#------------------------------------------------------------------------------ #$Date: 2023-12-07 04:52:34 +0200 (Thu, 07 Dec 2023) $ #$Revision: 288111 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/31/23/2312367.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2312367 loop_ _publ_author_name 'Whittington, Abigail A.' 'Keimowitz, Alison R.' 'Tanski, Joseph M.' _publ_section_title ; Crystal structures of three uranyl-acetate-bipyridine complexes crystallized from hydraulic fracking fluid. ; _journal_coeditor_code EQ3014 _journal_issue 1 _journal_name_full 'Acta crystallographica. Section C, Structural chemistry' _journal_paper_doi 10.1107/S2053229623010288 _journal_volume 80 _journal_year 2024 _chemical_formula_iupac '[U (C2 H3 O2)2 O2 (C10 H8 N2)2]' _chemical_formula_moiety 'C24 H22 N4 O6 U' _chemical_formula_sum 'C24 H22 N4 O6 U' _chemical_formula_weight 700.48 _chemical_name_systematic ; Bis(acetato-\k^2^O,O')(2,4'-bipyridine-\ \kN^1'^)dioxidouranium(VI) ; _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _atom_sites_solution_secondary difmap _cell_angle_alpha 78.274(5) _cell_angle_beta 84.648(5) _cell_angle_gamma 74.814(5) _cell_formula_units_Z 1 _cell_length_a 8.006(3) _cell_length_b 8.786(3) _cell_length_c 8.833(3) _cell_measurement_reflns_used 4878 _cell_measurement_temperature 125.(2) _cell_measurement_theta_max 30.4308 _cell_measurement_theta_min 2.3566 _cell_volume 586.6(4) _computing_cell_refinement ; SAINT (Bruker, 2013) ; _computing_data_collection ; APEX3 (Bruker, 2013) ; _computing_data_reduction ; SAINT (Bruker, 2013) ; _computing_molecular_graphics ; SHELXTL2014 (Sheldrick, 2008) ; _computing_publication_material ; SHELXTL2014 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009), and Mercury (Macrae et al., 2020) ; _computing_structure_refinement ; SHELXL2017 (Sheldrick, 2015b) ; _computing_structure_solution ; SHELXT2018 (Sheldrick, 2015a) ; _diffrn_ambient_temperature 125.(2) _diffrn_detector_area_resol_mean 8.3333 _diffrn_measured_fraction_theta_full 0.979 _diffrn_measured_fraction_theta_max 0.979 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker APEXII CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0266 _diffrn_reflns_av_unetI/netI 0.0345 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 5760 _diffrn_reflns_theta_full 25.24 _diffrn_reflns_theta_max 26.00 _diffrn_reflns_theta_min 2.36 _diffrn_source 'sealed X-ray tube' _diffrn_source_current 30.0 _diffrn_source_power 1.50 _diffrn_source_voltage 50 _exptl_absorpt_coefficient_mu 6.966 _exptl_absorpt_correction_T_max 0.72 _exptl_absorpt_correction_T_min 0.35 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; (SADABS: Bruker, 2013) ; _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.983 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 334 _exptl_crystal_size_max 0.240 _exptl_crystal_size_mid 0.140 _exptl_crystal_size_min 0.050 _refine_diff_density_max 2.263 _refine_diff_density_min -2.631 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 161 _refine_ls_number_reflns 2260 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.082 _refine_ls_R_factor_all 0.0266 _refine_ls_R_factor_gt 0.0266 _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/[\s^2^(Fo^2^)+(0.0285P)^2^+1.9118P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0613 _refine_ls_wR_factor_ref 0.0613 _reflns_number_gt 2260 _reflns_number_total 2260 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file eq3014sup1.cif _cod_data_source_block III_AW2913U _cod_original_cell_volume 586.6(3) _cod_database_code 2312367 _shelx_hkl_file ; -1 0 0 228.42 5.35 -1 0 0 252.07 5.26 1 0 0 253.07 5.34 1 0 0 229.79 5.36 -2 0 0 12.23 0.63 -2 0 0 10.33 0.79 2 0 0 12.89 0.75 2 0 0 11.55 0.87 -3 0 0 99.94 2.55 -3 0 0 94.91 2.83 3 0 0 97.25 2.80 3 0 0 101.60 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52.75 2.17 -3 4 0 49.59 2.09 2 -4 0 53.23 1.88 -2 4 0 58.54 2.01 -2 4 0 56.25 2.00 1 -4 0 185.59 4.42 -1 4 0 173.55 4.40 -1 4 0 171.65 4.39 -1 4 0 183.84 4.67 0 -4 0 93.11 2.65 0 4 0 100.87 2.89 -1 -4 0 28.92 1.33 1 4 0 32.57 1.43 -2 -4 0 55.96 2.00 2 4 0 53.66 1.91 -3 -4 0 129.21 3.67 3 4 0 126.23 3.47 -4 -4 0 121.41 3.73 -5 -4 0 158.61 4.83 -5 -4 0 163.23 4.26 5 4 0 172.54 4.62 -6 -4 0 48.44 2.77 -6 -4 0 48.15 2.06 -7 -4 0 44.96 2.88 -7 -4 0 40.60 2.11 -8 -4 0 45.60 2.99 -8 -4 0 38.62 2.30 8 4 0 43.68 2.76 -9 -4 0 22.77 2.26 -9 -4 0 20.67 1.94 9 4 0 26.99 2.54 -10 -4 0 10.49 1.90 -10 -4 0 12.83 1.94 10 4 0 15.37 2.15 -11 -4 0 10.20 2.03 -8 5 0 11.62 2.13 -7 5 0 8.21 1.88 -6 5 0 12.03 1.79 -5 5 0 35.16 2.44 -5 5 0 35.27 2.59 -4 5 0 78.93 3.14 -4 5 0 73.60 3.04 -3 5 0 36.84 1.97 -3 5 0 36.98 2.11 2 -5 0 55.31 2.05 -2 5 0 55.56 2.13 -2 5 0 53.24 2.21 1 -5 0 132.23 3.61 -1 5 0 130.02 3.59 -1 5 0 140.24 3.96 0 -5 0 108.14 3.14 0 5 0 119.00 3.45 -1 -5 0 163.09 4.34 1 5 0 173.36 4.58 -2 -5 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3 -2 11 9.94 2.32 4 1 -11 27.21 2.76 3 1 -11 15.36 3.30 3 1 -11 16.84 1.73 2 1 -11 13.57 1.64 -2 -1 11 9.62 1.57 1 1 -11 26.87 2.10 -1 -1 11 25.77 2.32 0 1 -11 22.48 1.96 0 -1 11 16.88 1.76 -1 1 -11 11.05 1.42 1 -1 11 10.25 1.50 -2 1 -11 16.30 1.57 2 -1 11 12.16 2.12 2 -1 11 11.92 1.57 -3 1 -11 8.21 1.42 3 -1 11 10.86 2.23 -4 1 -11 9.82 1.41 4 -1 11 10.94 2.39 4 0 -11 17.02 2.54 -4 0 11 15.91 1.80 3 0 -11 14.52 1.64 3 0 -11 11.37 2.22 2 0 -11 28.07 2.19 -2 0 11 28.62 2.24 1 0 -11 35.20 2.21 -1 0 11 29.89 2.27 0 0 11 16.56 1.66 -1 0 -11 12.94 1.48 1 0 11 9.83 1.45 -2 0 -11 13.65 1.49 2 0 11 11.61 2.29 2 0 11 10.23 1.51 -3 0 -11 18.57 1.64 3 0 11 12.38 1.58 3 0 11 12.12 2.38 -4 0 -11 16.11 1.60 -4 0 -11 15.09 2.57 4 0 11 15.33 2.61 -5 0 -11 3.91 2.69 -5 0 -11 9.46 