# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year 2011 _journal_volume 47 _journal_page_first 0 _publ_contact_author_name 'Teresa F. Mastropietro' _publ_contact_author_email teresa.mas@unical.it loop_ _publ_author_name 'Jose Martinez-Lillo' 'Teresa F. Mastropietro' 'Rosamaria Lappano' 'Antonio Madeo' ; M.E.Alberto ; 'Nino Russo' 'Marcello Maggiolini' 'G.De Munno' data_rebipy _database_code_depnum_ccdc_archive 'CCDC 797402' #TrackingRef 'cif compound1.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H8 Cl4 N2 Re' _chemical_formula_weight 484.18 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' Cl Cl 0.1484 0.1585 '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 Monoclinic _symmetry_space_group_name_H-M Pn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y, z+1/2' _cell_length_a 8.1950(12) _cell_length_b 6.7365(9) _cell_length_c 12.3971(18) _cell_angle_alpha 90.00 _cell_angle_beta 104.452(5) _cell_angle_gamma 90.00 _cell_volume 662.73(16) _cell_formula_units_Z 2 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 5343 _cell_measurement_theta_min 2.700 _cell_measurement_theta_max 31.510 _exptl_crystal_description Needle _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.426 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 450 _exptl_absorpt_coefficient_mu 9.950 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.160 _exptl_absorpt_correction_T_max 0.216 _exptl_absorpt_process_details sabads _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14857 _diffrn_reflns_av_R_equivalents 0.0242 _diffrn_reflns_av_sigmaI/netI 0.0369 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.70 _diffrn_reflns_theta_max 33.26 _reflns_number_total 4276 _reflns_number_gt 4062 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker-Nonius X8 APEX' _computing_cell_refinement 'Bruker-Nonius X8 APEX' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0000P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.019(4) _refine_ls_number_reflns 4276 _refine_ls_number_parameters 154 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0177 _refine_ls_R_factor_gt 0.0158 _refine_ls_wR_factor_ref 0.0286 _refine_ls_wR_factor_gt 0.0278 _refine_ls_goodness_of_fit_ref 0.767 _refine_ls_restrained_S_all 0.767 _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 0.687573(18) 0.204756(11) 0.725055(16) 0.02425(3) Uani 1 1 d . . . Cl4 Cl 0.82616(9) 0.02390(11) 0.88107(6) 0.03871(16) Uani 1 1 d . . . Cl1 Cl 0.52796(9) 0.38897(12) 0.57665(6) 0.03991(16) Uani 1 1 d . . . Cl2 Cl 0.91647(9) 0.41549(11) 0.74460(6) 0.04121(17) Uani 1 1 d . . . Cl3 Cl 0.77718(10) -0.00885(11) 0.60530(6) 0.04061(16) Uani 1 1 d . . . N1 N 0.4675(3) 0.0393(3) 0.72502(17) 0.0268(4) Uani 1 1 d . . . N2 N 0.5743(3) 0.3734(3) 0.83098(18) 0.0268(4) Uani 1 1 d . . . C6 C 0.4281(4) 0.2999(4) 0.8477(2) 0.0290(6) Uani 1 1 d . . . C5 C 0.3695(3) 0.1132(4) 0.7884(2) 0.0303(6) Uani 1 1 d . . . C3 C 0.1776(7) -0.1561(4) 0.7363(5) 0.0472(11) Uani 1 1 d . . . H3 H 0.0795 -0.2223 0.7400 0.057 