# 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_2a _database_code_depnum_ccdc_archive 'CCDC 915982' #TrackingRef 'mariusz.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H9 N5 O2' _chemical_formula_weight 267.25 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' 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.4645(12) _cell_length_b 6.6032(14) _cell_length_c 14.076(3) _cell_angle_alpha 97.978(11) _cell_angle_beta 91.056(10) _cell_angle_gamma 100.223(12) _cell_volume 585.0(2) _cell_formula_units_Z 2 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 1573 _cell_measurement_theta_min 2.93 _cell_measurement_theta_max 23.80 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.517 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 276 _exptl_absorpt_coefficient_mu 0.109 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9807 _exptl_absorpt_correction_T_max 0.9989 _exptl_absorpt_process_details 'SADABS (Bruker-AXS)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(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 kappa APEX-II CCD Quazar' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 7404 _diffrn_reflns_av_R_equivalents 0.0408 _diffrn_reflns_av_sigmaI/netI 0.0485 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 5.40 _diffrn_reflns_theta_max 25.68 _reflns_number_total 2178 _reflns_number_gt 1552 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0599P)^2^+0.0198P] 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 2178 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0711 _refine_ls_R_factor_gt 0.0443 _refine_ls_wR_factor_ref 0.1144 _refine_ls_wR_factor_gt 0.1008 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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 O4 O 0.8337(2) 0.7404(2) 0.16503(10) 0.0415(4) Uani 1 1 d . . . O5 O 0.5427(2) 0.7276(3) 0.08364(10) 0.0504(5) Uani 1 1 d . . . N1 N 0.2610(2) 0.7701(3) 0.79848(11) 0.0351(4) Uani 1 1 d . . . N2 N -0.0735(2) 0.7362(2) 0.58255(11) 0.0305(4) Uani 1 1 d . . . N3 N -0.0089(2) 0.7425(2) 0.49538(11) 0.0298(4) Uani 1 1 d . . . N4 N 0.2042(2) 0.7630(2) 0.50042(10) 0.0243(4) Uani 1 1 d . . . N5 N 0.6437(3) 0.7375(2) 0.15938(11) 0.0327(4) Uani 1 1 d . . . C4 C 0.2498(4) 0.7693(3) 0.89287(14) 0.0413(6) Uani 1 1 d . . . H4A H 0.3778 0.7864 0.9298 0.050 Uiso 1 1 calc R . . C5 C 0.0643(4) 0.7454(3) 0.94043(15) 0.0439(6) Uani 1 1 d . . . H5 H 0.0649 0.7444 1.0079 0.053 Uiso 1 1 calc R . . C6 C -0.1207(4) 0.7231(3) 0.88784(16) 0.0449(6) Uani 1 1 d . . . H6 H -0.2511 0.7062 0.9184 0.054 Uiso 1 1 calc R . . C7 C -0.1160(3) 0.7256(3) 0.78990(14) 0.0365(5) Uani 1 1 d . . . H7 H -0.2425 0.7114 0.7522 0.044 Uiso 1 1 calc R . . C8 C 0.0778(3) 0.7492(3) 0.74800(13) 0.0268(5) Uani 1 1 d . . . C9 C 0.0971(3) 0.7519(3) 0.64399(13) 0.0257(4) Uani 1 1 d . . . C10 C 0.2733(3) 0.7689(3) 0.59238(13) 0.0262(4) Uani 1 1 d . . . H10 H 0.4146 0.7821 0.6157 0.031 Uiso 1 1 calc R . . C11 C 0.3180(3) 0.7617(3) 0.41442(13) 0.0243(4) Uani 1 1 d . . . C12 C 0.5144(3) 0.7050(3) 0.41327(13) 0.0279(5) Uani 1 1 d . . . H12 H 0.5747 0.6711 0.4697 0.033 Uiso 1 1 calc R . . C13 C 0.6215(3) 0.6983(3) 0.32959(13) 0.0285(5) Uani 1 1 d . . . H13 H 0.7568 0.6610 0.3277 0.034 Uiso 1 1 calc R . . C14 C 0.5290(3) 0.7465(3) 0.24836(12) 0.0260(4) Uani 1 1 d . . . C15 C 0.3344(3) 0.8049(3) 