# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Sanjio Zade' _publ_contact_author_email sanjiozade@iiserkol.ac.in _publ_section_title ; Synthesis, characterization and coordination properties of bis(alkyl)selenosalen ligands ; _publ_author_name 'Dr Sanjio Zade' # Attachment '- cif458.cif' data_4 _database_code_depnum_ccdc_archive 'CCDC 808493' #TrackingRef '- cif458.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N'-bis[(2-methylseleno)phenylmethylene]-1,2-ethanediamine ; _chemical_name_common N,N'-bis((2-methylseleno)phenylmethylene)-1,2-ethanediamine _chemical_melting_point ? _chemical_formula_moiety 'C18 H20 N2 Se2' _chemical_formula_sum 'C18 H20 N2 Se2' _chemical_formula_weight 422.28 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' Se Se -0.0929 2.2259 '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 4.9264(3) _cell_length_b 7.4097(4) _cell_length_c 12.3868(7) _cell_angle_alpha 76.344(4) _cell_angle_beta 88.234(4) _cell_angle_gamma 79.904(3) _cell_volume 432.55(4) _cell_formula_units_Z 1 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5663 _cell_measurement_theta_min 2.87 _cell_measurement_theta_max 30.40 _exptl_crystal_description block _exptl_crystal_colour translucent _exptl_crystal_size_max 0.008 _exptl_crystal_size_mid 0.004 _exptl_crystal_size_min 0.003 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.621 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 210 _exptl_absorpt_coefficient_mu 4.272 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.980 _exptl_absorpt_correction_T_max 0.987 _exptl_absorpt_process_details 'Multiscan absorption correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 DUO' _diffrn_measurement_method '\ f and \ w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 9656 _diffrn_reflns_av_R_equivalents 0.0582 _diffrn_reflns_av_sigmaI/netI 0.0442 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 27.00 _reflns_number_total 1892 _reflns_number_gt 1707 _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^)+(0.1000P)^2^+0.9482P] 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 1886 _refine_ls_number_parameters 101 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0379 _refine_ls_R_factor_gt 0.0331 _refine_ls_wR_factor_ref 0.0953 _refine_ls_wR_factor_gt 0.0891 _refine_ls_goodness_of_fit_ref 0.658 _refine_ls_restrained_S_all 0.658 _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 Se1 Se -0.05431(6) 1.09388(4) 0.19669(2) 0.03543(14) Uani 1 1 d . . . N1 N -0.3261(6) 0.9139(4) 0.3825(2) 0.0362(5) Uani 1 1 d . . . C1 C -0.5451(7) 0.9441(5) 0.4622(3) 0.0377(7) Uani 1 1 d . . . H1A H -0.5812 0.8236 0.5057 0.045 Uiso 1 1 calc R . . H1B H -0.7135 1.0123 0.4230 0.045 