Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name ; Paul O'Brien ; 'David J. Crouch' 'Madeleine Helliwell' 'John Waters' 'David J. Williams' _publ_contact_author_name "Prof Paul O'Brien" _publ_contact_author_address ; Department of Chemistry University of Manchester Oxford Road Manchester Lancashire M13 9PL UNITED KINGDOM ; _publ_contact_author_email PAUL.OBRIEN@MAN.AC.UK _publ_requested_journal 'Dalton Transactions' _publ_section_title ; Imino-Bis(diisopropylphosphine Chalcogenide) Complexes of Arsenic, Antimony and Bismuth. Synthesis, CVD Studies and X-Ray Structure of Mn[N(EPiPr2)2]n (Where E = Se, S : M = As, Sb, Bi) ; data_s1305abs _database_code_CSD 199591 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _publ_section_exptl_refinement ; The structure was solved by direct methods. The asymmetric unit contains half the molecule. The non-H atoms were refined anisotropically. H atoms were included in calculated positions. ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H84 N3 P6 Sb Se6' _chemical_formula_weight 1340.39 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Sb Sb -0.5866 1.5461 '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 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 24.959(4) _cell_length_b 12.9416(17) _cell_length_c 19.316(3) _cell_angle_alpha 90.00 _cell_angle_beta 119.819(4) _cell_angle_gamma 90.00 _cell_volume 5413.1(14) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5870 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 26.40 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.645 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2664 _exptl_absorpt_coefficient_mu 4.749 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3831 _exptl_absorpt_correction_T_max 0.4502 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 21220 _diffrn_reflns_av_R_equivalents 0.0233 _diffrn_reflns_av_sigmaI/netI 0.0219 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 26.42 _reflns_number_total 5566 _reflns_number_gt 5185 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0180P)^2^+5.0793P] 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 5566 _refine_ls_number_parameters 248 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0203 _refine_ls_R_factor_gt 0.0181 _refine_ls_wR_factor_ref 0.0424 _refine_ls_wR_factor_gt 0.0418 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.002 _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 Sb1 Sb 0.0000 0.037128(12) 0.2500 0.01273(4) Uani 1 2 d S . . Se1 Se 0.037926(8) 0.028533(14) 0.131975(11) 0.01555(5) Uani 1 1 d . . . Se2 Se 0.100426(8) -0.101521(15) 0.355290(11) 0.01687(5) Uani 1 1 d . . . Se3 Se 0.079152(8) 0.192292(14) 0.359054(11) 0.01659(5) Uani 1 1 d . . . P1 P 0.08940(2) -0.11621(4) 0.15037(3) 0.01319(9) Uani 1 1 d . . . P2 P 0.17136(2) -0.08955(4) 0.31976(3) 0.01346(10) Uani 1 1 d . . . P3 P 0.06661(2) 0.35028(4) 0.31264(3) 0.01461(10) Uani 1 1 d . . . N1 N 0.15339(7) -0.12845(12) 0.23251(9) 0.0146(3) Uani 1 1 d . . . N2 