# 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_187alb _audit_creation_date 2013-11-06T16:03:27-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety "C12 H19 N2 Se, Cl, 2(H2 O)'" _chemical_formula_sum 'C12 H23 Cl N2 O2 Se' _chemical_formula_weight 341.73 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.7651(14) _cell_length_b 9.6342(18) _cell_length_c 11.281(2) _cell_angle_alpha 79.378(3) _cell_angle_beta 70.513(3) _cell_angle_gamma 87.642(3) _cell_volume 781.8(3) _cell_formula_units_Z 2 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 3257 _cell_measurement_theta_min 2.63 _cell_measurement_theta_max 24.89 _exptl_crystal_description block _exptl_crystal_colour colourless #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.452 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 352 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 2.57 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.442 _exptl_absorpt_correction_T_max 0.627 _exptl_absorpt_process_details 'Bruker, 2000.' #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _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 8347 _diffrn_reflns_av_unetI/netI 0.0365 _diffrn_reflns_av_R_equivalents 0.0276 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.947 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.994 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.994 _reflns_number_total 3175 _reflns_number_gt 2890 _reflns_threshold_expression 'I > 2\s(I)' #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_molecular_graphics 'Ortep for Windows (Farrugia, 2012)' _computing_publication_material 'WinGX publication routines (Farrugia, 2012)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_hydrogens mixed #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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 'w=1/[\s^2^(Fo^2^)+(0.0546P)^2^+0.8580P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 3175 _refine_ls_number_parameters 187 _refine_ls_number_restraints 11 _refine_ls_R_factor_all 0.0477 _refine_ls_R_factor_gt 0.0424 _refine_ls_wR_factor_ref 0.1073 _refine_ls_wR_factor_gt 0.1044 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.796 _refine_diff_density_min -0.64 _refine_diff_density_rms 0.085 _restr_special_details ; The same isotropic or anisotropic displacement parameters were used for O1 and Cl1, and O2 and Cl2, respectively ; loop_ _restr_distance_atom_site_label_1 _restr_distance_atom_site_label_2 _restr_distance_target O1 H14 0.89 O1 H15 0.89 O2 H16 0.89 O2 H17 0.89 O3 H18 0.89 O3 H19 0.89 H14 H15 1.45 H16 H17 1.45 H18 H19 1.45 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' O O 0.0106 0.006 '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' 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_calc_flag _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.7725(4) 0.4834(4) 0.7530(3) 0.0326(7) Uani 1 d . . C2 C 0.8392(5) 0.3481(4) 0.7612(3) 0.0374(7) Uani 1 d . . C3 C 0.9831(5) 0.3219(4) 0.8074(4) 0.0480(9) Uani 1 d . . H3 H 1.0316 0.232 0.8142 0.058 Uiso 1 calc . . C4 C 1.0553(5) 0.4302(5) 0.8437(4) 0.0537(10) Uani 1 d . . H4 H 1.1523 0.4122 0.8749 0.064 Uiso 1 calc . . C5 C 0.9842(5) 0.5655(5) 0.8341(4) 0.0512(10) Uani 1 d . . H5 H 1.0333 0.637 0.8591 0.061 Uiso 1 calc . . C6 C 0.8417(5) 0.5928(4) 0.7876(3) 0.0378(8) Uani 1 d . . C7 C 0.7555(5) 0.7340(4) 0.7647(4) 0.0458(9) Uani 1 d . . H7A H 0.7575 0.7888 0.8283 0.055 Uiso 1 calc . . H7B H 0.8228 0.7865 0.6808 0.055 Uiso 1 calc . . C8 C 0.4423(5) 0.6818(4) 0.9083(3) 0.0456(9) Uani 1 d . . H8A H 0.4287 0.7679 0.9416 0.068 Uiso 1 calc . . H8B H 0.4945 0.6117 0.9578 0.068 Uiso 1 calc . . H8C H 0.3249 0.6488 0.913 0.068 Uiso 1 calc . . C9 C 0.4955(6) 0.8265(4) 0.6984(4) 0.0534(10) Uani 1 d . . H9A H 0.4927 0.9105 0.7333 0.08 Uiso 1 calc . . H9B H 0.3745 0.8035 0.702 0.08 Uiso 1 calc . . H9C H 0.5751 0.8421 0.611 0.08 Uiso 1 calc . . C10 C 0.7418(5) 0.2409(4) 0.7246(3) 0.0408(8) Uani 1 d . . H10A H 0.8274 0.1728 0.6857 0.049 Uiso 1 calc . . H10B H 0.6489 0.1908 0.7997 0.049 Uiso 1 calc . . C11 C 0.7914(6) 0.3478(4) 0.5015(4) 0.0516(10) Uani 1 d . . H11A H 0.8353 0.2607 0.4737 0.077 Uiso 1 calc . . H11B H 0.8919 0.4021 0.5021 0.077 Uiso 1 calc . . H11C H 0.7348 0.4005 0.444 0.077 Uiso 1 calc . . C12 C 0.4955(6) 0.2394(4) 0.6325(4) 0.0512(10) Uani 1 d . . H12A H 0.4359 0.297 0.5796 0.077 Uiso 1 calc . . H12B H 0.4119 0.2166 0.7184 0.077 Uiso 1 calc . . H12C H 0.5347 0.1539 0.6 0.077 Uiso 1 calc . . N1 N 0.5640(4) 0.7081(3) 0.7736(3) 0.0357(6) Uani 1 d . . N2 N 0.6559(4) 0.3173(3) 0.6320(3) 0.0370(6) Uani 1 d . . Cl1 Cl 0.6694(3) -0.0463(2) 1.02299(18) 0.0725(5) Uani 0.5 d A 1 O1 O 0.6694(3) -0.0463(2) 1.02299(18) 0.0725(5) Uani 0.5 d B 2 H14 H 0.741(4) 0.016(4) 1.036(5) 0.087 Uiso 0.5 d C 2 H15 H 0.711(4) -0.130(3) 1.051(5) 0.087 