# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_request # Attachment 'final.cif' #'A Planar P6Se6 Macrocycle Incorporating P2N2 Scaffolds' #===END _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _publ_contact_author 'Tristram Chivers' _publ_contact_author_email chivers@ucalgary.ca _publ_contact_author_name 'Tristram Chivers' loop_ _publ_author_name 'Tristram Chivers' 'Andreas Nordheider' 'Ramalingam Thirumoorthi' 'Ignacio Vargas-Baca' J.Woollins data_compound2 _database_code_depnum_ccdc_archive 'CCDC 867162' #TrackingRef 'final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C48 H108 N12 P6 Se6' _chemical_formula_sum 'C48 H108 N12 P6 Se6' _chemical_formula_weight 1513.04 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' 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' _symmetry_cell_setting Trigonal _symmetry_space_group_name_H-M 'P 63/m ' _symmetry_space_group_name_HALL '-P 6c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-x, -y, z+1/2' 'y, -x+y, z+1/2' 'x-y, x, z+1/2' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' 'x, y, -z-1/2' '-y, x-y, -z-1/2' '-x+y, -x, -z-1/2' _cell_length_a 16.643(2) _cell_length_b 16.643(2) _cell_length_c 15.319(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 3674.7(11) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 8832 _cell_measurement_theta_min 1.9 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.367 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1548 _exptl_absorpt_coefficient_mu 3.155 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.5855 _exptl_absorpt_correction_T_max 0.8582 _exptl_absorpt_process_details 'SADABS (SHELXTL-NT v5.1, Bruker)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enraf Nonius FR590D, fine-focus sealed tube' _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_device_type 'KappaCCD (Nonius, FR540C)' _diffrn_measurement_method 'phi\omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7081 _diffrn_reflns_av_R_equivalents 0.0547 _diffrn_reflns_av_sigmaI/netI 0.0456 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.79 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2244 _reflns_number_gt 1628 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0760P)^2^+16.6374P] 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 2244 _refine_ls_number_parameters 121 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0916 _refine_ls_R_factor_gt 0.0606 _refine_ls_wR_factor_ref 0.1780 _refine_ls_wR_factor_gt 0.1553 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.8227(7) 0.0648(6) 0.2500 0.047(3) Uani 1 2 d S . . C2 C 0.9285(8) 0.1201(9) 0.2500 0.092(6) Uani 1 2 d S . . H2A H 0.9498 0.1589 0.3009 0.139 Uiso 0.50 1 calc PR . . H2B H 0.9498 0.1581 0.1986 0.139 Uiso 0.50 1 calc PR . . H2C H 0.9524 0.0782 0.2505 0.139 Uiso 1 2 calc SR . . C3 C 0.7861(7) 0.0015(6) 0.3298(7) 0.077(3) Uani 1 1 d . . . H3A H 0.7195 -0.0327 0.3282 0.116 Uiso 1 1 calc R . . H3B H 0.8064 0.0384 0.3819 0.116 Uiso 1 1 calc R . . H3C H 0.8093 -0.0409 0.3294 0.116 Uiso 1 1 calc R . . C5 C 0.9197(12) 0.4039(12) 0.4490(12) 0.066(5) Uiso 0.50 1 d P A 1 C5A C 0.8164(11) 0.3504(11) 0.4558(11) 0.056(4) Uiso 0.50 1 d P A 2 C6 C 0.9546(11) 0.2744(12) 0.4337(12) 0.061(4) Uiso 0.50 1 d P A 1 C6A C 0.9686(12) 0.3563(12) 0.4640(12) 0.065(5) Uiso 0.50 1 d P A 2 C7 C 0.7858(13) 0.2373(13) 0.4489(14) 0.061(5) Uiso 0.45 1 d P A 1 C7A C 0.8166(10) 0.2020(11) 0.4609(11) 0.059(4) Uiso 0.55 1 d P A 2 C9 C 1.2024(7) 0.4295(7) 0.2500 0.052(3) Uani 1 2 d S . . H9A H 1.1886 0.3919 0.1986 0.078 