N 0.0000 0.39148(17) 0.2500 0.0160(4) Uani 1 2 d S . . C1 C 0.03573(8) -0.22208(14) 0.13809(11) 0.0177(4) Uani 1 1 d . . . H1 H 0.0160 -0.2016 0.1701 0.021 Uiso 1 1 calc R . . C2 C 0.06738(10) -0.32594(16) 0.17230(14) 0.0315(5) Uani 1 1 d . . . H2A H 0.0822 -0.3551 0.1380 0.047 Uiso 1 1 calc R . . H2B H 0.0378 -0.3736 0.1746 0.047 Uiso 1 1 calc R . . H2C H 0.1024 -0.3155 0.2262 0.047 Uiso 1 1 calc R . . C3 C -0.01723(9) -0.23140(16) 0.05146(11) 0.0250(4) Uani 1 1 d . . . H3A H -0.0494 -0.2766 0.0495 0.038 Uiso 1 1 calc R . . H3B H -0.0014 -0.2607 0.0184 0.038 Uiso 1 1 calc R . . H3C H -0.0346 -0.1628 0.0313 0.038 Uiso 1 1 calc R . . C4 C 0.10844(9) -0.12422(15) 0.07040(11) 0.0185(4) Uani 1 1 d . . . H4 H 0.0691 -0.1314 0.0185 0.022 Uiso 1 1 calc R . . C5 C 0.14836(9) -0.21958(16) 0.08174(11) 0.0228(4) Uani 1 1 d . . . H5A H 0.1858 -0.2166 0.1343 0.034 Uiso 1 1 calc R . . H5B H 0.1599 -0.2210 0.0401 0.034 Uiso 1 1 calc R . . H5C H 0.1250 -0.2821 0.0781 0.034 Uiso 1 1 calc R . . C6 C 0.14160(10) -0.02670(16) 0.06649(13) 0.0255(5) Uani 1 1 d . . . H6A H 0.1476 -0.0307 0.0201 0.038 Uiso 1 1 calc R . . H6B H 0.1818 -0.0211 0.1153 0.038 Uiso 1 1 calc R . . H6C H 0.1166 0.0342 0.0615 0.038 Uiso 1 1 calc R . . C7 C 0.23648(8) -0.17002(15) 0.39015(11) 0.0176(4) Uani 1 1 d . . . H7 H 0.2503 -0.1438 0.4452 0.021 Uiso 1 1 calc R . . C8 C 0.21693(10) -0.28249(16) 0.38661(13) 0.0266(5) Uani 1 1 d . . . H8A H 0.2517 -0.3226 0.4271 0.040 Uiso 1 1 calc R . . H8B H 0.2043 -0.3108 0.3336 0.040 Uiso 1 1 calc R . . H8C H 0.1823 -0.2863 0.3968 0.040 Uiso 1 1 calc R . . C9 C 0.29160(9) -0.16340(17) 0.37615(12) 0.0250(4) Uani 1 1 d . . . H9A H 0.2784 -0.1826 0.3209 0.037 Uiso 1 1 calc R . . H9B H 0.3241 -0.2108 0.4125 0.037 Uiso 1 1 calc R . . H9C H 0.3076 -0.0926 0.3861 0.037 Uiso 1 1 calc R . . C10 C 0.19763(9) 0.04547(14) 0.33569(11) 0.0170(4) Uani 1 1 d . . . H10 H 0.1595 0.0887 0.3151 0.020 Uiso 1 1 calc R . . C11 C 0.23690(9) 0.07120(16) 0.42499(12) 0.0249(4) Uani 1 1 d . . . H11A H 0.2434 0.1460 0.4317 0.037 Uiso 1 1 calc R . . H11B H 0.2769 0.0362 0.4472 0.037 Uiso 1 1 calc R . . H11C H 0.2154 0.0477 0.4530 0.037 Uiso 1 1 calc R . . C12 C 0.22904(10) 0.07809(16) 0.28800(13) 0.0256(4) Uani 1 1 d . . . H12A H 0.2681 0.0406 0.3079 0.038 Uiso 1 1 calc R . . H12B H 0.2372 0.1526 0.2942 0.038 Uiso 1 1 calc R . . H12C H 0.2019 0.0619 0.2314 0.038 Uiso 1 1 calc R . . C13 C 0.09540(9) 0.43314(15) 0.40099(11) 0.0203(4) Uani 1 1 d . . . H13 H 0.1369 0.4066 0.4418 0.024 Uiso 1 1 calc R . . C14 C 0.05316(10) 0.42839(16) 0.43694(12) 0.0254(4) Uani 1 1 d . . . H14A H 0.0127 0.4572 0.3990 0.038 Uiso 1 1 calc R . . H14B H 0.0714 0.4686 0.4865 0.038 Uiso 1 1 calc R . . H14C H 0.0483 0.3563 0.4484 0.038 Uiso 1 1 calc R . . C15 C 0.10352(11) 0.54488(15) 0.38180(14) 0.0288(5) Uani 1 1 d . . . H15A H 0.1200 0.5867 0.4304 0.043 Uiso 1 1 calc R . . H15B H 0.0634 0.5727 0.3416 0.043 Uiso 1 1 calc R . . H15C H 0.1322 0.5467 0.3611 0.043 Uiso 1 1 calc R . . C16 C 0.11679(9) 0.37204(15) 