# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Anca Silvestru' _publ_contact_author_email ancas@chem.ubbcluj.ro loop_ _publ_author_name A.Pollnitz C.Silvestru J.-F.Carpentier A.Silvestru # Attachment '- Compound 8 - CCDC 811929.cif' data_494r _database_code_depnum_ccdc_archive 'CCDC 811929' #TrackingRef '- Compound 8 - CCDC 811929.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C38 H46 N2' _chemical_formula_sum 'C38 H46 N2' _chemical_formula_weight 530.77 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P-1 ' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.6487(10) _cell_length_b 11.7585(11) _cell_length_c 13.4318(12) _cell_angle_alpha 90.607(2) _cell_angle_beta 93.675(2) _cell_angle_gamma 106.769(2) _cell_volume 1606.3(3) _cell_formula_units_Z 2 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 6105 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 27.21 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.097 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.063 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9753 _exptl_absorpt_correction_T_max 0.9875 _exptl_absorpt_process_details 'Bruker, 2000.' _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 15517 _diffrn_reflns_av_R_equivalents 0.0557 _diffrn_reflns_av_sigmaI/netI 0.0601 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5617 _reflns_number_gt 4481 _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^)+(0.0380P)^2^+0.6600P] 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 5617 _refine_ls_number_parameters 377 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1026 _refine_ls_R_factor_gt 0.0799 _refine_ls_wR_factor_ref 0.1622 _refine_ls_wR_factor_gt 0.1532 _refine_ls_goodness_of_fit_ref 1.196 _refine_ls_restrained_S_all 1.196 _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 H2 H 0.672(3) 0.691(2) 0.1753(16) 0.059(9) Uiso 1 1 d D . . H1 H 0.941(2) 0.720(2) 0.2662(19) 0.062(9) Uiso 1 1 d D . . C1 C 0.8545(2) 0.7595(2) 0.43396(18) 0.0390(6) Uani 1 1 d . . . C2 C 0.7206(2) 0.7115(2) 0.40804(18) 0.0364(6) Uani 1 1 d . . . C3 C 0.6416(3) 0.6407(2) 0.4751(2) 0.0508(7) Uani 1 1 d . . . H3 H 0.5520 0.6094 0.4583 0.061 Uiso 1 1 calc R . . C4 C 0.6929(3) 0.6161(3) 0.5656(2) 0.0649(9) Uani 1 1 d . . . H4 H 0.6386 0.5688 0.6100 0.078 Uiso 1 1 calc R . . C5 C 0.8255(3) 0.6617(3) 0.5902(2) 0.0677(9) Uani 1 1 d . . . H5 H 0.8613 0.6440 0.6509 0.081 Uiso 1 1 calc R . . C6 C 0.9050(3) 0.7333(3) 0.5255(2) 0.0546(8) Uani 1 1 d . . . H6 H 0.9943 0.7647 0.5434 0.066 Uiso 1 1 calc R . . C7 C 0.8662(2) 0.9124(2) 0.30521(18) 0.0369(6) Uani 1 1 d . . . C8 C 0.7324(2) 0.8630(2) 0.27897(18) 0.0367(6) Uani 1 1 d . . . C9 C 0.6642(3) 0.9295(2) 0.2264(2) 0.0490(7) Uani 1 1 d . . . H9 H 0.5750 0.8967 0.2087 0.059 Uiso 1 1 calc R . . C10 C 0.7266(3) 1.0439(3) 0.1999(2) 0.0611(8) Uani 1 1 d . . . H10 H 0.6800 1.0880 0.1645 0.073 Uiso 1 1 calc R . . C11 C 0.8589(3) 1.0920(3) 0.2263(2) 0.0633(9) Uani 1 1 d . . . H11 H 0.9017 1.1692 0.2089 0.076 Uiso 1 1 calc R . . C12 C 0.9278(3) 1.0267(2) 0.2781(2) 0.0510(7) Uani 1 1 d . . . H12 H 1.0171 1.0599 0.2951 0.061 Uiso 1 1 calc R . . C13 C 0.9407(2) 0.8414(2) 0.36419(18) 0.0372(6) Uani 1 1 d . . . H13 H 1.0114 0.8978 0.4052 0.045 Uiso 1 1 calc R . . C14 C 0.6645(2) 0.7382(2) 0.30869(18) 0.0361(6) Uani 1 1 d . . . H14 H 0.5707 0.7295 0.3129 0.043 Uiso 1 1 calc R . . C15 C 1.1032(2) 0.8370(2) 0.24115(18) 0.0357(6) Uani 1 1 d . . . C16 C 1.0847(2) 0.8356(2) 0.13719(19) 0.0395(6) Uani 1 1 d . . . C17 C 1.1863(3) 0.9026(3) 0.0840(2) 0.0544(8) Uani 1 1 d . . . H17 H 1.1753 0.9021 0.0147 0.065 Uiso 1 1 calc R . . C18 C 1.3032(3) 0.9696(3) 0.1311(2) 0.0593(8) Uani 1 1 d . . . H18 H 1.3689 1.0162 0.0941 0.071 Uiso 1 1 calc R . . C19 C 1.3219(3) 0.9673(2) 0.2325(2) 0.0531(7) Uani 1 1 d . . . H19 H 1.4014 1.0119 0.2641 0.064 Uiso 1 1 calc R . . C20 C 1.2251(2) 0.9001(2) 0.2893(2) 0.0409(6) Uani 1 1 d . . . C21 C 0.9599(3) 0.7615(2) 0.07929(19) 0.0476(7) Uani 1 1 d . . . H21 H 0.9020 0.7156 0.1277 0.057 Uiso 1 1 calc R . . C22 C 0.9898(3) 0.6732(3) 0.0073(3) 0.0738(10) Uani 1 1 d . . . H22A H 1.0490 0.7156 -0.0397 0.111 Uiso 1 1 calc R . . H22B H 0.9096 0.6270 -0.0277 0.111 Uiso 1 1 calc R . . H22C H 1.0295 0.6215 0.0441 0.111 Uiso 1 1 calc R . . C23 C 0.8864(3) 0.8377(3) 0.0244(3) 0.0723(10) Uani 1 1 d . . . H23A H 0.9387 0.8802 -0.0264 0.108 Uiso 1 1 calc R . . H23B H 0.8693 0.8933 0.0707 0.108 Uiso 1 1 calc R . . H23C H 0.8046 0.7879 -0.0058 0.108 Uiso 1 1 calc R . . C24 C 1.2565(3) 0.8932(3) 0.4004(2) 0.0525(8) Uani 1 1 d . . . H24 H 1.1803 0.8372 0.4276 0.063 Uiso 1 1 calc R . . C25 C 1.2807(4) 1.0124(3) 0.4553(3) 0.0899(13) Uani 1 1 d . . . H25A H 1.3569 1.0684 0.4316 0.135 Uiso 1 1 calc R . . H25B H 1.2951 1.0027 0.5256 0.135 Uiso 1 1 calc R . . H25C H 1.2056 1.0412 0.4433 0.135 Uiso 1 1 calc R . . C26 C 1.3748(3) 0.8454(3) 0.4205(2) 0.0745(10) Uani 1 1 d . . . H26A H 1.3564 0.7679 0.3894 0.112 Uiso 1 1 calc R . . H26B H 1.3913 0.8402 0.4912 0.112 Uiso 1 1 calc R . . H26C H 1.4507 0.8981 0.3936 0.112 Uiso 1 1 calc R . . C27 C 0.5892(2) 0.5364(2) 0.22643(18) 0.0381(6) Uani 1 1 d . . . C28 C 0.4596(3) 0.5155(2) 0.18441(18) 0.0426(6) Uani 1 1 d . . . C29 C 0.3803(3) 0.3991(2) 0.1777(2) 0.0549(8) Uani 1 1 d . . . H29 H 0.2950 0.3834 0.1491 0.066 Uiso 1 1 calc R . . C30 C 0.4225(3) 0.3070(3) 0.2115(2) 0.0638(9) Uani 1 1 d . . . H30 H 0.3665 0.2298 0.2064 0.077 Uiso 1 1 calc R . . C31 C 0.5483(3) 0.3290(2) 0.2534(2) 0.0603(8) Uani 1 1 d . . . H31 H 0.5767 0.2659 0.2770 0.072 Uiso 1 1 calc R . . C32 C 0.6344(3) 0.4428(2) 0.2613(2) 0.0458(7) Uani 1 1 d . . . C33 C 0.4067(3) 0.6136(3) 0.1451(2) 0.0524(7) Uani 1 1 d . . . H33 H 0.4700 0.6896 0.1667 0.063 Uiso 1 1 calc R . . C34 C 0.3909(5) 0.6101(4) 0.0322(3) 0.1049(15) Uani 1 1 d . . . H34A H 0.4756 0.6242 0.0058 0.157 Uiso 1 1 calc R . . H34B H 0.3518 0.6704 0.0103 0.157 Uiso 1 1 calc R . . H34C H 0.3354 0.5335 0.0089 0.157 Uiso 1 1 calc R . . C35 C 0.2759(4) 0.6090(3) 0.1869(3) 0.0864(11) Uani 1 1 d . . . H35A H 0.2489 0.6764 0.1652 0.130 Uiso 1 1 calc R . . H35B H 0.2856 0.6104 0.2585 0.130 Uiso 1 1 calc R . . H35C H 0.2107 0.5372 0.1634 0.130 Uiso 1 1 calc R . . C36 C 0.7753(3) 0.4621(3) 0.3014(2) 0.0550(8) Uani 1 1 d . . . H36 H 0.8103 0.5460 0.3226 0.066 Uiso 1 1 calc R . . C37 C 0.8576(3) 0.4402(3) 0.2196(3) 0.0835(11) Uani 1 1 d . . . H37A H 0.8253 0.3588 0.1964 0.125 Uiso 1 1 calc R . . H37B H 0.9475 0.4566 0.2452 0.125 Uiso 1 1 calc R . . H37C H 0.8524 0.4914 0.1652 0.125 Uiso 1 1 calc R . . C38 C 0.7901(4) 0.3886(4) 0.3916(3) 0.0908(12) Uani 1 1 d . . . H38A H 0.7683 0.3063 0.3713 0.136 Uiso 1 1 calc R . . H38B H 0.7321 0.3985 0.4407 0.136 Uiso 1 1 calc R . . H38C H 0.8793 0.4147 0.4197 0.136 Uiso 1 1 calc R . . N1 N 1.0028(2) 0.77120(18) 0.30084(16) 0.0388(5) Uani 1 1 d D . . N2 N 0.6802(2) 0.65451(18) 