0.24881(13) 0.0293(5) Uani 1 1 d . . . H15 H 0.2743 0.8378 0.1921 0.035 Uiso 1 1 calc R . . C16 C 0.2287(3) 0.8149(3) 0.33301(13) 0.0284(5) Uani 1 1 d . . . H16 H 0.0959 0.8577 0.3353 0.034 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 O4 0.0321(9) 0.0553(10) 0.0400(9) 0.0112(7) 0.0115(7) 0.0114(7) O5 0.0477(9) 0.0778(12) 0.0235(8) 0.0054(8) -0.0012(7) 0.0073(8) N1 0.0384(10) 0.0422(11) 0.0257(9) 0.0067(8) 0.0025(8) 0.0088(8) N2 0.0304(9) 0.0345(10) 0.0271(9) 0.0049(7) 0.0035(7) 0.0064(7) N3 0.0247(9) 0.0364(10) 0.0292(9) 0.0051(7) 0.0033(7) 0.0072(7) N4 0.0220(8) 0.0265(9) 0.0237(9) 0.0038(7) 0.0006(6) 0.0027(6) N5 0.0373(10) 0.0335(10) 0.0271(10) 0.0047(7) 0.0038(8) 0.0052(8) C4 0.0494(13) 0.0470(14) 0.0281(12) 0.0066(10) -0.0002(10) 0.0099(11) C5 0.0624(16) 0.0451(14) 0.0257(11) 0.0064(10) 0.0093(11) 0.0119(11) C6 0.0494(13) 0.0465(14) 0.0388(13) 0.0068(10) 0.0192(11) 0.0068(11) C7 0.0376(12) 0.0369(12) 0.0337(12) 0.0031(9) 0.0069(9) 0.0041(9) C8 0.0314(11) 0.0223(10) 0.0261(11) 0.0033(8) 0.0044(8) 0.0031(8) C9 0.0280(10) 0.0217(10) 0.0261(10) 0.0028(8) 0.0015(8) 0.0017(8) C10 0.0287(10) 0.0264(10) 0.0218(10) 0.0029(8) -0.0026(8) 0.0013(8) C11 0.0250(10) 0.0229(10) 0.0237(10) 0.0032(8) 0.0018(8) 0.0005(8) C12 0.0250(10) 0.0319(11) 0.0276(10) 0.0092(8) -0.0005(8) 0.0039(8) C13 0.0244(10) 0.0311(11) 0.0309(11) 0.0077(9) 0.0029(8) 0.0052(8) C14 0.0287(10) 0.0238(10) 0.0244(10) 0.0037(8) 0.0024(8) 0.0014(8) C15 0.0300(10) 0.0349(12) 0.0237(10) 0.0068(8) -0.0017(8) 0.0064(9) C16 0.0269(10) 0.0318(11) 0.0288(11) 0.0074(9) 0.0002(8) 0.0091(8) _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 O4 N5 1.226(2) . ? O5 N5 1.228(2) . ? N1 C4 1.333(3) . ? N1 C8 1.345(2) . ? N2 N3 1.307(2) . ? N2 C9 1.369(2) . ? N3 N4 1.360(2) . ? N4 C10 1.355(2) . ? N4 C11 1.428(2) . ? N5 C14 1.467(2) . ? C4 C5 1.379(3) . ? C5 C6 1.369(3) . ? C6 C7 1.382(3) . ? C7 C8 1.388(3) . ? C8 C9 1.474(2) . ? C9 C10 1.359(3) . ? C11 C12 1.386(3) . ? C11 C16 1.389(3) . ? C12 C13 1.376(3) . ? C13 C14 1.382(2) . ? C14 C15 1.380(3) . ? C15 C16 1.378(3) . ? 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 C4 N1 C8 116.77(17) . . ? N3 N2 C9 108.98(15) . . ? N2 N3 N4 107.23(14) . . ? C10 N4 N3 110.15(15) . . ? C10 N4 C11 129.96(15) . . ? N3 N4 C11 119.74(14) . . ? O4 N5 O5 124.06(16) . . ? O4 N5 C14 118.26(15) . . ? O5 N5 C14 117.68(16) . . ? N1 C4 C5 124.2(2) . . ? C6 C5 C4 118.20(19) . . ? C5 C6 C7 119.5(2) . . ? C6 C7 C8 118.4(2) . . ? N1 C8 C7 122.94(17) . . ? N1 C8 C9 115.09(16) . . ? C7 C8 C9 121.97(17) . . ? C10 C9 N2 108.50(16) . . ? C10 C9 C8 128.92(17) . . ? N2 C9 C8 122.58(16) . . ? N4 C10 C9 105.14(16) . . ? C12 C11 C16 121.13(17) . . ? C12 C11 N4 119.46(16) . . ? C16 C11 N4 119.41(16) . . ? C13 C12 C11 119.43(17) . . ? C12 C13 C14 118.97(18) . . ? C15 C14 C13 122.15(17) . . ? C15 C14 N5 119.27(16) . . ? C13 C14 N5 118.58(17) . . ? C16 C15 C14 118.85(17) . . ? C15 C16 C11 119.45(18) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.168 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.048 data_3a _database_code_depnum_ccdc_archive 'CCDC 915983' #TrackingRef 'mariusz.