0.27010(11) 0.0195(4) Uani 1 1 d . . . H16 H 0.1089 0.4440 0.2483 0.023 Uiso 1 1 calc R . . C17 C 0.18570(9) 0.36416(17) 0.33068(13) 0.0267(5) Uani 1 1 d . . . H17A H 0.2096 0.3758 0.3037 0.040 Uiso 1 1 calc R . . H17B H 0.1949 0.2952 0.3549 0.040 Uiso 1 1 calc R . . H17C H 0.1968 0.4164 0.3723 0.040 Uiso 1 1 calc R . . C18 C 0.09862(9) 0.29859(16) 0.19990(12) 0.0234(4) Uani 1 1 d . . . H18A H 0.1135 0.2289 0.2201 0.035 Uiso 1 1 calc R . . H18B H 0.1171 0.3224 0.1683 0.035 Uiso 1 1 calc R . . H18C H 0.0536 0.2975 0.1663 0.035 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Sb1 0.01080(8) 0.01618(9) 0.01182(8) 0.000 0.00607(7) 0.000 Se1 0.01620(10) 0.01910(10) 0.01292(9) 0.00288(7) 0.00842(8) 0.00444(7) Se2 0.01390(9) 0.02534(10) 0.01356(9) 0.00263(7) 0.00847(8) 0.00132(7) Se3 0.01437(9) 0.01794(10) 0.01388(9) 0.00082(7) 0.00432(7) -0.00050(7) P1 0.0119(2) 0.0175(2) 0.0102(2) 0.00034(17) 0.00545(18) 0.00159(18) P2 0.0109(2) 0.0191(2) 0.0101(2) 0.00034(17) 0.00504(18) 0.00018(18) P3 0.0118(2) 0.0171(2) 0.0136(2) -0.00044(18) 0.00537(19) -0.00089(18) N1 0.0133(8) 0.0192(8) 0.0110(7) 0.0007(6) 0.0059(6) 0.0011(6) N2 0.0131(11) 0.0182(11) 0.0155(11) 0.000 0.0062(9) 0.000 C1 0.0137(9) 0.0204(10) 0.0160(9) -0.0013(7) 0.0052(8) -0.0020(7) C2 0.0251(11) 0.0237(11) 0.0357(13) 0.0059(9) 0.0075(10) -0.0018(9) C3 0.0196(10) 0.0296(11) 0.0186(10) -0.0041(8) 0.0040(8) -0.0050(9) C4 0.0156(9) 0.0290(10) 0.0105(9) 0.0010(7) 0.0061(7) 0.0055(8) C5 0.0206(10) 0.0309(11) 0.0169(10) -0.0042(8) 0.0093(8) 0.0054(8) C6 0.0267(11) 0.0327(12) 0.0255(11) 0.0079(9) 0.0194(9) 0.0074(9) C7 0.0144(9) 0.0251(10) 0.0109(9) 0.0024(7) 0.0046(7) 0.0025(8) C8 0.0228(11) 0.0275(11) 0.0274(11) 0.0087(9) 0.0109(9) 0.0054(9) C9 0.0164(10) 0.0341(12) 0.0243(11) 0.0070(9) 0.0101(9) 0.0059(9) C10 0.0144(9) 0.0200(9) 0.0149(9) -0.0014(7) 0.0060(8) -0.0014(7) C11 0.0201(10) 0.0281(11) 0.0196(10) -0.0068(8) 0.0047(9) -0.0025(8) C12 0.0269(11) 0.0261(11) 0.0282(11) 0.0000(9) 0.0169(10) -0.0057(9) C13 0.0179(10) 0.0224(10) 0.0153(9) -0.0036(8) 0.0042(8) -0.0013(8) C14 0.0322(12) 0.0267(11) 0.0190(10) -0.0031(8) 0.0142(9) 0.0005(9) C15 0.0335(12) 0.0230(11) 0.0313(12) -0.0079(9) 0.0171(10) -0.0077(9) C16 0.0153(9) 0.0215(10) 0.0238(10) 0.0028(8) 0.0114(8) -0.0012(8) C17 0.0150(10) 0.0340(12) 0.0307(12) -0.0033(9) 0.0111(9) -0.0036(9) C18 0.0206(10) 0.0293(11) 0.0249(11) -0.0008(8) 0.0149(9) -0.0001(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Sb1 Se3 2.8694(3) . ? Sb1 Se3 2.8694(3) 2 ? Sb1 Se1 2.8726(4) . ? Sb1 Se1 2.8726(4) 2 ? Sb1 Se2 2.9273(4) 2 ? Sb1 Se2 2.9273(4) . ? Se1 P1 2.1982(5) . ? Se2 P2 2.1996(6) . ? Se3 P3 2.1916(6) . ? P1 N1 1.6041(15) . ? P1 C4 1.8310(19) . ? P1 C1 1.8471(19) . ? P2 N1 1.5947(15) . ? P2 C10 1.8377(19) . ? P2 C7 1.8378(19) . ? P3 N2 1.5849(9) . ? P3 C16 1.8294(19) . ? P3 C13 1.8327(19) . ? N2 P3 1.5849(9) 2 ? C1 C2 1.532(3) . ? C1 C3 1.537(3) . ? C1 H1 1.0000 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 C6 1.532(3) . ? C4 C5 