Uiso 1 1 calc R . . C10 C 0.6356(4) 0.5437(4) 0.8811(2) 0.0344(6) Uani 1 1 d . . . H10 H 0.7362 0.5932 0.8703 0.041 Uiso 1 1 calc R . . C7 C 0.3434(4) 0.3982(4) 0.9144(2) 0.0388(7) Uani 1 1 d . . . H7 H 0.2438 0.3466 0.9259 0.047 Uiso 1 1 calc R . . C4 C 0.2247(4) 0.0169(4) 0.7957(3) 0.0414(7) Uani 1 1 d . . . H4 H 0.1590 0.0679 0.8405 0.050 Uiso 1 1 calc R . . C1 C 0.4226(4) -0.1295(4) 0.6679(2) 0.0363(6) Uani 1 1 d . . . H1 H 0.4908 -0.1806 0.6248 0.044 Uiso 1 1 calc R . . C9 C 0.5552(4) 0.6466(5) 0.9472(3) 0.0417(7) Uani 1 1 d . . . H9 H 0.6001 0.7649 0.9805 0.050 Uiso 1 1 calc R . . C2 C 0.2772(5) -0.2284(5) 0.6720(3) 0.0458(8) Uani 1 1 d . . . H2 H 0.2469 -0.3442 0.6310 0.055 Uiso 1 1 calc R . . C8 C 0.4080(4) 0.5741(5) 0.9642(3) 0.0430(8) Uani 1 1 d . . . H8 H 0.3516 0.6429 1.0090 0.052 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 0.02246(4) 0.02557(4) 0.02577(4) -0.00072(6) 0.00799(3) -0.00256(6) Cl4 0.0351(4) 0.0440(4) 0.0352(3) 0.0098(3) 0.0052(3) 0.0005(3) Cl1 0.0411(4) 0.0418(4) 0.0345(4) 0.0066(3) 0.0051(3) 0.0065(3) Cl2 0.0338(4) 0.0422(4) 0.0498(4) -0.0017(3) 0.0146(3) -0.0143(3) Cl3 0.0445(4) 0.0400(4) 0.0417(4) -0.0078(3) 0.0188(3) 0.0040(3) N1 0.0244(11) 0.0265(11) 0.0287(11) 0.0002(8) 0.0050(9) -0.0047(8) N2 0.0269(11) 0.0278(11) 0.0275(11) -0.0010(9) 0.0101(9) -0.0009(9) C6 0.0267(14) 0.0306(15) 0.0316(15) 0.0035(10) 0.0105(11) 0.0003(10) C5 0.0268(13) 0.0284(14) 0.0359(15) 0.0032(11) 0.0086(11) 0.0011(10) C3 0.0278(17) 0.0368(14) 0.076(3) 0.009(2) 0.0109(17) -0.0067(19) C10 0.0336(15) 0.0347(15) 0.0354(15) -0.0073(11) 0.0095(12) -0.0068(11) C7 0.0364(16) 0.0404(17) 0.0459(18) 0.0011(13) 0.0223(14) 0.0021(13) C4 0.0276(15) 0.0390(16) 0.062(2) 0.0074(14) 0.0189(15) -0.0004(12) C1 0.0340(16) 0.0346(15) 0.0406(16) -0.0039(12) 0.0097(12) -0.0061(12) C9 0.053(2) 0.0364(15) 0.0356(17) -0.0102(12) 0.0111(14) -0.0010(14) C2 0.0403(19) 0.0320(16) 0.060(2) -0.0042(14) 0.0033(17) -0.0133(13) C8 0.054(2) 0.0451(19) 0.0359(17) -0.0054(13) 0.0223(15) 0.0071(14) _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 N2 2.118(2) . ? Re1 N1 2.120(2) . ? Re1 Cl3 2.3148(7) . ? Re1 Cl2 2.3164(7) . ? Re1 Cl4 2.3278(7) . ? Re1 Cl1 2.3312(7) . ? N1 C1 1.342(3) . ? N1 C5 1.351(3) . ? N2 C10 1.341(3) . ? N2 C6 1.359(4) . ? C6 C7 1.375(4) . ? C6 C5 1.475(4) . ? C5 C4 1.375(4) . ? C3 C2 1.366(7) . ? C3 C4 1.381(5) . ? C10 C9 1.362(4) . ? C7 C8 1.379(4) . ? C1 C2 1.377(5) . ? C9 C8 1.366(5) . ? 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 N2 Re1 N1 77.15(8) . . ? N2 Re1 Cl3 171.67(6) . . ? N1 Re1 Cl3 94.54(6) . . ? N2 Re1 Cl2 94.31(6) . . ? N1 Re1 Cl2 171.44(6) . . ? Cl3 Re1 Cl2 94.00(3) . . ? N2 Re1 Cl4 87.94(6) . . ? N1 Re1 Cl4 87.92(6) . . ? Cl3 Re1 Cl4 92.32(3) . . ? Cl2 Re1 Cl4 91.11(3) . . ? N2 Re1 Cl1 87.56(6) . . ? N1 Re1 Cl1 88.28(6) . . ? Cl3 Re1 Cl1 91.72(3) . . ? Cl2 Re1 Cl1 92.09(3) . . ? Cl4 Re1 Cl1 174.65(3) . . ? C1 N1 C5 119.7(2) . . ? C1 N1 Re1 124.52(19) . . ? C5 N1 Re1 115.79(17) . . ? C10 N2 C6 118.9(2) . . ? C10 N2 Re1 