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H15 Cl N5 O6 Re' _chemical_formula_weight 631.01 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' Re Re -1.0185 7.2310 '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' _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 9.3391(2) _cell_length_b 11.0822(3) _cell_length_c 11.5507(3) _cell_angle_alpha 62.6070(10) _cell_angle_beta 86.5330(10) _cell_angle_gamma 83.7290(10) _cell_volume 1055.00(5) _cell_formula_units_Z 2 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 9574 _cell_measurement_theta_min 2.12 _cell_measurement_theta_max 33.06 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.986 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 5.933 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3552 _exptl_absorpt_correction_T_max 0.5362 _exptl_absorpt_process_details 'SADABS (Bruker-AXS)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 16972 _diffrn_reflns_av_R_equivalents 0.0224 _diffrn_reflns_av_sigmaI/netI 0.0328 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 5.26 _diffrn_reflns_theta_max 30.51 _reflns_number_total 6314 _reflns_number_gt 5645 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0152P)^2^+0.8076P] 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 6314 _refine_ls_number_parameters 319 _refine_ls_number_restraints 43 _refine_ls_R_factor_all 0.0296 _refine_ls_R_factor_gt 0.0229 _refine_ls_wR_factor_ref 0.0501 _refine_ls_wR_factor_gt 0.0475 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.065 _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 Re1 Re 0.738485(11) 0.685017(10) 0.303943(10) 0.02495(4) Uani 1 1 d D . . Cl1 Cl 0.95137(13) 0.61506(11) 0.20618(11) 0.0322(3) Uani 0.855(5) 1 d PDU A 1 C3 C 0.5760(5) 0.7426(5) 0.3824(5) 0.0297(9) Uani 0.855(5) 1 d PDU A 1 O3 O 0.4779(4) 0.7697(3) 0.4356(4) 0.0474(8) Uani 0.855(5) 1 d PDU A 1 Cl1' Cl 0.5472(10) 0.7911(9) 0.3803(9) 0.040(2) Uani 0.145(5) 1 d PDU A 2 C3' C 0.901(3) 0.608(3) 0.237(4) 0.049(8) Uani 0.145(5) 1 d PDU A 2 O3' O 0.9973(19) 0.565(2) 0.194(2) 0.049(5) Uani 0.145(5) 1 d PDU A 2 C1 C 0.6077(3) 0.6104(3) 0.2377(3) 0.0340(6) Uani 1 1 d . A . O1 O 0.5286(3) 0.5678(3) 0.1965(3) 0.0514(6) Uani 1 1 d . . . C2 C 0.7498(3) 0.5172(3) 0.4644(3) 0.0306(6) Uani 1 1 d . A . O2 O 0.7545(3) 0.4191(2) 0.5610(2) 0.0452(6) Uani 1 1 d . . . N1 N 0.7502(2) 0.8835(2) 0.1277(2) 0.0254(4) Uani 1 1 d . A . N2 N 0.8874(2) 0.7913(2) 0.3500(2) 0.0241(4) Uani 1 1 d . A . N3 N 0.9659(2) 0.7560(2) 0.4530(2) 0.0255(4) Uani 1 1 d . . . N4 N 1.0455(2) 0.8614(2) 0.4228(2) 0.0232(4) Uani 1 1 d . A . N5 N 1.4316(3) 0.8312(3) 0.7923(3) 0.0386(6) Uani 1 1 d . . . O4 O 1.4417(3) 0.7299(3) 0.8960(2) 0.0572(7) Uani 1 1 d . . . O5 O 1.4990(4) 0.9295(3) 0.7642(3) 0.0792(11) Uani 1 1 d . . . C4 C 0.6798(3) 0.9239(3) 0.0152(3) 0.0313(6) Uani 1 1 d . . . H4 H 0.6198 0.8632 0.0089 0.038 Uiso 1 1 calc R A . C5 C 0.6917(3) 1.0505(3) -0.0916(3) 0.0352(6) Uani 1 1 d . A . H5A H 0.6401 1.0758 -0.1690 0.042 Uiso 1 1 calc R . . C6 C 0.7795(3) 1.1391(3) -0.0842(3) 0.0342(6) Uani 1 1 d . . . H6 H 0.7875 1.2267 -0.1559 0.041 Uiso 1 1 calc R A . C7 C 0.8554(3) 1.0991(3) 0.0285(3) 0.0296(6) Uani 1 1 d . A . H7 H 0.9178 1.1579 0.0351 0.036 Uiso 1 1 calc R . . C8 C 0.8390(3) 0.9712(2) 0.1323(2) 0.0239(5) Uani 1 1 d . . . C9 C 0.9158(3) 0.9177(2) 0.2546(2) 0.0231(5) Uani 1 1 d . A . C10 C 1.0179(3) 0.9635(2) 0.3007(2) 0.0247(5) Uani 1 1 d . . . H10 H 1.0602 1.0476 0.2572 0.030 Uiso 1 1 calc R A . C11 C 1.1435(3) 0.8539(2) 0.5169(2) 