1.45 5 0 11 11.91 3.11 4 -1 -11 15.22 2.51 -4 1 11 15.30 1.77 3 -1 -11 15.54 1.70 3 -1 -11 18.99 2.46 -3 1 11 14.95 1.73 2 -1 -11 8.78 1.97 2 -1 -11 7.78 1.35 -2 1 11 7.00 1.40 1 -1 -11 18.82 1.61 -1 1 11 15.70 1.62 0 -1 -11 50.96 2.37 0 1 11 44.78 2.45 -1 -1 -11 28.03 2.00 1 1 11 27.76 2.05 -2 -1 -11 27.09 2.01 2 1 11 25.54 2.82 2 1 11 27.18 2.08 -3 -1 -11 10.46 1.39 3 1 11 11.30 2.21 3 1 11 9.96 1.43 -4 -1 -11 10.04 1.43 -4 -1 -11 13.05 2.25 4 1 11 9.15 2.32 -5 -1 -11 21.57 2.83 -5 -1 -11 22.86 2.08 5 1 11 18.03 2.88 4 -2 -11 18.83 2.63 -4 2 11 17.89 1.91 3 -2 -11 24.23 2.64 3 -2 -11 18.92 1.76 -3 2 11 20.80 1.86 2 -2 -11 18.37 2.30 2 -2 -11 17.32 1.66 -2 2 11 15.50 1.69 1 -2 -11 20.29 1.87 1 -2 -11 20.31 2.28 -1 2 11 22.38 1.96 0 -2 -11 23.01 1.85 0 2 11 26.09 1.98 -1 -2 -11 26.98 2.08 -1 -2 -11 27.55 1.92 1 2 11 24.81 1.96 -2 -2 -11 23.31 2.14 -2 -2 -11 20.98 1.85 2 2 11 18.41 1.81 -3 -2 -11 26.50 2.31 -3 -2 -11 25.06 1.89 3 2 11 21.77 2.66 3 2 11 21.66 1.93 -4 -2 -11 31.10 2.08 -4 -2 -11 32.83 2.70 4 2 11 23.42 2.97 4 2 11 28.62 2.15 -5 -2 -11 14.51 1.58 -5 -2 -11 16.93 2.42 5 2 11 11.26 2.46 -6 -2 -11 6.62 2.38 4 -3 -11 14.28 2.21 3 -3 -11 29.86 2.43 3 -3 -11 25.76 2.08 3 -3 -11 29.42 3.37 -3 3 11 24.22 2.25 2 -3 -11 31.48 2.15 2 -3 -11 33.25 3.14 2 -3 -11 33.40 2.32 -2 3 11 34.41 2.29 1 -3 -11 26.31 2.04 1 -3 -11 22.56 1.88 1 -3 -11 23.68 2.69 -1 3 11 24.30 2.02 0 -3 -11 28.45 2.61 0 -3 -11 24.62 2.02 0 -3 -11 25.82 1.82 0 3 11 28.00 2.00 -1 -3 -11 29.49 2.10 -1 -3 -11 29.09 1.91 1 3 11 29.66 1.94 -2 -3 -11 17.27 1.94 -2 -3 -11 17.99 1.55 2 3 11 16.73 1.98 2 3 11 18.28 1.70 -3 -3 -11 17.89 1.70 -3 -3 -11 19.61 2.17 3 3 11 16.36 1.53 3 3 11 15.54 2.08 -4 -3 -11 18.28 1.79 -4 -3 -11 20.49 2.14 4 3 11 13.50 1.47 4 3 11 11.47 2.11 -5 -3 -11 18.78 2.31 -5 -3 -11 15.01 1.56 5 3 11 13.80 2.47 6 3 11 6.67 2.94 3 -4 -11 22.11 2.22 3 -4 -11 19.82 1.87 3 -4 -11 19.38 2.54 -3 4 11 17.81 1.85 2 -4 -11 15.12 2.17 2 -4 -11 12.32 1.45 2 -4 -11 15.60 1.89 -2 4 11 15.21 1.68 1 -4 -11 36.61 2.11 1 -4 -11 39.44 2.32 1 -4 -11 33.40 2.84 -1 4 11 37.11 2.30 0 -4 -11 45.88 2.46 0 -4 -11 44.64 2.21 0 -4 -11 45.92 2.93 0 4 11 47.28 2.39 -1 -4 -11 25.61 1.79 -1 -4 -11 26.86 2.04 -1 -4 -11 30.29 2.57 1 4 11 25.02 1.91 -2 -4 -11 14.03 1.35 -2 -4 -11 17.77 1.83 2 4 11 17.27 1.52 -3 -4 -11 22.31 2.03 -3 -4 -11 20.44 1.69 3 4 11 19.77 2.14 -4 -4 -11 15.49 1.94 -4 -4 -11 11.42 1.33 4 4 11 12.18 2.02 -5 -4 -11 18.24 2.54 -5 -4 -11 15.31 1.57 5 4 11 12.78 2.28 -6 -4 -11 8.68 1.62 6 4 11 7.57 2.83 3 -5 -11 12.61 1.87 2 -5 -11 20.26 2.08 2 -5 -11 17.43 2.35 2 -5 -11 15.42 1.51 -2 5 11 16.59 1.83 1 -5 -11 17.58 1.70 1 -5 -11 21.29 2.26 1 -5 -11 20.65 2.08 -1 5 11 21.92 1.88 0 -5 -11 22.27 2.20 0 -5 -11 19.97 1.88 0 -5 -11 16.36 1.60 0 5 11 19.10 1.89 -1 -5 -11 27.96 2.09 -1 -5 -11 28.61 2.31 -1 -5 -11 27.49 1.74 