125.08(19) . . ? C6 N2 Re1 116.00(18) . . ? N2 C6 C7 120.8(3) . . ? N2 C6 C5 115.1(2) . . ? C7 C6 C5 124.0(3) . . ? N1 C5 C4 120.8(3) . . ? N1 C5 C6 115.9(2) . . ? C4 C5 C6 123.3(3) . . ? C2 C3 C4 118.9(4) . . ? N2 C10 C9 122.2(3) . . ? C6 C7 C8 119.2(3) . . ? C5 C4 C3 119.6(3) . . ? N1 C1 C2 121.1(3) . . ? C10 C9 C8 119.3(3) . . ? C3 C2 C1 119.9(3) . . ? C9 C8 C7 119.6(3) . . ? _diffrn_measured_fraction_theta_max 0.898 _diffrn_reflns_theta_full 33.26 _diffrn_measured_fraction_theta_full 0.898 _refine_diff_density_max 0.510 _refine_diff_density_min -0.519 _refine_diff_density_rms 0.084 # Attachment 'cif compound3.CIF' data_remebpy _database_code_depnum_ccdc_archive 'CCDC 797403' #TrackingRef 'cif compound3.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H12 Cl4 N2 Re' _chemical_formula_weight 512.24 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' Cl Cl 0.1484 0.1585 '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 Orthorhombic _symmetry_space_group_name_H-M Pccn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-x, y+1/2, -z+1/2' 'x+1/2, -y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'x, -y-1/2, z-1/2' '-x-1/2, y, z-1/2' _cell_length_a 6.9640(2) _cell_length_b 13.4511(4) _cell_length_c 17.4989(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1639.18(8) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 9318 _cell_measurement_theta_min 2.327 _cell_measurement_theta_max 31.632 _exptl_crystal_description Needle _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.076 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 964 _exptl_absorpt_coefficient_mu 8.052 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.142 _exptl_absorpt_correction_T_max 0.211 _exptl_absorpt_process_details sabads _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32431 _diffrn_reflns_av_R_equivalents 0.0257 _diffrn_reflns_av_sigmaI/netI 0.0108 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 32.10 _reflns_number_total 2674 _reflns_number_gt 2289 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker-Nonius X8 APEX' _computing_cell_refinement 'Bruker-Nonius X8 APEX' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0205P)^2^+1.2154P] 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 2674 _refine_ls_number_parameters 88 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0242 _refine_ls_R_factor_gt 0.0192 _refine_ls_wR_factor_ref 0.0510 _refine_ls_wR_factor_gt 0.0482 _refine_ls_goodness_of_fit_ref 1.180 _refine_ls_restrained_S_all 1.180 _refine_ls_shift/su_max 0.008 _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 1.2500 0.7500 1.059865(6) 0.03399(5) Uani 1 2 d S . . Cl1 Cl 1.03798(11) 0.88361(6) 1.05306(4) 0.05615(17) Uani 1 1 d . . . Cl2 Cl 1.06467(11) 0.66955(6) 1.15082(4) 0.05507(17) Uani 1 1 d . . . N1 N 1.0999(3) 0.69070(15) 0.96524(11) 0.0383(4) Uani 1 1 d . . . C5 C 1.1662(3) 0.71693(18) 0.89534(12) 0.0368(4) Uani 1 1 d . . . C4 C 1.0794(4) 0.6823(2) 0.82998(14) 0.0436(5) Uani 1 1 d . . . H4 H 1.1289 0.6998 0.7825 0.052 