0.22875(15) 0.0370(5) Uani 1 1 d 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 0.0399(15) 0.0464(15) 0.0325(14) -0.0091(11) 0.0016(11) 0.0162(12) C2 0.0344(14) 0.0416(14) 0.0339(14) -0.0083(11) 0.0011(11) 0.0128(11) C3 0.0415(16) 0.0593(18) 0.0460(17) -0.0026(13) 0.0078(13) 0.0049(13) C4 0.069(2) 0.079(2) 0.0402(18) 0.0065(15) 0.0107(16) 0.0097(18) C5 0.074(2) 0.088(2) 0.0400(18) 0.0082(16) 0.0003(16) 0.023(2) C6 0.0492(18) 0.070(2) 0.0436(17) -0.0043(14) -0.0034(14) 0.0175(15) C7 0.0373(15) 0.0357(14) 0.0375(14) -0.0115(11) 0.0067(11) 0.0099(11) C8 0.0397(15) 0.0386(14) 0.0360(14) -0.0080(11) 0.0036(11) 0.0181(12) C9 0.0465(17) 0.0497(17) 0.0538(18) -0.0043(13) -0.0004(14) 0.0200(14) C10 0.071(2) 0.0519(18) 0.069(2) 0.0059(15) 0.0061(17) 0.0322(17) C11 0.078(2) 0.0398(16) 0.074(2) 0.0045(15) 0.0196(18) 0.0176(16) C12 0.0479(17) 0.0426(16) 0.0604(19) -0.0086(13) 0.0073(14) 0.0094(13) C13 0.0290(13) 0.0420(14) 0.0379(14) -0.0142(11) -0.0012(11) 0.0072(11) C14 0.0267(13) 0.0437(14) 0.0389(14) -0.0068(11) 0.0015(11) 0.0119(11) C15 0.0302(14) 0.0346(13) 0.0437(15) -0.0062(11) 0.0036(11) 0.0117(11) C16 0.0384(15) 0.0423(14) 0.0392(15) -0.0040(11) 0.0025(12) 0.0141(12) C17 0.0534(19) 0.0597(18) 0.0478(17) 0.0056(14) 0.0086(14) 0.0115(15) C18 0.0448(18) 0.0563(18) 0.072(2) 0.0068(16) 0.0170(16) 0.0047(14) C19 0.0341(16) 0.0526(17) 0.067(2) -0.0082(15) 0.0012(14) 0.0043(13) C20 0.0306(14) 0.0440(15) 0.0499(16) -0.0121(12) 0.0000(12) 0.0148(12) C21 0.0452(16) 0.0571(17) 0.0372(15) -0.0042(13) -0.0009(12) 0.0107(13) C22 0.078(2) 0.065(2) 0.075(2) -0.0231(17) -0.0133(19) 0.0218(18) C23 0.064(2) 0.085(2) 0.072(2) -0.0163(18) -0.0190(18) 0.0346(19) C24 0.0282(14) 0.076(2) 0.0494(17) -0.0190(14) -0.0054(12) 0.0120(14) C25 0.072(2) 0.111(3) 0.081(3) -0.055(2) -0.018(2) 0.025(2) C26 0.051(2) 0.110(3) 0.064(2) -0.0027(19) -0.0052(16) 0.0287(19) C27 0.0430(16) 0.0392(14) 0.0318(14) -0.0078(11) 0.0033(11) 0.0116(12) C28 0.0435(16) 0.0483(16) 0.0345(14) -0.0084(12) -0.0002(12) 0.0122(13) C29 0.0446(17) 0.0535(18) 0.0578(19) -0.0165(14) -0.0035(14) 0.0024(14) C30 0.064(2) 0.0411(17) 0.079(2) -0.0112(15) 0.0039(18) 0.0034(15) C31 0.073(2) 0.0423(17) 0.069(2) -0.0003(14) 0.0068(17) 0.0211(16) C32 0.0549(18) 0.0404(15) 0.0445(16) -0.0061(12) 0.0046(13) 0.0176(13) C33 0.0447(17) 0.0554(17) 0.0539(18) -0.0110(14) -0.0151(14) 0.0140(14) C34 0.147(4) 0.141(4) 0.055(2) 0.014(2) 0.004(2) 0.086(3) C35 0.073(2) 0.092(3) 0.105(3) -0.018(2) 0.005(2) 0.043(2) C36 0.0565(19) 0.0488(16) 0.066(2) 0.0018(14) -0.0030(15) 0.0272(14) C37 0.065(2) 0.095(3) 0.104(3) 0.008(2) 0.017(2) 0.042(2) C38 0.094(3) 0.103(3) 0.086(3) 0.015(2) -0.011(2) 0.048(2) N1 0.0313(12) 0.0427(12) 0.0400(12) -0.0115(10) 0.0024(10) 0.0076(10) N2 0.0400(13) 0.0394(12) 0.0319(12) -0.0024(10) 0.0020(10) 0.0121(10) _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 1.383(4) . ? C1 C2 1.393(3) . ? C1 C13 1.506(3) . ? C2 C3 1.386(3) . ? C2 C14 1.500(3) . ? C3 C4 1.369(4) . ? C3 H3 0.9300 . ? C4 C5 1.375(4) . ? C4 H4 0.9300 . ? C5 C6 1.371(4) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C12 1.378(4) . ? C7 C8 1.395(3) . ? C7 C13 1.507(3) . ? C8 C9 1.382(4) . ? C8 C14 1.507(3) . ? C9 C10 1.379(4) . ? C9 H9 0.9300 . ? C10 C11 1.379(4) . ? C10 H10 0.9300 . ? C11 C12 1.372(4) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 N1 1.489(3) . ? C13 H13 0.9800 . ? C14 N2 1.498(3) . ? C14 H14 0.9800 . ? C15 C16 1.397(3) . ? C15 C20 1.407(3) . ? C15 N1 1.425(3) . ? C16 C17 1.386(4) . ? C16 C21 1.521(3) . ? C17 C18 1.376(4) . ? C17 H17 0.9300 . ? C18 C19 1.366(4) . ? C18 H18 0.9300 . ? C19 C20 1.384(4) . ? C19 H19 0.9300 . ? C20 C24 1.516(4) . ? C21 C23 1.518(4) . ? C21 C22 1.523(4) . ? C21 H21 0.9800 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 C25 1.523(4) . ? C24 C26 1.531(4) . ? C24 H24 0.9800 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 C32 1.396(4) . ? C27 C28 1.409(4) . ? C27 N2 1.445(3) . ? C28 C29 1.383(4) . ? C28 C33 1.509(4) . ? C29 C30 1.359(4) . ? C29 H29 0.9300 . ? C30 C31 1.371(4) . ? C30 H30 0.9300 . ? C31 C32 1.385(4) . ? C31 H31 0.9300 . ? C32 C36 1.513(4) . ? C33 C34 1.513(4) . ? C33 C35 1.522(4) . ? C33 H33 0.9800 . ? C34 H34A 0.9600 . ? C34 H34B 0.9600 . ? C34 H34C 0.9600 . ? C35 H35A 0.9600 . ? C35 H35B 0.9600 . ? C35 H35C 0.9600 . ? C36 C37 1.514(4) . ? C36 C38 1.522(4) . ? C36 H36 0.9800 . ? C37 H37A 0.9600 . ? C37 H37B 0.9600 . ? C37 H37C 0.9600 . ? C38 H38A 0.9600 . ? C38 H38B 0.9600 . ? C38 H38C 0.9600 . ? N1 H1 0.858(17) . ? N2 H2 0.850(17) . ? 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 118.8(2) . . ? C6 C1 C13 121.2(2) . . ? C2 C1 C13 120.0(2) . . ? C3 C2 C1 119.2(2) . . ? C3 C2 C14 121.3(2) . . ? C1 C2 C14 119.5(2) . . ? C4 C3 C2 121.2(3) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? C3 C4 C5 119.4(3) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? C6 C5 C4 120.2(3) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C5 C6 C1 121.1(3) . . ? C5 C6 H6 119.5 . . ? C1 C6 H6 119.5 . . ? C12 C7 C8 119.3(2) . . ? C12 C7 C13 121.0(2) . . ? C8 C7 C13 119.7(2) . . ? C9 C8 C7 119.4(2) . . ? C9 C8 C14 121.2(2) . . ? C7 C8 C14 119.5(2) . . ? C10 C9 C8 120.9(3) . . ? C10 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? C9 C10 C11 119.3(3) . . ? C9 C10 H10 120.4 . . ? C11 C10 H10 120.4 . . ? C12 C11 C10 120.4(3) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C11 C12 C7 120.8(3) . . ? C11 C12 H12 119.6 . . ? C7 C12 H12 119.6 . . ? N1 C13 C1 109.11(19) . . ? N1 C13 C7 113.6(2) . . ? C1 C13 C7 111.6(2) . . ? N1 C13 H13 107.4 . . ? C1 C13 H13 107.4 . . ? C7 C13 H13 107.4 . . ? N2 C14 C2 110.93(19) . . ? N2 C14 C8 107.88(19) . . ? C2 C14 C8 111.19(19) . . ? N2 C14 H14 108.9 . . ? C2 C14 H14 108.9 . . ? C8 C14 H14 108.9 . . ? C16 C15 C20 120.2(2) . . ? C16 C15 N1 121.6(2) . . ? C20 C15 N1 118.2(2) . . ? C17 C16 C15 118.4(2) . . ? C17 C16 C21 118.3(2) . . ? C15 C16 C21 123.2(2) . . ? C18 C17 C16 121.6(3) . . ? C18 C17 H17 119.2 . . ? C16 C17 H17 119.2 . . ? C19 C18 C17 119.5(3) . . ? C19 C18 H18 120.3 . . ? C17 C18 H18 120.3 . . ? C18 C19 C20 121.4(3) . . ? C18 C19 H19 119.3 . . ? C20 C19 H19 119.3 . . ? C19 C20 C15 118.7(2) . . ? C19 C20 C24 118.6(2) . . ? C15 C20 C24 122.6(2) . . ? C23 C21 C16 112.3(2) . . ? C23 C21 C22 110.7(2) . . ? C16 C21 C22 111.0(2) . . ? C23 C21 H21 107.5 . . ? C16 C21 H21 107.5 . . ? C22 C21 H21 107.5 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C20 C24 C25 112.5(3) . . ? C20 C24 C26 111.1(2) . . ? C25 C24 C26 109.9(3) . . ? C20 C24 H24 107.7 . . ? C25 C24 H24 107.7 . . ? C26 C24 H24 107.7 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C24 C26 H26A 109.5 . . ? C24 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C24 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C32 C27 C28 120.8(2) . . ? C32 C27 N2 118.7(2) . . ? C28 C27 N2 120.4(2) . . ? C29 C28 C27 117.6(3) . . ? C29 C28 C33 119.7(2) . . ? C27 C28 C33 122.7(2) . . ? C30 C29 C28 122.4(3) . . ? C30 C29 H29 118.8 . . ? C28 C29 H29 118.8 . . ? C29 C30 C31 119.3(3) . . ? C29 C30 H30 120.4 . . ? C31 C30 H30 120.4 . . ? C30 C31 C32 121.8(3) . . ? C30 C31 H31 119.1 . . ? C32 C31 H31 119.1 . . ? C31 C32 C27 118.1(3) . . ? C31 C32 C36 120.0(3) . . ? C27 C32 C36 121.8(2) . . ? C28 C33 C34 112.0(3) . . ? C28 C33 C35 111.6(3) . . ? C34 C33 C35 109.4(3) . . ? C28 C33 H33 107.9 . . ? C34 C33 H33 107.9 . . ? C35 C33 H33 107.9 . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C33 C35 H35A 109.5 . . ? C33 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C33 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C32 C36 C37 110.4(3) . . ? C32 C36 C38 114.0(3) . . ? C37 C36 C38 110.4(3) . . ? C32 C36 H36 107.2 . . ? C37 C36 H36 107.2 . . ? C38 C36 H36 107.2 . . ? C36 C37 H37A 109.5 . . ? C36 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C36 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C36 C38 H38A 109.5 . . ? C36 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C36 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C15 N1 C13 116.58(19) . . ? C15 N1 H1 112(2) . . ? C13 N1 H1 108(2) . . ? C27 N2 C14 115.94(19) . . ? C27 N2 H2 112(2) . . ? C14 N2 H2 103(2) . . ? 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 1.1(4) . . . . ? C13 C1 C2 C3 -177.0(2) . . . . ? C6 C1 C2 C14 -179.5(2) . . . . ? C13 C1 C2 C14 2.5(3) . . . . ? C1 C2 C3 C4 -0.8(4) . . . . ? C14 C2 C3 C4 179.7(3) . . . . ? C2 C3 C4 C5 -0.4(5) . . . . ? C3 C4 C5 C6 1.3(5) . . . . ? C4 C5 C6 C1 -1.0(5) . . . . ? C2 C1 C6 C5 -0.2(4) . . . . ? C13 C1 C6 C5 177.9(3) . . . . ? C12 C7 C8 C9 -0.1(3) . . . . ? C13 C7 C8 C9 178.8(2) . . . . ? C12 C7 C8 C14 -179.9(2) . . . . ? C13 C7 C8 C14 -1.0(3) . . . . ? C7 C8 C9 C10 -0.1(4) . . . . ? C14 C8 C9 C10 179.7(2) . . . . ? C8 C9 C10 C11 0.0(4) . . . . ? C9 C10 C11 C12 0.3(5) . . . . ? C10 C11 C12 C7 -0.5(4) . . . . ? C8 C7 C12 C11 0.4(4) . . . . ? C13 C7 C12 C11 -178.5(2) . . . . ? C6 C1 C13 N1 87.1(3) . . . . ? C2 C1 C13 N1 -94.9(3) . . . . ? C6 C1 C13 C7 -146.6(2) . . . . ? C2 C1 C13 C7 31.4(3) . . . . ? C12 C7 C13 N1 -89.4(3) . . . . ? C8 C7 C13 N1 91.7(3) . . . . ? C12 C7 C13 C1 146.8(2) . . . . ? C8 C7 C13 C1 -32.1(3) . . . . ? C3 C2 C14 N2 -95.9(3) . . . . ? C1 C2 C14 N2 84.6(3) . . . . ? C3 C2 C14 C8 144.0(2) . . . . ? C1 C2 C14 C8 -35.4(3) . . . . ? C9 C8 C14 N2 93.0(3) . . . . ? C7 C8 C14 N2 -87.2(2) . . . . ? C9 C8 C14 C2 -145.2(2) . . . . ? C7 C8 C14 C2 34.6(3) . . . . ? C20 C15 C16 C17 -3.4(4) . . . . ? N1 C15 C16 C17 179.5(2) . . . . ? C20 C15 C16 C21 174.8(2) . . . . ? N1 C15 C16 C21 -2.3(4) . . . . ? C15 C16 C17 C18 -0.2(4) . . . . ? C21 C16 C17 C18 -178.5(3) . . . . ? C16 C17 C18 C19 2.4(5) . . . . ? C17 C18 C19 C20 -0.9(5) . . . . ? C18 C19 C20 C15 -2.7(4) . . . . ? C18 C19 C20 C24 174.8(3) . . . . ? C16 C15 C20 C19 4.8(4) . . . . ? N1 C15 C20 C19 -178.0(2) . . . . ? C16 C15 C20 C24 -172.6(2) . . . . ? N1 C15 C20 C24 4.6(3) . . . . ? C17 C16 C21 C23 -66.2(3) . . . . ? C15 C16 C21 C23 115.6(3) . . . . ? C17 C16 C21 C22 58.3(3) . . . . ? C15 C16 C21 C22 -119.9(3) . . . . ? C19 C20 C24 C25 66.2(3) . . . . ? C15 C20 C24 C25 -116.4(3) . . . . ? C19 C20 C24 C26 -57.6(3) . . . . ? C15 C20 C24 C26 119.8(3) . . . . ? C32 C27 C28 C29 -1.0(4) . . . . ? N2 C27 C28 C29 175.3(2) . . . . ? C32 C27 C28 C33 -179.5(2) . . . . ? N2 C27 C28 C33 -3.2(4) . . . . ? C27 C28 C29 C30 1.2(4) . . . . ? C33 C28 C29 C30 179.8(3) . . . . ? C28 C29 C30 C31 -0.4(5) . . . . ? C29 C30 C31 C32 -0.6(5) . . . . ? C30 C31 C32 C27 0.8(4) . . . . ? C30 C31 C32 C36 -175.8(3) . . . . ? C28 C27 C32 C31 0.0(4) . . . . ? N2 C27 C32 C31 -176.3(2) . . . . ? C28 C27 C32 C36 176.5(2) . . . . ? N2 C27 C32 C36 0.2(4) . . . . ? C29 C28 C33 C34 -71.3(4) . . . . ? C27 C28 C33 C34 107.2(3) . . . . ? C29 C28 C33 C35 51.8(3) . . . . ? C27 C28 C33 C35 -129.7(3) . . . . ? C31 C32 C36 C37 82.6(3) . . . . ? C27 C32 C36 C37 -93.9(3) . . . . ? C31 C32 C36 C38 -42.3(4) . . . . ? C27 C32 C36 C38 141.2(3) . . . . ? C16 C15 N1 C13 -111.4(3) . . . . ? C20 C15 N1 C13 71.5(3) . . . . ? C1 C13 N1 C15 -170.6(2) . . . . ? C7 C13 N1 C15 64.2(3) . . . . ? C32 C27 N2 C14 -105.2(3) . . . . ? C28 C27 N2 C14 78.5(3) . . . . ? C2 C14 N2 C27 77.0(3) . . . . ? C8 C14 N2 C27 -161.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.203 _refine_diff_density_min -0.207 _refine_diff_density_rms 0.036 # Attachment '- Compound 11 - CCDC 811930.cif' data_549r _database_code_depnum_ccdc_archive 'CCDC 811930' #TrackingRef '- Compound 11 - CCDC 811930.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H24 N2 Se2 Zn' _chemical_formula_sum 'C28 H24 N2 Se2 Zn' _chemical_formula_weight 611.78 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' Zn Zn 0.2839 1.4301 '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 Monoclinic _symmetry_space_group_name_H-M 'P2(1)/n ' _symmetry_space_group_name_Hall '-P 2yn' 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 13.398(5) _cell_length_b 14.424(6) _cell_length_c 13.532(5) _cell_angle_alpha 90.00 _cell_angle_beta 110.608(7) _cell_angle_gamma 90.00 _cell_volume 2447.7(17) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 3579 _cell_measurement_theta_min 2.15 _cell_measurement_theta_max 23.62 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.660 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1216 _exptl_absorpt_coefficient_mu 3.997 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2350 _exptl_absorpt_correction_T_max 0.4874 _exptl_absorpt_process_details 'Bruker, 2000.' _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 11492 _diffrn_reflns_av_R_equivalents 0.0953 _diffrn_reflns_av_sigmaI/netI 0.1416 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4214 _reflns_number_gt 3246 _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^)+(0.0000P)^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_number_reflns 4214 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0768 _refine_ls_R_factor_gt 0.0584 _refine_ls_wR_factor_ref 0.1604 _refine_ls_wR_factor_gt 0.1490 _refine_ls_goodness_of_fit_ref 0.978 _refine_ls_restrained_S_all 0.978 _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 0.7749(5) 0.1767(4) 0.3917(4) 0.0324(13) Uani 1 1 d . . . C2 C 0.6637(5) 0.1932(4) 0.3606(4) 0.0347(14) Uani 1 1 d . . . C3 C 0.6009(5) 0.1816(4) 0.2534(4) 0.0400(15) Uani 1 1 d . . . H3 H 0.5276 0.1907 0.2326 0.048 Uiso 1 1 calc R . . C4 C 0.6429(6) 0.1576(4) 0.1789(5) 0.0458(16) Uani 1 1 d . . . H4 H 0.5996 0.1531 0.1082 0.055 Uiso 1 1 calc R . . C5 C 0.7504(6) 0.1402(4) 0.2101(5) 0.0500(18) Uani 1 1 d . . . H5 H 0.7802 0.1219 0.1606 0.060 Uiso 1 1 calc R . . C6 C 0.8143(6) 0.1497(4) 0.3148(5) 0.0454(15) Uani 1 1 d . . . H6 H 0.8868 0.1374 0.3343 0.054 