1 5 11 25.54 1.98 -2 -5 -11 26.62 2.08 -2 -5 -11 41.92 3.11 -2 -5 -11 29.84 1.76 -3 -5 -11 16.73 1.57 -3 -5 -11 19.90 1.89 3 5 11 18.59 2.09 -4 -5 -11 11.06 1.29 4 5 11 10.74 1.84 -5 -5 -11 19.00 1.82 5 5 11 17.55 2.38 -6 -5 -11 7.68 1.53 2 -6 -11 15.02 3.59 1 -6 -11 22.25 2.39 -1 6 11 18.23 1.89 0 -6 -11 14.34 1.87 0 6 11 15.88 1.67 -1 -6 -11 15.27 1.35 -1 -6 -11 13.08 1.82 -2 -6 -11 15.11 1.47 -2 -6 -11 18.81 2.07 -3 -6 -11 19.99 1.58 3 6 11 21.82 2.13 -4 -6 -11 26.35 1.77 4 6 11 29.17 2.54 -5 -6 -11 11.40 1.30 5 6 11 12.77 2.11 -6 -6 -11 10.52 1.90 0 -7 -11 32.45 2.88 0 7 11 30.40 2.34 -1 -7 -11 29.25 2.58 -2 -7 -11 12.03 1.71 -3 -7 -11 17.87 2.05 3 7 11 19.05 2.03 4 7 11 22.32 2.41 -5 -7 -11 16.45 1.57 -2 -8 -11 15.81 1.95 -3 -8 -11 21.20 2.33 1 0 -12 13.11 1.98 -1 0 12 11.68 2.33 0 0 -12 28.60 2.18 0 0 12 23.63 2.30 -1 0 -12 14.28 1.54 1 0 12 11.86 1.84 -2 0 -12 5.71 1.54 3 0 12 5.06 2.09 1 -1 -12 16.08 1.66 -1 1 12 15.96 1.72 0 -1 -12 12.25 1.53 0 1 12 9.85 1.52 -1 -1 -12 10.90 1.44 1 1 12 7.37 1.44 -2 -1 -12 17.00 1.65 2 1 12 14.01 1.65 -3 -1 -12 16.10 2.19 3 1 12 11.81 2.31 3 1 12 12.95 1.66 2 -2 -12 17.97 2.63 1 -2 -12 20.00 1.74 -1 2 12 14.87 1.75 0 -2 -12 16.80 1.65 0 2 12 17.16 1.65 -1 -2 -12 14.45 1.89 -1 -2 -12 13.79 1.47 1 2 12 13.98 1.61 -2 -2 -12 11.64 1.47 -2 -2 -12 15.07 1.97 2 2 12 9.60 1.44 2 2 12 7.34 1.79 -3 -2 -12 13.52 1.57 -3 -2 -12 21.77 2.34 3 2 12 6.44 1.94 3 2 12 12.24 1.54 -4 -2 -12 23.12 2.72 4 2 12 14.88 2.62 4 2 12 14.11 1.70 2 -3 -12 12.70 2.31 1 -3 -12 24.50 2.93 1 -3 -12 22.44 2.13 1 -3 -12 24.48 2.06 -1 3 12 21.54 1.97 0 -3 -12 31.19 2.12 0 -3 -12 32.16 2.29 0 3 12 29.25 2.23 -1 -3 -12 19.78 1.83 -1 -3 -12 18.64 2.09 1 3 12 18.09 1.68 -2 -3 -12 19.85 2.01 -2 -3 -12 15.55 1.57 2 3 12 14.46 1.59 -3 -3 -12 12.33 1.49 -3 -3 -12 19.07 2.12 3 3 12 13.00 1.51 3 3 12 11.63 1.97 -4 -3 -12 20.56 2.29 4 3 12 11.80 2.23 1 -4 -12 27.53 2.59 1 -4 -12 25.46 2.04 1 -4 -12 26.53 2.26 0 -4 -12 13.09 1.49 0 -4 -12 22.89 3.14 0 -4 -12 13.37 1.76 0 4 12 14.37 1.68 -1 -4 -12 23.07 1.86 -1 -4 -12 20.65 2.08 1 4 12 20.75 1.99 -2 -4 -12 30.74 2.29 -2 -4 -12 28.11 1.99 2 4 12 30.73 2.05 -3 -4 -12 17.61 2.09 -3 -4 -12 18.80 1.83 -4 -4 -12 9.80 1.78 4 4 12 8.37 1.85 0 -5 -12 20.20 2.07 0 -5 -12 20.04 1.63 0 -5 -12 19.97 2.31 0 5 12 22.57 2.22 -1 -5 -12 14.31 1.79 -1 -5 -12 13.66 1.40 1 5 12 12.70 1.54 -2 -5 -12 11.55 1.67 -2 -5 -12 11.46 1.34 -3 -5 -12 23.70 2.21 -3 -5 -12 22.86 1.86 3 5 12 23.38 2.34 4 5 12 13.85 2.05 -1 -6 -12 15.34 2.00 -1 -6 -12 15.54 1.45 1 6 12 16.45 2.36 -2 -6 -12 6.21 1.11 -3 -6 -12 14.64 1.43 3 6 12 15.14 1.89 0 0 0 0.00 0.00 ; _shelx_hkl_checksum 80438 _shelx_res_file ; TITL AW2913U_a.res in P-1 AW2913U_a.res created by SHELXL-2017/1 at 11:54:32 on 08-Nov-2023 REM Old TITL AW2913U in P1 REM SHELXT solution in P-1: R1 0.045, Rweak 0.299, Alpha 0.042 