0.0231(5) Uani 1 1 d . . . C12 C 1.2242(3) 0.9627(3) 0.4856(3) 0.0281(5) Uani 1 1 d . A . H12 H 1.2146 1.0410 0.4031 0.034 Uiso 1 1 calc R . . C13 C 1.3196(3) 0.9553(3) 0.5771(3) 0.0302(6) Uani 1 1 d . . . H13 H 1.3760 1.0286 0.5585 0.036 Uiso 1 1 calc R A . C14 C 1.3304(3) 0.8392(3) 0.6953(3) 0.0292(5) Uani 1 1 d . A . C15 C 1.2509(3) 0.7309(3) 0.7264(3) 0.0345(6) Uani 1 1 d . . . H15 H 1.2614 0.6525 0.8089 0.041 Uiso 1 1 calc R A . C16 C 1.1550(3) 0.7374(3) 0.6360(3) 0.0322(6) Uani 1 1 d . A . H16 H 1.0987 0.6638 0.6553 0.039 Uiso 1 1 calc R . . C17 C 0.7897(4) 0.6632(3) 0.8169(3) 0.0377(7) Uani 1 1 d . . . C18 C 0.7811(4) 0.5462(3) 0.9502(3) 0.0498(9) Uani 1 1 d . . . H18A H 0.8270 0.5664 1.0126 0.075 Uiso 1 1 calc R . . H18B H 0.8309 0.4636 0.9503 0.075 Uiso 1 1 calc R . . H18C H 0.6799 0.5318 0.9752 0.075 Uiso 1 1 calc R . . C19 C 0.7256(4) 0.6502(3) 0.7089(3) 0.0450(8) Uani 1 1 d . . . H19A H 0.7204 0.7387 0.6307 0.067 Uiso 1 1 calc R . . H19B H 0.6285 0.6206 0.7344 0.067 Uiso 1 1 calc R . . H19C H 0.7858 0.5826 0.6906 0.067 Uiso 1 1 calc R . . O6 O 0.8468(3) 0.7634(3) 0.7985(3) 0.0655(8) 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 Re1 0.02449(5) 0.02426(5) 0.02909(6) -0.01348(4) -0.00133(4) -0.00759(3) Cl1 0.0313(7) 0.0294(5) 0.0387(6) -0.0182(4) 0.0059(5) -0.0054(5) C3 0.024(2) 0.032(2) 0.038(2) -0.020(2) 0.0051(16) -0.0094(17) O3 0.0374(15) 0.0504(16) 0.061(2) -0.0320(15) 0.0204(15) -0.0104(13) Cl1' 0.041(5) 0.048(5) 0.041(4) -0.031(4) -0.009(3) 0.007(3) C3' 0.022(13) 0.046(13) 0.08(2) -0.025(13) 0.017(12) -0.013(11) O3' 0.041(10) 0.044(10) 0.067(12) -0.030(9) 0.013(9) -0.012(8) C1 0.0361(14) 0.0351(13) 0.0339(14) -0.0167(12) 0.0013(12) -0.0125(11) O1 0.0533(14) 0.0597(14) 0.0536(14) -0.0313(12) -0.0057(12) -0.0265(12) C2 0.0303(13) 0.0310(12) 0.0364(14) -0.0195(11) 0.0011(11) -0.0081(10) O2 0.0566(14) 0.0340(10) 0.0367(12) -0.0080(9) 0.0024(10) -0.0101(10) N1 0.0241(10) 0.0274(10) 0.0275(11) -0.0146(9) -0.0012(8) -0.0029(8) N2 0.0235(10) 0.0241(9) 0.0265(10) -0.0123(8) -0.0012(8) -0.0048(8) N3 0.0257(10) 0.0240(9) 0.0278(11) -0.0114(8) -0.0006(8) -0.0081(8) N4 0.0238(10) 0.0237(9) 0.0249(10) -0.0127(8) -0.0017(8) -0.0058(8) N5 0.0374(13) 0.0478(14) 0.0358(13) -0.0234(12) -0.0099(11) 0.0011(11) O4 0.0623(16) 0.0616(15) 0.0395(13) -0.0137(12) -0.0219(12) -0.0055(12) O5 0.090(2) 0.0746(19) 0.0667(19) -0.0165(15) -0.0398(17) -0.0363(17) C4 0.0283(13) 0.0375(13) 0.0324(14) -0.0186(11) -0.0066(11) -0.0047(11) C5 0.0347(15) 0.0439(15) 0.0273(13) -0.0164(12) -0.0079(11) -0.0004(12) C6 0.0371(15) 0.0314(13) 0.0277(13) -0.0075(11) -0.0004(11) -0.0051(11) C7 0.0292(13) 0.0293(12) 0.0294(13) -0.0116(10) -0.0001(10) -0.0068(10) C8 0.0217(11) 0.0257(11) 0.0260(12) -0.0133(9) -0.0009(9) -0.0020(9) C9 0.0237(11) 0.0231(10) 0.0240(12) -0.0116(9) 0.0012(9) -0.0047(9) C10 0.0260(12) 0.0244(11) 0.0254(12) -0.0123(9) 0.0009(9) -0.0060(9) C11 0.0226(11) 0.0264(11) 0.0240(11) -0.0147(9) 0.0014(9) -0.0038(9) C12 0.0303(13) 0.0270(11) 0.0274(13) -0.0119(10) -0.0028(10) -0.0052(10) C13 0.0297(13) 0.0334(13) 0.0325(14) -0.0182(11) -0.0026(11) -0.0079(10) C14 0.0267(12) 0.0369(13) 0.0298(13) -0.0204(11) -0.0073(10) 0.0012(10) C15 0.0396(15) 0.0330(13) 0.0262(13) -0.0088(11) -0.0069(11) -0.0022(11) C16 0.0376(15) 0.0289(12) 0.0293(13) -0.0108(11) -0.0039(11) -0.0093(11) C17 