Uiso 1 1 calc R . . C7 C 0.6025(5) 0.2242(4) 0.4238(4) 0.0357(13) Uani 1 1 d . . . H7 H 0.5298 0.2306 0.3866 0.043 Uiso 1 1 calc R . . C8 C 0.5479(5) 0.2765(4) 0.5617(4) 0.0406(14) Uani 1 1 d . . . H8A H 0.4863 0.2963 0.5025 0.049 Uiso 1 1 calc R . . H8B H 0.5743 0.3297 0.6074 0.049 Uiso 1 1 calc R . . C9 C 0.5144(5) 0.2023(4) 0.6221(4) 0.0367(14) Uani 1 1 d . . . C10 C 0.4920(6) 0.1146(5) 0.5850(5) 0.060(2) Uani 1 1 d . . . H10 H 0.5017 0.0979 0.5226 0.072 Uiso 1 1 calc R . . C11 C 0.4544(7) 0.0488(6) 0.6400(7) 0.079(2) Uani 1 1 d . . . H11 H 0.4404 -0.0114 0.6143 0.095 Uiso 1 1 calc R . . C12 C 0.4384(6) 0.0723(6) 0.7303(6) 0.068(2) Uani 1 1 d . . . H12 H 0.4123 0.0293 0.7663 0.082 Uiso 1 1 calc R . . C13 C 0.4618(7) 0.1613(6) 0.7672(6) 0.069(2) Uani 1 1 d . . . H13 H 0.4534 0.1782 0.8302 0.083 Uiso 1 1 calc R . . C14 C 0.4971(6) 0.2254(5) 0.7128(5) 0.0522(17) Uani 1 1 d . . . H14 H 0.5096 0.2859 0.7379 0.063 Uiso 1 1 calc R . . C15 C 0.7579(6) 0.2923(4) 0.8565(4) 0.0432(16) Uani 1 1 d . . . C16 C 0.7517(5) 0.3862(4) 0.8251(4) 0.0383(14) Uani 1 1 d . . . C17 C 0.7125(6) 0.4500(5) 0.8816(5) 0.063(2) Uani 1 1 d . . . H17 H 0.7100 0.5122 0.8630 0.075 Uiso 1 1 calc R . . C18 C 0.6781(7) 0.4260(5) 0.9618(5) 0.070(2) Uani 1 1 d . . . H18 H 0.6520 0.4703 0.9965 0.084 Uiso 1 1 calc R . . C19 C 0.6836(7) 0.3328(6) 0.9897(6) 0.068(2) Uani 1 1 d . . . H19 H 0.6590 0.3137 1.0426 0.082 Uiso 1 1 calc R . . C20 C 0.7252(6) 0.2687(5) 0.9397(5) 0.0543(18) Uani 1 1 d . . . H20 H 0.7315 0.2074 0.9624 0.065 Uiso 1 1 calc R . . C21 C 0.7833(5) 0.4288(4) 0.7432(4) 0.0407(14) Uani 1 1 d . . . H21 H 0.7952 0.4924 0.7495 0.049 Uiso 1 1 calc R . . C22 C 0.8238(5) 0.4543(5) 0.5908(4) 0.0495(17) Uani 1 1 d . . . H22A H 0.8911 0.4356 0.5852 0.059 Uiso 1 1 calc R . . H22B H 0.8320 0.5168 0.6189 0.059 Uiso 1 1 calc R . . C23 C 0.7379(5) 0.4531(4) 0.4828(4) 0.0366(14) Uani 1 1 d . . . C24 C 0.7570(6) 0.4160(4) 0.3965(5) 0.0463(16) Uani 1 1 d . . . H24 H 0.8241 0.3924 0.4050 0.056 Uiso 1 1 calc R . . C25 C 0.6780(7) 0.4138(5) 0.2984(5) 0.063(2) Uani 1 1 d . . . H25 H 0.6926 0.3892 0.2414 0.076 Uiso 1 1 calc R . . C26 C 0.5787(7) 0.4472(5) 0.2840(5) 0.0580(19) Uani 1 1 d . . . H26 H 0.5251 0.4441 0.2180 0.070 Uiso 1 1 calc R . . C27 C 0.5585(5) 0.4860(5) 0.3693(5) 0.0523(17) Uani 1 1 d . . . H27 H 0.4913 0.5099 0.3599 0.063 Uiso 1 1 calc R . . C28 C 0.6373(5) 0.4893(5) 0.4673(4) 0.0447(16) Uani 1 1 d . . . H28 H 0.6232 0.5158 0.5236 0.054 Uiso 1 1 calc R . . N1 N 0.6313(4) 0.2444(3) 0.5223(3) 0.0297(11) Uani 1 1 d . . . N2 N 0.7968(4) 0.3908(3) 0.6641(3) 0.0360(11) Uani 1 1 d . . . Se2 Se 0.81092(5) 0.19217(4) 0.79714(4) 0.0410(2) Uani 1 1 d . . . Se1 Se 0.88145(5) 0.19066(5) 0.52862(4) 0.0440(2) Uani 1 1 d . . . Zn1 Zn 0.78212(6) 0.25164(5) 0.62636(5) 0.0362(2) 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 0.045(4) 0.023(3) 0.032(3) 0.002(2) 0.016(3) 0.001(3) C2 0.050(4) 0.022(3) 0.033(3) -0.005(2) 0.016(3) -0.005(3) C3 0.043(4) 0.042(4) 0.035(3) -0.003(3) 0.014(3) -0.003(3) C4 0.064(5) 0.040(4) 0.035(3) -0.003(3) 0.020(3) -0.002(3) C5 0.082(6) 0.036(4) 0.047(4) -0.009(3) 0.043(4) -0.009(4) C6 0.057(4) 0.037(4) 0.049(3) 0.002(3) 0.027(3) 0.003(3) C7 0.034(4) 0.038(3) 0.038(3) 0.001(3) 0.016(3) 0.001(3) C8 0.049(4) 0.039(3) 0.039(3) -0.002(3) 0.021(3) -0.001(3) C9 0.031(3) 0.040(4) 0.040(3) -0.001(3) 0.014(3) -0.003(3) C10 0.085(6) 0.048(4) 0.066(4) -0.007(3) 0.050(4) -0.011(4) C11 0.102(7) 0.049(5) 0.108(6) -0.004(4) 0.064(6) -0.005(5) C12 0.079(6) 0.055(5) 0.095(6) 0.018(4) 0.061(5) 0.003(4) C13 0.095(6) 0.067(5) 0.073(5) 0.010(4) 0.065(5) 0.009(5) C14 0.064(5) 0.046(4) 0.058(4) -0.005(3) 0.036(4) 0.005(4) C15 0.057(4) 0.043(4) 0.029(3) -0.005(3) 0.013(3) -0.004(3) C16 0.053(4) 0.028(3) 0.033(3) 0.000(2) 0.014(3) 0.003(3) C17 0.101(7) 0.044(4) 0.055(4) 0.001(3) 0.043(4) 0.005(4) C18 0.123(7) 0.047(5) 0.060(4) -0.003(3) 0.057(5) 0.011(5) C19 0.097(6) 0.071(5) 0.054(4) 0.005(4) 0.048(4) 0.009(5) C20 0.074(5) 0.051(4) 0.043(3) 0.009(3) 0.027(4) -0.003(4) C21 0.048(4) 0.039(4) 0.034(3) 0.000(3) 0.013(3) -0.005(3) C22 0.063(5) 0.044(4) 0.045(3) 0.010(3) 0.024(3) -0.012(3) C23 0.051(4) 0.027(3) 0.041(3) 0.005(2) 0.027(3) -0.007(3) C24 0.066(5) 0.035(4) 0.047(3) 0.014(3) 0.033(3) 0.006(3) C25 0.106(7) 0.050(5) 0.045(4) 0.001(3) 0.041(4) -0.008(5) C26 0.066(5) 0.056(5) 0.046(4) 0.004(3) 0.011(4) -0.019(4) C27 0.037(4) 0.061(5) 0.061(4) 0.009(3) 0.019(3) 0.002(3) C28 0.058(4) 0.041(4) 0.046(3) 0.000(3) 0.032(3) -0.008(3) N1 0.036(3) 0.027(3) 0.030(2) -0.0036(18) 0.016(2) -0.002(2) N2 0.045(3) 0.032(3) 0.031(2) 0.001(2) 0.013(2) -0.010(2) Se2 0.0553(5) 0.0350(4) 0.0333(3) 0.0056(2) 0.0161(3) 0.0046(3) Se1 0.0401(4) 0.0531(5) 0.0407(4) -0.0017(3) 0.0165(3) 0.0080(3) Zn1 0.0432(5) 0.0368(5) 0.0306(4) 0.0002(3) 0.0154(3) 0.0001(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.378(8) . ? C1 C2 1.418(9) . ? C1 Se1 1.910(6) . ? C2 C3 1.407(8) . ? C2 C7 1.449(8) . ? C3 C4 1.361(8) . ? C3 H3 0.9300 . ? C4 C5 1.374(9) . ? C4 H4 0.9300 . ? C5 C6 1.381(8) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 N1 1.284(7) . ? C7 H7 0.9300 . ? C8 N1 1.472(7) . ? C8 C9 1.508(8) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.355(9) . ? C9 C14 1.368(8) . ? C10 C11 1.405(10) . ? C10 H10 0.9300 . ? C11 C12 1.356(10) . ? C11 H11 0.9300 . ? C12 C13 1.373(11) . ? C12 H12 0.9300 . ? C13 C14 1.366(10) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C20 1.386(9) . ? C15 C16 1.412(8) . ? C15 Se2 1.908(6) . ? C16 C17 1.410(9) . ? C16 C21 1.455(8) . ? C17 C18 1.365(9) . ? C17 H17 0.9300 . ? C18 C19 1.391(11) . ? C18 H18 0.9300 . ? C19 C20 1.374(10) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 N2 1.271(7) . ? C21 H21 0.9300 . ? C22 N2 1.485(7) . ? C22 C23 1.509(8) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.387(8) . ? C23 C28 1.391(8) . ? C24 C25 1.375(10) . ? C24 H24 0.9300 . ? C25 C26 1.363(11) . ? C25 H25 0.9300 . ? C26 C27 1.392(9) . ? C26 H26 0.9300 . ? C27 C28 1.374(8) . ? C27 H27 0.9300 . ? C28 H28 0.9300 . ? N1 Zn1 2.018(5) . ? N2 Zn1 2.063(5) . ? Se2 Zn1 2.3659(12) . ? Se1 Zn1 2.3523(11) . ? 