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: C26 N2 O6 U CELL 0.71073 8.00630 8.78640 8.83310 78.2745 84.6484 74.8141 ZERR 1.00 0.00270 0.00290 0.00290 0.0050 0.0045 0.0047 LATT 1 SFAC C H N O U UNIT 24 22 4 6 1 TEMP -148 SIZE 0.24 0.14 0.05 REM light yellow block L.S. 16 CONF BOND $H HTAB EQIV $2 -x+1, -y+2, -z+1 HTAB C4 O2_$2 HTAB C12 N2_$2 MPLA 6 N1 C1 C2 C3 C4 C5 MPLA 6 N2 C6 C7 C8 C9 C10 ACTA OMIT 0 52 LIST 4 FMAP 2 PLAN 20 REM EXTI 0.000955 WGHT 0.028500 1.911800 FVAR 0.18033 U 5 0.500000 1.000000 1.000000 10.50000 0.01675 0.01482 = 0.01439 -0.00708 0.00165 -0.00319 O1 4 0.437405 0.841643 1.132843 11.00000 0.02321 0.01557 = 0.02251 -0.00543 0.00029 -0.00715 O2 4 0.284262 1.002652 0.817760 11.00000 0.02100 0.02527 = 0.02345 -0.01312 -0.00081 -0.00234 O3 4 0.192304 1.154237 0.991652 11.00000 0.02182 0.02410 = 0.02019 -0.00948 -0.00086 -0.00152 N1 3 0.600001 0.806833 0.807861 11.00000 0.02184 0.01933 = 0.01613 -0.00794 -0.00049 -0.00365 N2 3 0.825602 0.559392 0.342277 11.00000 0.03908 0.02649 = 0.02413 -0.01264 0.00612 -0.00929 C1 1 0.609522 0.648682 0.849034 11.00000 0.02847 0.02166 = 0.02027 -0.00890 -0.00041 -0.00218 AFIX 43 H1B 2 0.583062 0.607259 0.953926 11.00000 -1.20000 AFIX 0 C2 1 0.656163 0.542839 0.745696 11.00000 0.02624 0.01716 = 0.02334 -0.00917 -0.00086 -0.00039 AFIX 43 H2B 2 0.659233 0.432421 0.779693 11.00000 -1.20000 AFIX 0 C3 1 0.698380 0.600614 0.591599 11.00000 0.01898 0.02074 = 0.02190 -0.00957 -0.00028 -0.00380 C4 1 0.689461 0.764144 0.549356 11.00000 0.03423 0.02251 = 0.01766 -0.00707 0.00434 -0.00998 AFIX 43 H4A 2 0.717602 0.808646 0.445814 11.00000 -1.20000 AFIX 0 C5 1 0.639203 0.861606 0.659503 11.00000 0.03050 0.02010 = 0.02495 -0.00824 0.00085 -0.00580 AFIX 43 H5A 2 0.632250 0.973022 0.627986 11.00000 -1.20000 AFIX 0 C6 1 0.750600 0.495202 0.473171 11.00000 0.02035 0.02198 = 0.02031 -0.00885 -0.00059 -0.00310 C7 1 0.723565 0.341260 0.498509 11.00000 0.02581 0.02368 = 0.01784 -0.00629 -0.00117 -0.00824 AFIX 43 H7A 2 0.668701 0.299732 0.592049 11.00000 -1.20000 AFIX 0 C8 1 0.779066 0.250217 0.383197 11.00000 0.03232 0.02173 = 0.02907 -0.01288 -0.00199 -0.00393 AFIX 43 H8A 2 0.762534 0.144998 0.396903 11.00000 -1.20000 AFIX 0 C9 1 0.858265 0.314066 0.248871 11.00000 0.03244 0.03049 = 0.02688 -0.01856 0.00262 -0.00426 AFIX 43 H9A 2 0.898205 0.253572 0.169094 11.00000 -1.20000 AFIX 0 C10 1 0.878179 0.468003 0.232998 11.00000 0.04247 0.03371 = 0.02379 -0.01558 0.00791 -0.00752 AFIX 43 H10A 2 0.931921 0.511925 0.139886 11.00000 -1.20000 AFIX 0 C11 1 0.162099 1.099754 0.877632 11.00000 0.02128 0.02042 = 0.02118 -0.00431 -0.00132 -0.00751 C12 1 -0.014739 1.149094 0.812769 11.00000 0.02080 0.02477 = 0.02923 -0.00569 -0.00610 -0.00238 AFIX 137 H12A 2 -0.039326 1.057500 0.779774 11.00000 -1.50000 H12B 2 -0.019017 1.237007 0.723752 11.00000 -1.50000 H12C 