1.532(3) . ? C4 H4 1.0000 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.526(3) . ? C7 C9 1.531(3) . ? C7 H7 1.0000 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C12 1.536(3) . ? C10 C11 1.538(3) . ? C10 H10 1.0000 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.525(3) . ? C13 C15 1.531(3) . ? C13 H13 1.0000 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.529(3) . ? C16 C18 1.528(3) . ? C16 H16 1.0000 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Se3 Sb1 Se3 91.176(14) . 2 ? Se3 Sb1 Se1 103.380(12) . . ? Se3 Sb1 Se1 79.793(12) 2 . ? Se3 Sb1 Se1 79.793(12) . 2 ? Se3 Sb1 Se1 103.379(12) 2 2 ? Se1 Sb1 Se1 175.562(10) . 2 ? Se3 Sb1 Se2 167.986(6) . 2 ? Se3 Sb1 Se2 83.099(12) 2 2 ? Se1 Sb1 Se2 86.051(12) . 2 ? Se1 Sb1 Se2 91.226(12) 2 2 ? Se3 Sb1 Se2 83.099(12) . . ? Se3 Sb1 Se2 167.986(6) 2 . ? Se1 Sb1 Se2 91.226(12) . . ? Se1 Sb1 Se2 86.051(12) 2 . ? Se2 Sb1 Se2 104.390(14) 2 . ? P1 Se1 Sb1 107.547(15) . . ? P2 Se2 Sb1 106.502(18) . . ? P3 Se3 Sb1 116.517(17) . . ? N1 P1 C4 106.28(8) . . ? N1 P1 C1 110.83(8) . . ? C4 P1 C1 109.00(9) . . ? N1 P1 Se1 117.28(6) . . ? C4 P1 Se1 106.73(6) . . ? C1 P1 Se1 106.45(6) . . ? N1 P2 C10 111.51(8) . . ? N1 P2 C7 106.47(8) . . ? C10 P2 C7 107.72(9) . . ? N1 P2 Se2 117.41(6) . . ? C10 P2 Se2 106.87(6) . . ? C7 P2 Se2 106.39(6) . . ? N2 P3 C16 107.33(7) . . ? N2 P3 C13 106.91(9) . . ? C16 P3 C13 106.81(9) . . ? N2 P3 Se3 120.55(7) . . ? C16 P3 Se3 109.69(7) . . ? C13 P3 Se3 104.77(7) . . ? P2 N1 P1 129.25(10) . . ? P3 N2 P3 140.68(15) . 2 ? C2 C1 C3 112.37(16) . . ? C2 C1 P1 114.19(13) . . ? C3 C1 P1 111.97(13) . . ? C2 C1 H1 105.8 . . ? C3 C1 H1 105.8 . . ? P1 C1 H1 105.8 . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C6 C4 C5 109.99(16) . . ? C6 C4 P1 111.61(13) . . ? C5 C4 P1 110.38(13) . . ? C6 C4 H4 108.3 . . ? C5 C4 H4 108.3 . . ? P1 C4 H4 108.3 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C8 C7 C9 109.93(16) . . ? C8 C7 P2 111.22(13) . . ? C9 C7 P2 112.30(13) . . ? C8 C7 H7 107.7 . . ? C9 C7 H7 107.7 . . ? P2 C7 H7 107.7 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C12 C10 C11 112.48(16) . . ? C12 C10 P2 114.00(13) . . ? C11 C10 P2 111.66(13) . . ? C12 C10 H10 106.0 . . ? C11 C10 H10 106.0 . . ? P2 C10 H10 106.0 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C15 110.67(17) . . ? C14 C13 P3 111.14(14) . . ? C15 C13 P3 111.41(14) . . ? C14 C13 H13 107.8 . . ? C15 C13 H13 107.8 . . ? P3 C13 H13 107.8 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 C18 111.23(16) . . ? C17 C16 P3 114.01(14) . . ? C18 C16 P3 109.60(13) . . ? C17 C16 H16 107.2 . . ? C18 C16 H16 107.2 . . ? P3 C16 H16 107.2 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? 