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 117.7(5) . . ? C6 C1 Se1 114.1(5) . . ? C2 C1 Se1 128.2(4) . . ? C3 C2 C1 118.1(5) . . ? C3 C2 C7 112.8(6) . . ? C1 C2 C7 129.0(5) . . ? C4 C3 C2 122.7(6) . . ? C4 C3 H3 118.6 . . ? C2 C3 H3 118.6 . . ? C3 C4 C5 118.8(6) . . ? C3 C4 H4 120.6 . . ? C5 C4 H4 120.6 . . ? C4 C5 C6 120.0(6) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C1 C6 C5 122.7(6) . . ? C1 C6 H6 118.7 . . ? C5 C6 H6 118.7 . . ? N1 C7 C2 131.1(6) . . ? N1 C7 H7 114.4 . . ? C2 C7 H7 114.4 . . ? N1 C8 C9 112.5(5) . . ? N1 C8 H8A 109.1 . . ? C9 C8 H8A 109.1 . . ? N1 C8 H8B 109.1 . . ? C9 C8 H8B 109.1 . . ? H8A C8 H8B 107.8 . . ? C10 C9 C14 118.4(6) . . ? C10 C9 C8 122.1(5) . . ? C14 C9 C8 119.3(6) . . ? C9 C10 C11 120.5(6) . . ? C9 C10 H10 119.7 . . ? C11 C10 H10 119.7 . . ? C12 C11 C10 120.5(7) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C11 C12 C13 118.3(7) . . ? C11 C12 H12 120.8 . . ? C13 C12 H12 120.8 . . ? C14 C13 C12 121.0(7) . . ? C14 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C13 C14 C9 121.2(7) . . ? C13 C14 H14 119.4 . . ? C9 C14 H14 119.4 . . ? C20 C15 C16 118.5(6) . . ? C20 C15 Se2 115.3(5) . . ? C16 C15 Se2 126.2(5) . . ? C17 C16 C15 117.2(6) . . ? C17 C16 C21 113.6(5) . . ? C15 C16 C21 129.2(5) . . ? C18 C17 C16 124.1(7) . . ? C18 C17 H17 118.0 . . ? C16 C17 H17 118.0 . . ? C17 C18 C19 117.3(6) . . ? C17 C18 H18 121.3 . . ? C19 C18 H18 121.3 . . ? C20 C19 C18 120.6(7) . . ? C20 C19 H19 119.7 . . ? C18 C19 H19 119.7 . . ? C19 C20 C15 122.2(7) . . ? C19 C20 H20 118.9 . . ? C15 C20 H20 118.9 . . ? N2 C21 C16 128.7(6) . . ? N2 C21 H21 115.6 . . ? C16 C21 H21 115.6 . . ? N2 C22 C23 111.0(5) . . ? N2 C22 H22A 109.4 . . ? C23 C22 H22A 109.4 . . ? N2 C22 H22B 109.4 . . ? C23 C22 H22B 109.4 . . ? H22A C22 H22B 108.0 . . ? C24 C23 C28 118.2(6) . . ? C24 C23 C22 121.1(6) . . ? C28 C23 C22 120.6(5) . . ? C25 C24 C23 121.0(7) . . ? C25 C24 H24 119.5 . . ? C23 C24 H24 119.5 . . ? C26 C25 C24 120.6(6) . . ? C26 C25 H25 119.7 . . ? C24 C25 H25 119.7 . . ? C25 C26 C27 119.3(6) . . ? C25 C26 H26 120.4 . . ? C27 C26 H26 120.4 . . ? C28 C27 C26 120.4(6) . . ? C28 C27 H27 119.8 . . ? C26 C27 H27 119.8 . . ? C27 C28 C23 120.5(6) . . ? C27 C28 H28 119.8 . . ? C23 C28 H28 119.8 . . ? C7 N1 C8 117.3(5) . . ? C7 N1 Zn1 126.7(4) . . ? C8 N1 Zn1 115.6(3) . . ? C21 N2 C22 115.9(5) . . ? C21 N2 Zn1 126.8(4) . . ? C22 N2 Zn1 117.3(4) . . ? C15 Se2 Zn1 100.38(18) . . ? C1 Se1 Zn1 101.95(18) . . ? N1 Zn1 N2 101.98(18) . . ? N1 Zn1 Se1 102.36(12) . . ? N2 Zn1 Se1 118.66(14) . . ? N1 Zn1 Se2 116.21(12) . . ? N2 Zn1 Se2 98.18(12) . . ? Se1 Zn1 Se2 118.92(4) . . ? 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(8) . . . . ? Se1 C1 C2 C3 177.4(4) . . . . ? C6 C1 C2 C7 -178.1(6) . . . . ? Se1 C1 C2 C7 -0.3(9) . . . . ? C1 C2 C3 C4 -1.7(9) . . . . ? C7 C2 C3 C4 176.4(6) . . . . ? C2 C3 C4 C5 2.8(9) . . . . ? C3 C4 C5 C6 -1.9(10) . . . . ? C2 C1 C6 C5 1.2(9) . . . . ? Se1 C1 C6 C5 -176.9(5) . . . . ? C4 C5 C6 C1 -0.1(10) . . . . ? C3 C2 C7 N1 -178.0(6) . . . . ? C1 C2 C7 N1 -0.2(10) . . . . ? N1 C8 C9 C10 -47.0(8) . . . . ? N1 C8 C9 C14 138.6(6) . . . . ? C14 C9 C10 C11 -1.5(11) . . . . ? C8 C9 C10 C11 -175.9(7) . . . . ? C9 C10 C11 C12 1.0(13) . . . . ? C10 C11 C12 C13 -1.2(13) . . . . ? C11 C12 C13 C14 2.0(13) . . . . ? C12 C13 C14 C9 -2.6(12) . . . . ? C10 C9 C14 C13 2.3(11) . . . . ? C8 C9 C14 C13 176.9(7) . . . . ? C20 C15 C16 C17 0.2(10) . . . . ? Se2 C15 C16 C17 -178.2(5) . . . . ? C20 C15 C16 C21 178.2(6) . . . . ? Se2 C15 C16 C21 -0.3(10) . . . . ? C15 C16 C17 C18 -1.8(11) . . . . ? C21 C16 C17 C18 179.9(7) . . . . ? C16 C17 C18 C19 0.8(13) . . . . ? C17 C18 C19 C20 1.9(13) . . . . ? C18 C19 C20 C15 -3.5(13) . . . . ? C16 C15 C20 C19 2.4(11) . . . . ? Se2 C15 C20 C19 -179.0(6) . . . . ? C17 C16 C21 N2 -161.4(6) . . . . ? C15 C16 C21 N2 20.6(11) . . . . ? N2 C22 C23 C24 -112.0(6) . . . . ? N2 C22 C23 C28 67.9(8) . . . . ? C28 C23 C24 C25 -0.9(9) . . . . ? C22 C23 C24 C25 179.0(6) . . . . ? C23 C24 C25 C26 -0.7(10) . . . . ? C24 C25 C26 C27 1.7(11) . . . . ? C25 C26 C27 C28 -1.1(11) . . . . ? C26 C27 C28 C23 -0.5(10) . . . . ? C24 C23 C28 C27 1.5(9) . . . . ? C22 C23 C28 C27 -178.4(6) . . . . ? C2 C7 N1 C8 178.5(6) . . . . ? C2 C7 N1 Zn1 6.4(9) . . . . ? C9 C8 N1 C7 103.3(6) . . . . ? C9 C8 N1 Zn1 -83.8(5) . . . . ? C16 C21 N2 C22 176.9(6) . . . . ? C16 C21 N2 Zn1 -1.9(9) . . . . ? C23 C22 N2 C21 -116.8(6) . . . . ? C23 C22 N2 Zn1 62.1(6) . . . . ? C20 C15 Se2 Zn1 156.5(5) . . . . ? C16 C15 Se2 Zn1 -25.0(6) . . . . ? C6 C1 Se1 Zn1 174.0(4) . . . . ? C2 C1 Se1 Zn1 -3.8(5) . . . . ? C7 N1 Zn1 N2 114.2(5) . . . . ? C8 N1 Zn1 N2 -58.0(4) . . . . ? C7 N1 Zn1 Se1 -9.1(5) . . . . ? C8 N1 Zn1 Se1 178.7(3) . . . . ? C7 N1 Zn1 Se2 -140.4(4) . . . . ? C8 N1 Zn1 Se2 47.4(4) . . . . ? C21 N2 Zn1 N1 96.0(5) . . . . ? C22 N2 Zn1 N1 -82.7(4) . . . . ? C21 N2 Zn1 Se1 -152.6(5) . . . . ? C22 N2 Zn1 Se1 28.7(4) . . . . ? C21 N2 Zn1 Se2 -23.2(5) . . . . ? C22 N2 Zn1 Se2 158.1(4) . . . . ? C1 Se1 Zn1 N1 6.6(2) . . . . ? C1 Se1 Zn1 N2 -104.6(2) . . . . ? C1 Se1 Zn1 Se2 136.20(17) . . . . ? C15 Se2 Zn1 N1 -78.5(2) . . . . ? C15 Se2 Zn1 N2 29.3(3) . . . . ? C15 Se2 Zn1 Se1 158.5(2) . . . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.670 _refine_diff_density_min -0.666 _refine_diff_density_rms 0.126 # Attachment '- Compound 12 - CCDC 811931.cif' data_558r _database_code_depnum_ccdc_archive 'CCDC 811931' #TrackingRef '- Compound 12 - CCDC 811931.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C38 H44 N2 Se2 Zn' _chemical_formula_sum 'C38 H44 N2 Se2 Zn' _chemical_formula_weight 752.04 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' Zn Zn 0.2839 1.4301 '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 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 15.0512(16) _cell_length_b 13.1067(14) _cell_length_c 18.4747(19) _cell_angle_alpha 90.00 _cell_angle_beta 101.281(2) _cell_angle_gamma 90.00 _cell_volume 3574.1(7) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 3526 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 23.52 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.398 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1536 _exptl_absorpt_coefficient_mu 2.751 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5463 _exptl_absorpt_correction_T_max 0.6372 _exptl_absorpt_process_details 'Bruker, 2000.' _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 12649 _diffrn_reflns_av_R_equivalents 0.0582 _diffrn_reflns_av_sigmaI/netI 0.0559 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3143 _reflns_number_gt 2617 _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^)+(0.0352P)^2^+10.9839P] 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 3143 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0851 _refine_ls_R_factor_gt 0.0660 _refine_ls_wR_factor_ref 0.1252 _refine_ls_wR_factor_gt 0.1190 _refine_ls_goodness_of_fit_ref 1.211 _refine_ls_restrained_S_all 1.211 _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 C2 C 0.2172(4) 0.2685(4) 0.2574(3) 0.0441(14) Uani 1 1 d . . . C1 C 0.1950(4) 0.3408(4) 0.2004(3) 0.0449(14) Uani 1 1 d . . . C6 C 0.2492(4) 0.3402(5) 0.1467(4) 0.0629(18) Uani 1 1 d . . . H6 H 0.2364 0.3870 0.1082 0.075 Uiso 1 1 calc R . . C5 C 0.3188(5) 0.2753(6) 0.1479(4) 0.082(2) Uani 1 1 d . . . H5 H 0.3517 0.2772 0.1102 0.098 Uiso 1 1 calc R . . C4 C 0.3414(5) 0.2066(6) 0.2042(4) 0.080(2) Uani 1 1 d . . . H4 H 0.3900 0.1623 0.2056 0.096 Uiso 1 1 calc R . . C3 C 0.2909(4) 0.2044(5) 0.2584(4) 0.0638(19) Uani 1 