Uiso 0.5 d D 2 Cl2 Cl 0.1242(3) 1.0158(2) 0.5678(2) 0.0830(6) Uani 0.5 d E 2 O2 O 0.1242(3) 1.0158(2) 0.5678(2) 0.0830(6) Uani 0.5 d F 1 H16 H 0.208(11) 0.956(8) 0.585(11) 0.1 Uiso 0.5 d G 1 H17 H 0.144(14) 1.096(6) 0.592(11) 0.1 Uiso 0.5 d H 1 O3 O 1.0682(5) -0.0726(4) 0.8505(4) 0.0767(10) Uani 1 d . . H18 H 1.120(6) 0.012(2) 0.831(4) 0.092 Uiso 1 d . . H19 H 0.953(3) -0.068(5) 0.900(5) 0.092 Uiso 1 d . . Se1 Se 0.57241(4) 0.51815(3) 0.69351(3) 0.03400(13) Uani 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0295(16) 0.0371(18) 0.0300(16) -0.0059(13) -0.0085(13) 0.0014(13) C2 0.0338(17) 0.0385(18) 0.0347(17) -0.0064(14) -0.0051(14) 0.0055(14) C3 0.047(2) 0.050(2) 0.043(2) -0.0072(17) -0.0130(17) 0.0132(18) C4 0.038(2) 0.075(3) 0.050(2) -0.012(2) -0.0177(18) 0.0042(19) C5 0.041(2) 0.066(3) 0.047(2) -0.0194(19) -0.0091(17) -0.0123(19) C6 0.0338(17) 0.0421(19) 0.0338(17) -0.0114(15) -0.0034(14) -0.0028(14) C7 0.045(2) 0.0366(19) 0.052(2) -0.0129(17) -0.0084(17) -0.0049(16) C8 0.049(2) 0.039(2) 0.0405(19) -0.0105(16) -0.0019(17) 0.0033(16) C9 0.078(3) 0.034(2) 0.046(2) -0.0080(16) -0.019(2) 0.0163(19) C10 0.046(2) 0.0304(17) 0.0420(19) -0.0055(14) -0.0113(16) 0.0080(15) C11 0.065(3) 0.045(2) 0.0366(19) -0.0108(17) -0.0044(18) -0.0001(19) C12 0.064(3) 0.038(2) 0.057(2) -0.0109(17) -0.025(2) -0.0056(18) N1 0.0383(15) 0.0279(14) 0.0367(15) -0.0080(11) -0.0059(12) 0.0035(11) N2 0.0447(16) 0.0298(14) 0.0346(15) -0.0094(12) -0.0091(13) 0.0024(12) Cl1 0.0762(12) 0.0677(11) 0.0637(10) -0.0267(9) -0.0008(9) -0.0136(9) O1 0.0762(12) 0.0677(11) 0.0637(10) -0.0267(9) -0.0008(9) -0.0136(9) Cl2 0.0960(15) 0.0730(13) 0.0610(11) -0.0085(10) -0.0039(10) 0.0090(11) O2 0.0960(15) 0.0730(13) 0.0610(11) -0.0085(10) -0.0039(10) 0.0090(11) O3 0.068(2) 0.094(3) 0.071(2) -0.033(2) -0.0173(18) 0.0056(19) Se1 0.0356(2) 0.0314(2) 0.0365(2) -0.00892(13) -0.01287(14) 0.00426(13) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.374(5) . ? C1 C2 1.381(5) . ? C1 Se1 1.883(3) . ? C2 C3 1.379(5) . ? C2 C10 1.497(5) . ? C3 C4 1.389(6) . ? C3 H3 0.93 . ? C4 C5 1.394(6) . ? C4 H4 0.93 . ? C5 C6 1.372(5) . ? C5 H5 0.93 . ? C6 C7 1.509(5) . ? C7 N1 1.485(5) . ? C7 H7A 0.97 . ? C7 H7B 0.97 . ? C8 N1 1.478(4) . ? C8 H8A 0.96 . ? C8 H8B 0.96 . ? C8 H8C 0.96 . ? C9 N1 1.482(5) . ? C9 H9A 0.96 . ? C9 H9B 0.96 . ? C9 H9C 0.96 . ? C10 N2 1.490(4) . ? C10 H10A 0.97 . ? C10 H10B 0.97 . ? C11 N2 1.481(5) . ? C11 H11A 0.96 . ? C11 H11B 0.96 . ? C11 H11C 0.96 . ? C12 N2 1.478(5) . ? C12 H12A 0.96 . ? C12 H12B 0.96 . ? C12 H12C 0.96 . ? N1 Se1 2.175(3) . ? N2 Se1 2.177(3) . ? O3 H18 0.88(3) . ? O3 H19 0.88(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 C6 C1 C2 123.9(3) . . ? C6 C1 Se1 118.4(3) . . ? C2 C1 Se1 117.7(3) . . ? C3 C2 C1 117.7(3) . . ? C3 C2 C10 125.7(3) . . ? C1 C2 C10 116.5(3) . . ? C2 C3 C4 119.7(4) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C3 C4 C5 120.9(4) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C6 C5 C4 119.8(4) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C5 C6 C1 118.0(3) . . ? C5 C6 C7 126.6(3) . . ? C1 C6 C7 115.4(3) . . ? N1 C7 C6 108.1(3) . . ? N1 C7 H7A 110.1 . . ? C6 C7 H7A 110.1 . . ? N1 C7 H7B 110.1 . . ? C6 C7 H7B 110.1 . . ? H7A C7 H7B 108.4 . . ? N1 C8 H8A 109.5 . . ? N1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N1 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N2 C10 C2 107.7(3) . . ? N2 C10 H10A 110.2 . . ? C2 C10 H10A 110.2 . . ? N2 C10 H10B 110.2 . . ? C2 C10 H10B 110.2 . . ? H10A C10 H10B 108.5 . . ? N2 C11 H11A 109.5 . . ? N2 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N2 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N2 C12 H12A 109.5 . . ? N2 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N2 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C8 N1 C9 110.3(3) . . ? C8 N1 C7 110.9(3) . . ? C9 N1 C7 111.9(3) . . ? C8 N1 Se1 109.1(2) . . ? C9 N1 Se1 109.5(2) . . ? C7 N1 Se1 105.0(2) . . ? C12 N2 C11 110.6(3) . . ? C12 N2 C10 112.2(3) . . ? C11 N2 C10 110.7(3) . . ? C12 N2 Se1 110.1(2) . . ? C11 N2 Se1 107.8(2) . . ? C10 N2 Se1 105.2(2) . . ? H18 O3 H19 109(2) . . ? C1 Se1 N1 81.08(13) . . ? C1 Se1 N2 80.96(13) . . ? N1 Se1 N2 162.02(11) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.4(5) . . . . ? Se1 C1 C2 C3 -178.6(3) . . . . ? C6 C1 C2 C10 177.5(3) . . . . ? Se1 C1 C2 C10 -1.5(4) . . . . ? C1 C2 C3 C4 0.0(6) . . . . ? C10 C2 C3 C4 -176.8(4) . . . . ? C2 C3 C4 C5 0.0(6) . . . . ? C3 C4 C5 C6 -0.3(6) . . . . ? C4 C5 C6 C1 0.6(5) . . . . ? C4 C5 C6 C7 -176.7(4) . . . . ? C2 C1 C6 C5 -0.7(5) . . . . ? Se1 C1 C6 C5 178.3(3) . . . . ? C2 C1 C6 C7 176.9(3) . . . . ? Se1 C1 C6 C7 -4.1(4) . . . . ? C5 C6 C7 N1 -154.0(3) . . . . ? C1 C6 C7 N1 28.6(4) . . . . ? C3 C2 C10 N2 -156.5(3) . . . . ? C1 C2 C10 N2 26.7(4) . . . . ? C6 C7 N1 C8 82.4(3) . . . . ? C6 