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 Se3 Sb1 Se1 P1 107.197(18) . . . . ? Se3 Sb1 Se1 P1 -164.028(15) 2 . . . ? Se1 Sb1 Se1 P1 -28.092(15) 2 . . . ? Se2 Sb1 Se1 P1 -80.341(18) 2 . . . ? Se2 Sb1 Se1 P1 24.000(15) . . . . ? Se3 Sb1 Se2 P2 -80.732(18) . . . . ? Se3 Sb1 Se2 P2 -18.73(4) 2 . . . ? Se1 Sb1 Se2 P2 22.598(15) . . . . ? Se1 Sb1 Se2 P2 -160.911(15) 2 . . . ? Se2 Sb1 Se2 P2 108.835(17) 2 . . . ? Se3 Sb1 Se3 P3 -13.885(14) 2 . . . ? Se1 Sb1 Se3 P3 65.902(19) . . . . ? Se1 Sb1 Se3 P3 -117.269(19) 2 . . . ? Se2 Sb1 Se3 P3 -75.14(4) 2 . . . ? Se2 Sb1 Se3 P3 155.522(16) . . . . ? Sb1 Se1 P1 N1 -64.83(7) . . . . ? Sb1 Se1 P1 C4 176.19(7) . . . . ? Sb1 Se1 P1 C1 59.88(6) . . . . ? Sb1 Se2 P2 N1 -64.59(7) . . . . ? Sb1 Se2 P2 C10 61.49(6) . . . . ? Sb1 Se2 P2 C7 176.37(6) . . . . ? Sb1 Se3 P3 N2 35.17(4) . . . . ? Sb1 Se3 P3 C16 -90.19(7) . . . . ? Sb1 Se3 P3 C13 155.49(7) . . . . ? C10 P2 N1 P1 -84.95(14) . . . . ? C7 P2 N1 P1 157.81(12) . . . . ? Se2 P2 N1 P1 38.81(14) . . . . ? C4 P1 N1 P2 155.67(12) . . . . ? C1 P1 N1 P2 -86.03(14) . . . . ? Se1 P1 N1 P2 36.45(14) . . . . ? C16 P3 N2 P3 106.42(7) . . . 2 ? C13 P3 N2 P3 -139.28(7) . . . 2 ? Se3 P3 N2 P3 -20.03(2) . . . 2 ? N1 P1 C1 C2 -34.22(17) . . . . ? C4 P1 C1 C2 82.42(16) . . . . ? Se1 P1 C1 C2 -162.80(13) . . . . ? N1 P1 C1 C3 -163.35(13) . . . . ? C4 P1 C1 C3 -46.71(16) . . . . ? Se1 P1 C1 C3 68.07(14) . . . . ? N1 P1 C4 C6 -72.40(15) . . . . ? C1 P1 C4 C6 168.10(13) . . . . ? Se1 P1 C4 C6 53.51(14) . . . . ? N1 P1 C4 C5 50.24(15) . . . . ? C1 P1 C4 C5 -69.25(15) . . . . ? Se1 P1 C4 C5 176.15(12) . . . . ? N1 P2 C7 C8 -65.77(15) . . . . ? C10 P2 C7 C8 174.50(13) . . . . ? Se2 P2 C7 C8 60.20(14) . . . . ? N1 P2 C7 C9 57.91(16) . . . . ? C10 P2 C7 C9 -61.82(16) . . . . ? Se2 P2 C7 C9 -176.12(12) . . . . ? N1 P2 C10 C12 -29.88(17) . . . . ? C7 P2 C10 C12 86.60(15) . . . . ? Se2 P2 C10 C12 -159.42(13) . . . . ? N1 P2 C10 C11 -158.72(13) . . . . ? C7 P2 C10 C11 -42.25(16) . . . . ? Se2 P2 C10 C11 71.74(14) . . . . ? N2 P3 C13 C14 60.16(16) . . . . ? C16 P3 C13 C14 174.80(14) . . . . ? Se3 P3 C13 C14 -68.86(14) . . . . ? N2 P3 C13 C15 -63.76(16) . . . . ? C16 P3 C13 C15 50.89(17) . . . . ? Se3 P3 C13 C15 167.23(13) . . . . ? N2 P3 C16 C17 164.34(15) . . . . ? C13 P3 C16 C17 49.98(17) . . . . ? Se3 P3 C16 C17 -63.03(15) . . . . ? N2 P3 C16 C18 -70.26(16) . . . . ? C13 P3 C16 C18 175.38(13) . . . . ? Se3 P3 C16 C18 62.37(14) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.42 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.430 _refine_diff_density_min -0.297 _refine_diff_density_rms 0.065 data_Complex_3 _database_code_CSD 199592 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C36 H84 Bi N3 P6 Se6' _chemical_formula_weight 1427.62 _chemical_melting_point ? _chemical_compound_source ? 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Bi Bi -4.1077 10.2566 '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 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 25.300(3) _cell_length_b 13.0081(14) _cell_length_c 19.672(3) _cell_angle_alpha 90.00 _cell_angle_beta 120.203(10) _cell_angle_gamma 90.00 _cell_volume 5595.1(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 28 _cell_measurement_theta_min 4.80 _cell_measurement_theta_max 12.48 _exptl_crystal_description