0.0404(15) 0.0331(13) 0.0361(15) -0.0124(12) 0.0041(12) -0.0081(12) C18 0.065(2) 0.0444(17) 0.0337(16) -0.0106(14) 0.0001(15) -0.0135(16) C19 0.0508(19) 0.0449(16) 0.0384(17) -0.0161(14) 0.0028(14) -0.0161(14) O6 0.090(2) 0.0417(12) 0.0589(16) -0.0113(12) -0.0103(15) -0.0321(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 Re1 C1 1.917(3) . ? Re1 C3 1.920(5) . ? Re1 C2 1.927(3) . ? Re1 C3' 1.948(16) . ? Re1 N2 2.151(2) . ? Re1 N1 2.214(2) . ? Re1 Cl1' 2.378(8) . ? Re1 Cl1 2.4548(14) . ? C3 O3 1.161(6) . ? C3' O3' 1.166(17) . ? C1 O1 1.150(4) . ? C2 O2 1.144(3) . ? N1 C4 1.351(3) . ? N1 C8 1.365(3) . ? N2 N3 1.312(3) . ? N2 C9 1.368(3) . ? N3 N4 1.350(3) . ? N4 C10 1.360(3) . ? N4 C11 1.430(3) . ? N5 O4 1.207(3) . ? N5 O5 1.219(4) . ? N5 C14 1.475(3) . ? C4 C5 1.389(4) . ? C4 H4 0.9500 . ? C5 C6 1.381(4) . ? C5 H5A 0.9500 . ? C6 C7 1.382(4) . ? C6 H6 0.9500 . ? C7 C8 1.390(3) . ? C7 H7 0.9500 . ? C8 C9 1.456(3) . ? C9 C10 1.366(3) . ? C10 H10 0.9500 . ? C11 C12 1.384(3) . ? C11 C16 1.388(3) . ? C12 C13 1.392(4) . ? C12 H12 0.9500 . ? C13 C14 1.379(4) . ? C13 H13 0.9500 . ? C14 C15 1.374(4) . ? C15 C16 1.388(4) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 O6 1.209(4) . ? C17 C19 1.486(5) . ? C17 C18 1.493(4) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? 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 C1 Re1 C3 88.15(18) . . ? C1 Re1 C2 89.42(12) . . ? C3 Re1 C2 86.09(17) . . ? C1 Re1 C3' 90.0(10) . . ? C3 Re1 C3' 174.4(10) . . ? C2 Re1 C3' 88.6(11) . . ? C1 Re1 N2 171.79(10) . . ? C3 Re1 N2 94.18(15) . . ? C2 Re1 N2 98.58(10) . . ? C3' Re1 N2 88.3(10) . . ? C1 Re1 N1 97.50(10) . . ? C3 Re1 N1 96.10(15) . . ? C2 Re1 N1 172.79(9) . . ? C3' Re1 N1 89.4(11) . . ? N2 Re1 N1 74.44(8) . . ? C1 Re1 Cl1' 92.4(2) . . ? C3 Re1 Cl1' 8.8(3) . . ? C2 Re1 Cl1' 93.9(3) . . ? C3' Re1 Cl1' 176.5(9) . . ? N2 Re1 Cl1' 88.9(2) . . ? N1 Re1 Cl1' 87.9(2) . . ? C1 Re1 Cl1 93.73(10) . . ? C3 Re1 Cl1 178.12(15) . . ? C2 Re1 Cl1 94.05(9) . . ? C3' Re1 Cl1 6.5(10) . . ? N2 Re1 Cl1 83.94(7) . . ? N1 Re1 Cl1 83.54(6) . . ? Cl1' Re1 Cl1 170.0(3) . . ? O3 C3 Re1 176.0(4) . . ? O3' C3' Re1 179(3) . . ? O1 C1 Re1 178.9(3) . . ? O2 C2 Re1 178.4(3) . . ? C4 N1 C8 117.3(2) . . ? C4 N1 Re1 125.62(18) . . ? C8 N1 Re1 117.03(16) . . ? N3 N2 C9 110.5(2) . . ? N3 N2 Re1 132.27(16) . . ? C9 N2 Re1 117.12(16) . . ? N2 N3 N4 105.53(19) . . ? N3 N4 C10 111.9(2) . . ? N3 N4 C11 119.18(19) . . ? C10 N4 C11 128.9(2) . . ? O4 N5 O5 123.3(3) . . ? O4 N5 C14 118.9(3) . . ? O5 N5 C14 117.8(3) . . ? N1 C4 C5 122.5(3) . . ? N1 C4 H4 118.7 . . ? C5 C4 H4 118.7 . . ? C6 C5 C4 119.3(3) . . ? C6 C5 H5A 120.3 . . ? C4 C5 H5A 120.3 . . ? C5 C6 C7 119.3(2) . . ? C5 C6 H6 120.4 . . ? C7 C6 H6 120.4 . . ? C6 C7 C8 118.8(3) . . ? C6 C7 H7 120.6 . . ? C8 C7 H7 120.6 . . ? N1 C8 C7 122.7(2) . . ? N1 C8 C9 113.9(2) . . ? C7 C8 C9 123.4(2) . . ? C10 C9 N2 107.7(2) . . ? C10 C9 C8 134.8(2) . . ? N2 C9 C8 117.4(2) . . ? N4 C10 C9 104.4(2) . . ? N4 C10 H10 127.8 . . ? C9 C10 H10 127.8 . . ? C12 C11 C16 122.3(2) . . ? C12 C11 N4 118.9(2) . . ? C16 C11 N4 118.8(2) . . ? C11 C12 C13 118.9(2) . . ? C11 C12 H12 120.6 . . ? C13 C12 H12 120.6 . . ? C14 C13 C12 118.5(2) . . ? C14 C13 H13 120.8 . . ? C12 C13 H13 120.8 . . ? C15 C14 C13 122.8(2) . . ? C15 C14 N5 118.7(2) . . ? C13 C14 N5 118.5(2) . . ? C14 C15 C16 119.2(2) . . ? C14 C15 H15 120.4 . . ? C16 C15 H15 120.4 . . ? C11 C16 C15 118.3(2) . . ? C11 C16 H16 120.8 . . ? C15 C16 H16 120.8 . . ? O6 C17 C19 121.9(3) . . ? O6 C17 C18 121.1(3) . . ? C19 C17 C18 117.0(3) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? 