Uiso 1 1 calc R . . C2 C -0.2291(6) 0.7479(4) 0.3783(2) 0.0344(6) Uani 1 1 d . . . H2 H -0.3047 0.6506 0.4237 0.041 Uiso 1 1 calc R . . C3 C -0.0020(6) 0.6995(4) 0.3054(2) 0.0307(6) Uani 1 1 d . . . C4 C 0.1142(7) 0.5083(5) 0.3207(3) 0.0407(7) Uani 1 1 d . . . H4 H 0.0405 0.4191 0.3737 0.049 Uiso 1 1 calc R . . C5 C 0.3356(7) 0.4495(5) 0.2588(3) 0.0451(8) Uani 1 1 d . . . H5 H 0.4112 0.3223 0.2703 0.054 Uiso 1 1 calc R . . C6 C 0.4427(7) 0.5817(5) 0.1799(3) 0.0447(8) Uani 1 1 d . . . H6 H 0.5933 0.5436 0.1384 0.054 Uiso 1 1 calc R . . C7 C 0.3293(7) 0.7700(5) 0.1616(3) 0.0378(6) Uani 1 1 d . . . H7 H 0.4030 0.8569 0.1071 0.045 Uiso 1 1 calc R . . C8 C 0.1057(6) 0.8334(4) 0.2233(2) 0.0286(5) Uani 1 1 d . . . C9 C 0.1556(8) 1.1938(5) 0.0669(3) 0.0479(8) Uani 1 1 d . . . H9A H 0.3466 1.1760 0.0872 0.072 Uiso 1 1 calc R . . H9B H 0.0868 1.3259 0.0397 0.072 Uiso 1 1 calc R . . H9C H 0.1368 1.1286 0.0099 0.072 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 Se1 0.0399(2) 0.03277(19) 0.02979(19) -0.00565(12) 0.00566(12) 0.00087(12) N1 0.0419(13) 0.0450(14) 0.0209(11) -0.0098(10) 0.0119(10) -0.0044(11) C1 0.0376(15) 0.0491(17) 0.0263(14) -0.0118(13) 0.0114(12) -0.0054(13) C2 0.0395(15) 0.0409(15) 0.0226(13) -0.0070(11) 0.0072(11) -0.0079(12) C3 0.0350(14) 0.0361(14) 0.0216(12) -0.0103(10) 0.0022(10) -0.0029(11) C4 0.0492(17) 0.0358(15) 0.0352(16) -0.0065(12) 0.0054(13) -0.0058(13) C5 0.0512(19) 0.0375(16) 0.0458(19) -0.0174(14) 0.0030(15) 0.0041(14) C6 0.0417(17) 0.052(2) 0.0398(17) -0.0192(15) 0.0105(14) 0.0042(15) C7 0.0385(15) 0.0439(16) 0.0296(14) -0.0099(12) 0.0103(12) -0.0034(13) C8 0.0314(13) 0.0331(13) 0.0223(12) -0.0114(10) 0.0005(10) -0.0017(10) C9 0.056(2) 0.0481(19) 0.0331(16) 0.0026(14) 0.0076(15) -0.0101(15) _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 Se1 C8 1.907(3) . ? Se1 C9 1.951(3) . ? N1 C2 1.251(4) . ? N1 C1 1.464(4) . ? C1 C1 1.511(6) 2_476 ? C2 C3 1.465(4) . ? C3 C4 1.402(4) . ? C3 C8 1.405(4) . ? C4 C5 1.381(5) . ? C5 C6 1.375(5) . ? C6 C7 1.377(5) . ? C7 C8 1.398(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 C8 Se1 C9 99.73(14) . . ? C2 N1 C1 118.1(3) . . ? N1 C1 C1 108.9(3) . 2_476 ? N1 C2 C3 123.2(3) . . ? C4 C3 C8 119.1(3) . . ? C4 C3 C2 117.2(3) . . ? C8 C3 C2 123.7(3) . . ? C5 C4 C3 121.5(3) . . ? C6 C5 C4 119.1(3) . . ? C5 C6 C7 120.6(3) . . ? C6 C7 C8 121.4(3) . . ? C7 C8 C3 118.2(3) . . ? C7 C8 Se1 121.4(2) . . ? C3 C8 Se1 120.3(2) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.457 _refine_diff_density_min -1.154 _refine_diff_density_rms 0.141 data_5 _database_code_depnum_ccdc_archive 'CCDC 808494' #TrackingRef '- cif458.