Uiso 1 1 calc R . . C1 C 0.9432(4) 0.6331(2) 0.96991(15) 0.0486(6) Uani 1 1 d . . . H1 H 0.8955 0.6163 1.0178 0.058 Uiso 1 1 calc R . . C3 C 0.9183(4) 0.6215(2) 0.83415(15) 0.0455(6) Uani 1 1 d . . . C2 C 0.8509(4) 0.5982(2) 0.90573(16) 0.0517(6) Uani 1 1 d . . . H2 H 0.7422 0.5586 0.9109 0.062 Uiso 1 1 calc R . . C6 C 0.8227(5) 0.5838(3) 0.76306(19) 0.0660(9) Uani 1 1 d . . . H6A H 0.8866 0.6106 0.7190 0.099 Uiso 1 1 calc R . . H6B H 0.6906 0.6042 0.7628 0.099 Uiso 1 1 calc R . . H6C H 0.8297 0.5126 0.7618 0.099 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 0.03638(7) 0.03969(8) 0.02589(7) 0.000 0.000 -0.00884(4) Cl1 0.0499(4) 0.0501(4) 0.0685(4) -0.0030(3) -0.0098(3) 0.0018(3) Cl2 0.0626(4) 0.0657(4) 0.0369(3) 0.0035(3) 0.0145(3) -0.0176(3) N1 0.0392(10) 0.0468(11) 0.0291(8) -0.0013(8) 0.0010(7) -0.0158(8) C5 0.0363(11) 0.0435(11) 0.0305(10) 0.0008(9) -0.0011(8) -0.0119(9) C4 0.0468(13) 0.0529(14) 0.0311(11) 0.0006(10) -0.0055(9) -0.0146(11) C1 0.0466(13) 0.0598(15) 0.0395(12) -0.0002(11) 0.0038(10) -0.0255(12) C3 0.0442(13) 0.0477(13) 0.0447(13) 0.0006(11) -0.0152(10) -0.0112(10) C2 0.0439(14) 0.0581(16) 0.0531(15) 0.0008(12) -0.0060(11) -0.0234(12) C6 0.0680(19) 0.074(2) 0.0564(17) 0.0031(15) -0.0305(16) -0.0231(17) _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 N1 2.1144(19) . ? Re1 N1 2.1144(19) 2_765 ? Re1 Cl2 2.3174(6) 2_765 ? Re1 Cl2 2.3174(6) . ? Re1 Cl1 2.3290(7) . ? Re1 Cl1 2.3290(7) 2_765 ? N1 C1 1.341(3) . ? N1 C5 1.354(3) . ? C5 C4 1.375(3) . ? C5 C5 1.468(4) 2_765 ? C4 C3 1.390(3) . ? C1 C2 1.376(4) . ? C3 C2 1.374(4) . ? C3 C6 1.499(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 N1 Re1 N1 76.91(10) . 2_765 ? N1 Re1 Cl2 171.64(5) . 2_765 ? N1 Re1 Cl2 94.95(5) 2_765 2_765 ? N1 Re1 Cl2 94.95(5) . . ? N1 Re1 Cl2 171.64(5) 2_765 . ? Cl2 Re1 Cl2 93.24(4) 2_765 . ? N1 Re1 Cl1 86.42(6) . . ? N1 Re1 Cl1 88.99(6) 2_765 . ? Cl2 Re1 Cl1 91.60(3) 2_765 . ? Cl2 Re1 Cl1 92.43(3) . . ? N1 Re1 Cl1 88.99(6) . 2_765 ? N1 Re1 Cl1 86.42(6) 2_765 2_765 ? Cl2 Re1 Cl1 92.43(3) 2_765 2_765 ? Cl2 Re1 Cl1 91.60(3) . 2_765 ? Cl1 Re1 Cl1 174.14(4) . 2_765 ? C1 N1 C5 118.9(2) . . ? C1 N1 Re1 124.94(16) . . ? C5 N1 Re1 116.15(14) . . ? N1 C5 C4 120.9(2) . . ? N1 C5 C5 115.40(12) . 2_765 ? C4 C5 C5 123.70(14) . 2_765 ? C5 C4 C3 120.7(2) . . ? N1 C1 C2 121.8(2) . . ? C2 C3 C4 117.2(2) . . ? C2 C3 C6 121.9(2) . . ? C4 C3 C6 120.9(3) . . ? C3 C2 C1 120.5(2) . . ? _diffrn_measured_fraction_theta_max 0.929 _diffrn_reflns_theta_full 32.10 _diffrn_measured_fraction_theta_full 0.929 _refine_diff_density_max 0.367 _refine_diff_density_min -1.276 _refine_diff_density_rms 0.128 # Attachment 'cif compound4.CIF' data_rep21c _database_code_depnum_ccdc_archive 'CCDC 797404' #TrackingRef 'cif compound4.