2 -0.101419 1.185014 0.892399 11.00000 -1.50000 AFIX 0 HKLF 4 REM AW2913U_a.res in P-1 REM R1 = 0.0266 for 2260 Fo > 4sig(Fo) and 0.0266 for all 2260 data REM 161 parameters refined using 0 restraints END WGHT 0.0285 1.9118 REM Instructions for potential hydrogen bonds HTAB C4 O2_$2 HTAB C12 N2_$2 REM Highest difference peak 2.263, deepest hole -2.631, 1-sigma level 0.156 Q1 1 0.4803 0.9606 1.1003 11.00000 0.05 2.26 Q2 1 0.3913 1.0309 0.9559 11.00000 0.05 1.70 Q3 1 0.5038 1.0761 1.0133 11.00000 0.05 0.93 Q4 1 0.3258 1.0545 1.0220 11.00000 0.05 0.88 Q5 1 0.3301 0.9815 1.0589 11.00000 0.05 0.85 Q6 1 0.3589 0.9401 1.0743 11.00000 0.05 0.80 Q7 1 0.4990 0.8256 1.0677 11.00000 0.05 0.79 Q8 1 0.6069 0.8394 1.0705 11.00000 0.05 0.79 Q9 1 0.0755 1.1184 0.8484 11.00000 0.05 0.62 Q10 1 0.4656 0.8435 1.1822 11.00000 0.05 0.57 Q11 1 0.3903 0.7982 1.1248 11.00000 0.05 0.48 Q12 1 0.3329 1.0979 1.0928 11.00000 0.05 0.47 Q13 1 0.2831 1.0281 0.9196 11.00000 0.05 0.44 Q14 1 0.2018 1.1079 1.0754 11.00000 0.05 0.39 Q15 1 0.2456 0.9243 1.1408 11.00000 0.05 0.35 Q16 1 0.2794 1.0933 0.7743 11.00000 0.05 0.35 Q17 1 0.2484 1.1971 0.9852 11.00000 0.05 0.34 Q18 1 0.5631 0.7941 1.1896 11.00000 0.05 0.33 Q19 1 0.4416 0.9019 0.6844 11.00000 0.05 0.33 Q20 1 0.1668 1.0780 0.9977 11.00000 0.05 0.33 ; _shelx_res_checksum 958 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group U U 0.5 1.0 1.0 0.01498(9) Uani d 1 . . O O1 0.4374(4) 0.8416(4) 1.1328(4) 0.0198(7) Uani d 1 . . O O2 0.2843(4) 1.0027(4) 0.8178(4) 0.0227(7) Uani d 1 . . O O3 0.1923(4) 1.1542(4) 0.9917(4) 0.0221(7) Uani d 1 . . N N1 0.6000(5) 0.8068(5) 0.8079(4) 0.0187(8) Uani d 1 . . N N2 0.8256(6) 0.5594(5) 0.3423(5) 0.0290(10) Uani d 1 . . C C1 0.6095(7) 0.6487(6) 0.8490(6) 0.0236(10) Uani d 1 . . H H1B 0.583062 0.607259 0.953926 0.028 Uiso calc 1 . . C C2 0.6562(6) 0.5428(6) 0.7457(5) 0.0224(10) Uani d 1 . . H H2B 0.659233 0.432421 0.779693 0.027 Uiso calc 1 . . C C3 0.6984(6) 0.6006(6) 0.5916(5) 0.0200(10) Uani d 1 . . C C4 0.6895(7) 0.7641(6) 0.5494(5) 0.0241(10) Uani d 1 . . H H4A 0.717602 0.808646 0.445814 0.029 Uiso calc 1 . . C C5 0.6392(7) 0.8616(6) 0.6595(6) 0.0248(11) Uani d 1 . . H H5A 0.63225 0.973022 0.627986 0.03 Uiso calc 1 . . C C6 0.7506(6) 0.4952(6) 0.4732(5) 0.0206(10) Uani d 1 . . C C7 0.7236(6) 0.3413(6) 0.4985(5) 0.0217(10) Uani d 1 . . H H7A 0.668701 0.299732 0.592049 0.026 Uiso calc 1 . . C C8 0.7791(7) 0.2502(6) 0.3832(6) 0.0270(11) Uani d 1 . . H H8A 0.762534 0.144998 0.396903 0.032 Uiso calc 1 . . C C9 0.8583(7) 0.3141(7) 0.2489(6) 0.0289(12) Uani d 1 . . H H9A 0.898205 0.253572 0.169094 0.035 Uiso calc 1 . . C C10 0.8782(8) 0.4680(7) 0.2330(6) 0.0328(13) Uani d 1 . . H H10A 0.931921 0.511925 0.139886 0.039 Uiso calc 1 . . C C11 0.1621(6) 1.0998(6) 0.8776(5) 0.0204(10) Uani d 1 . . C C12 -0.0147(6) 1.1491(6) 0.8128(6) 