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N'-bis[(2-decylseleno)phenylmethylene]-1,2-ethanediamine ; _chemical_name_common N,N'-bis((2-decylseleno)phenylmethylene)-1,2-ethanediamine _chemical_melting_point 335.5 _chemical_formula_moiety 'C36 H56 N2 Se2 ' _chemical_formula_sum 'C36 H56 N2 Se2 ' _chemical_formula_weight 674.75 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' Se Se -0.0929 2.2259 '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 4.8148(2) _cell_length_b 7.2403(2) _cell_length_c 24.6213(8) _cell_angle_alpha 96.012(2) _cell_angle_beta 91.398(2) _cell_angle_gamma 98.086(2) _cell_volume 844.44(5) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8580 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 36.87 _exptl_crystal_description Needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.006 _exptl_crystal_size_mid 0.0002 _exptl_crystal_size_min 0.00012 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.327 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 354 _exptl_absorpt_coefficient_mu 2.215 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.999 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'Multiscan absorption correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 DUO' _diffrn_measurement_method '\ f and \ w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 10775 _diffrn_reflns_av_R_equivalents 0.0400 _diffrn_reflns_av_sigmaI/netI 0.0466 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 0.83 _diffrn_reflns_theta_max 27.00 _reflns_number_total 3692 _reflns_number_gt 3436 _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^)+(0.1000P)^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 3692 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0313 _refine_ls_R_factor_gt 0.0285 _refine_ls_wR_factor_ref 0.0959 _refine_ls_wR_factor_gt 0.0881 _refine_ls_goodness_of_fit_ref 0.815 _refine_ls_restrained_S_all 0.815 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 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 Se1 Se 0.51252(3) 0.41907(2) 0.349903(6) 0.01095(10) Uani 1 1 d . . . N1 N 0.8039(3) 0.3436(2) 0.44273(7) 0.0126(3) Uani 1 1 d . . . C1 C 1.0394(4) 0.4173(3) 0.48111(8) 0.0131(4) Uani 1 1 d . . . H1A H 1.2040 0.4588 0.4612 0.016 Uiso 1 1 calc R . . H1B H 1.0834 0.3197 0.5026 0.016 Uiso 1 1 calc R . . C2 C 0.7098(4) 0.1700(3) 0.44035(8) 0.0116(4) Uani 1 1 d . . . H2 H 0.7966 0.0961 0.4623 0.014 Uiso 1 1 calc R . . C3 C 0.4687(4) 0.0809(3) 0.40429(8) 0.0114(4) Uani 1 1 d . . . C4 C 0.3518(4) -0.1021(3) 0.41255(8) 0.0139(4) Uani 1 1 d . . . H4 H 0.4336 -0.1627 0.4389 0.017 Uiso 1 1 calc R . . C5 C 0.1171(4) -0.1948(3) 0.38236(8) 0.0144(4) Uani 1 1 d . . . H5 H 0.0403 -0.3154 0.3888 0.017 Uiso 1 1 calc R . . C6 C -0.0014(4) -0.1050(3) 