C7 N1 C9 -154.1(3) . . . . ? C6 C7 N1 Se1 -35.4(3) . . . . ? C2 C10 N2 C12 -154.6(3) . . . . ? C2 C10 N2 C11 81.2(3) . . . . ? C2 C10 N2 Se1 -35.0(3) . . . . ? C6 C1 Se1 N1 -13.7(3) . . . . ? C2 C1 Se1 N1 165.3(3) . . . . ? C6 C1 Se1 N2 165.4(3) . . . . ? C2 C1 Se1 N2 -15.6(3) . . . . ? _iucr_refine_instructions_details ; TITL 187alb in P-1 CELL 0.71073 7.7651 9.6342 11.2814 79.378 70.513 87.642 ZERR 2.00 0.0014 0.0018 0.0021 0.003 0.003 0.003 LATT 1 SFAC C H N Se O Cl UNIT 24 46 4 2 4 2 LIST 4 ! automatically inserted. Change 6 to 4 for CHECKCIF!! rem OMIT 0.00 50.02 FMAP 2 EADP Cl1 O1 EADP Cl2 O2 EXYZ Cl1 O1 EXYZ Cl2 O2 DFIX 0.89 0.01 O1 H14 O1 H15 DANG 1.45 0.02 H14 H15 DFIX 0.89 0.01 O2 H16 O2 H17 DANG 1.45 0.02 H16 H17 DFIX 0.89 0.01 O3 H18 O3 H19 DANG 1.45 0.02 H18 H19 SIZE 0.38 0.31 0.20 ACTA BUMP CONF BOND BOND $H PLAN 20 L.S. 50 WGHT 0.0546 0.8580 SWAT 0.000019 191.6429 FVAR 0.17565 C1 1 0.772485 0.483439 0.753042 11.00000 0.02948 0.03712 = 0.03001 -0.00585 -0.00846 0.00140 C2 1 0.839232 0.348129 0.761158 11.00000 0.03381 0.03854 = 0.03467 -0.00637 -0.00510 0.00547 C3 1 0.983115 0.321870 0.807397 11.00000 0.04749 0.05043 = 0.04287 -0.00717 -0.01296 0.01323 AFIX 43 H3 2 1.031626 0.232033 0.814232 11.00000 -1.20000 AFIX 0 C4 1 1.055307 0.430157 0.843728 11.00000 0.03798 0.07519 = 0.05024 -0.01157 -0.01775 0.00424 AFIX 43 H4 2 1.152326 0.412177 0.874908 11.00000 -1.20000 AFIX 0 C5 1 0.984217 0.565462 0.834060 11.00000 0.04062 0.06649 = 0.04727 -0.01943 -0.00907 -0.01226 AFIX 43 H5 2 1.033332 0.636993 0.859056 11.00000 -1.20000 AFIX 0 C6 1 0.841651 0.592812 0.787588 11.00000 0.03383 0.04210 = 0.03380 -0.01141 -0.00342 -0.00284 C7 1 0.755471 0.734025 0.764733 11.00000 0.04493 0.03660 = 0.05245 -0.01290 -0.00841 -0.00495 AFIX 23 H7A 2 0.757530 0.788836 0.828277 11.00000 -1.20000 H7B 2 0.822805 0.786511 0.680779 11.00000 -1.20000 AFIX 0 C8 1 0.442348 0.681808 0.908307 11.00000 0.04865 0.03892 = 0.04050 -0.01055 -0.00193 0.00327 AFIX 137 H8A 2 0.428663 0.767889 0.941646 11.00000 -1.50000 H8B 2 0.494522 0.611671 0.957785 11.00000 -1.50000 H8C 2 0.324890 0.648789 0.912962 11.00000 -1.50000 AFIX 0 C9 1 0.495522 0.826475 0.698361 11.00000 0.07843 0.03385 = 0.04558 -0.00805 -0.01884 0.01628 AFIX 137 H9A 2 0.492688 0.910516 0.733284 11.00000 -1.50000 H9B 2 0.374506 0.803478 0.702035 11.00000 -1.50000 H9C 2 0.575055 0.842085 0.611039 11.00000 -1.50000 AFIX 0 C10 1 0.741756 0.240876 0.724567 11.00000 0.04648 0.03037 = 0.04197 -0.00548 -0.01128 0.00799 AFIX 23 H10A 2 0.827404 0.172756 0.685697 11.00000 -1.20000 H10B 2 0.648947 0.190783 0.799693 11.00000 -1.20000 AFIX 0 C11 1 0.791371 0.347850 0.501476 11.00000 0.06484 0.04523 = 0.03660 -0.01084 -0.00438 -0.00011 AFIX 137 H11A 2 0.835255 0.260686 0.473716 11.00000 -1.50000 H11B 2 0.891882 0.402129 0.502141 11.00000 -1.50000 H11C 2 0.734809 0.400531 0.443980 11.00000 -1.50000 AFIX 0 C12 1 0.495529 0.239398 0.632540 11.00000 0.06426 0.03774 = 0.05709 -0.01095 -0.02530 -0.00557 AFIX 137 H12A 2 0.435859 0.297034 0.579552 11.00000 -1.50000 H12B 2 0.411875 0.216640 0.718382 11.00000 -1.50000 H12C 2 0.534687 0.153904 0.600045 11.00000 -1.50000 AFIX 0 N1 3 0.563956 0.708104 0.773607 11.00000 0.03830 0.02786 = 0.03669 -0.00798 -0.00594 0.00349 N2 3 0.655860 0.317308 0.631985 11.00000 0.04471 0.02977 = 0.03460 -0.00936 -0.00905 0.00241 PART 1 CL1 6 0.669431 -0.046317 1.022994 10.50000 0.07619 0.06766 = 0.06375 -0.02674 -0.00077 -0.01357 PART 2 O1 5 0.669431 -0.046317 1.022994 10.50000 0.07619 0.06766 = 0.06375 -0.02674 -0.00077 -0.01357 H14 2 0.740611 0.016364 1.036169 10.50000 -1.20000 H15 2 0.710744 -0.130051 1.051247 10.50000 -1.20000 PART 2 CL2 6 0.124167 1.015816 0.567773 10.50000 0.09602 0.07296 = 0.06099 -0.00853 -0.00391 0.00905 PART 1 O2 5 0.124167 1.015816 0.567773 10.50000 0.09602 0.07296 = 0.06099 -0.00853 -0.00391 0.00905 H16 2 0.208109 0.956379 0.585111 10.50000 -1.20000 H17 2 0.143776 1.096014 0.591558 10.50000 -1.20000 PART 0 O3 5 1.068237 -0.072577 0.850539 11.00000 0.06766 0.09378 = 0.07120 -0.03304 -0.01727 0.00563 H18 2 1.120121 0.012181 0.831108 11.00000 -1.20000 H19 2 0.953036 -0.067590 0.900220 11.00000 -1.20000 SE1 4 0.572411 0.518153 0.693509 11.00000 0.03560 0.03137 = 0.03651 -0.00892 -0.01287 0.00426 HKLF 4 REM 187alb in P-1 REM R1 = 0.0424 for 2890 Fo > 4sig(Fo) and 0.0477 for all 3175 data REM 187 parameters refined using 11 restraints END WGHT 0.0546 0.8580 REM Highest difference peak 0.796, deepest hole -0.640, 1-sigma level 0.085 Q1 1 0.7569 -0.0621 1.0649 11.00000 0.05 0.80 Q2 1 0.8033 -0.0476 1.0060 11.00000 0.05 0.63 Q3 1 0.1820 1.0945 0.5593 11.00000 0.05 0.55 Q4 1 0.6870 0.5323 0.7012 11.00000 0.05 0.55 Q5 1 0.4886 0.4917 0.6596 11.00000 0.05 0.54 Q6 1 0.5812 0.2156 0.6780 11.00000 0.05 0.53 Q7 1 0.2284 1.0014 0.5996 11.00000 0.05 0.50 