . ? C8 N1 C5 C7 68.6(3) . . . . ? C1 N1 C5 C6 123.0(3) . . . . ? C8 N1 C5 C6 -57.1(3) . . . . ? C1 N1 C8 C10 60.9(3) . . . . ? C5 N1 C8 C10 -119.0(3) . . . . ? C1 N1 C8 C9 -68.3(3) . . . . ? C5 N1 C8 C9 111.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.11 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.305 _refine_diff_density_min -1.438 _refine_diff_density_rms 0.136