1 d . . . H3 H 0.3066 0.1585 0.2972 0.077 Uiso 1 1 calc R . . C7 C 0.1720(4) 0.2553(4) 0.3198(3) 0.0471(14) Uani 1 1 d . . . H7 H 0.2073 0.2252 0.3613 0.057 Uiso 1 1 calc R . . C8 C 0.0708(3) 0.2647(4) 0.3994(3) 0.0396(13) Uani 1 1 d . . . C9 C 0.1036(4) 0.3359(4) 0.4534(3) 0.0407(14) Uani 1 1 d . . . C10 C 0.0823(4) 0.3197(5) 0.5233(3) 0.0560(17) Uani 1 1 d . . . H10 H 0.1033 0.3659 0.5610 0.067 Uiso 1 1 calc R . . C11 C 0.0317(5) 0.2383(6) 0.5376(3) 0.0628(19) Uani 1 1 d . . . H11 H 0.0201 0.2285 0.5847 0.075 Uiso 1 1 calc R . . C12 C -0.0017(4) 0.1714(5) 0.4820(4) 0.0609(19) Uani 1 1 d . . . H12 H -0.0376 0.1175 0.4921 0.073 Uiso 1 1 calc R . . C13 C 0.0161(4) 0.1808(4) 0.4112(3) 0.0466(15) Uani 1 1 d . . . C14 C 0.1584(4) 0.4288(5) 0.4414(3) 0.0507(16) Uani 1 1 d . . . H14 H 0.1653 0.4287 0.3897 0.061 Uiso 1 1 calc R . . C15 C 0.2540(5) 0.4259(6) 0.4904(4) 0.080(2) Uani 1 1 d . . . H15A H 0.2490 0.4226 0.5414 0.120 Uiso 1 1 calc R . . H15B H 0.2866 0.4863 0.4822 0.120 Uiso 1 1 calc R . . H15C H 0.2859 0.3669 0.4782 0.120 Uiso 1 1 calc R . . C16 C 0.1113(4) 0.5265(5) 0.4551(4) 0.0656(19) Uani 1 1 d . . . H16A H 0.0512 0.5272 0.4255 0.098 Uiso 1 1 calc R . . H16B H 0.1448 0.5837 0.4422 0.098 Uiso 1 1 calc R . . H16C H 0.1077 0.5308 0.5063 0.098 Uiso 1 1 calc R . . C17 C -0.0167(4) 0.1046(5) 0.3512(4) 0.0584(17) Uani 1 1 d . . . H17 H -0.0256 0.1407 0.3039 0.070 Uiso 1 1 calc R . . C18 C 0.0553(5) 0.0221(5) 0.3504(4) 0.073(2) Uani 1 1 d . . . H18A H 0.1088 0.0526 0.3387 0.110 Uiso 1 1 calc R . . H18B H 0.0322 -0.0283 0.3138 0.110 Uiso 1 1 calc R . . H18C H 0.0701 -0.0097 0.3980 0.110 Uiso 1 1 calc R . . C19 C -0.1073(5) 0.0548(6) 0.3578(5) 0.091(3) Uani 1 1 d . . . H19A H -0.0980 0.0092 0.3992 0.137 Uiso 1 1 calc R . . H19B H -0.1307 0.0174 0.3135 0.137 Uiso 1 1 calc R . . H19C H -0.1498 0.1069 0.3647 0.137 Uiso 1 1 calc R . . N1 N 0.0916(3) 0.2785(3) 0.3265(2) 0.0366(10) Uani 1 1 d . . . Se1 Se 0.10541(4) 0.44408(4) 0.19109(3) 0.0490(2) Uani 1 1 d . . . Zn1 Zn 0.0000 0.36138(6) 0.2500 0.0343(2) Uani 1 2 d S . . 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 C2 0.041(3) 0.053(4) 0.041(3) 0.007(3) 0.015(3) 0.003(3) C1 0.042(3) 0.046(4) 0.047(3) 0.000(3) 0.012(3) -0.003(3) C6 0.055(4) 0.071(5) 0.068(4) 0.025(4) 0.024(4) 0.013(4) C5 0.088(6) 0.090(6) 0.083(5) 0.016(5) 0.056(5) 0.006(5) C4 0.074(5) 0.087(6) 0.090(6) 0.015(5) 0.044(4) 0.030(4) C3 0.065(4) 0.072(5) 0.061(4) 0.016(4) 0.028(4) 0.028(4) C7 0.052(4) 0.049(4) 0.040(3) 0.010(3) 0.009(3) 0.015(3) C8 0.041(3) 0.046(3) 0.034(3) 0.014(3) 0.013(2) 0.021(3) C9 0.045(3) 0.045(3) 0.034(3) 0.011(3) 0.012(3) 0.015(3) C10 0.059(4) 0.074(5) 0.039(3) 0.009(3) 0.021(3) 0.016(4) C11 0.075(5) 0.085(5) 0.037(4) 0.022(4) 0.030(3) 0.019(4) C12 0.053(4) 0.072(5) 0.063(4) 0.036(4) 0.027(3) 0.007(3) C13 0.045(3) 0.049(4) 0.047(4) 0.019(3) 0.013(3) 0.012(3) C14 0.065(4) 0.057(4) 0.031(3) 0.005(3) 0.011(3) 0.008(3) C15 0.059(4) 0.095(6) 0.085(5) 0.020(5) 0.014(4) 0.006(4) C16 0.065(4) 0.056(4) 0.071(5) 0.001(3) 0.003(4) 0.009(3) C17 0.061(4) 0.057(4) 0.058(4) 0.018(3) 0.012(3) -0.003(3) C18 0.089(5) 0.061(4) 0.068(5) 0.007(4) 0.011(4) 0.004(4) C19 0.081(5) 0.088(6) 0.104(6) 0.035(5) 0.018(5) -0.023(5) N1 0.046(3) 0.035(3) 0.029(2) 0.0114(19) 0.009(2) 0.007(2) Se1 0.0479(4) 0.0429(4) 0.0568(4) 0.0188(3) 0.0117(3) -0.0015(3) Zn1 0.0370(5) 0.0339(5) 0.0310(5) 0.000 0.0042(4) 0.000 _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 C2 C3 1.389(8) . ? C2 C1 1.408(7) . ? C2 C7 1.459(7) . ? C1 C6 1.404(8) . ? C1 Se1 1.894(6) . ? C6 C5 1.345(9) . ? C6 H6 0.9300 . ? C5 C4 1.367(10) . ? C5 H5 0.9300 . ? C4 C3 1.371(8) . ? C4 H4 0.9300 . ? C3 H3 0.9300 . ? C7 N1 1.277(6) . ? C7 H7 0.9300 . ? C8 C9 1.384(7) . ? C8 C13 1.417(8) . ? C8 N1 1.451(6) . ? C9 C10 1.406(7) . ? C9 C14 1.511(8) . ? C10 C11 1.366(9) . ? C10 H10 0.9300 . ? C11 C12 1.368(9) . ? C11 H11 0.9300 . ? C12 C13 1.392(8) . ? C12 H12 0.9300 . ? C13 C17 1.501(9) . ? C14 C16 1.509(8) . ? C14 C15 1.544(9) . ? C14 H14 0.9800 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 C18 1.533(9) . ? C17 C19 1.538(9) . ? C17 H17 0.9800 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? N1 Zn1 2.078(4) . ? Se1 Zn1 2.3562(7) . ? Zn1 N1 2.078(4) 2 ? Zn1 Se1 2.3562(7) 2 ? 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 C3 C2 C1 119.2(5) . . ? C3 C2 C7 114.4(5) . . ? C1 C2 C7 126.3(5) . . ? C6 C1 C2 116.0(5) . . ? C6 C1 Se1 116.3(4) . . ? C2 C1 Se1 127.6(4) . . ? C5 C6 C1 123.4(6) . . ? C5 C6 H6 118.3 . . ? C1 C6 H6 118.3 . . ? C6 C5 C4 120.5(7) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C4 C3 118.5(7) . . ? C5 C4 H4 120.8 . . ? C3 C4 H4 120.8 . . ? C4 C3 C2 122.3(6) . . ? C4 C3 H3 118.9 . . ? C2 C3 H3 118.9 . . ? N1 C7 C2 130.2(5) . . ? N1 C7 H7 114.9 . . ? C2 C7 H7 114.9 . . ? C9 C8 C13 123.2(5) . . ? C9 C8 N1 118.3(5) . . ? C13 C8 N1 118.4(5) . . ? C8 C9 C10 116.6(5) . . ? C8 C9 C14 124.4(5) . . ? C10 C9 C14 119.0(5) . . ? C11 C10 C9 122.1(6) . . ? C11 C10 H10 119.0 . . ? C9 C10 H10 119.0 . . ? C10 C11 C12 119.5(6) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? C11 C12 C13 122.6(6) . . ? C11 C12 H12 118.7 . . ? C13 C12 H12 118.7 . . ? C12 C13 C8 115.9(6) . . ? C12 C13 C17 122.6(6) . . ? C8 C13 C17 121.4(5) . . ? C16 C14 C9 111.8(5) . . ? C16 C14 C15 109.7(5) . . ? C9 C14 C15 111.6(5) . . ? C16 C14 H14 107.9 . . ? C9 C14 H14 107.9 . . ? C15 C14 H14 107.9 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C13 C17 C18 110.2(5) . . ? C13 C17 C19 113.1(6) . . ? C18 C17 C19 110.0(6) . . ? C13 C17 H17 107.8 . . ? C18 C17 H17 107.8 . . ? C19 C17 H17 107.8 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C7 N1 C8 116.1(4) . . ? C7 N1 Zn1 125.0(4) . . ? C8 N1 Zn1 117.5(3) . . ? C1 Se1 Zn1 99.26(17) . . ? N1 Zn1 N1 117.0(2) 2 . ? N1 Zn1 Se1 97.93(12) 2 2 ? N1 Zn1 Se1 110.06(12) . 2 ? N1 Zn1 Se1 110.06(12) 2 . ? N1 Zn1 Se1 97.93(12) . . ? Se1 Zn1 Se1 125.22(5) 2 . ? 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 C3 C2 C1 C6 1.8(9) . . . . ? C7 C2 C1 C6 179.0(6) . . . . ? C3 C2 C1 Se1 -174.0(5) . . . . ? C7 C2 C1 Se1 3.2(9) . . . . ? C2 C1 C6 C5 0.0(10) . . . . ? Se1 C1 C6 C5 176.3(6) . . . . ? C1 C6 C5 C4 -1.4(12) . . . . ? C6 C5 C4 C3 0.9(12) . . . . ? C5 C4 C3 C2 0.9(12) . . . . ? C1 C2 C3 C4 -2.4(10) . . . . ? C7 C2 C3 C4 -179.9(7) . . . . ? C3 C2 C7 N1 -158.3(6) . . . . ? C1 C2 C7 N1 24.4(10) . . . . ? C13 C8 C9 C10 2.0(8) . . . . ? N1 C8 C9 C10 -179.8(5) . . . . ? C13 C8 C9 C14 -177.1(5) . . . . ? N1 C8 C9 C14 1.2(8) . . . . ? C8 C9 C10 C11 -0.2(8) . . . . ? C14 C9 C10 C11 178.9(5) . . . . ? C9 C10 C11 C12 -1.8(10) . . . . ? C10 C11 C12 C13 2.1(10) . . . . ? C11 C12 C13 C8 -0.4(9) . . . . ? C11 C12 C13 C17 177.0(6) . . . . ? C9 C8 C13 C12 -1.7(8) . . . . ? N1 C8 C13 C12 -179.9(5) . . . . ? C9 C8 C13 C17 -179.1(5) . . . . ? N1 C8 C13 C17 2.7(7) . . . . ? C8 C9 C14 C16 118.9(6) . . . . ? C10 C9 C14 C16 -60.1(7) . . . . ? C8 C9 C14 C15 -117.8(6) . . . . ? C10 C9 C14 C15 63.2(7) . . . . ? C12 C13 C17 C18 -92.0(7) . . . . ? C8 C13 C17 C18 85.2(7) . . . . ? C12 C13 C17 C19 31.6(8) . . . . ? C8 C13 C17 C19 -151.2(5) . . . . ? C2 C7 N1 C8 -173.7(6) . . . . ? C2 C7 N1 Zn1 -7.5(9) . . . . ? C9 C8 N1 C7 76.2(6) . . . . ? C13 C8 N1 C7 -105.5(6) . . . . ? C9 C8 N1 Zn1 -91.1(5) . . . . ? C13 C8 N1 Zn1 87.3(5) . . . . ? C6 C1 Se1 Zn1 153.2(5) . . . . ? C2 C1 Se1 Zn1 -30.9(5) . . . . ? C7 N1 Zn1 N1 95.1(5) . . . 