Q8 1 0.9226 -0.0368 0.8130 11.00000 0.05 0.48 Q9 1 0.5798 0.5987 0.6521 11.00000 0.05 0.47 Q10 1 0.9212 0.6398 0.8136 11.00000 0.05 0.45 Q11 1 0.9100 0.3367 0.7818 11.00000 0.05 0.44 Q12 1 0.5831 0.8588 0.6842 11.00000 0.05 0.43 Q13 1 0.6026 0.4491 0.7440 11.00000 0.05 0.43 Q14 1 0.5386 0.4340 0.7485 11.00000 0.05 0.39 Q15 1 0.8046 0.6539 0.7787 11.00000 0.05 0.36 Q16 1 1.1403 -0.0494 0.8874 11.00000 0.05 0.34 Q17 1 0.8166 0.2875 0.7469 11.00000 0.05 0.30 Q18 1 0.6897 0.2815 0.6789 11.00000 0.05 0.29 Q19 1 0.5409 0.7677 0.7417 11.00000 0.05 0.29 Q20 1 0.4768 0.5111 0.7602 11.00000 0.05 0.28 ; # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF _database_code_depnum_ccdc_archive 'CCDC 952118' ####################################################################### # # 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_5ale _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H21 Cl N2 O Se' _chemical_formula_sum 'C12 H21 Cl N2 O Se' _chemical_formula_weight 323.72 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' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C2/c ' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 14.7558(18) _cell_length_b 11.3558(14) _cell_length_c 18.666(2) _cell_angle_alpha 90.00 _cell_angle_beta 109.722(2) _cell_angle_gamma 90.00 _cell_volume 2944.3(6) _cell_formula_units_Z 8 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 3782 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 22.67 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.461 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1328 _exptl_absorpt_coefficient_mu 2.720 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4168 _exptl_absorpt_correction_T_max 0.5613 _exptl_absorpt_process_details 'Bruker, 2001.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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 13720 _diffrn_reflns_av_R_equivalents 0.0401 _diffrn_reflns_av_sigmaI/netI 0.0337 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2588 _reflns_number_gt 2283 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.0319P)^2^+2.2368P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2588 _refine_ls_number_parameters 167 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0347 _refine_ls_R_factor_gt 0.0292 _refine_ls_wR_factor_ref 0.0710 _refine_ls_wR_factor_gt 0.0690 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.028 _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 C1 C 0.33987(16) 0.9224(2) 0.93430(13) 0.0331(5) Uani 1 1 d . . . C2 C 0.38456(17) 0.9260(2) 1.01239(13) 0.0369(6) Uani 1 1 d . . . C3 C 0.3551(2) 1.0116(2) 1.05262(15) 0.0470(7) Uani 1 1 d . . . H3 H 0.3840 1.0168 1.1051 0.056 Uiso 1 1 calc R . . C4 C 0.2826(2) 1.0892(2) 1.01473(16) 0.0491(7) Uani 1 1 d . . . H4 H 0.2628 1.1460 1.0422 0.059 Uiso 1 1 calc R . . C5 C 0.23894(19) 1.0838(2) 0.93656(16) 0.0440(6) Uani 1 1 d . . . H5 H 0.1909 1.1373 0.9117 0.053 Uiso 1 1 calc R . . C6 C 0.26705(17) 0.9986(2) 0.89557(14) 0.0360(6) Uani 1 1 d . . . C7 C 0.46474(19) 0.8388(2) 1.04484(14) 0.0436(6) Uani 1 1 d . . . H7A H 0.5262 0.8749 1.0501 0.052 Uiso 1 1 calc R . . H7B H 0.4661 0.8130 1.0947 0.052 Uiso 1 1 calc R . . C8 C 0.3777(2) 0.6534(3) 1.00463(19) 0.0593(8) Uani 1 1 d . . . H8A H 0.4043 0.6194 1.0544 0.089 Uiso 1 1 calc R . . H8B H 0.3643 0.5922 0.9670 0.089 Uiso 1 1 calc R . . H8C H 0.3192 0.6942 1.0005 0.089 Uiso 1 1 calc R . . C9 C 0.5376(2) 0.6738(3) 0.99803(18) 0.0554(8) Uani 1 1 d . . . H9A H 0.5647 0.6402 1.0479 0.083 Uiso 1 1 calc R . . H9B H 0.5827 0.7281 0.9894 0.083 Uiso 1 1 calc R . . H9C H 0.5238 0.6123 0.9606 0.083 Uiso 1 1 calc R . . C10 C 0.22131(19) 0.9749(2) 0.81153(14) 0.0446(6) Uani 1 1 d . . . H10A H 0.1666 0.9226 0.8026 0.053 Uiso 1 1 calc R . . H10B H 0.1988 1.0480 0.7845 0.053 Uiso 1 1 calc R . . C11 C 0.2495(2) 0.8451(3) 0.71594(16) 0.0613(8) Uani 1 1 d . . . H11A H 0.2140 0.8940 0.6739 0.092 Uiso 1 1 calc R . . H11B H 0.2067 0.7896 0.7267 0.092 Uiso 1 1 calc R . . H11C H 0.2987 0.8034 0.7032 0.092 Uiso 1 1 calc R . . C12 C 0.3586(2) 1.0087(3) 0.76800(17) 0.0578(8) Uani 1 1 d . . . H12A H 0.3221 1.0563 0.7256 0.087 Uiso 1 1 calc R . . H12B H 0.4095 0.9697 0.7561 0.087 Uiso 1 1 calc R . . H12C H 0.3857 1.0578 0.8119 0.087 Uiso 1 1 calc R . . Cl1 Cl 1.0000 0.76536(11) 0.7500 0.0696(3) Uani 1 2 d S . . Cl2 Cl 1.0000 0.21786(13) 0.7500 0.0969(5) Uani 1 2 d S . . H13 H 0.990(3) 1.055(2) 0.8148(19) 0.103(14) Uiso 1 1 d D . . H14 H 0.974(4) 0.930(2) 0.815(3) 0.19(3) Uiso 1 1 d D . . N1 N 0.44734(14) 0.73693(19) 0.99219(12) 0.0394(5) Uani 1 1 d . . . N2 N 0.29483(15) 0.91972(19) 0.78404(11) 0.0416(5) Uani 1 1 d . . . O1 O 0.9753(2) 0.9957(3) 0.84395(14) 0.0845(8) Uani 1 1 d D . . Se1 Se 0.381504(17) 0.80932(2) 0.877972(14) 0.03926(11) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0340(13) 