0.34242(8) 0.0145(4) Uani 1 1 d . . . H6 H -0.1598 -0.1656 0.3221 0.017 Uiso 1 1 calc R . . C7 C 0.1145(4) 0.0746(3) 0.33248(8) 0.0133(4) Uani 1 1 d . . . H7 H 0.0341 0.1319 0.3052 0.016 Uiso 1 1 calc R . . C8 C 0.3506(4) 0.1708(3) 0.36290(7) 0.0106(4) Uani 1 1 d . . . C9 C 0.3060(4) 0.4462(3) 0.28202(8) 0.0129(4) Uani 1 1 d . . . H9A H 0.1076 0.4066 0.2864 0.016 Uiso 1 1 calc R . . H9B H 0.3300 0.5778 0.2762 0.016 Uiso 1 1 calc R . . C10 C 0.3977(4) 0.3344(3) 0.23152(8) 0.0141(4) Uani 1 1 d . . . H10A H 0.3529 0.2014 0.2351 0.017 Uiso 1 1 calc R . . H10B H 0.5996 0.3633 0.2291 0.017 Uiso 1 1 calc R . . C11 C 0.2541(4) 0.3777(3) 0.17874(8) 0.0125(4) Uani 1 1 d . . . H11A H 0.0523 0.3495 0.1814 0.015 Uiso 1 1 calc R . . H11B H 0.2993 0.5107 0.1753 0.015 Uiso 1 1 calc R . . C12 C 0.3420(4) 0.2667(3) 0.12747(8) 0.0127(4) Uani 1 1 d . . . H12A H 0.2792 0.1342 0.1291 0.015 Uiso 1 1 calc R . . H12B H 0.5452 0.2847 0.1267 0.015 Uiso 1 1 calc R . . C13 C 0.2219(4) 0.3251(3) 0.07480(8) 0.0123(4) Uani 1 1 d . . . H13A H 0.0187 0.3078 0.0759 0.015 Uiso 1 1 calc R . . H13B H 0.2852 0.4577 0.0733 0.015 Uiso 1 1 calc R . . C14 C 0.3059(4) 0.2153(3) 0.02283(8) 0.0126(4) Uani 1 1 d . . . H14A H 0.5091 0.2301 0.0221 0.015 Uiso 1 1 calc R . . H14B H 0.2384 0.0831 0.0238 0.015 Uiso 1 1 calc R . . C15 C 0.1908(4) 0.2782(3) -0.02936(8) 0.0126(4) Uani 1 1 d . . . H15A H 0.2580 0.4106 -0.0301 0.015 Uiso 1 1 calc R . . H15B H -0.0124 0.2636 -0.0285 0.015 Uiso 1 1 calc R . . C16 C 0.2727(4) 0.1703(3) -0.08174(8) 0.0129(4) Uani 1 1 d . . . H16A H 0.2035 0.0380 -0.0813 0.015 Uiso 1 1 calc R . . H16B H 0.4758 0.1840 -0.0826 0.015 Uiso 1 1 calc R . . C17 C 0.1571(5) 0.2372(3) -0.13351(8) 0.0158(4) Uani 1 1 d . . . H17A H -0.0458 0.2247 -0.1324 0.019 Uiso 1 1 calc R . . H17B H 0.2275 0.3693 -0.1340 0.019 Uiso 1 1 calc R . . C18 C 0.2354(5) 0.1295(3) -0.18605(9) 0.0231(5) Uani 1 1 d . . . H18A H 0.4360 0.1440 -0.1880 0.035 Uiso 1 1 calc R . . H18B H 0.1565 0.1777 -0.2169 0.035 Uiso 1 1 calc R . . H18C H 0.1629 -0.0011 -0.1863 0.035 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 Se1 0.01240(14) 0.00980(13) 0.00972(14) 0.00050(8) -0.00006(8) -0.00112(8) N1 0.0127(8) 0.0149(8) 0.0093(8) -0.0010(6) -0.0002(6) 0.0004(6) C1 0.0112(9) 0.0157(9) 0.0111(9) -0.0012(7) -0.0008(7) -0.0005(7) C2 0.0115(9) 0.0151(9) 0.0082(8) 0.0008(7) 0.0000(7) 0.0025(7) C3 0.0109(9) 0.0119(9) 0.0107(9) -0.0014(7) 0.0028(7) 0.0006(7) C4 0.0147(9) 0.0131(9) 0.0141(9) 0.0009(7) 0.0014(7) 0.0026(7) C5 0.0152(10) 0.0099(8) 0.0171(10) 0.0009(7) 0.0031(8) -0.0019(7) C6 0.0135(10) 0.0147(9) 0.0130(9) -0.0030(7) 0.0007(8) -0.0032(7) C7 0.0137(9) 0.0143(9) 0.0110(9) 0.0006(7) 0.0000(7) 0.0002(7) C8 