2 ? C8 N1 Zn1 N1 -98.9(4) . . . 2 ? C7 N1 Zn1 Se1 -154.4(4) . . . 2 ? C8 N1 Zn1 Se1 11.6(4) . . . 2 ? C7 N1 Zn1 Se1 -22.3(5) . . . . ? C8 N1 Zn1 Se1 143.7(4) . . . . ? C1 Se1 Zn1 N1 -89.9(2) . . . 2 ? C1 Se1 Zn1 N1 32.6(2) . . . . ? C1 Se1 Zn1 Se1 154.12(17) . . . 2 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.567 _refine_diff_density_min -0.867 _refine_diff_density_rms 0.082 data_576r _database_code_depnum_ccdc_archive 'CCDC 811932' #TrackingRef '- Compound 6 - CCDC 811932.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H24 N2 Se2' _chemical_formula_sum 'C28 H24 N2 Se2' _chemical_formula_weight 546.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' _symmetry_space_group_name_Hall '-P 2ybc' 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 10.8520(8) _cell_length_b 22.7903(18) _cell_length_c 9.6203(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.1520(10) _cell_angle_gamma 90.00 _cell_volume 2379.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 5149 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 23.29 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.525 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1096 _exptl_absorpt_coefficient_mu 3.126 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4441 _exptl_absorpt_correction_T_max 0.4970 _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 22703 _diffrn_reflns_av_R_equivalents 0.0476 _diffrn_reflns_av_sigmaI/netI 0.0354 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4190 _reflns_number_gt 3485 _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^)+(0.0331P)^2^+0.3057P] 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 4190 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0396 _refine_ls_R_factor_gt 0.0291 _refine_ls_wR_factor_ref 0.0710 _refine_ls_wR_factor_gt 0.0681 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _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 0.2708(2) 0.35198(11) 0.8861(3) 0.0395(6) Uani 1 1 d . . . C2 C 0.2358(2) 0.29618(12) 0.9317(3) 0.0427(6) Uani 1 1 d . . . C3 C 0.1300(3) 0.27068(13) 0.8738(3) 0.0547(8) Uani 1 1 d . . . H3 H 0.1052 0.2338 0.9044 0.066 Uiso 1 1 calc R . . C4 C 0.0622(3) 0.29856(14) 0.7736(3) 0.0605(8) Uani 1 1 d . . . H4 H -0.0074 0.2807 0.7360 0.073 Uiso 1 1 calc R . . C5 C 0.0979(3) 0.35308(14) 0.7293(3) 0.0568(8) Uani 1 1 d . . . H5 H 0.0524 0.3722 0.6608 0.068 Uiso 1 1 calc R . . C6 C 0.2005(3) 0.37989(12) 0.7851(3) 0.0496(7) Uani 1 1 d . . . H6 H 0.2229 0.4171 0.7547 0.060 Uiso 1 1 calc R . . C7 C 0.3070(3) 0.26093(12) 1.0304(3) 0.0472(7) Uani 1 1 d . . . H7 H 0.2763 0.2244 1.0559 0.057 Uiso 1 1 calc R . . C8 C 0.4733(3) 0.23726(13) 1.1735(3) 0.0527(7) Uani 1 1 d . . . H8A H 0.4229 0.2027 1.1893 0.063 Uiso 1 1 calc R . . H8B H 0.4870 0.2561 1.2626 0.063 Uiso 1 1 calc R . . C9 C 0.5959(2) 0.21853(11) 1.1138(3) 0.0414(6) Uani 1 1 d . . . C10 C 0.6537(3) 0.25000(12) 1.0106(3) 0.0477(7) Uani 1 1 d . . . H10 H 0.6173 0.2840 0.9763 0.057 Uiso 1 1 calc R . . C11 C 0.7648(3) 0.23159(15) 0.9578(3) 0.0613(8) Uani 1 1 d . . . H11 H 0.8030 0.2533 0.8883 0.074 Uiso 1 1 calc R . . C12 C 0.8199(3) 0.18127(16) 1.0069(4) 0.0672(9) Uani 1 1 d . . . H12 H 0.8946 0.1687 0.9701 0.081 Uiso 1 1 calc R . . C13 C 0.7634(3) 0.14975(14) 1.1109(4) 0.0643(9) Uani 1 1 d . . . H13 H 0.8004 0.1159 1.1454 0.077 Uiso 1 1 calc R . . C14 C 0.6528(3) 0.16820(13) 1.1638(3) 0.0525(7) Uani 1 1 d . . . H14 H 0.6154 0.1467 1.2342 0.063 Uiso 1 1 calc R . . C15 C 0.3167(2) 0.52557(11) 0.8851(3) 0.0402(6) Uani 1 1 d . . . C16 C 0.3096(2) 0.58155(11) 0.8274(3) 0.0421(6) Uani 1 1 d . . . C17 C 0.2198(3) 0.62026(13) 0.8752(3) 0.0548(8) Uani 1 1 d . . . H17 H 0.2144 0.6575 0.8364 0.066 Uiso 1 1 calc R . . C18 C 0.1393(3) 0.60457(14) 0.9782(3) 0.0630(9) Uani 1 1 d . . . H18 H 0.0802 0.6310 1.0094 0.076 Uiso 1 1 calc R . . C19 C 0.1469(3) 0.54952(15) 1.0345(3) 0.0632(9) Uani 1 1 d . . . H19 H 0.0923 0.5386 1.1042 0.076 Uiso 1 1 calc R . . C20 C 0.2342(3) 0.51016(13) 0.9895(3) 0.0529(7) Uani 1 1 d . . . H20 H 0.2381 0.4730 1.0291 0.063 Uiso 1 1 calc R . . C21 C 0.3949(3) 0.60144(12) 0.7193(3) 0.0481(7) Uani 1 1 d . . . H21 H 0.3907 0.6401 0.6885 0.058 Uiso 1 1 calc R . . C22 C 0.5584(3) 0.59042(15) 0.5638(3) 0.0624(8) Uani 1 1 d . . . H22A H 0.5464 0.6324 0.5539 0.075 Uiso 1 1 calc R . . H22B H 0.5411 0.5722 0.4747 0.075 Uiso 1 1 calc R . . C23 C 0.6896(3) 0.57841(13) 0.6042(3) 0.0477(7) Uani 1 1 d . . . C24 C 0.7483(3) 0.52814(14) 0.5620(4) 0.0658(9) Uani 1 1 d . . . H24 H 0.7065 0.5010 0.5070 0.079 Uiso 1 1 calc R . . C25 C 0.8680(4) 0.51757(15) 0.6001(4) 0.0765(11) Uani 1 1 d . . . H25 H 0.9070 0.4835 0.5705 0.092 Uiso 1 1 calc R . . C26 C 0.9310(3) 0.55724(17) 0.6823(4) 0.0748(10) Uani 1 1 d . . . H26 H 1.0122 0.5501 0.7081 0.090 Uiso 1 1 calc R . . C27 C 0.8729(3) 0.60659(16) 0.7248(4) 0.0703(9) Uani 1 1 d . . . H27 H 0.9144 0.6335 0.7805 0.084 Uiso 1 1 calc R . . C28 C 0.7540(3) 0.61716(14) 0.6865(3) 0.0607(8) Uani 1 1 d . . . H28 H 0.7156 0.6513 0.7166 0.073 Uiso 1 1 calc R . . N1 N 0.4072(2) 0.27744(10) 1.0824(2) 0.0461(5) Uani 1 1 d . . . N2 N 0.4730(2) 0.56770(10) 0.6676(2) 0.0480(6) Uani 1 1 d . . . Se1 Se 0.41515(2) 0.389425(12) 0.96440(3) 0.04361(10) Uani 1 1 d . . . Se2 Se 0.44045(2) 0.471609(12) 0.81825(3) 0.04269(10) 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 0.0376(14) 0.0434(15) 0.0374(14) -0.0067(12) 0.0025(11) 0.0044(12) C2 0.0390(15) 0.0452(16) 0.0439(15) -0.0037(12) 0.0081(12) 0.0022(12) C3 0.0449(18) 0.0542(18) 0.065(2) 0.0020(15) 0.0082(15) -0.0071(14) C4 0.0391(17) 0.071(2) 0.071(2) -0.0116(18) -0.0017(15) -0.0069(15) C5 0.0450(17) 0.066(2) 0.0589(19) 0.0001(16) -0.0084(14) 0.0069(15) C6 0.0466(17) 0.0472(16) 0.0550(18) -0.0015(14) -0.0053(14) 0.0036(13) C7 0.0528(18) 0.0404(16) 0.0485(17) 0.0049(13) 0.0155(14) 0.0027(13) C8 0.0596(19) 0.0529(18) 0.0456(17) 0.0085(14) 0.0019(14) 0.0040(14) C9 0.0463(16) 0.0404(15) 0.0374(15) -0.0022(12) -0.0067(12) -0.0013(12) C10 0.0468(17) 0.0472(16) 0.0490(17) 0.0027(13) -0.0026(13) -0.0006(13) C11 0.0529(19) 0.072(2) 0.059(2) 0.0036(17) 0.0005(15) -0.0092(17) C12 0.0446(18) 0.084(3) 0.073(2) -0.013(2) -0.0045(16) 0.0049(18) C13 0.058(2) 0.058(2) 0.077(2) -0.0012(17) -0.0177(18) 0.0121(16) C14 0.0573(19) 0.0497(17) 0.0504(17) 0.0067(14) -0.0073(14) -0.0020(15) C15 