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 C5 H5A O5 0.95 2.59 3.279(4) 129.8 1_454 C10 H10 O6 0.95 2.16 3.088(3) 167.0 2_776 C12 H12 O6 0.95 2.39 3.329(4) 171.5 2_776 C16 H16 N3 0.95 2.43 2.757(3) 99.7 . C16 H16 Cl1 0.95 2.83 3.693(3) 151.7 2_766 C19 H19B O1 0.98 2.48 3.343(4) 147.0 2_666 _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 30.51 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 1.395 _refine_diff_density_min -0.848 _refine_diff_density_rms 0.107 #===END data_3b _database_code_depnum_ccdc_archive 'CCDC 915984' #TrackingRef 'mariusz.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H9 Cl2 N4 O3 Re, C H4 O' _chemical_formula_sum 'C17 H13 Cl2 N4 O4 Re' _chemical_formula_weight 594.41 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Re Re -1.0185 7.2310 '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 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.2075(4) _cell_length_b 10.3218(5) _cell_length_c 10.5372(4) _cell_angle_alpha 64.434(5) _cell_angle_beta 88.975(3) _cell_angle_gamma 85.241(4) _cell_volume 997.85(7) _cell_formula_units_Z 2 _cell_measurement_temperature 295.0(2) _cell_measurement_reflns_used 4653 _cell_measurement_theta_min 3.6644 _cell_measurement_theta_max 29.2300 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.085 _exptl_crystal_size_mid 0.075 _exptl_crystal_size_min 0.037 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.978 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 6.387 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details ;CrysAlis RED, (2005) ; _exptl_absorpt_correction_T_min 0.63679 _exptl_absorpt_correction_T_max 1.00000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 295.0(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7528 _diffrn_reflns_av_R_equivalents 0.0333 _diffrn_reflns_av_sigmaI/netI 0.0513 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.67 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3518 _reflns_number_gt 2985 _reflns_threshold_expression >2sigma(I) #========================================================================== # # REFINEMENT DATA _computing_data_collection 'CrysAlis CCD v. 1.163 (UNIL IC & KUMA 2000)' _computing_cell_refinement 'CrysAlis RED v. 1.163 (UNIL IC & KUMA 2000)' _computing_data_reduction 'CrysAlis RED v. 1.163 (UNIL IC & KUMA 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ;XP in SHELXTL/PC (Sheldrick, 1990b) ORTEP-3 W v. 1.062 (Farrugia 1997) ; _computing_publication_material ;SHELXL-97 (Sheldrick, 1997) and PLATON (Spek, 1990) ; _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^)+(0.0078P)^2^+0.0000P] 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 3518 _refine_ls_number_parameters 255 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0362 _refine_ls_R_factor_gt 0.0266 _refine_ls_wR_factor_ref 0.0448 _refine_ls_wR_factor_gt 0.0433 _refine_ls_goodness_of_fit_ref 0.955 _refine_ls_restrained_S_all 0.955 _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 Re1 Re 0.226119(17) 0.295279(19) 