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H8 Cl4 N2 Re' _chemical_formula_weight 508.20 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' Cl Cl 0.1484 0.1585 '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 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 7.5973(2) _cell_length_b 18.9753(6) _cell_length_c 10.3352(3) _cell_angle_alpha 90.00 _cell_angle_beta 108.2490(10) _cell_angle_gamma 90.00 _cell_volume 1415.00(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7277 _cell_measurement_theta_min 2.335 _cell_measurement_theta_max 30.0722 _exptl_crystal_description Needle _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.386 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 948 _exptl_absorpt_coefficient_mu 9.327 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.1342 _exptl_absorpt_correction_T_max 0.6045 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22670 _diffrn_reflns_av_R_equivalents 0.0290 _diffrn_reflns_av_sigmaI/netI 0.0175 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 31.65 _reflns_number_total 4255 _reflns_number_gt 3837 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker-Nonius X8 APEX' _computing_cell_refinement 'Bruker-Nonius X8 APEX' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0623P)^2^+28.1049P] 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 4255 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0789 _refine_ls_R_factor_gt 0.0721 _refine_ls_wR_factor_ref 0.1860 _refine_ls_wR_factor_gt 0.1809 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.090 _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 0.05788(6) 0.64974(3) 0.17130(4) 0.05223(18) Uani 1 1 d . . . Cl1 Cl -0.1588(4) 0.68054(18) 0.2789(3) 0.0567(7) Uani 1 1 d . . . Cl4 Cl 0.2880(4) 0.60595(17) 0.0858(3) 0.0541(6) Uani 1 1 d . . . Cl3 Cl -0.1750(5) 0.6159(2) -0.0192(3) 0.0712(10) Uani 1 1 d . . . Cl2 Cl 0.0768(7) 0.7568(2) 0.1042(5) 0.0825(11) Uani 1 1 d . . . N2 N 0.0717(11) 0.5484(4) 0.2698(8) 0.0376(16) Uani 1 1 d . . . C12 C 0.2962(13) 0.6092(5) 0.4486(9) 0.0382(19) Uani 1 1 d . . . N1 N 0.2684(12) 0.6650(4) 0.3634(9) 0.0405(18) Uani 1 1 d . . . C11 C 0.1929(12) 0.5467(5) 0.4000(9) 0.0373(18) Uani 1 1 d . . . C6 C 0.3482(14) 0.4893(6) 0.6157(10) 0.045(2) Uani 1 1 d . . . H6A H 0.3637 0.4499 0.6717 0.055 Uiso 1 1 calc R . . C4 C 0.4254(13) 0.6096(6) 0.5805(10) 0.043(2) Uani 1 1 d . . . C7 C 0.2178(13) 0.4864(6) 0.4802(10) 0.040(2) Uani 1 1 d . . . C3 C 0.5294(16) 0.6726(7) 0.6185(12) 0.053(3) Uani 1 1 d . . . H3A H 0.6169 0.6763 0.7043 0.064 Uiso 1 1 calc R . . C5 C 0.4468(15) 0.5469(7) 0.6622(10) 0.049(2) Uani 1 1 d . . . H5A H 0.5314 0.5467 0.7495 0.058 Uiso 1 1 calc R . . C1 C 0.3694(18) 0.7232(6) 0.4037(13) 0.054(3) Uani 1 1 d . . . H1A H 0.3506 0.7619 0.3457 0.065 Uiso 1 1 calc R . . C2 C 0.5016(18) 0.7267(7) 0.5309(13) 0.058(3) Uani 1 1 d . . . H2A H 0.5727 0.7673 0.5561 0.070 Uiso 1 1 calc R . . C10 C -0.0192(16) 0.4908(6) 0.2177(11) 0.047(2) Uani 1 1 d . . . H10A H -0.1002 0.4921 0.1291 0.056 Uiso 1 1 calc R . . C9 C 0.0013(16) 0.4278(6) 0.2903(11) 0.048(2) Uani 1 1 d . . . H9A H -0.0636 0.3877 0.2503 0.058 Uiso 1 1 calc R . . C8 C 0.1190(15) 0.4258(6) 0.4222(12) 0.048(2) Uani 1 1 d . . . H8A H 0.1329 0.3844 0.4726 0.058 