0.0108(8) 0.0100(8) 0.0097(8) -0.0021(7) 0.0026(7) -0.0007(7) C9 0.0135(9) 0.0145(9) 0.0107(9) 0.0009(7) 0.0005(7) 0.0018(7) C10 0.0135(9) 0.0184(9) 0.0115(9) 0.0016(7) 0.0009(7) 0.0057(7) C11 0.0113(9) 0.0147(9) 0.0115(9) 0.0007(7) 0.0017(7) 0.0024(7) C12 0.0118(9) 0.0143(9) 0.0120(9) 0.0012(7) 0.0014(7) 0.0023(7) C13 0.0134(9) 0.0130(9) 0.0106(9) 0.0018(7) 0.0025(7) 0.0020(7) C14 0.0128(9) 0.0114(9) 0.0136(9) 0.0009(7) 0.0031(7) 0.0016(7) C15 0.0124(9) 0.0135(9) 0.0117(9) -0.0001(7) 0.0006(7) 0.0023(7) C16 0.0134(9) 0.0134(9) 0.0116(9) 0.0015(7) 0.0015(7) 0.0007(7) C17 0.0170(10) 0.0175(9) 0.0128(9) 0.0024(7) -0.0009(8) 0.0014(8) C18 0.0299(12) 0.0247(11) 0.0132(10) -0.0001(8) 0.0015(9) -0.0002(9) _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 Se1 C8 1.9183(18) . ? Se1 C9 1.965(2) . ? N1 C2 1.269(3) . ? N1 C1 1.461(3) . ? C1 C1 1.534(4) 2_766 ? C2 C3 1.474(3) . ? C3 C4 1.402(3) . ? C3 C8 1.414(3) . ? C4 C5 1.386(3) . ? C5 C6 1.388(3) . ? C6 C7 1.390(3) . ? C7 C8 1.401(3) . ? C9 C10 1.521(3) . ? C10 C11 1.539(3) . ? C11 C12 1.526(3) . ? C12 C13 1.530(3) . ? C13 C14 1.528(3) . ? C14 C15 1.525(3) . ? C15 C16 1.526(3) . ? C16 C17 1.530(3) . ? C17 C18 1.523(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 C8 Se1 C9 100.50(8) . . ? C2 N1 C1 117.83(17) . . ? N1 C1 C1 109.23(19) . 2_766 ? N1 C2 C3 122.69(18) . . ? C4 C3 C8 119.30(18) . . ? C4 C3 C2 117.20(17) . . ? C8 C3 C2 123.50(17) . . ? C5 C4 C3 121.56(18) . . ? C4 C5 C6 119.00(18) . . ? C5 C6 C7 120.58(19) . . ? C6 C7 C8 121.12(18) . . ? C7 C8 C3 118.40(17) . . ? C7 C8 Se1 121.67(14) . . ? C3 C8 Se1 119.93(14) . . ? C10 C9 Se1 114.25(13) . . ? C9 C10 C11 112.16(16) . . ? C12 C11 C10 113.16(15) . . ? C11 C12 C13 112.80(16) . . ? C14 C13 C12 113.81(15) . . ? C15 C14 C13 113.24(15) . . ? C14 C15 C16 114.04(16) . . ? C15 C16 C17 113.06(16) . . ? C18 C17 C16 113.55(17) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.527 _refine_diff_density_min -0.643 _refine_diff_density_rms 0.115 data_8 _database_code_depnum_ccdc_archive 'CCDC 808495' #TrackingRef '- cif458.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H17 N2 Pt Se2, F6 P' _chemical_formula_sum 'C17 H17 F6 N2 P Pt Se2' _chemical_formula_weight 747.30 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pt Pt -1.7033 8.3905 '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)/n ' 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 14.6757(5) _cell_length_b 8.3057(3) _cell_length_c 17.3588(6) _cell_angle_alpha 90.00 _cell_angle_beta 97.908(2) _cell_angle_gamma 90.00 _cell_volume 2095.78(13) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9954 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 26.33 _exptl_crystal_description