0.178283(19) 0.03531(7) Uani 1 1 d . . . N1 N 0.2391(3) 0.1111(3) 0.3881(4) 0.0348(8) Uani 1 1 d . . . N2 N 0.3757(3) 0.3398(3) 0.2923(3) 0.0314(8) Uani 1 1 d . . . N3 N 0.4521(3) 0.4456(3) 0.2558(4) 0.0369(9) Uani 1 1 d . . . N4 N 0.5310(3) 0.4101(3) 0.3699(3) 0.0304(8) Uani 1 1 d . . . O1 O 0.2460(4) 0.5672(4) -0.0954(4) 0.0757(11) Uani 1 1 d . . . O2 O 0.0227(4) 0.1863(4) 0.0460(5) 0.0933(14) Uani 1 1 d . . . O3 O 0.0036(4) 0.4605(5) 0.2529(4) 0.0799(12) Uani 1 1 d . . . O99 O 0.3150(5) 0.8426(4) 0.2332(4) 0.0865(12) Uani 1 1 d . . . H99 H 0.3431 0.9226 0.2009 0.130 Uiso 1 1 calc R . . Cl1 Cl 0.40909(12) 0.15690(13) 0.12207(12) 0.0531(3) Uani 1 1 d . . . Cl2 Cl 0.94552(13) 0.78853(15) 0.33783(17) 0.0706(4) Uani 1 1 d . . . C1 C 0.2371(4) 0.4633(5) 0.0063(5) 0.0447(12) Uani 1 1 d . . . C2 C 0.0991(5) 0.2291(5) 0.0943(5) 0.0553(13) Uani 1 1 d . . . C3 C 0.0852(5) 0.3981(5) 0.2296(5) 0.0435(12) Uani 1 1 d . . . C4 C 0.1670(4) -0.0027(5) 0.4326(5) 0.0433(11) Uani 1 1 d . . . H4 H 0.1052 -0.0066 0.3708 0.052 Uiso 1 1 calc R . . C5 C 0.1801(5) -0.1142(5) 0.5657(5) 0.0520(13) Uani 1 1 d . . . H5 H 0.1288 -0.1918 0.5923 0.062 Uiso 1 1 calc R . . C6 C 0.2685(5) -0.1093(5) 0.6574(5) 0.0534(13) Uani 1 1 d . . . H6 H 0.2774 -0.1829 0.7482 0.064 Uiso 1 1 calc R . . C7 C 0.3449(4) 0.0050(5) 0.6156(5) 0.0442(11) Uani 1 1 d . . . H7 H 0.4068 0.0095 0.6770 0.053 Uiso 1 1 calc R . . C8 C 0.3281(4) 0.1126(4) 0.4809(4) 0.0310(10) Uani 1 1 d . . . C9 C 0.4036(4) 0.2383(4) 0.4261(4) 0.0297(9) Uani 1 1 d . . . C10 C 0.5036(4) 0.2847(4) 0.4754(4) 0.0323(10) Uani 1 1 d . . . H10 H 0.5443 0.2390 0.5638 0.039 Uiso 1 1 calc R . . C11 C 0.6285(4) 0.5051(4) 0.3639(4) 0.0325(10) Uani 1 1 d . . . C12 C 0.7195(4) 0.4601(5) 0.4727(5) 0.0406(11) Uani 1 1 d . . . H12 H 0.7164 0.3709 0.5496 0.049 Uiso 1 1 calc R . . C13 C 0.8157(4) 0.5501(5) 0.4656(5) 0.0447(12) Uani 1 1 d . . . H13 H 0.8769 0.5228 0.5388 0.054 Uiso 1 1 calc R . . C14 C 0.8198(4) 0.6792(5) 0.3502(5) 0.0441(12) Uani 1 1 d . . . C15 C 0.7301(4) 0.7237(5) 0.2418(5) 0.0472(12) Uani 1 1 d . . . H15 H 0.7346 0.8122 0.1643 0.057 Uiso 1 1 calc R . . C16 C 0.6323(4) 0.6356(4) 0.2487(5) 0.0422(11) Uani 1 1 d . . . H16 H 0.5701 0.6645 0.1762 0.051 Uiso 1 1 calc R . . C99 C 0.2673(7) 0.8170(7) 0.1242(7) 0.096(2) Uani 1 1 d . . . H99A H 0.2397 0.7211 0.1614 0.144 Uiso 1 1 calc R . . H99B H 0.3355 0.8271 0.0574 0.144 Uiso 1 1 calc R . . H99C H 0.1939 0.8852 0.0786 0.144 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 Re1 0.03755(11) 0.03342(11) 0.03081(11) -0.00853(8) -0.00629(7) -0.00962(7) N1 0.034(2) 0.033(2) 0.036(2) -0.0113(17) 0.0000(17) -0.0097(16) N2 0.0323(19) 0.0285(19) 0.030(2) -0.0076(16) -0.0022(16) -0.0092(16) N3 0.039(2) 0.034(2) 0.036(2) -0.0115(17) -0.0032(17) -0.0114(17) N4 0.0320(19) 0.031(2) 0.026(2) -0.0092(16) -0.0015(16) -0.0066(15) O1 0.110(3) 0.044(2) 0.048(2) 0.0046(19) -0.009(2) -0.012(2) O2 0.085(3) 0.103(3) 0.102(3) -0.048(3) -0.036(3) -0.035(2) O3 0.069(3) 0.098(3) 0.084(3) -0.052(3) -0.011(2) 0.007(2) O99 0.123(4) 0.065(3) 0.057(3) -0.008(2) -0.019(2) -0.025(3) Cl1 0.0569(8) 0.0528(8) 0.0415(7) -0.0132(6) -0.0030(6) -0.0009(6) Cl2 0.0543(8) 0.0681(9) 0.1017(12) -0.0440(9) 0.0035(8) -0.0307(7) C1 0.052(3) 0.041(3) 0.040(3) -0.016(2) -0.015(2) -0.005(2) C2 0.059(3) 0.049(3) 0.048(3) -0.011(3) -0.010(3) -0.009(3) C3 