0.0310(12) 0.0369(13) -0.0025(10) 0.0155(10) -0.0039(10) C2 0.0407(14) 0.0390(14) 0.0336(13) 0.0014(11) 0.0159(11) -0.0045(11) C3 0.0587(17) 0.0514(17) 0.0347(14) -0.0067(12) 0.0208(13) -0.0082(14) C4 0.0602(18) 0.0410(15) 0.0563(18) -0.0115(13) 0.0332(15) -0.0024(13) C5 0.0437(15) 0.0367(14) 0.0555(17) 0.0011(12) 0.0219(13) 0.0032(11) C6 0.0362(13) 0.0350(13) 0.0390(14) -0.0015(11) 0.0155(11) -0.0025(10) C7 0.0431(15) 0.0521(16) 0.0334(13) 0.0042(12) 0.0102(12) -0.0029(12) C8 0.0446(17) 0.0490(17) 0.083(2) 0.0211(16) 0.0194(16) -0.0019(13) C9 0.0397(15) 0.0571(18) 0.066(2) 0.0074(15) 0.0135(14) 0.0135(13) C10 0.0416(15) 0.0458(15) 0.0414(15) 0.0013(12) 0.0076(12) 0.0054(12) C11 0.068(2) 0.064(2) 0.0427(17) -0.0160(15) 0.0070(15) 0.0030(16) C12 0.066(2) 0.063(2) 0.0487(17) 0.0059(14) 0.0258(15) -0.0064(16) Cl1 0.0786(8) 0.0581(7) 0.0761(8) 0.000 0.0314(6) 0.000 Cl2 0.1318(13) 0.0684(8) 0.1300(13) 0.000 0.0958(12) 0.000 N1 0.0330(11) 0.0386(11) 0.0453(12) 0.0082(10) 0.0114(9) 0.0010(9) N2 0.0462(13) 0.0435(12) 0.0320(11) -0.0035(9) 0.0093(10) 0.0001(10) O1 0.107(2) 0.0876(19) 0.0498(14) 0.0000(14) 0.0144(14) -0.0092(17) Se1 0.04093(17) 0.03856(17) 0.03777(16) -0.00458(11) 0.01259(12) 0.00308(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.379(3) . ? C1 C2 1.383(3) . ? C1 Se1 1.889(2) . ? C2 C3 1.385(4) . ? C2 C7 1.505(4) . ? C3 C4 1.383(4) . ? C3 H3 0.9300 . ? C4 C5 1.383(4) . ? C4 H4 0.9300 . ? C5 C6 1.381(3) . ? C5 H5 0.9300 . ? C6 C10 1.508(3) . ? C7 N1 1.483(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 N1 1.473(3) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 N1 1.484(3) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 N2 1.486(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 N2 1.486(3) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 N2 1.479(4) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? N1 Se1 2.183(2) . ? N2 Se1 2.184(2) . ? O1 H13 0.935(18) . ? O1 H14 0.919(19) . ? 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 C6 C1 C2 122.9(2) . . ? C6 C1 Se1 118.50(17) . . ? C2 C1 Se1 118.56(18) . . ? C1 C2 C3 117.8(2) . . ? C1 C2 C7 115.8(2) . . ? C3 C2 C7 126.3(2) . . ? C4 C3 C2 120.0(2) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C5 121.0(2) . . ? C3 C4 H4 119.5 . . ? C5 C4 H4 119.5 . . ? C6 C5 C4 119.7(2) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C1 C6 C5 118.4(2) . . ? C1 C6 C10 115.4(2) . . ? C5 C6 C10 126.1(2) . . ? N1 C7 C2 108.1(2) . . ? N1 C7 H7A 110.1 . . ? C2 C7 H7A 110.1 . . ? N1 C7 H7B 110.1 . . ? C2 C7 H7B 110.1 . . ? H7A C7 H7B 108.4 . . ? N1 C8 H8A 109.5 . . ? N1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N1 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N2 C10 C6 108.2(2) . . ? N2 C10 H10A 110.1 . . ? C6 C10 H10A 110.1 . . ? N2 C10 H10B 110.1 . . ? C6 C10 H10B 110.1 . . ? H10A C10 H10B 108.4 . . ? N2 C11 H11A 109.5 . . ? N2 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N2 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N2 C12 H12A 109.5 . . ? N2 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N2 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C8 N1 C7 111.8(2) . . ? C8 N1 C9 109.5(2) . . ? C7 N1 C9 112.2(2) . . ? C8 N1 Se1 106.99(16) . . ? C7 N1 Se1 105.89(15) . . ? C9 N1 Se1 110.25(17) . . ? C12 N2 C11 110.5(2) . . ? C12 N2 C10 111.7(2) . . ? C11 N2 C10 111.5(2) . . ? C12 N2 Se1 108.33(17) . . ? C11 N2 Se1 109.39(17) . . ? C10 N2 Se1 105.25(15) . . ? H13 O1 H14 102(2) . . ? C1 Se1 N1 80.41(9) . . ? C1 Se1 N2 81.04(9) . . ? N1 Se1 N2 161.31(8) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.9(4) . . . . ? Se1 C1 C2 C3 178.20(18) . . . . ? C6 C1 C2 C7 -178.1(2) . . . . ? Se1 C1 C2 C7 1.1(3) . . . . ? C1 C2 C3 C4 0.5(4) . . . . ? C7 C2 C3 C4 177.3(3) . . . . ? C2 C3 C4 C5 -0.5(4) . . . . ? C3 C4 C5 C6 0.9(4) . . . . ? C2 C1 C6 C5 1.3(4) . . . . ? Se1 C1 C6 C5 -177.83(18) . . . . ? C2 C1 C6 C10 -175.1(2) . . . . ? Se1 C1 C6 C10 5.8(3) . . . . ? C4 C5 C6 C1 -1.3(4) . . . . ? C4 C5 C6 C10 174.7(3) . . . . ? C1 C2 C7 N1 -25.8(3) . . . . ? C3 C2 C7 N1 157.4(2) . . . . ? C1 C6 C10 N2 -29.4(3) . . . . ? C5 C6 C10 N2 154.6(2) . . . . ? C2 C7 N1 C8 -82.0(3) . . . . ? C2 C7 N1 C9 154.5(2) . . . . ? C2 C7 N1 Se1 34.2(2) . . . . ? C6 C10 N2 C12 -82.3(3) . . . . ? C6 C10 N2 C11 153.6(2) . . . . ? C6 C10 N2 Se1 35.1(2) . . . . ? C6 C1 Se1 N1 -165.5(2) . . . . ? C2 C1 Se1 N1 15.36(19) . . . . ? C6 C1 Se1 N2 12.19(19) . . . . ? C2 C1 Se1 N2 -167.0(2) . . . . ? C8 N1 Se1 C1 91.41(19) . . . . ? C7 N1 Se1 C1 -27.99(16) . . . . ? C9 N1 Se1 C1 -149.58(19) . . . . ? C8 N1 Se1 N2 84.1(3) . . . . ? C7 N1 Se1 N2 -35.3(3) . . . . ? C9 N1 Se1 N2 -156.8(2) . . . . ? C12 N2 Se1 C1 92.82(18) . . . . ? C11 N2 Se1 C1 -146.7(2) . . . . ? C10 N2 Se1 C1 -26.83(16) . . . . ? C12 N2 Se1 N1 100.1(3) . . . . ? C11 N2 Se1 N1 -139.4(2) . . . . ? C10 N2 Se1 N1 -19.6(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.455 _refine_diff_density_min -0.230 _refine_diff_density_rms 0.052 _database_code_depnum_ccdc_archive 'CCDC 952119' ####################################################################### # # 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_196alb _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H10 Cl4 Sb, C12 H19 N2 Se' _chemical_formula_sum 'C24 H29 Cl4 N2 Sb Se' _chemical_formula_weight 688.00 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' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Sb Sb -0.5866 1.5461 '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 9.4870(7) _cell_length_b 12.6148(9) _cell_length_c 12.9073(9) _cell_angle_alpha 109.2860(10) _cell_angle_beta 101.6220(10) _cell_angle_gamma 104.8360(10) _cell_volume 1338.37(17) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3587 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 27.89 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.48 _exptl_crystal_size_min 0.47 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.707 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 2.806 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3232 _exptl_absorpt_correction_T_max 0.3522 _exptl_absorpt_process_details 'Bruker, 2001.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 11219 _diffrn_reflns_av_R_equivalents 0.0293 _diffrn_reflns_av_sigmaI/netI 0.0371 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4662 _reflns_number_gt 4346 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^ > 2\s(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^)+(0.0324P)^2^+0.2009P] 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 4662 _refine_ls_number_parameters 293 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0341 _refine_ls_R_factor_gt 0.0307 _refine_ls_wR_factor_ref 0.0754 _refine_ls_wR_factor_gt 0.0739 _refine_ls_goodness_of_fit_ref 1.177 _refine_ls_restrained_S_all 1.177 _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 C1 C 0.7204(4) 0.5286(3) -0.0545(3) 0.0284(7) Uani 1 1 d . . . C2 C 0.6918(4) 0.4818(3) -0.1720(3) 0.0346(8) Uani 1 1 d . . . C3 C 0.6163(4) 0.3584(3) -0.2316(3) 0.0455(10) Uani 1 1 d . . . H3 H 0.5934 0.3230 -0.3114 0.055 Uiso 1 1 calc R . . C4 C 0.5757(5) 0.2894(3) -0.1722(4) 0.0487(10) Uani 1 1 d . . . H4 H 0.5256 0.2071 -0.2128 0.058 Uiso 1 1 calc R . . C5 C 0.6072(4) 0.3389(3) -0.0540(4) 0.0432(9) Uani 1 1 d . . . H5 H 0.5797 0.2903 -0.0154 0.052 Uiso 1 1 calc R . . C6 C 0.6800(4) 0.4612(3) 0.0069(3) 0.0309(8) Uani 1 1 d . . . C7 C 0.7545(5) 0.5704(4) -0.2204(3) 0.0442(9) Uani 1 1 d . . . H7A H 0.8571 0.5736 -0.2225 0.053 Uiso 1 1 calc R . . H7B H 0.6897 0.5461 -0.2987 0.053 Uiso 1 1 calc R . . C8 C 0.6059(5) 0.7018(4) -0.1764(4) 0.0542(11) Uani 1 1 d . . . H8A H 0.5790 0.6979 -0.2537 0.081 Uiso 1 1 calc R . . H8B H 0.6098 0.7775 -0.1234 0.081 Uiso 1 1 calc R . . H8C H 0.5302 0.6381 -0.1715 0.081 Uiso 1 1 calc R . . C9 C 0.8781(5) 0.7880(4) -0.1498(4) 0.0608(12) Uani 1 1 d . . . H9A H 0.9748 0.7759 -0.1345 0.091 Uiso 1 1 calc R . . H9B H 0.8864 0.8626 -0.0923 0.091 Uiso 1 1 calc R . . H9C H 0.8509 0.7897 -0.2249 0.091 Uiso 1 1 calc R . . C10 C 0.7166(4) 0.5309(3) 0.1335(3) 0.0382(9) Uani 1 1 d . . . H10A H 0.6286 0.5506 0.1492 0.046 Uiso 1 1 calc R . . H10B H 0.7409 0.4835 0.1756 0.046 Uiso 1 1 calc R . . C11 C 0.9946(5) 0.6171(4) 0.1885(4) 0.0574(12) Uani 1 1 d . . . H11A H 1.0148 0.6000 0.2560 0.086 Uiso 1 1 calc R . . H11B H 1.0774 0.6859 0.1985 0.086 Uiso 1 1 calc R . . H11C H 0.9859 0.5494 0.1222 0.086 Uiso 1 1 calc R . . C12 C 0.8562(6) 0.7387(4) 0.2771(3) 0.0585(12) Uani 1 1 d . . . H12A H 0.8700 0.7141 0.3402 0.088 Uiso 1 1 calc R . . H12B H 0.7621 0.7550 0.2650 0.088 Uiso 1 1 calc R . . H12C H 0.9407 0.8098 0.2950 0.088 Uiso 1 1 calc R . . C13 C -0.0266(4) 0.7578(3) 0.5802(3) 0.0296(7) Uani 1 1 d . . . C14 C -0.1262(4) 0.8200(3) 0.5755(3) 0.0338(8) Uani 1 1 d . . . H14 H -0.0888 0.9032 0.6043 0.041 Uiso 1 1 calc R . . C15 C -0.2820(4) 0.7573(3) 0.5276(3) 0.0437(9) Uani 1 1 d . . . H15 H -0.3502 0.7985 0.5251 0.052 Uiso 1 1 calc R . . C16 C -0.3368(5) 0.6342(4) 0.4834(4) 0.0494(10) Uani 1 1 d . . . H16 H -0.4419 0.5924 0.4512 0.059 Uiso 1 1 calc R . . C17 C -0.2367(5) 0.5729(3) 0.4868(4) 0.0495(11) Uani 1 1 d . . . H17 H -0.2742 0.4896 0.4561 0.059 Uiso 1 1 calc R . . C18 C -0.0810(4) 0.6344(3) 0.5356(3) 0.0410(9) Uani 1 1 d . . . H18 H -0.0131 0.5930 0.5385 0.049 Uiso 1 1 calc R . . C19 C 0.4574(4) 0.9474(3) 0.7341(3) 0.0315(8) Uani 1 1 d . . . C20 C 0.5234(4) 0.9813(3) 0.8507(3) 0.0417(9) Uani 1 1 d . . . H20 H 0.4632 0.9634 0.8956 0.050 Uiso 1 1 calc R . . C21 C 0.6796(5) 1.0419(4) 0.9003(4) 0.0516(11) Uani 1 1 d . . . H21 H 0.7251 1.0655 0.9790 0.062 Uiso 1 1 calc R . . C22 C 