Block _exptl_crystal_colour Red _exptl_crystal_size_max 0.003 _exptl_crystal_size_mid 0.001 _exptl_crystal_size_min 0.0008 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.368 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1392.0 _exptl_absorpt_coefficient_mu 10.303 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.988 _exptl_absorpt_correction_T_max 0.992 _exptl_absorpt_process_details 'Multiscan absorption correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 DUO' _diffrn_measurement_method '\ f and \ w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 52549 _diffrn_reflns_av_R_equivalents 0.0574 _diffrn_reflns_av_sigmaI/netI 0.0263 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 27.00 _reflns_number_total 4589 _reflns_number_gt 3731 _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^)+(0.1000P)^2^+0.7142P] 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 4589 _refine_ls_number_parameters 263 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0384 _refine_ls_R_factor_gt 0.0250 _refine_ls_wR_factor_ref 0.0947 _refine_ls_wR_factor_gt 0.0794 _refine_ls_goodness_of_fit_ref 0.725 _refine_ls_restrained_S_all 0.725 _refine_ls_shift/su_max 0.003 _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 Pt1 Pt 0.710543(13) 0.27639(3) 0.016509(10) 0.03563(9) Uani 1 1 d . . . Se1 Se 0.81226(4) 0.09419(7) 0.08904(3) 0.04484(15) Uani 1 1 d . . . Se2 Se 0.69256(5) 0.39625(7) 0.13665(3) 0.05495(18) Uani 1 1 d . . . P1 P 0.93415(13) 0.2999(3) 0.76970(10) 0.0580(4) Uani 1 1 d . . . C1 C 0.9339(5) 0.1817(9) 0.0801(5) 0.078(2) Uani 1 1 d . . . H1A H 0.9798 0.1010 0.0950 0.117 Uiso 1 1 calc R . . H1B H 0.9454 0.2735 0.1137 0.117 Uiso 1 1 calc R . . H1C H 0.9364 0.2136 0.0273 0.117 Uiso 1 1 calc R . . C2 C 0.8206(4) -0.0886(7) 0.0230(3) 0.0427(12) Uani 1 1 d . . . C3 C 0.8573(4) -0.2225(7) 0.0620(4) 0.0514(14) Uani 1 1 d . . . H3 H 0.8717 -0.2197 0.1158 0.062 Uiso 1 1 calc R . . C4 C 0.8731(5) -0.3609(8) 0.0221(4) 0.0637(18) Uani 1 1 d . . . H4 H 0.8985 -0.4508 0.0489 0.076 Uiso 1 1 calc R . . C5 C 0.8509(5) -0.3651(8) -0.0573(4) 0.0628(18) Uani 1 1 d . . . H5 H 0.8616 -0.4579 -0.0847 0.075 Uiso 1 1 calc R . . C6 C 0.8134(5) -0.2340(8) -0.0957(4) 0.0577(17) Uani 1 1 d . . . H6 H 0.7990 -0.2391 -0.1495 0.069 Uiso 1 1 calc R . . C7 C 0.7955(4) -0.0909(7) -0.0577(3) 0.0451(13) Uani 1 1 d . . . C8 C 0.7542(4) 0.0396(7) -0.1069(3) 0.0478(13) Uani 1 1 d . . . H8 H 0.7523 0.0226 -0.1601 0.057 Uiso 1 1 calc R . . C9 C 0.6800(5) 0.2816(7) -0.1514(3) 0.0495(14) Uani 1 1 d . . . H9A H 0.6616 0.2206 -0.1987 0.059 Uiso 1 1 calc R . . H9B H 0.7250 0.3614 -0.1619 0.059 Uiso 1 1 calc R . . C10 C 0.5976(4) 0.3633(7) -0.1260(3) 0.0474(13) Uani 