prisms _exptl_crystal_colour Red _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.33 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.695 _exptl_crystal_density_method ? _exptl_crystal_F_000 2792 _exptl_absorpt_coefficient_mu 7.252 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.2339 _exptl_absorpt_correction_T_max 0.2844 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 11.36 _diffrn_reflns_number 4997 _diffrn_reflns_av_R_equivalents 0.0447 _diffrn_reflns_av_sigmaI/netI 0.0932 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4880 _reflns_number_observed 3002 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 522 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0315P)^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 riding _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00000(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4358 _refine_ls_number_parameters 237 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1059 _refine_ls_R_factor_obs 0.0517 _refine_ls_wR_factor_all 0.1107 _refine_ls_wR_factor_obs 0.0903 _refine_ls_goodness_of_fit_all 0.992 _refine_ls_goodness_of_fit_obs 1.077 _refine_ls_restrained_S_all 1.021 _refine_ls_restrained_S_obs 1.077 _refine_ls_shift/esd_max 0.007 _refine_ls_shift/esd_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Bi Bi 0.0000 0.03939(6) 0.2500 0.0443(2) Uani 1 d S . Se1 Se 0.03773(5) 0.03148(11) 0.13169(6) 0.0545(3) Uani 1 d . . Se2 Se 0.10057(5) -0.10329(11) 0.35334(7) 0.0600(4) Uani 1 d . . Se3 Se 0.08005(5) 0.19833(10) 0.36054(7) 0.0583(3) Uani 1 d . . P1 P 0.09008(11) -0.1097(2) 0.1501(2) 0.0438(6) Uani 1 d . . P2 P 0.17067(11) -0.0898(2) 0.3190(2) 0.0447(6) Uani 1 d . . P3 P 0.06625(11) 0.3540(2) 0.3130(2) 0.0497(7) Uani 1 d . . N1 N 0.1524(3) -0.1228(7) 0.2337(5) 0.047(2) Uani 1 d . . N2 N 0.0000 0.3902(11) 0.2500 0.054(3) Uani 1 d S . C1 C 0.0381(5) -0.2191(10) 0.1349(7) 0.063(3) Uani 1 d . . H1A H 0.0189 -0.2031 0.1662 0.076 Uiso 1 calc R . C2 C 0.0683(7) -0.3196(12) 0.1638(10) 0.100(6) Uani 1 d . . H2A H 0.1006 -0.3129 0.2175 0.151 Uiso 1 calc R . H2B H 0.0851 -0.3422 0.1322 0.151 Uiso 1 calc R . H2C H 0.0389 -0.3689 0.1606 0.151 Uiso 1 calc R . C3 C -0.0155(5) -0.2229(12) 0.0471(8) 0.080(4) Uani 1 d . . H3A H -0.0335 -0.1558 0.0313 0.119 Uiso 1 calc R . H3B H -0.0459 -0.2709 0.0424 0.119 Uiso 1 calc R . H3C H 0.0002 -0.2442 0.0139 0.119 Uiso 1 calc R . C4 C 0.1116(5) -0.1108(10) 0.0746(6) 0.057(3) Uani 1 d . . H4A H 0.0740 -0.1165 0.0234 0.068 Uiso 1 calc R . C5 C 0.1520(6) -0.2052(12) 0.0839(8) 0.080(4) Uani 1 d . . H5A H 0.1314 -0.2669 0.0844 0.120 Uiso 1 calc R . H5B H 0.1903 -0.1997 0.1324 0.120 Uiso 1 calc R . H5C H 0.1595 -0.2076 0.0407 0.120 Uiso 1 calc R . C6 C 0.1436(6) -0.0144(13) 0.0737(8) 0.086(5) Uani 1 d . . H6A H 0.1184 0.0439 0.0679 0.129 Uiso 1 calc R . H6B H 0.1510 -0.0166 0.0305 0.129 Uiso 1 calc R . H6C H 0.1818 -0.0087 0.1222 0.129 Uiso 1 calc R . C7 C 0.2345(5) -0.1726(11) 0.3872(7) 0.062(3) Uani 1 d . . H7A