0.0251(11) Uani d 1 . . H H12A -0.039326 1.0575 0.779774 0.038 Uiso calc 1 . . H H12B -0.019017 1.237007 0.723752 0.038 Uiso calc 1 . . H H12C -0.101419 1.185014 0.892399 0.038 Uiso calc 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 U 0.01675(14) 0.01482(13) 0.01439(13) -0.00319(9) 0.00165(8) -0.00708(9) O1 0.0232(17) 0.0156(16) 0.0225(16) -0.0071(14) 0.0003(13) -0.0054(14) O2 0.0210(17) 0.0253(18) 0.0235(17) -0.0023(14) -0.0008(13) -0.0131(15) O3 0.0218(18) 0.0241(18) 0.0202(16) -0.0015(14) -0.0009(13) -0.0095(14) N1 0.022(2) 0.019(2) 0.0161(18) -0.0036(16) -0.0005(15) -0.0079(16) N2 0.039(3) 0.026(2) 0.024(2) -0.009(2) 0.0061(19) -0.0126(19) C1 0.028(3) 0.022(3) 0.020(2) -0.002(2) -0.0004(19) -0.009(2) C2 0.026(3) 0.017(2) 0.023(2) 0.000(2) -0.0009(19) -0.009(2) C3 0.019(2) 0.021(2) 0.022(2) -0.0038(19) -0.0003(18) -0.010(2) C4 0.034(3) 0.023(3) 0.018(2) -0.010(2) 0.004(2) -0.007(2) C5 0.031(3) 0.020(3) 0.025(2) -0.006(2) 0.001(2) -0.008(2) C6 0.020(2) 0.022(2) 0.020(2) -0.0031(19) -0.0006(18) -0.009(2) C7 0.026(3) 0.024(3) 0.018(2) -0.008(2) -0.0012(18) -0.006(2) C8 0.032(3) 0.022(3) 0.029(3) -0.004(2) -0.002(2) -0.013(2) C9 0.032(3) 0.030(3) 0.027(3) -0.004(2) 0.003(2) -0.019(2) C10 0.042(3) 0.034(3) 0.024(3) -0.008(3) 0.008(2) -0.016(2) C11 0.021(2) 0.020(2) 0.021(2) -0.008(2) -0.0013(18) -0.004(2) C12 0.021(3) 0.025(3) 0.029(3) -0.002(2) -0.006(2) -0.006(2) 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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O1 U O1 2_677 . 180.0 ? O1 U O2 2_677 . 88.92(13) ? O1 U O2 . . 91.08(13) ? O1 U O2 2_677 2_677 91.08(13) ? O1 U O2 . 2_677 88.92(13) ? O2 U O2 . 2_677 180.0 ? O1 U O3 2_677 2_677 89.22(14) ? O1 U O3 . 2_677 90.78(14) ? O2 U O3 . 2_677 127.48(10) ? O2 U O3 2_677 2_677 52.52(10) ? O1 U O3 2_677 . 90.78(14) ? O1 U O3 . . 89.22(14) ? O2 U O3 . . 52.52(10) ? O2 U O3 2_677 . 127.48(10) ? O3 U O3 2_677 . 180.0 ? O1 U N1 2_677 . 91.78(13) ? O1 U N1 . . 88.22(13) ? O2 U N1 . . 63.91(11) ? O2 U N1 2_677 . 116.09(11) ? O3 U N1 2_677 . 63.70(11) ? O3 U N1 . . 116.30(11) ? O1 U N1 2_677 2_677 88.22(13) ? O1 U N1 . 2_677 91.78(13) ? O2 U N1 . 2_677 116.10(11) ? O2 U N1 2_677 2_677 63.90(11) ? O3 U N1 2_677 2_677 116.30(11) ? O3 U N1 . 2_677 63.70(11) ? N1 U N1 . 2_677 180.0 ? O1 U C11 2_677 2_677 89.91(15) ? O1 U C11 . 2_677 90.09(14) ? O2 U C11 . 2_677 153.71(12) ? O2 U C11 2_677 2_677 26.29(12) ? O3 U C11 2_677 2_677 26.23(12) ? O3 U C11 . 2_677 153.77(12) ? N1 U C11 . 2_677 89.89(13) ? N1 U C11 2_677 2_677 90.11(13) ? O1 U C11 2_677 . 90.09(14) ? O1 U C11 . . 89.91(15) ? O2 U C11 . . 26.29(12) ? O2 U C11 2_677 . 153.71(12) ? O3 U C11 2_677 . 153.77(12) ? O3 U C11 . . 26.23(12) ? N1 U C11 . . 90.11(13) ? N1 U C11 2_677 . 89.89(13) ? C11 U C11 2_677 . 180.0(3) ? C11 O2 U . . 94.6(3) ? C11 O3 U . . 93.8(3) ? C5 N1 C1 . . 117.0(4) ? C5 N1 U . . 