# Electronic Supplementary Material (ESI) for Dalton Transactions # 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_oct-15-1 _database_code_depnum_ccdc_archive 'CCDC 897457' #TrackingRef 'Oct-15-1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Ditallium(I) di-N,N-(2-cyano-2-oximinoacetyl)piperazine ; _chemical_name_common 'Ditallium(i) di-N,N-(2-cyano-2-oximinoacetyl)piperazine' _chemical_melting_point ? _chemical_formula_moiety 'C10 H8 N6 O4 Tl2' _chemical_formula_sum 'C10 H8 N6 O4 Tl2' _chemical_formula_weight 684.96 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' Tl Tl -2.8358 9.6688 '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/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 4.2757(8) _cell_length_b 13.674(2) _cell_length_c 12.009(2) _cell_angle_alpha 90.00 _cell_angle_beta 99.347(2) _cell_angle_gamma 90.00 _cell_volume 692.8(2) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 264 _cell_measurement_theta_min 2.18 _cell_measurement_theta_max 27.27 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 3.284 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 23.258 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.1894 _exptl_absorpt_correction_T_max 0.2930 _exptl_absorpt_process_details 'SADABS (Bruker AXS, 2005)' _exptl_special_details ; Overal quality of crystalline specimen of this complex was not good. We have tried numerous attempts to crystallize that compound at different conditions, and even prepared several bathes of Tl2BiPipCO. All suitable for diffraction experiments crystals were not entirely clear and exhibited some degree of opacity. The latter could have been due to preparative conditions when Tl2CO3 was used to make this complex, and a very small bubbles of CO2 may have been trapped inside crystals. Small, almost clear yellow block-like crystal was selected in a thick paraton oil and then placed into the Kryollop, centered and used for data collection at 120 K with the use of the Kryoflex system. Data were corrected for decay and absorption using the program SADABS (Sheldrick, G.M. (2003). SADABS. Version 2.10. University of Gottingen, Germany) ; _diffrn_ambient_temperature 120(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 APEX2 CCD area detector' _diffrn_measurement_method '4 omega full-sphere scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 8049 _diffrn_reflns_av_R_equivalents 0.0425 _diffrn_reflns_av_sigmaI/netI 0.0325 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 27.21 _reflns_number_total 1555 _reflns_number_gt 1369 _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, 1990)' _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^)+(0.0229P)^2^+23.0230P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1555 _refine_ls_number_parameters 100 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.0514 _refine_ls_R_factor_gt 0.0451 _refine_ls_wR_factor_ref 0.1013 _refine_ls_wR_factor_gt 0.0987 _refine_ls_goodness_of_fit_ref 1.272 _refine_ls_restrained_S_all 1.267 _refine_ls_shift/su_max 0.000 _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 C1 C 0.222(3) 0.6282(9) 0.2455(9) 0.013(2) Uani 1 1 d U . . C2 C 0.053(3) 0.7113(9) 0.2812(10) 0.016(2) Uani 1 1 d . . . C3 C 0.331(3) 0.6440(9) 0.1344(9) 0.015(2) Uani 1 1 d . . . C4 C 0.570(3) 0.5987(9) -0.0276(9) 0.013(2) Uani 1 1 d U . . H4A H 0.8044 0.5990 -0.0172 0.015 Uiso 1 1 calc R . . H4B H 0.4945 0.6648 -0.0524 0.015 Uiso 1 1 calc R . . C5 C 0.557(3) 0.4752(8) 0.1183(9) 0.014(2) Uani 1 1 d . . . H5A H 0.4722 0.4602 0.1883 0.017 Uiso 1 1 calc R . . H5B H 0.7910 0.4702 0.1351 0.017 Uiso 1 1 calc R . . N1 N 0.271(3) 0.5509(8) 0.3096(9) 0.022(2) Uani 1 1 d . . . N2 N -0.091(3) 0.7741(9) 0.3093(10) 0.028(3) Uani 1 1 d . . . N3 N 0.466(2) 0.5756(7) 0.0814(8) 0.014(2) Uani 1 1 d U . . O1 O 0.165(2) 0.5534(7) 0.4058(7) 0.024(2) Uani 1 1 d . . . O2 O 0.276(2) 0.7282(6) 0.0933(7) 0.0177(18) Uani 1 1 d . . . Tl1 Tl 0.23934(11) 0.36607(3) 0.46135(4) 0.01847(16) Uani 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 C1 0.016(4) 0.012(4) 0.013(4) -0.003(3) 0.006(3) 0.000(3) C2 0.022(6) 0.015(6) 0.012(5) -0.003(4) 0.001(5) -0.002(5) C3 0.011(5) 0.019(6) 0.013(5) 0.001(5) 0.003(4) -0.004(4) C4 0.018(4) 0.012(4) 0.008(4) -0.002(3) 0.004(3) -0.001(3) C5 0.021(6) 0.010(5) 0.011(5) -0.004(4) 0.003(4) 0.000(4) N1 0.032(6) 0.025(6) 0.010(5) 0.001(4) 0.007(4) 0.003(5) N2 0.037(7) 0.026(6) 0.023(6) -0.005(5) 0.011(5) 0.009(5) N3 0.015(3) 0.013(3) 0.014(3) 0.003(2) 0.002(2) -0.001(2) O1 0.042(6) 0.021(5) 0.012(4) 0.003(4) 0.012(4) 0.010(4) O2 0.025(5) 0.014(4) 0.016(4) -0.001(3) 0.010(3) 0.001(3) Tl1 0.0223(3) 0.0126(2) 0.0217(2) -0.0034(2) 0.00734(17) -0.00052(19) _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 C1 N1 1.304(16) . yes C1 C2 1.447(16) . yes C1 C3 1.499(15) . yes C2 N2 1.139(16) . yes C3 O2 1.258(14) . yes C3 N3 1.319(15) . yes C4 N3 1.483(14) . yes C4 C5 1.519(15) 3_665 yes C4 H4A 0.9900 . no C4 H4B 0.9900 . no C5 N3 1.475(14) . yes C5 C4 1.519(15) 3_665 yes C5 H5A 0.9900 . no C5 H5B 0.9900 . no N1 O1 1.307(13) . yes O1 Tl1 2.653(9) . yes O1 Tl1 2.766(9) 3_566 yes Tl1 O1 2.766(9) 3_566 yes 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 N1 C1 C2 120.2(10) . . yes N1 C1 C3 126.8(11) . . yes C2 C1 C3 113.1(10) . . yes N2 C2 C1 177.0(14) . . yes O2 C3 N3 121.9(10) . . yes O2 C3 C1 114.6(10) . . yes N3 C3 C1 123.5(11) . . yes N3 C4 C5 111.6(9) . 3_665 yes N3 C4 H4A 109.3 . . no C5 C4 H4A 109.3 3_665 . no N3 C4 H4B 109.3 . . no C5 C4 H4B 109.3 3_665 . no H4A C4 H4B 108.0 . . no N3 C5 C4 110.9(9) . 3_665 yes N3 C5 H5A 109.5 . . no C4 C5 H5A 109.5 3_665 . no N3 C5 H5B 109.5 . . no C4 C5 H5B 109.5 3_665 . no H5A C5 H5B 108.0 . . no C1 N1 O1 117.0(10) . . yes C3 N3 C5 129.1(10) . . yes C3 N3 C4 119.6(10) . . yes C5 N3 C4 111.2(9) . . yes N1 O1 Tl1 98.8(7) . . yes N1 O1 Tl1 149.2(8) . 3_566 yes Tl1 O1 Tl1 107.4(3) . 3_566 yes O1 Tl1 O1 72.6(3) . 