0.7683(5) 1.0673(4) 0.8332(4) 0.0563(12) Uani 1 1 d . . . H22 H 0.8738 1.1070 0.8663 0.068 Uiso 1 1 calc R . . C23 C 0.7002(5) 1.0338(4) 0.7173(4) 0.0511(11) Uani 1 1 d . . . H23 H 0.7600 1.0518 0.6723 0.061 Uiso 1 1 calc R . . C24 C 0.5453(4) 0.9742(3) 0.6674(3) 0.0403(9) Uani 1 1 d . . . H24 H 0.4998 0.9521 0.5889 0.048 Uiso 1 1 calc R . . Cl1 Cl 0.16911(11) 0.99679(8) 0.81919(7) 0.0392(2) Uani 1 1 d . . . Cl2 Cl 0.22932(11) 0.72300(8) 0.76357(8) 0.0425(2) Uani 1 1 d . . . Cl3 Cl 0.26265(12) 0.71398(9) 0.49432(8) 0.0473(2) Uani 1 1 d . . . Cl4 Cl 0.20049(12) 0.98434(9) 0.55456(8) 0.0448(2) Uani 1 1 d . . . N1 N 0.7587(3) 0.6891(3) -0.1465(3) 0.0384(7) Uani 1 1 d . . . N2 N 0.8495(3) 0.6421(3) 0.1713(2) 0.0361(7) Uani 1 1 d . . . Sb2 Sb 0.21529(2) 0.854891(18) 0.657271(17) 0.02574(9) Uani 1 1 d . . . Se1 Se 0.81760(4) 0.69574(3) 0.02817(3) 0.03397(11) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0235(17) 0.0276(17) 0.0314(18) 0.0097(14) 0.0079(14) 0.0084(14) C2 0.0298(19) 0.040(2) 0.033(2) 0.0117(16) 0.0116(15) 0.0141(16) C3 0.042(2) 0.045(2) 0.035(2) -0.0009(18) 0.0088(18) 0.0168(19) C4 0.048(2) 0.031(2) 0.059(3) 0.0085(19) 0.017(2) 0.0129(18) C5 0.045(2) 0.036(2) 0.055(3) 0.0212(19) 0.0197(19) 0.0168(18) C6 0.0301(19) 0.0303(18) 0.0371(19) 0.0148(15) 0.0130(15) 0.0144(15) C7 0.046(2) 0.060(3) 0.031(2) 0.0202(19) 0.0161(18) 0.020(2) C8 0.046(3) 0.072(3) 0.068(3) 0.050(3) 0.023(2) 0.026(2) C9 0.054(3) 0.075(3) 0.066(3) 0.049(3) 0.025(2) 0.010(2) C10 0.044(2) 0.046(2) 0.038(2) 0.0256(18) 0.0197(17) 0.0188(18) C11 0.040(2) 0.081(3) 0.048(3) 0.028(2) 0.0016(19) 0.024(2) C12 0.071(3) 0.056(3) 0.033(2) 0.005(2) 0.015(2) 0.015(2) C13 0.0327(19) 0.0312(18) 0.0238(17) 0.0114(14) 0.0068(14) 0.0108(15) C14 0.037(2) 0.0332(18) 0.0327(19) 0.0125(15) 0.0085(16) 0.0167(16) C15 0.036(2) 0.050(2) 0.047(2) 0.0200(19) 0.0090(18) 0.0192(18) C16 0.032(2) 0.055(3) 0.049(2) 0.023(2) -0.0005(18) 0.0040(19) C17 0.052(3) 0.0293(19) 0.053(3) 0.0142(18) 0.004(2) 0.0030(18) C18 0.044(2) 0.0326(19) 0.045(2) 0.0166(17) 0.0065(18) 0.0146(17) C19 0.0315(19) 0.0281(17) 0.0328(19) 0.0097(15) 0.0088(15) 0.0115(15) C20 0.035(2) 0.049(2) 0.037(2) 0.0197(18) 0.0077(17) 0.0072(18) C21 0.042(2) 0.056(3) 0.045(2) 0.021(2) 0.0009(19) 0.007(2) C22 0.032(2) 0.049(2) 0.069(3) 0.014(2) 0.007(2) 0.0036(19) C23 0.042(2) 0.054(3) 0.055(3) 0.015(2) 0.028(2) 0.013(2) C24 0.046(2) 0.039(2) 0.038(2) 0.0126(17) 0.0204(18) 0.0160(18) Cl1 0.0449(5) 0.0374(5) 0.0332(5) 0.0079(4) 0.0152(4) 0.0174(4) Cl2 0.0443(5) 0.0432(5) 0.0485(6) 0.0301(4) 0.0100(4) 0.0168(4) Cl3 0.0537(6) 0.0447(5) 0.0391(5) 0.0061(4) 0.0202(5) 0.0200(5) Cl4 0.0530(6) 0.0485(5) 0.0473(6) 0.0340(5) 0.0165(5) 0.0206(5) N1 0.0345(17) 0.0471(18) 0.0407(18) 0.0285(15) 0.0135(14) 0.0098(14) N2 0.0373(17) 0.0414(17) 0.0277(15) 0.0132(13) 0.0096(13) 0.0117(14) Sb2 0.02975(14) 0.02595(13) 0.02390(13) 0.01137(10) 0.00862(10) 0.01158(10) Se1 0.0319(2) 0.03121(19) 0.0335(2) 0.01286(16) 0.00850(15) 0.00419(15) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.371(5) . ? C1 C6 1.378(5) . ? C1 Se1 1.886(3) . ? C2 C3 1.394(5) . ? C2 C7 1.506(5) . ? C3 C4 1.372(6) . ? C3 H3 0.9300 . ? C4 C5 1.379(6) . ? C4 H4 0.9300 . ? C5 C6 1.382(5) . ? C5 H5 0.9300 . ? C6 C10 1.494(5) . ? C7 N1 1.471(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 N1 1.487(5) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 N1 1.474(5) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 N2 1.479(5) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 N2 1.480(5) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 N2 1.477(5) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C18 1.377(5) . ? C13 C14 1.378(5) . ? C13 Sb2 2.143(3) . ? C14 C15 1.379(5) . ? C14 H14 0.9300 . ? C15 C16 1.374(6) . ? C15 H15 0.9300 . ? C16 C17 1.372(6) . ? C16 H16 0.9300 . ? C17 C18 1.377(5) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 C24 1.374(5) . ? C19 C20 1.377(5) . ? C19 Sb2 2.137(3) . ? C20 C21 1.381(5) . ? C20 H20 0.9300 . ? C21 C22 1.378(6) . ? C21 H21 0.9300 . ? C22 C23 1.374(6) . ? C22 H22 0.9300 . ? C23 C24 1.369(6) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? Cl1 Sb2 2.4623(9) . ? Cl2 Sb2 2.4932(8) . ? Cl3 Sb2 2.4710(9) . ? Cl4 Sb2 2.4323(8) . ? N1 Se1 2.178(3) . ? N2 Se1 2.160(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 C2 C1 C6 124.0(3) . . ? C2 C1 Se1 118.2(3) . . ? C6 C1 Se1 117.7(2) . . ? C1 C2 C3 117.2(3) . . ? C1 C2 C7 115.2(3) . . ? C3 C2 C7 127.5(3) . . ? C4 C3 C2 119.9(4) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C5 121.6(4) . . ? C3 C4 H4 119.2 . . ? C5 C4 H4 119.2 . . ? C4 C5 C6 119.6(4) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C1 C6 C5 117.7(3) . . ? C1 C6 C10 115.2(3) . . ? C5 C6 C10 127.1(3) . . ? N1 C7 C2 108.7(3) . . ? N1 C7 H7A 110.0 . . ? C2 C7 H7A 110.0 . . ? N1 C7 H7B 