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 0.0462(3) 0.0712(3) 0.0313(2) -0.00157(19) 0.00076(16) 0.0143(2) Cl1 0.0550(15) 0.0664(18) 0.0463(13) 0.0117(13) 0.0124(12) 0.0196(13) Cl4 0.0557(15) 0.0551(15) 0.0515(14) -0.0056(12) 0.0170(12) -0.0003(12) Cl3 0.0653(19) 0.093(3) 0.0393(13) -0.0056(15) -0.0071(13) 0.0054(18) Cl2 0.105(3) 0.060(2) 0.082(3) 0.0113(19) 0.029(2) -0.001(2) N2 0.039(4) 0.040(4) 0.031(3) -0.001(3) 0.006(3) 0.004(3) C12 0.032(4) 0.047(5) 0.031(4) -0.004(4) 0.003(3) 0.006(4) N1 0.040(4) 0.040(4) 0.035(4) -0.006(3) 0.002(3) 0.004(3) C11 0.032(4) 0.048(5) 0.031(4) 0.002(4) 0.007(3) 0.009(4) C6 0.042(5) 0.056(6) 0.037(5) 0.017(4) 0.011(4) 0.011(4) C4 0.033(4) 0.060(6) 0.031(4) -0.006(4) 0.002(3) 0.011(4) C7 0.035(4) 0.055(6) 0.033(4) 0.003(4) 0.013(3) 0.007(4) C3 0.043(5) 0.061(7) 0.045(6) -0.016(5) -0.003(4) 0.008(5) C5 0.042(5) 0.069(7) 0.030(4) 0.004(4) 0.005(4) 0.011(5) C1 0.058(7) 0.044(6) 0.051(6) -0.001(5) 0.004(5) 0.004(5) C2 0.055(6) 0.048(6) 0.057(7) -0.013(5) -0.002(5) -0.003(5) C10 0.049(6) 0.046(6) 0.043(5) -0.008(4) 0.009(4) -0.001(4) C9 0.054(6) 0.043(5) 0.048(5) -0.014(4) 0.016(5) -0.007(4) C8 0.046(5) 0.051(6) 0.050(6) 0.009(5) 0.019(5) 0.013(5) _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 N1 2.143(8) . ? Re1 N2 2.164(8) . ? Re1 Cl2 2.166(4) . ? Re1 Cl3 2.289(3) . ? Re1 Cl1 2.331(3) . ? Re1 Cl4 2.344(3) . ? N2 C10 1.315(13) . ? N2 C11 1.372(11) . ? C12 N1 1.352(13) . ? C12 C4 1.409(12) . ? C12 C11 1.424(14) . ? N1 C1 1.335(15) . ? C11 C7 1.390(14) . ? C6 C5 1.328(17) . ? C6 C7 1.441(14) . ? C4 C3 1.419(17) . ? C4 C5 1.438(16) . ? C7 C8 1.402(16) . ? C3 C2 1.342(19) . ? C1 C2 1.384(16) . ? C10 C9 1.394(16) . ? C9 C8 1.376(16) . ? 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 Re1 N2 76.8(3) . . ? N1 Re1 Cl2 93.7(3) . . ? N2 Re1 Cl2 170.5(2) . . ? N1 Re1 Cl3 170.5(3) . . ? N2 Re1 Cl3 93.8(2) . . ? Cl2 Re1 Cl3 95.67(17) . . ? N1 Re1 Cl1 87.6(3) . . ? N2 Re1 Cl1 86.3(2) . . ? Cl2 Re1 Cl1 92.60(16) . . ? Cl3 Re1 Cl1 90.55(13) . . ? N1 Re1 Cl4 88.2(2) . . ? N2 Re1 Cl4 86.0(2) . . ? Cl2 Re1 Cl4 94.56(15) . . ? Cl3 Re1 Cl4 92.49(13) . . ? Cl1 Re1 Cl4 171.90(11) . . ? C10 N2 C11 119.2(9) . . ? C10 N2 Re1 127.2(7) . . ? C11 N2 Re1 113.6(7) . . ? N1 C12 C4 123.1(10) . . ? N1 C12 C11 117.8(8) . . ? C4 C12 C11 119.1(10) . . ? C1 N1 C12 119.2(9) . . ? C1 N1 Re1 126.2(8) . . ? C12 N1 Re1 114.6(6) . . ? N2 C11 C7 121.9(9) . . ? N2 C11 C12 117.0(9) . . ? C7 C11 C12 121.2(8) . . ? C5 C6 C7 121.4(10) . . ? C12 C4 C3 115.5(10) . . ? C12 C4 C5 118.7(10) . . ? C3 C4 C5 125.7(9) . . ? C11 C7 C8 117.7(9) . . ? C11 C7 C6 118.2(10) . . ? C8 C7 C6 124.0(10) . . ? C2 C3 C4 120.2(10) . . ? C6 C5 C4 121.4(9) . . ? N1 C1 C2 120.8(12) . . ? C3 C2 C1 121.2(12) . . ? N2 C10 C9 122.4(10) . . ? C8 C9 C10 119.0(10) . . ? C9 C8 C7 119.7(10) . . ? _diffrn_measured_fraction_theta_max 0.892 _diffrn_reflns_theta_full 31.65 _diffrn_measured_fraction_theta_full 0.892 _refine_diff_density_max 4.758 _refine_diff_density_min -5.374 _refine_diff_density_rms 0.223