1 1 d . . . H10A H 0.5757 0.4481 -0.1623 0.057 Uiso 1 1 calc R . . H10B H 0.5482 0.2862 -0.1243 0.057 Uiso 1 1 calc R . . C11 C 0.5991(4) 0.5739(7) -0.0329(3) 0.0440(12) Uani 1 1 d . . . H11 H 0.5639 0.6259 -0.0741 0.053 Uiso 1 1 calc R . . C12 C 0.6154(3) 0.6657(7) 0.0386(3) 0.0430(12) Uani 1 1 d . . . C13 C 0.5877(4) 0.8279(8) 0.0306(4) 0.0519(14) Uani 1 1 d . . . H13 H 0.5636 0.8671 -0.0182 0.062 Uiso 1 1 calc R . . C14 C 0.5957(4) 0.9292(8) 0.0941(4) 0.0589(17) Uani 1 1 d . . . H14 H 0.5775 1.0363 0.0880 0.071 Uiso 1 1 calc R . . C15 C 0.6307(4) 0.8713(8) 0.1666(4) 0.0621(17) Uani 1 1 d . . . H15 H 0.6353 0.9387 0.2098 0.075 Uiso 1 1 calc R . . C16 C 0.6588(5) 0.7119(8) 0.1750(4) 0.0601(17) Uani 1 1 d . . . H16 H 0.6828 0.6740 0.2240 0.072 Uiso 1 1 calc R . . C17 C 0.6521(4) 0.6079(6) 0.1120(3) 0.0431(12) Uani 1 1 d . . . F1 F 0.9383(4) 0.3409(8) 0.6812(3) 0.1038(17) Uani 1 1 d . . . F2 F 0.8599(4) 0.4394(6) 0.7740(3) 0.0957(15) Uani 1 1 d . . . F3 F 0.9261(4) 0.2589(5) 0.8577(3) 0.0830(14) Uani 1 1 d . . . F4 F 1.0025(4) 0.1539(7) 0.7677(3) 0.1064(17) Uani 1 1 d . . . F5 F 0.8506(4) 0.1799(7) 0.7419(3) 0.0992(16) Uani 1 1 d . . . F6 F 1.0158(4) 0.4157(7) 0.7971(3) 0.0964(16) Uani 1 1 d . . . N1 N 0.7205(3) 0.1726(6) -0.0885(2) 0.0434(10) Uani 1 1 d . . . N2 N 0.6260(3) 0.4314(5) -0.0481(2) 0.0379(9) 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 Pt1 0.03591(13) 0.04071(14) 0.02953(13) 0.00192(7) 0.00185(8) -0.00095(7) Se1 0.0505(3) 0.0448(3) 0.0363(3) -0.0024(2) -0.0044(2) 0.0068(2) Se2 0.0805(4) 0.0512(3) 0.0321(3) 0.0020(2) 0.0039(3) 0.0181(3) P1 0.0513(9) 0.0780(12) 0.0443(9) -0.0059(8) 0.0051(7) -0.0005(8) C1 0.042(3) 0.064(4) 0.118(7) -0.022(5) -0.022(4) -0.004(3) C2 0.038(3) 0.046(3) 0.044(3) -0.001(2) 0.004(2) -0.003(2) C3 0.046(3) 0.047(3) 0.059(4) -0.004(3) 0.000(3) 0.004(3) C4 0.067(4) 0.043(4) 0.078(5) -0.005(3) -0.001(4) 0.005(3) C5 0.063(4) 0.043(3) 0.082(5) -0.020(3) 0.010(4) -0.001(3) C6 0.051(4) 0.061(4) 0.062(4) -0.026(3) 0.011(3) -0.008(3) C7 0.038(3) 0.051(3) 0.047(3) -0.007(3) 0.007(2) -0.004(2) C8 0.052(3) 0.053(3) 0.040(3) -0.009(3) 0.010(2) -0.007(3) C9 0.067(4) 0.052(3) 0.029(3) 0.005(2) 0.004(3) -0.001(3) C10 0.047(3) 0.054(3) 0.038(3) 0.002(2) -0.007(2) -0.004(3) C11 0.039(3) 0.052(3) 0.040(3) 0.011(2) 0.001(2) -0.001(2) C12 0.032(2) 0.046(3) 0.052(3) 0.003(3) 0.007(2) 0.001(2) C13 0.043(3) 0.049(3) 0.061(4) 0.010(3) 0.001(3) 0.003(3) C14 0.049(3) 0.040(3) 0.088(5) 0.000(3) 0.010(3) -0.004(3) C15 0.054(4) 0.061(4) 0.070(4) -0.016(3) 0.004(3) 0.003(3) C16 0.064(4) 0.056(4) 0.057(4) -0.014(3) -0.002(3) 0.014(3) C17 0.044(3) 0.041(3) 0.043(3) 0.002(2) 0.002(2) 0.004(2) F1 0.103(4) 0.165(5) 0.047(2) -0.003(3) 