3_566 yes 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 N1 C1 C3 O2 -174.3(12) . . . . yes C2 C1 C3 O2 4.1(14) . . . . yes N1 C1 C3 N3 7.1(19) . . . . yes C2 C1 C3 N3 -174.4(11) . . . . yes C2 C1 N1 O1 -0.8(17) . . . . yes C3 C1 N1 O1 177.5(11) . . . . yes O2 C3 N3 C5 177.7(11) . . . . yes C1 C3 N3 C5 -3.9(18) . . . . yes O2 C3 N3 C4 2.4(16) . . . . yes C1 C3 N3 C4 -179.2(10) . . . . yes C4 C5 N3 C3 129.2(12) 3_665 . . . yes C4 C5 N3 C4 -55.2(13) 3_665 . . . yes C5 C4 N3 C3 -128.3(11) 3_665 . . . yes C5 C4 N3 C5 55.6(13) 3_665 . . . yes C1 N1 O1 Tl1 168.5(9) . . . . yes C1 N1 O1 Tl1 20(2) . . . 3_566 yes N1 O1 Tl1 O1 -163.5(9) . . . 3_566 yes Tl1 O1 Tl1 O1 0.0 3_566 . . 3_566 yes _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.21 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 2.775 _refine_diff_density_min -3.146 _refine_diff_density_rms 0.339 data_newest-lig _database_code_depnum_ccdc_archive 'CCDC 897458' #TrackingRef 'newest-lig.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Di-N,N-(2-cyano-2-oximinoacetyl)piperazine ; _chemical_name_common Di-N,N-(2-cyano-2-oximinoacetyl)piperazine _chemical_melting_point 'decomposes: 173 C beginning' _chemical_formula_moiety 'C10 H10 N6 O4' _chemical_formula_sum 'C10 H10 N6 O4' _chemical_formula_weight 278.24 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 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 6.298(5) _cell_length_b 15.488(12) _cell_length_c 6.453(5) _cell_angle_alpha 90.00 _cell_angle_beta 102.648(13) _cell_angle_gamma 90.00 _cell_volume 614.2(8) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 173 _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 54.52 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.505 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 288 _exptl_absorpt_coefficient_mu 0.120 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.662 _exptl_absorpt_correction_T_max 0.745 _exptl_absorpt_process_details 'SADABS (Bruker AXS, 2005)' _exptl_special_details ; Data were corrected for decay and absorption using the program SADABS (Sheldrick, G.M. (2003). SADABS. Version 2.10. University of Gottingen, Germany) A clear and colorless crystalline specimen was selected for studies in thick paraton oil, and then was pooled out by the Cryoloop. The Cryloop was placed using magnetic Cu-pin holder on the goniometer head of APEX2 diffractemeter. Cold N2 gas stream from the Kryoflex cooled the crystal to 120 K, and intensity data was measured using 4 runs of 364 frames covering the full-sphere of reflections. ; _diffrn_ambient_temperature 120(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 'APEX 2, CCD area detector' _diffrn_measurement_method '4 omega and 2 phi scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 1201 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0327 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.63 _diffrn_reflns_theta_max 26.00 _reflns_number_total 1201 _reflns_number_gt 853 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _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^ > 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. This crystal specimen was a non-merohedral twin. Normal twined crystal workup procedure was applied. Specifically: 1) 4 runs with 360 frames were examined and 1592 reflections with I > or equal 20 sigma(I) were harvested; 2) two domains were selected that absorbed over 96% of these reflections; 3) domain #1 had 951 reflections, domain #2 had 634 reflections; 4) both domains generated monoclinic cells with the volume 611 A(3), and P2(1)/n space group, Z=2; 5) the TWIN law is 0.9970 -0.0003 -0.0129 0.00107 -1.0000 0.0052 -0.4608 -0.0008 -0.9970; both domains are related through 178.2 dgree rotation; 6) twin4.hkl and twin5.hkl files were generated in TWINABS; 7) the structure has emegred using the twin4.hkl file and *_0m.p4p files; 8) the XPREP used for data conditioning 1309 reflections that gave mean I/sigma = 16.08; 9) |E x E(-1)| = 0.970, for centrosymmetric structures. On a top of the twinning problem this specimen also had a specific for oximes "disorder" - coexistence of the syn- and anti- isomers. A successful modeling of this complication with the following refinement has lead to syn- (51.24%) and anti- (48.76%) isomers contribution into the overall structure. ; _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^)+(0.1111P)^2^+0.1467P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1201 _refine_ls_number_parameters 112 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.0843 _refine_ls_R_factor_gt 0.0605 _refine_ls_wR_factor_ref 0.1859 _refine_ls_wR_factor_gt 0.1695 _refine_ls_goodness_of_fit_ref 1.096 _refine_ls_restrained_S_all 1.142 _refine_ls_shift/su_max 0.000 _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 C1 C 0.8267(4) 0.66557(19) 0.6015(4) 0.0353(7) Uani 1 1 d . A 1 C2 C 0.8844(5) 0.7495(2) 0.5406(5) 0.0483(9) Uani 1 1 d . A 1 C3 C 1.0086(4) 0.60205(17) 0.6647(4) 0.0296(6) Uani 1 1 d . . . C4 C 0.9163(5) 0.58514(18) 1.0178(4) 0.0335(7) Uani 1 1 d . . . H4A H 0.8051 0.6297 0.9646 0.040 Uiso 1 1 calc R A . H4B H 1.0220 0.6096 1.1402 0.040 Uiso 1 1 calc R . . C5 C 1.1916(4) 0.49339(17) 0.9115(4) 0.0315(7) Uani 1 1 d . . . H5A H 1.3096 0.5139 1.0289 0.038 Uiso 1 1 calc R A . H5B H 1.2563 0.4782 0.7896 0.038 Uiso 1 1 calc R . . N1A N 0.6346(14) 0.6247(7) 0.5941(12) 0.037(2) Uani 0.488(9) 1 d PU A 1 N2 N 0.9302(6) 0.8171(2) 0.4962(6) 0.0724(11) Uani 1 1 d U A 1 N3 N 1.0288(4) 0.56178(14) 0.8496(3) 0.0299(6) Uani 1 1 d . A . O1 O 0.5622(8) 0.5799(4) 0.5962(7) 0.0383(14) Uani 0.512(9) 1 d P A 1 H1 H 0.4260 0.5771 0.5753 0.057 Uiso 0.512(9) 1 calc PR A 1 O2 O 1.1287(3) 0.59127(12) 0.5385(3) 0.0345(6) Uani 1 1 d . A . O1A O 0.4724(10) 0.6846(3) 0.5069(7) 0.0413(17) Uani 0.488(9) 1 d P A 1 H1A H 0.3508 0.6598 0.4796 0.062 Uiso 0.488(9) 1 calc PR A 1 N1 N 0.6213(13) 0.6611(5) 0.5601(11) 0.032(2) Uani 0.512(9) 1 d PU A 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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0325(17) 