H 0.2488 -0.1487 0.4410 0.074 Uiso 1 calc R . C8 C 0.2131(7) -0.2833(13) 0.3807(11) 0.105(6) Uani 1 d . . H8A H 0.1793 -0.2861 0.3899 0.158 Uiso 1 calc R . H8B H 0.2460 -0.3247 0.4191 0.158 Uiso 1 calc R . H8C H 0.2004 -0.3089 0.3290 0.158 Uiso 1 calc R . C9 C 0.2882(6) -0.1688(14) 0.3724(9) 0.094(5) Uani 1 d . . H9A H 0.3019 -0.0991 0.3765 0.141 Uiso 1 calc R . H9B H 0.2754 -0.1947 0.3207 0.141 Uiso 1 calc R . H9C H 0.3211 -0.2104 0.4108 0.141 Uiso 1 calc R . C10 C 0.1988(4) 0.0435(11) 0.3393(6) 0.056(3) Uani 1 d . . H10A H 0.1619 0.0864 0.3165 0.067 Uiso 1 calc R . C11 C 0.2324(6) 0.0663(13) 0.4286(8) 0.087(5) Uani 1 d . . H11A H 0.2078 0.0435 0.4502 0.131 Uiso 1 calc R . H11B H 0.2395 0.1389 0.4371 0.131 Uiso 1 calc R . H11C H 0.2708 0.0305 0.4541 0.131 Uiso 1 calc R . C12 C 0.2335(6) 0.0763(11) 0.2970(9) 0.084(4) Uani 1 d . . H12A H 0.2095 0.0594 0.2422 0.126 Uiso 1 calc R . H12B H 0.2719 0.0408 0.3198 0.126 Uiso 1 calc R . H12C H 0.2406 0.1491 0.3028 0.126 Uiso 1 calc R . C13 C 0.0934(5) 0.4378(10) 0.3988(7) 0.066(3) Uani 1 d . . H13A H 0.1352 0.4172 0.4376 0.079 Uiso 1 calc R . C14 C 0.0546(7) 0.4304(12) 0.4371(8) 0.081(4) Uani 1 d . . H14A H 0.0536 0.3604 0.4518 0.122 Uiso 1 calc R . H14B H 0.0138 0.4530 0.4006 0.122 Uiso 1 calc R . H14C H 0.0718 0.4731 0.4831 0.122 Uiso 1 calc R . C15 C 0.0949(7) 0.5479(14) 0.3758(11) 0.103(5) Uani 1 d . . H15A H 0.1196 0.5528 0.3515 0.155 Uiso 1 calc R . H15B H 0.1121 0.5905 0.4219 0.155 Uiso 1 calc R . H15C H 0.0541 0.5704 0.3395 0.155 Uiso 1 calc R . C16 C 0.1157(4) 0.3738(10) 0.2710(8) 0.064(3) Uani 1 d . . H16A H 0.1077 0.4437 0.2495 0.076 Uiso 1 calc R . C17 C 0.1847(5) 0.3691(14) 0.3332(10) 0.095(5) Uani 1 d . . H17A H 0.1933 0.4158 0.3754 0.143 Uiso 1 calc R . H17B H 0.2083 0.3881 0.3093 0.143 Uiso 1 calc R . H17C H 0.1952 0.3004 0.3536 0.143 Uiso 1 calc R . C18 C 0.0986(6) 0.3021(13) 0.2026(9) 0.082(4) Uani 1 d . . H18A H 0.0556 0.3077 0.1657 0.123 Uiso 1 calc R . H18B H 0.1082 0.2326 0.2214 0.123 Uiso 1 calc R . H18C H 0.1212 0.3203 0.1771 0.123 Uiso 1 calc R . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Bi 0.0333(3) 0.0566(4) 0.0474(4) 0.000 0.0235(3) 0.000 Se1 0.0540(6) 0.0659(8) 0.0519(6) 0.0115(6) 0.0329(5) 0.0168(6) Se2 0.0439(5) 0.0902(10) 0.0552(7) 0.0172(6) 0.0317(5) 0.0091(6) Se3 0.0451(6) 0.0615(8) 0.0547(7) 0.0007(6) 0.0150(5) -0.0002(5) P1 0.0345(12) 0.056(2) 0.0426(14) 0.0016(13) 0.0203(11) 0.0043(12) P2 0.0321(11) 0.063(2) 0.0386(14) 0.0020(13) 0.0173(11) 0.0018(12) P3 0.0312(12) 0.060(2) 0.052(2) -0.0035(14) 0.0164(12) -0.0043(12) N1 0.032(4) 0.061(6) 0.045(5) 0.002(4) 0.017(4) 0.012(4) N2 0.044(6) 0.061(9) 0.054(8) 0.000 0.023(6) 0.000 C1 0.057(6) 0.062(8) 0.063(7) 0.002(6) 0.024(6) -0.009(6) C2 0.074(9) 0.071(11) 0.110(13) 0.006(9) 0.012(9) -0.018(8) C3 0.056(7) 0.080(10) 0.076(9) -0.012(8) 0.013(6) -0.014(7) C4 0.047(5) 0.095(10) 0.035(5) 0.001(6) 0.025(5) 0.005(6) C5 0.062(7) 0.103(12) 0.072(8) -0.015(8) 0.031(7) 0.023(8) C6 0.086(9) 0.122(14) 0.083(9) 0.027(9) 