110.0 . . ? C2 C7 H7B 110.0 . . ? H7A C7 H7B 108.3 . . ? N1 C8 H8A 109.5 . . ? N1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N1 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N2 C10 C6 108.8(3) . . ? N2 C10 H10A 109.9 . . ? C6 C10 H10A 109.9 . . ? N2 C10 H10B 109.9 . . ? C6 C10 H10B 109.9 . . ? H10A C10 H10B 108.3 . . ? N2 C11 H11A 109.5 . . ? N2 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N2 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N2 C12 H12A 109.5 . . ? N2 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N2 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C18 C13 C14 120.7(3) . . ? C18 C13 Sb2 120.0(3) . . ? C14 C13 Sb2 119.4(2) . . ? C13 C14 C15 119.2(3) . . ? C13 C14 H14 120.4 . . ? C15 C14 H14 120.4 . . ? C16 C15 C14 120.2(4) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C17 C16 C15 120.2(4) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C16 C17 C18 120.2(4) . . ? C16 C17 H17 119.9 . . ? C18 C17 H17 119.9 . . ? C17 C18 C13 119.5(3) . . ? C17 C18 H18 120.3 . . ? C13 C18 H18 120.3 . . ? C24 C19 C20 120.7(3) . . ? C24 C19 Sb2 119.8(3) . . ? C20 C19 Sb2 119.5(3) . . ? C19 C20 C21 119.3(4) . . ? C19 C20 H20 120.3 . . ? C21 C20 H20 120.3 . . ? C22 C21 C20 120.1(4) . . ? C22 C21 H21 120.0 . . ? C20 C21 H21 120.0 . . ? C23 C22 C21 119.7(4) . . ? C23 C22 H22 120.1 . . ? C21 C22 H22 120.1 . . ? C24 C23 C22 120.7(4) . . ? C24 C23 H23 119.7 . . ? C22 C23 H23 119.7 . . ? C23 C24 C19 119.5(4) . . ? C23 C24 H24 120.3 . . ? C19 C24 H24 120.3 . . ? C7 N1 C9 112.6(3) . . ? C7 N1 C8 111.1(3) . . ? C9 N1 C8 110.6(3) . . ? C7 N1 Se1 104.8(2) . . ? C9 N1 Se1 108.2(2) . . ? C8 N1 Se1 109.2(2) . . ? C12 N2 C10 113.1(3) . . ? C12 N2 C11 109.9(3) . . ? C10 N2 C11 110.5(3) . . ? C12 N2 Se1 110.0(2) . . ? C10 N2 Se1 104.6(2) . . ? C11 N2 Se1 108.6(2) . . ? C19 Sb2 C13 178.48(11) . . ? C19 Sb2 Cl4 90.35(9) . . ? C13 Sb2 Cl4 90.91(9) . . ? C19 Sb2 Cl1 90.40(9) . . ? C13 Sb2 Cl1 90.44(9) . . ? Cl4 Sb2 Cl1 89.42(3) . . ? C19 Sb2 Cl3 89.37(9) . . ? C13 Sb2 Cl3 89.80(9) . . ? Cl4 Sb2 Cl3 90.12(4) . . ? Cl1 Sb2 Cl3 179.49(3) . . ? C19 Sb2 Cl2 89.81(9) . . ? C13 Sb2 Cl2 88.93(9) . . ? Cl4 Sb2 Cl2 179.53(3) . . ? Cl1 Sb2 Cl2 90.14(3) . . ? Cl3 Sb2 Cl2 90.32(3) . . ? C1 Se1 N2 81.02(13) . . ? C1 Se1 N1 81.06(13) . . ? N2 Se1 N1 161.95(11) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.5(5) . . . . ? Se1 C1 C2 C3 -178.4(3) . . . . ? C6 C1 C2 C7 -176.3(3) . . . . ? Se1 C1 C2 C7 4.9(4) . . . . ? C1 C2 C3 C4 -0.8(5) . . . . ? C7 C2 C3 C4 175.5(4) . . . . ? C2 C3 C4 C5 0.2(6) . . . . ? C3 C4 C5 C6 0.7(6) . . . . ? C2 C1 C6 C5 0.5(5) . . . . ? Se1 C1 C6 C5 179.3(3) . . . . ? C2 C1 C6 C10 -177.7(3) . . . . ? Se1 C1 C6 C10 1.1(4) . . . . ? C4 C5 C6 C1 -1.1(5) . . . . ? C4 C5 C6 C10 176.9(4) . . . . ? C1 C2 C7 N1 -29.4(4) . . . . ? C3 C2 C7 N1 154.2(3) . . . . ? C1 C6 C10 N2 -27.4(4) . . . . ? C5 C6 C10 N2 154.6(3) . . . . ? C18 C13 C14 C15 1.3(5) . . . . ? Sb2 C13 C14 C15 -178.9(3) . . . . ? C13 C14 C15 C16 -1.0(6) . . . . ? C14 C15 C16 C17 0.0(6) . . . . ? C15 C16 C17 C18 0.7(7) . . . . ? C16 C17 C18 C13 -0.5(6) . . . . ? C14 C13 C18 C17 -0.5(6) . . . . ? Sb2 C13 C18 C17 179.6(3) . . . . ? C24 C19 C20 C21 -0.5(5) . . . . ? Sb2 C19 C20 C21 -179.5(3) . . . . ? C19 C20 C21 C22 -0.4(6) . . . . ? C20 C21 C22 C23 1.0(7) . . . . ? C21 C22 C23 C24 -0.7(7) . . . . ? C22 C23 C24 C19 -0.2(6) . . . . ? C20 C19 C24 C23 0.8(5) . . . . ? Sb2 C19 C24 C23 179.8(3) . . . . ? C2 C7 N1 C9 153.0(3) . . . . ? C2 C7 N1 C8 -82.2(4) . . . . ? C2 C7 N1 Se1 35.7(3) . . . . ? C6 C10 N2 C12 156.0(3) . . . . ? C6 C10 N2 C11 -80.3(3) . . . . ? C6 C10 N2 Se1 36.3(3) . . . . ? C24 C19 Sb2 Cl4 -44.7(3) . . . . ? C20 C19 Sb2 Cl4 134.3(3) . . . . ? C24 C19 Sb2 Cl1 -134.1(3) . . . . ? C20 C19 Sb2 Cl1 44.9(3) . . . . ? C24 C19 Sb2 Cl2 135.8(3) . . . . ? C20 C19 Sb2 Cl2 -45.3(3) . . . . ? C18 C13 Sb2 Cl4 134.8(3) . . . . ? C14 C13 Sb2 Cl4 -45.0(3) . . . . ? C18 C13 Sb2 Cl1 -135.8(3) . . . . ? C14 C13 Sb2 Cl1 44.4(3) . . . . ? C18 C13 Sb2 Cl3 44.7(3) . . . . ? C14 C13 Sb2 Cl3 -135.2(3) . . . . ? C18 C13 Sb2 Cl2 -45.6(3) . . . . ? C14 C13 Sb2 Cl2 134.5(3) . . . . ? C2 C1 Se1 N2 -164.7(3) . . . . ? C6 C1 Se1 N2 16.4(3) . . . . ? C2 C1 Se1 N1 13.1(3) . . . . ? C6 C1 Se1 N1 -165.8(3) . . . . ? C12 N2 Se1 C1 -151.1(3) . . . . ? C10 N2 Se1 C1 -29.4(2) . . . . ? C11 N2 Se1 C1 88.5(3) . . . . ? C12 N2 Se1 N1 -158.1(3) . . . . ? C10 N2 Se1 N1 -36.4(5) . . . . ? C11 N2 Se1 N1 81.5(4) . . . . ? C7 N1 Se1 C1 -27.6(2) . . . . ? C9 N1 Se1 C1 -147.9(3) . . . . ? C8 N1 Se1 C1 91.6(3) . . . . ? C7 N1 Se1 N2 -20.6(5) . . . . ? C9 N1 Se1 N2 -141.0(4) . . . . ? C8 N1 Se1 N2 98.6(4) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.358 _refine_diff_density_min -0.859 _refine_diff_density_rms 0.111 _database_code_depnum_ccdc_archive 'CCDC 952120'