0.021(2) -0.005(4) F2 0.110(4) 0.106(4) 0.069(3) 0.000(3) 0.005(3) 0.043(3) F3 0.090(4) 0.109(4) 0.049(3) 0.012(2) 0.006(2) 0.002(3) F4 0.091(4) 0.109(4) 0.118(4) -0.024(4) 0.009(3) 0.031(3) F5 0.079(3) 0.118(4) 0.095(4) -0.017(3) -0.010(3) -0.020(3) F6 0.096(3) 0.113(4) 0.075(3) 0.008(3) -0.005(3) -0.048(3) N1 0.044(2) 0.056(3) 0.030(2) 0.005(2) 0.0042(18) -0.005(2) N2 0.033(2) 0.046(3) 0.034(2) 0.0064(18) 0.0049(17) -0.0043(18) _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 Pt1 N2 2.017(4) . ? Pt1 N1 2.039(5) . ? Pt1 Se2 2.3583(6) . ? Pt1 Se1 2.3636(6) . ? Se1 C2 1.916(6) . ? Se1 C1 1.953(7) . ? Se2 C17 1.885(5) . ? P1 F6 1.559(5) . ? P1 F4 1.577(6) . ? P1 F1 1.583(5) . ? P1 F3 1.585(5) . ? P1 F2 1.600(5) . ? P1 F5 1.602(5) . ? C2 C3 1.372(8) . ? C2 C7 1.400(8) . ? C3 C4 1.377(9) . ? C4 C5 1.373(10) . ? C5 C6 1.353(10) . ? C6 C7 1.402(8) . ? C7 C8 1.459(8) . ? C8 N1 1.270(7) . ? C9 N1 1.479(7) . ? C9 C10 1.505(9) . ? C10 N2 1.473(7) . ? C11 N2 1.287(7) . ? C11 C12 1.448(8) . ? C12 C17 1.398(8) . ? C12 C13 1.409(9) . ? C13 C14 1.379(9) . ? C14 C15 1.380(10) . ? C15 C16 1.389(9) . ? C16 C17 1.386(8) . ? 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 Pt1 N1 83.54(18) . . ? N2 Pt1 Se2 94.99(13) . . ? N1 Pt1 Se2 177.72(13) . . ? N2 Pt1 Se1 178.27(12) . . ? N1 Pt1 Se1 95.03(14) . . ? Se2 Pt1 Se1 86.48(2) . . ? C2 Se1 C1 96.5(3) . . ? C2 Se1 Pt1 106.05(16) . . ? C1 Se1 Pt1 103.7(2) . . ? C17 Se2 Pt1 105.23(17) . . ? F6 P1 F4 90.9(4) . . ? F6 P1 F1 91.9(3) . . ? F4 P1 F1 92.0(3) . . ? F6 P1 F3 89.7(3) . . ? F4 P1 F3 89.3(3) . . ? F1 P1 F3 178.0(3) . . ? F6 P1 F2 92.3(3) . . ? F4 P1 F2 175.9(4) . . ? F1 P1 F2 90.4(3) . . ? F3 P1 F2 88.2(3) . . ? F6 P1 F5 179.6(4) . . ? F4 P1 F5 88.7(3) . . ? F1 P1 F5 88.3(3) . . ? F3 P1 F5 90.1(3) . . ? F2 P1 F5 88.1(3) . . ? C3 C2 C7 120.9(5) . . ? C3 C2 Se1 113.6(4) . . ? C7 C2 Se1 125.5(4) . . ? C2 C3 C4 120.7(7) . . ? C5 C4 C3 119.5(6) . . ? C6 C5 C4 119.9(6) . . ? C5 C6 C7 122.7(7) . . ? C2 C7 C6 116.3(6) . . ? C2 C7 C8 127.4(5) . . ? C6 C7 C8 116.4(6) . . ? N1 C8 C7 130.1(5) . . ? N1 C9 C10 108.5(5) . . ? N2 C10 C9 107.7(4) . . ? N2 C11 C12 129.9(5) . . ? C17 C12 C13 119.2(5) . . ? C17 C12 C11 126.7(5) . . ? C13 C12 C11 114.1(5) . . ? C14 C13 C12 120.9(6) . . ? C13 C14 C15 119.8(6) . . ? C14 C15 C16 119.7(6) . . ? C17 C16 C15 121.6(6) . . ? C16 C17 C12 118.8(5) . . ? C16 C17 Se2 114.6(4) . . ? C12 C17 Se2 126.6(4) . . ? C8 N1 C9 118.5(5) . . ? C8 N1 Pt1 132.2(4) . . ? C9 N1 Pt1 109.3(4) . . ? C11 N2 C10 119.0(4) . . ? C11 N2 Pt1 131.0(4) . . ? C10 N2 Pt1 109.9(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.787 _refine_diff_density_min -0.774 _refine_diff_density_rms 0.100 # END of CIF