0.039(3) 0.045(3) 0.045(3) -0.018(2) -0.017(2) 0.005(2) C4 0.042(3) 0.040(3) 0.049(3) -0.018(2) 0.006(2) -0.017(2) C5 0.054(3) 0.033(3) 0.060(4) -0.010(3) 0.011(3) -0.019(2) C6 0.064(3) 0.033(3) 0.044(3) 0.002(2) 0.010(3) -0.006(2) C7 0.052(3) 0.036(3) 0.034(3) -0.005(2) -0.002(2) -0.006(2) C8 0.028(2) 0.029(2) 0.030(2) -0.0074(19) 0.0003(19) 0.0009(18) C9 0.029(2) 0.025(2) 0.029(2) -0.0050(19) -0.0020(19) -0.0016(18) C10 0.036(2) 0.033(2) 0.022(2) -0.006(2) -0.0023(19) -0.0044(19) C11 0.032(2) 0.032(2) 0.036(3) -0.016(2) 0.002(2) -0.0087(18) C12 0.040(3) 0.040(3) 0.046(3) -0.022(2) -0.003(2) -0.007(2) C13 0.041(3) 0.045(3) 0.057(3) -0.030(3) -0.004(2) -0.004(2) C14 0.034(3) 0.049(3) 0.063(3) -0.034(3) 0.008(2) -0.014(2) C15 0.056(3) 0.036(3) 0.048(3) -0.014(2) 0.006(3) -0.019(2) C16 0.048(3) 0.041(3) 0.036(3) -0.012(2) -0.001(2) -0.017(2) C99 0.098(5) 0.099(5) 0.085(5) -0.034(4) -0.003(4) -0.011(4) _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 Re1 C1 1.901(5) . ? Re1 C2 1.907(5) . ? Re1 C3 1.924(5) . ? Re1 N2 2.155(3) . ? Re1 N1 2.205(3) . ? Re1 Cl1 2.4753(12) . ? N1 C4 1.341(5) . ? N1 C8 1.353(5) . ? N2 N3 1.310(4) . ? N2 C9 1.363(5) . ? N3 N4 1.354(4) . ? N4 C10 1.341(5) . ? N4 C11 1.436(5) . ? O1 C1 1.153(5) . ? O2 C2 1.152(6) . ? O3 C3 1.100(5) . ? O99 C99 1.389(7) . ? Cl2 C14 1.745(4) . ? C4 C5 1.377(6) . ? C5 C6 1.353(7) . ? C6 C7 1.373(6) . ? C7 C8 1.376(5) . ? C8 C9 1.454(5) . ? C9 C10 1.362(5) . ? C11 C16 1.373(6) . ? C11 C12 1.379(6) . ? C12 C13 1.386(6) . ? C13 C14 1.366(6) . ? C14 C15 1.367(6) . ? C15 C16 1.385(6) . ? 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 C1 Re1 C2 90.12(19) . . ? C1 Re1 C3 88.0(2) . . ? C2 Re1 C3 88.8(2) . . ? C1 Re1 N2 96.90(15) . . ? C2 Re1 N2 172.24(16) . . ? C3 Re1 N2 94.69(15) . . ? C1 Re1 N1 171.42(16) . . ? C2 Re1 N1 98.35(17) . . ? C3 Re1 N1 93.53(16) . . ? N2 Re1 N1 74.57(12) . . ? C1 Re1 Cl1 93.98(14) . . ? C2 Re1 Cl1 92.07(16) . . ? C3 Re1 Cl1 177.78(14) . . ? N2 Re1 Cl1 84.19(9) . . ? N1 Re1 Cl1 84.33(9) . . ? C4 N1 C8 116.7(4) . . ? C4 N1 Re1 126.1(3) . . ? C8 N1 Re1 117.1(3) . . ? N3 N2 C9 111.3(3) . . ? N3 N2 Re1 132.1(3) . . ? C9 N2 Re1 116.4(2) . . ? N2 N3 N4 104.8(3) . . ? C10 N4 N3 111.7(3) . . ? C10 N4 C11 129.4(3) . . ? N3 N4 C11 119.0(3) . . ? O1 C1 Re1 177.6(4) . . ? O2 C2 Re1 178.6(5) . . ? O3 C3 Re1 177.0(4) . . ? N1 C4 C5 123.0(4) . . ? C6 C5 C4 119.2(4) . . ? C5 C6 C7 119.6(4) . . ? C6 C7 C8 118.6(4) . . ? N1 C8 C7 122.8(4) . . ? N1 C8 C9 114.1(3) . . ? C7 C8 C9 123.1(4) . . ? C10 C9 N2 106.6(3) . . ? C10 C9 C8 135.7(4) . . ? N2 C9 C8 117.7(3) . . ? N4 C10 C9 105.6(3) . . ? C16 C11 C12 121.5(4) . . ? C16 C11 N4 119.8(4) . . ? C12 C11 N4 118.8(4) . . ? C11 C12 C13 118.9(4) . . ? C14 C13 C12 119.4(4) . . ? C13 C14 C15 121.8(4) . . ? C13 C14 Cl2 119.3(4) . . ? C15 C14 Cl2 118.9(4) . . ? C14 C15 C16 119.3(4) . . ? C11 C16 C15 119.2(4) . . ? 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 O99 H99 Cl1 0.82 2.35 3.164(4) 174.6 1_565 C6 H6 O1 0.93 2.43 3.253(6) 147.1 1_546 C7 H7 Cl1 0.93 2.73 3.507(5) 142.2 2_656 C10 H10 O99 0.93 2.39 3.301(5) 167.4 2_666 C12 H12 O99 0.93 2.44 3.358(6) 171.0 2_666 C16 H16 N3 0.93 2.46 2.776(5) 100.1 . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.741 _refine_diff_density_min -0.734 _refine_diff_density_rms 0.103 #===END