0.0392(15) 0.0443(16) 0.0370(14) -0.0064(12) -0.0038(11) -0.0011(12) C16 0.0418(16) 0.0431(16) 0.0415(15) -0.0037(12) -0.0067(12) -0.0033(12) C17 0.0589(19) 0.0422(17) 0.063(2) -0.0044(14) -0.0063(16) 0.0079(14) C18 0.061(2) 0.066(2) 0.062(2) -0.0128(17) 0.0078(17) 0.0170(17) C19 0.062(2) 0.071(2) 0.057(2) -0.0045(17) 0.0180(16) 0.0050(17) C20 0.0564(19) 0.0490(17) 0.0534(18) -0.0006(14) 0.0096(15) 0.0019(14) C21 0.0513(18) 0.0416(16) 0.0512(17) 0.0072(13) -0.0097(14) -0.0026(14) C22 0.058(2) 0.081(2) 0.0478(18) 0.0178(16) 0.0051(15) -0.0006(17) C23 0.0514(18) 0.0537(18) 0.0381(16) 0.0071(13) 0.0103(13) -0.0060(14) C24 0.068(2) 0.060(2) 0.069(2) -0.0045(17) 0.0064(18) -0.0117(17) C25 0.071(3) 0.058(2) 0.101(3) 0.001(2) 0.024(2) 0.0089(18) C26 0.052(2) 0.084(3) 0.088(3) 0.017(2) 0.0021(19) -0.008(2) C27 0.067(2) 0.074(2) 0.070(2) -0.0074(18) -0.0070(18) -0.0119(19) C28 0.068(2) 0.058(2) 0.056(2) -0.0043(15) 0.0079(17) 0.0024(16) N1 0.0474(14) 0.0458(13) 0.0453(14) 0.0047(11) 0.0015(11) 0.0028(11) N2 0.0475(14) 0.0539(15) 0.0426(13) 0.0067(11) -0.0009(11) -0.0062(12) Se1 0.04618(18) 0.04321(17) 0.04139(17) 0.00047(12) -0.00695(12) -0.00094(12) Se2 0.04438(17) 0.04439(17) 0.03932(16) -0.00153(12) 0.00234(12) 0.00201(12) _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 1.388(4) . ? C1 C2 1.398(4) . ? C1 Se1 1.935(3) . ? C2 C3 1.401(4) . ? C2 C7 1.463(4) . ? C3 C4 1.367(4) . ? C3 H3 0.9300 . ? C4 C5 1.370(4) . ? C4 H4 0.9300 . ? C5 C6 1.378(4) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 N1 1.254(3) . ? C7 H7 0.9300 . ? C8 N1 1.455(3) . ? C8 C9 1.512(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.378(4) . ? C9 C14 1.388(4) . ? C10 C11 1.375(4) . ? C10 H10 0.9300 . ? C11 C12 1.377(4) . ? C11 H11 0.9300 . ? C12 C13 1.378(4) . ? C12 H12 0.9300 . ? C13 C14 1.371(4) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C20 1.393(4) . ? C15 C16 1.393(4) . ? C15 Se2 1.932(3) . ? C16 C17 1.393(4) . ? C16 C21 1.466(4) . ? C17 C18 1.370(4) . ? C17 H17 0.9300 . ? C18 C19 1.369(4) . ? C18 H18 0.9300 . ? C19 C20 1.375(4) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 N2 1.249(3) . ? C21 H21 0.9300 . ? C22 N2 1.459(3) . ? C22 C23 1.501(4) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.373(4) . ? C23 C28 1.376(4) . ? C24 C25 1.370(5) . ? C24 H24 0.9300 . ? C25 C26 1.381(5) . ? C25 H25 0.9300 . ? C26 C27 1.353(5) . ? C26 H26 0.9300 . ? C27 C28 1.362(5) . ? C27 H27 0.9300 . ? C28 H28 0.9300 . ? Se1 Se2 2.3585(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 C6 C1 C2 119.1(2) . . ? C6 C1 Se1 120.9(2) . . ? C2 C1 Se1 119.98(19) . . ? C1 C2 C3 118.4(3) . . ? C1 C2 C7 124.0(2) . . ? C3 C2 C7 117.4(3) . . ? C4 C3 C2 121.7(3) . . ? C4 C3 H3 119.1 . . ? C2 C3 H3 119.1 . . ? C3 C4 C5 119.3(3) . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? C4 C5 C6 120.6(3) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C5 C6 C1 120.8(3) . . ? C5 C6 H6 119.6 . . ? C1 C6 H6 119.6 . . ? N1 C7 C2 123.4(3) . . ? N1 C7 H7 118.3 . . ? C2 C7 H7 118.3 . . ? N1 C8 C9 112.4(2) . . ? N1 C8 H8A 109.1 . . ? C9 C8 H8A 109.1 . . ? N1 C8 H8B 109.1 . . ? C9 C8 H8B 109.1 . . ? H8A C8 H8B 107.8 . . ? C10 C9 C14 118.5(3) . . ? C10 C9 C8 122.0(2) . . ? C14 C9 C8 119.5(2) . . ? C11 C10 C9 120.6(3) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C10 C11 C12 120.5(3) . . ? C10 C11 H11 119.7 . . ? C12 C11 H11 119.7 . . ? C11 C12 C13 119.3(3) . . ? C11 C12 H12 120.3 . . ? C13 C12 H12 120.3 . . ? C14 C13 C12 120.1(3) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C13 C14 C9 121.0(3) . . ? C13 C14 H14 119.5 . . ? C9 C14 H14 119.5 . . ? C20 C15 C16 118.9(2) . . ? C20 C15 Se2 121.9(2) . . ? C16 C15 Se2 119.2(2) . . ? C15 C16 C17 119.1(3) . . ? C15 C16 C21 122.1(2) . . ? C17 C16 C21 118.8(3) . . ? C18 C17 C16 121.4(3) . . ? C18 C17 H17 119.3 . . ? C16 C17 H17 119.3 . . ? C19 C18 C17 119.2(3) . . ? C19 C18 H18 120.4 . . ? C17 C18 H18 120.4 . . ? C18 C19 C20 121.0(3) . . ? C18 C19 H19 119.5 . . ? C20 C19 H19 119.5 . . ? C19 C20 C15 120.5(3) . . ? C19 C20 H20 119.8 . . ? C15 C20 H20 119.8 . . ? N2 C21 C16 121.5(3) . . ? N2 C21 H21 119.2 . . ? C16 C21 H21 119.2 . . ? N2 C22 C23 111.2(2) . . ? N2 C22 H22A 109.4 . . ? C23 C22 H22A 109.4 . . ? N2 C22 H22B 109.4 . . ? C23 C22 H22B 109.4 . . ? H22A C22 H22B 108.0 . . ? C24 C23 C28 118.1(3) . . ? C24 C23 C22 121.1(3) . . ? C28 C23 C22 120.8(3) . . ? C25 C24 C23 120.5(3) . . ? C25 C24 H24 119.8 . . ? C23 C24 H24 119.8 . . ? C24 C25 C26 120.4(3) . . ? C24 C25 H25 119.8 . . ? C26 C25 H25 119.8 . . ? C27 C26 C25 119.2(3) . . ? C27 C26 H26 120.4 . . ? C25 C26 H26 120.4 . . ? C26 C27 C28 120.4(3) . . ? C26 C27 H27 119.8 . . ? C28 C27 H27 119.8 . . ? C27 C28 C23 121.4(3) . . ? C27 C28 H28 119.3 . . ? C23 C28 H28 119.3 . . ? C7 N1 C8 118.5(2) . . ? C21 N2 C22 119.2(3) . . ? C1 Se1 Se2 102.34(8) . . ? C15 Se2 Se1 103.01(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 -0.5(4) . . . . ? Se1 C1 C2 C3 179.3(2) . . . . ? C6 C1 C2 C7 175.7(2) . . . . ? Se1 C1 C2 C7 -4.6(3) . . . . ? C1 C2 C3 C4 0.9(4) . . . . ? C7 C2 C3 C4 -175.5(3) . . . . ? C2 C3 C4 C5 -0.5(5) . . . . ? C3 C4 C5 C6 -0.3(5) . . . . ? C4 C5 C6 C1 0.8(4) . . . . ? C2 C1 C6 C5 -0.4(4) . . . . ? Se1 C1 C6 C5 179.8(2) . . . . ? C1 C2 C7 N1 -0.8(4) . . . . ? C3 C2 C7 N1 175.4(3) . . . . ? N1 C8 C9 C10 19.4(4) . . . . ? N1 C8 C9 C14 -160.6(2) . . . . ? C14 C9 C10 C11 0.5(4) . . . . ? C8 C9 C10 C11 -179.5(3) . . . . ? C9 C10 C11 C12 0.2(5) . . . . ? C10 C11 C12 C13 -0.8(5) . . . . ? C11 C12 C13 C14 0.6(5) . . . . ? C12 C13 C14 C9 0.1(5) . . . . ? C10 C9 C14 C13 -0.7(4) . . . . ? C8 C9 C14 C13 179.4(3) . . . . ? C20 C15 C16 C17 -0.4(4) . . . . ? Se2 C15 C16 C17 179.6(2) . . . . ? C20 C15 C16 C21 178.7(2) . . . . ? Se2 C15 C16 C21 -1.3(3) . . . . ? C15 C16 C17 C18 0.5(4) . . . . ? C21 C16 C17 C18 -178.6(3) . . . . ? C16 C17 C18 C19 -0.4(5) . . . . ? C17 C18 C19 C20 0.2(5) . . . . ? C18 C19 C20 C15 -0.1(5) . . . . ? C16 C15 C20 C19 0.2(4) . . . . ? Se2 C15 C20 C19 -179.8(2) . . . . ? C15 C16 C21 N2 4.6(4) . . . . ? C17 C16 C21 N2 -176.3(3) . . . . ? N2 C22 C23 C24 91.1(3) . . . . ? N2 C22 C23 C28 -87.9(3) . . . . ? C28 C23 C24 C25 -0.7(5) . . . . ? C22 C23 C24 C25 -179.7(3) . . . . ? C23 C24 C25 C26 0.4(5) . . . . ? C24 C25 C26 C27 0.1(6) . . . . ? C25 C26 C27 C28 -0.3(5) . . . . ? C26 C27 C28 C23 0.0(5) . . . . ? C24 C23 C28 C27 0.5(5) . . . . ? C22 C23 C28 C27 179.5(3) . . . . ? C2 C7 N1 C8 -176.6(2) . . . . ? C9 C8 N1 C7 115.1(3) . . . . ? C16 C21 N2 C22 -177.8(2) . . . . ? C23 C22 N2 C21 125.9(3) . . . . ? C6 C1 Se1 Se2 -9.7(2) . . . . ? C2 C1 Se1 Se2 170.51(18) . . . . ? C20 C15 Se2 Se1 -3.9(2) . . . . ? C16 C15 Se2 Se1 176.00(18) . . . . ? C1 Se1 Se2 C15 77.83(11) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.271 _refine_diff_density_min -0.374 _refine_diff_density_rms 0.090