120.7(3) ? C1 N1 U . . 122.2(3) ? C6 N2 C10 . . 117.4(5) ? N1 C1 C2 . . 123.3(5) ? N1 C1 H1B . . 118.3 ? C2 C1 H1B . . 118.3 ? C1 C2 C3 . . 119.3(5) ? C1 C2 H2B . . 120.3 ? C3 C2 H2B . . 120.3 ? C4 C3 C2 . . 117.3(4) ? C4 C3 C6 . . 119.9(4) ? C2 C3 C6 . . 122.8(4) ? C5 C4 C3 . . 119.6(5) ? C5 C4 H4A . . 120.2 ? C3 C4 H4A . . 120.2 ? N1 C5 C4 . . 123.5(5) ? N1 C5 H5A . . 118.3 ? C4 C5 H5A . . 118.3 ? N2 C6 C7 . . 122.9(4) ? N2 C6 C3 . . 115.0(4) ? C7 C6 C3 . . 122.1(4) ? C8 C7 C6 . . 118.3(5) ? C8 C7 H7A . . 120.9 ? C6 C7 H7A . . 120.9 ? C9 C8 C7 . . 119.4(5) ? C9 C8 H8A . . 120.3 ? C7 C8 H8A . . 120.3 ? C8 C9 C10 . . 118.4(4) ? C8 C9 H9A . . 120.8 ? C10 C9 H9A . . 120.8 ? N2 C10 C9 . . 123.6(5) ? N2 C10 H10A . . 118.2 ? C9 C10 H10A . . 118.2 ? O3 C11 O2 . . 119.1(4) ? O3 C11 C12 . . 120.9(4) ? O2 C11 C12 . . 120.0(4) ? O3 C11 U . . 60.0(2) ? O2 C11 U . . 59.1(2) ? C12 C11 U . . 179.0(3) ? C11 C12 H12A . . 109.5 ? C11 C12 H12B . . 109.5 ? H12A C12 H12B . . 109.5 ? C11 C12 H12C . . 109.5 ? H12A C12 H12C . . 109.5 ? H12B C12 H12C . . 109.5 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag U O1 2_677 1.777(3) ? U O1 . 1.777(3) y U O2 . 2.461(3) y U O2 2_677 2.461(3) ? U O3 2_677 2.481(3) ? U O3 . 2.481(3) y U N1 . 2.571(4) y U N1 2_677 2.571(4) ? U C11 2_677 2.859(5) ? U C11 . 2.859(5) ? O2 C11 . 1.270(6) ? O3 C11 . 1.267(5) ? N1 C5 . 1.339(6) ? N1 C1 . 1.347(6) ? N2 C6 . 1.341(7) ? N2 C10 . 1.348(6) ? C1 C2 . 1.392(6) ? C1 H1B . 0.95 ? C2 C3 . 1.396(7) ? C2 H2B . 0.95 ? C3 C4 . 1.394(7) ? C3 C6 . 1.495(6) ? C4 C5 . 1.388(6) ? C4 H4A . 0.95 ? C5 H5A . 0.95 ? C6 C7 . 1.396(7) ? C7 C8 . 1.391(6) ? C7 H7A . 0.95 ? C8 C9 . 1.378(8) ? C8 H8A . 0.95 ? C9 C10 . 1.381(8) ? C9 H9A . 0.95 ? C10 H10A . 0.95 ? C11 C12 . 1.500(7) ? C12 H12A . 0.98 ? C12 H12B . 0.98 ? C12 H12C . 0.98 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag C4 H4A O2 2_676 0.95 2.57 3.487(6) 162.7 y C12 H12B N2 2_676 0.98 2.61 3.309(7) 128.6 y 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C5 N1 C1 C2 . . . . -0.5(7) ? U N1 C1 C2 . . . . 177.2(4) ? N1 C1 C2 C3 . . . . 1.1(8) ? C1 C2 C3 C4 . . . . -0.6(7) ? C1 C2 C3 C6 . . . . 179.7(4) ? C2 C3 C4 C5 . . . . -0.3(7) ? C6 C3 C4 C5 . . . . 179.4(5) ? C1 N1 C5 C4 . . . . -0.6(7) ? U N1 C5 C4 . . . . -178.2(4) ? C3 C4 C5 N1 . . . . 0.9(8) ? C10 N2 C6 C7 . . . . -0.9(8) ? C10 N2 C6 C3 . . . . 178.7(5) ? C4 C3 C6 N2 . . . . 15.5(7) ? C2 C3 C6 N2 . . . . -164.8(5) ? C4 C3 C6 C7 . . . . -164.8(5) ? C2 C3 C6 C7 . . . . 14.8(7) ? N2 C6 C7 C8 . . . . 0.8(7) ? C3 C6 C7 C8 . . . . -178.8(4) ? C6 C7 C8 C9 . . . . 0.0(7) ? C7 C8 C9 C10 . . . . -0.6(8) ? C6 N2 C10 C9 . . . . 0.2(8) ? C8 C9 C10 N2 . . . . 0.5(9) ? U O3 C11 O2 . . . . -1.0(5) ? U O3 C11 C12 . . . . 179.3(4) ? U O2 C11 O3 . . . . 1.0(5) ? U O2 C11 C12 . . . . -179.3(4) ? _cod_database_fobs_code 2312367