0.0441(17) 0.0278(14) 0.0049(12) 0.0035(12) -0.0001(13) C2 0.0421(18) 0.056(2) 0.0509(19) 0.0262(16) 0.0191(15) 0.0151(16) C3 0.0278(14) 0.0313(14) 0.0283(13) 0.0006(11) 0.0033(11) -0.0078(11) C4 0.0377(16) 0.0326(14) 0.0297(14) 0.0005(11) 0.0061(12) 0.0033(12) C5 0.0292(15) 0.0341(15) 0.0323(14) 0.0030(11) 0.0091(11) 0.0028(11) N1A 0.031(4) 0.041(4) 0.037(3) 0.013(3) 0.001(2) -0.001(4) N2 0.073(2) 0.0596(19) 0.093(2) 0.0385(17) 0.0354(18) 0.0200(16) N3 0.0321(13) 0.0304(12) 0.0267(12) 0.0025(9) 0.0053(9) -0.0007(9) O1 0.031(2) 0.031(3) 0.051(3) 0.0040(19) 0.004(2) -0.009(2) O2 0.0351(11) 0.0389(11) 0.0305(10) 0.0035(8) 0.0092(9) -0.0052(8) O1A 0.032(4) 0.043(3) 0.046(3) 0.016(2) 0.003(2) 0.005(2) N1 0.030(5) 0.032(4) 0.033(3) 0.001(3) 0.005(3) 0.001(3) _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 C1 N1 1.264(8) . yes C1 N1A 1.357(10) . yes C1 C2 1.428(5) . yes C1 C3 1.497(4) . yes C2 N2 1.138(5) . yes C3 O2 1.238(3) . yes C3 N3 1.327(4) . yes C4 N3 1.466(4) . yes C4 C5 1.512(4) 3_767 yes C4 H4A 0.9900 . no C4 H4B 0.9900 . no C5 N3 1.468(3) . yes C5 C4 1.512(4) 3_767 yes C5 H5A 0.9900 . no C5 H5B 0.9900 . no N1A O1A 1.403(8) . yes O1 N1 1.345(8) . yes O1 H1 0.8400 . no O1A H1A 0.8400 . no 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 N1 C1 C2 107.6(5) . . yes N1A C1 C2 133.9(5) . . yes N1 C1 C3 135.0(4) . . yes N1A C1 C3 109.0(5) . . yes C2 C1 C3 116.6(3) . . yes N2 C2 C1 178.5(4) . . yes O2 C3 N3 125.2(3) . . yes O2 C3 C1 116.8(2) . . yes N3 C3 C1 118.1(3) . . yes N3 C4 C5 110.3(2) . 3_767 yes N3 C4 H4A 109.6 . . no C5 C4 H4A 109.6 3_767 . no N3 C4 H4B 109.6 . . no C5 C4 H4B 109.6 3_767 . no H4A C4 H4B 108.1 . . no N3 C5 C4 109.2(2) . 3_767 yes N3 C5 H5A 109.8 . . no C4 C5 H5A 109.8 3_767 . no N3 C5 H5B 109.8 . . no C4 C5 H5B 109.8 3_767 . no H5A C5 H5B 108.3 . . no C1 N1A O1A 105.8(8) . . yes C3 N3 C4 125.7(2) . . yes C3 N3 C5 120.5(2) . . yes C4 N3 C5 113.5(2) . . yes N1A O1A H1A 109.5 . . no C1 N1 O1 108.9(7) . . yes 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 N1 C1 C3 O2 116.3(6) . . . . yes N1A C1 C3 O2 121.1(4) . . . . yes C2 C1 C3 O2 -52.3(4) . . . . yes N1 C1 C3 N3 -63.6(6) . . . . yes N1A C1 C3 N3 -58.8(5) . . . . yes C2 C1 C3 N3 127.9(3) . . . . yes N1 C1 N1A O1A 0.1(9) . . . . yes C2 C1 N1A O1A -0.5(9) . . . . yes C3 C1 N1A O1A -172.2(4) . . . . yes O2 C3 N3 C4 167.6(2) . . . . yes C1 C3 N3 C4 -12.5(4) . . . . yes O2 C3 N3 C5 -5.3(4) . . . . yes C1 C3 N3 C5 174.6(2) . . . . yes C5 C4 N3 C3 129.6(3) 3_767 . . . yes C5 C4 N3 C5 -57.1(3) 3_767 . . . yes C4 C5 N3 C3 -129.8(3) 3_767 . . . yes C4 C5 N3 C4 56.5(3) 3_767 . . . yes N1A C1 N1 O1 -5.6(10) . . . . yes C2 C1 N1 O1 174.0(4) . . . . yes C3 C1 N1 O1 4.7(9) . . . . yes 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 O1 H1 O2 0.84 1.85 2.680(5) 170.0 1_455 O1A H1A O2 0.84 1.86 2.648(6) 155.4 1_455 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.300 _refine_diff_density_min -0.189 _refine_diff_density_rms 0.065