0.067(8) 0.016(9) C7 0.061(6) 0.080(9) 0.046(6) 0.010(6) 0.027(6) 0.010(6) C8 0.094(11) 0.088(12) 0.113(13) 0.039(10) 0.038(10) 0.026(9) C9 0.058(7) 0.126(14) 0.104(11) 0.045(10) 0.047(8) 0.033(8) C10 0.039(5) 0.065(7) 0.057(6) -0.004(7) 0.018(5) -0.004(6) C11 0.065(8) 0.103(13) 0.068(8) -0.008(8) 0.014(7) 0.011(8) C12 0.081(9) 0.080(10) 0.109(12) -0.026(8) 0.061(9) -0.030(7) C13 0.057(6) 0.058(9) 0.063(7) -0.011(6) 0.015(6) -0.005(6) C14 0.095(10) 0.085(11) 0.060(8) -0.019(7) 0.036(7) -0.007(8) C15 0.094(10) 0.094(13) 0.132(14) -0.024(12) 0.065(10) -0.032(10) C16 0.038(5) 0.062(8) 0.094(9) 0.002(7) 0.035(6) -0.001(5) C17 0.047(7) 0.124(14) 0.122(13) -0.019(11) 0.047(8) -0.015(8) C18 0.072(8) 0.102(12) 0.097(10) 0.001(9) 0.062(8) 0.002(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Bi Se1 2.9281(10) . ? Bi Se1 2.9281(10) 2 ? Bi Se3 2.9451(14) . ? Bi Se3 2.9451(13) 2 ? Bi Se2 2.9744(13) 2 ? Bi Se2 2.9744(13) . ? Se1 P1 2.185(3) . ? Se2 P2 2.200(3) . ? Se3 P3 2.184(3) . ? P1 N1 1.616(8) . ? P1 C4 1.823(9) . ? P1 C1 1.857(12) . ? P2 N1 1.560(9) . ? P2 C10 1.839(13) . ? P2 C7 1.841(12) . ? P3 N2 1.574(5) . ? P3 C13 1.829(12) . ? P3 C16 1.832(11) . ? N2 P3 1.574(5) 2 ? C1 C2 1.48(2) . ? C1 C3 1.57(2) . ? C4 C6 1.50(2) . ? C4 C5 1.55(2) . ? C7 C8 1.52(2) . ? C7 C9 1.53(2) . ? C10 C12 1.54(2) . ? C10 C11 1.55(2) . ? C13 C15 1.51(2) . ? C13 C14 1.51(2) . ? C16 C18 1.51(2) . ? C16 C17 1.55(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 Se1 Bi Se1 175.97(7) . 2 ? Se1 Bi Se3 103.50(4) . . ? Se1 Bi Se3 79.39(4) 2 . ? Se1 Bi Se3 79.39(4) . 2 ? Se1 Bi Se3 103.50(4) 2 2 ? Se3 Bi Se3 90.82(5) . 2 ? Se1 Bi Se2 86.77(4) . 2 ? Se1 Bi Se2 90.71(3) 2 2 ? Se3 Bi Se2 167.62(3) . 2 ? Se3 Bi Se2 84.22(4) 2 2 ? Se1 Bi Se2 90.71(3) . . ? Se1 Bi Se2 86.77(4) 2 . ? Se3 Bi Se2 84.22(4) . . ? Se3 Bi Se2 167.62(3) 2 . ? Se2 Bi Se2 102.78(6) 2 . ? P1 Se1 Bi 108.07(8) . . ? P2 Se2 Bi 106.55(9) . . ? P3 Se3 Bi 115.61(8) . . ? N1 P1 C4 106.8(4) . . ? N1 P1 C1 109.4(5) . . ? C4 P1 C1 109.9(6) . . ? N1 P1 Se1 117.3(3) . . ? C4 P1 Se1 106.0(4) . . ? C1 P1 Se1 107.3(4) . . ? N1 P2 C10 111.5(5) . . ? N1 P2 C7 107.4(5) . . ? C10 P2 C7 107.0(5) . . ? N1 P2 Se2 117.4(3) . . ? C10 P2 Se2 107.0(3) . . ? C7 P2 Se2 106.0(4) . . ? N2 P3 C13 107.8(6) . . ? N2 P3 C16 107.6(4) . . ? C13 P3 C16 107.9(6) . . ? N2 P3 Se3 119.5(5) . . ? C13 P3 Se3 104.6(4) . . ? C16 P3 Se3 109.0(4) . . ? P2 N1 P1 132.4(5) . . ? P3 N2 P3 145.2(10) 2 . ? C2 C1 C3 112.9(12) . . ? C2 C1 P1 115.4(9) . . ? C3 C1 P1 110.5(9) . . ? C6 C4 C5 109.8(10) . . ? C6 C4 P1 112.8(9) . . ? C5 C4 P1 111.1(9) . . ? C8 C7 C9 109.1(13) . . ? C8 C7 P2 110.4(9) . . ? C9 C7 P2 112.4(9) . . ? C12 C10 C11 114.9(10) . . ? C12 C10 P2 114.0(9) . . ? C11 C10 P2 111.0(10) . . ? C15 C13 C14 109.3(12) . . ? C15 C13 P3 110.1(10) . . ? C14 C13 P3 112.7(9) . . ? C18 C16 C17 112.6(11) . . ? C18 C16 P3 111.1(8) . . ? C17 C16 P3 113.1(10) . . ? _refine_diff_density_max 0.855 _refine_diff_density_min -0.560 _refine_diff_density_rms 0.130