Uiso 0.50 1 calc PR . . H9B H 1.1879 0.3911 0.3009 0.078 Uiso 0.50 1 calc PR . . H9C H 1.2671 0.4756 0.2505 0.078 Uiso 1 2 calc SR . . C10- C 1.1661(5) 0.5367(5) 0.3313(5) 0.0473(19) Uani 1 1 d . . . H10A H 1.1518 0.4982 0.3821 0.071 Uiso 1 1 calc R . . H10B H 1.1295 0.5665 0.3315 0.071 Uiso 1 1 calc R . . H10C H 1.2307 0.5828 0.3316 0.071 Uiso 1 1 calc R . . N1 N 0.7797(5) 0.1229(5) 0.2500 0.042(2) Uani 1 2 d S A . C4 C 0.8762(5) 0.3038(5) 0.4197(5) 0.0487(19) Uani 1 1 d . . . C8 C 1.1443(6) 0.4774(6) 0.2500 0.037(2) Uani 1 2 d S . . N2 N 0.8736(3) 0.3048(3) 0.3239(4) 0.0347(13) Uani 1 1 d . . . N3 N 1.0471(5) 0.4024(5) 0.2500 0.0371(19) Uani 1 2 d S . . P1 P 0.80514(15) 0.22341(15) 0.2500 0.0345(6) Uani 1 2 d S . . P2 P 0.94838(15) 0.38176(15) 0.2500 0.0348(6) Uani 1 2 d S . . Se1 Se 0.66749(6) 0.21876(6) 0.2500 0.0609(5) Uani 1 2 d S . . Se2 Se 0.94141(6) 0.51403(6) 0.2500 0.0573(4) 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 C1 0.040(5) 0.031(5) 0.078(9) 0.000 0.000 0.023(4) C2 0.044(7) 0.061(8) 0.184(18) 0.000 0.000 0.035(6) C3 0.104(8) 0.053(5) 0.094(8) 0.015(5) 0.002(6) 0.053(5) C9 0.031(5) 0.045(6) 0.087(9) 0.000 0.000 0.024(5) C10- 0.039(4) 0.045(4) 0.050(5) -0.012(4) -0.006(3) 0.015(3) N1 0.026(4) 0.029(4) 0.068(6) 0.000 0.000 0.011(3) C4 0.051(4) 0.044(4) 0.049(5) -0.001(4) -0.011(4) 0.022(3) C8 0.018(4) 0.030(4) 0.061(7) 0.000 0.000 0.010(4) N2 0.028(3) 0.031(3) 0.041(4) -0.005(2) -0.001(2) 0.011(2) N3 0.022(4) 0.021(4) 0.062(6) 0.000 0.000 0.007(3) P1 0.0218(11) 0.0245(11) 0.0558(18) 0.000 0.000 0.0104(9) P2 0.0228(11) 0.0241(11) 0.0558(18) 0.000 0.000 0.0104(9) Se1 0.0231(5) 0.0248(5) 0.1334(13) 0.000 0.000 0.0110(4) Se2 0.0236(5) 0.0245(5) 0.1246(12) 0.000 0.000 0.0127(4) _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 N1 1.462(11) . ? C1 C2 1.525(15) . ? C1 C3 1.527(10) 10_556 ? C1 C3 1.527(10) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C5 C4 1.514(18) . ? C5A C4 1.633(18) . ? C6 C4 1.622(18) . ? C6A C4 1.499(19) . ? C7 C4 1.42(2) . ? C7A C4 1.605(17) . ? C9 C8 1.529(12) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10- C8 1.516(9) . ? C10- H10A 0.9600 . ? C10- H10B 0.9600 . ? C10- H10C 0.9600 . ? N1 P1 1.507(8) . ? C4 N2 1.469(10) . ? C8 N3 1.468(10) . ? C8 C10- 1.516(9) 10_556 ? N2 P1 1.695(5) . ? N2 P2 1.695(6) . ? N3 P2 1.501(7) . ? P1 N2 1.695(5) 10_556 ? P1 Se1 2.253(2) . ? P1 P2 2.519(3) . ? P2 N2 1.695(6) 10_556 ? P2 Se2 2.262(2) . ? Se1 Se2 2.3217(14) 3_665 ? Se2 Se1 2.3217(14) 2_655 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 113.5(8) . . ? N1 C1 C3 107.3(6) . 10_556 ? C2 C1 C3 111.0(6) . 10_556 ? N1 C1 C3 107.3(6) . . ? C2 C1 C3 111.0(6) . . ? C3 C1 C3 106.4(9) 10_556 . ? 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 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10- H10A 109.5 . . ? C8 C10- H10B 109.5 . . ? H10A C10- H10B 109.5 . . ? C8 C10- H10C 109.5 . . ? H10A C10- H10C 109.5 . . ? H10B C10- H10C 109.5 . . ? C1 N1 P1 140.9(7) . . ? C7 C4 N2 107.3(10) . . ? C7 C4 C6A 133.5(13) . . ? N2 C4 C6A 118.3(9) . . ? C7 C4 C5 120.0(12) . . ? N2 C4 C5 106.5(9) . . ? C6A C4 C5 55.8(10) . . ? C7 C4 C7A 36.8(8) . . ? N2 C4 C7A 113.5(8) . . ? C6A C4 C7A 110.4(10) . . ? C5 C4 C7A 138.4(11) . . ? C7 C4 C6 114.9(11) . . ? N2 C4 C6 99.7(8) . . ? C6A C4 C6 51.0(9) . . ? C5 C4 C6 106.2(10) . . ? C7A C4 C6 78.1(9) . . ? C7 C4 C5A 66.7(10) . . ? N2 C4 C5A 107.8(8) . . ? C6A C4 C5A 105.1(10) . . ? C5 C4 C5A 56.5(9) . . ? C7A C4 C5A 99.6(9) . . ? C6 C4 C5A 150.7(11) . . ? N3 C8 C10- 110.9(5) . . ? N3 C8 C10- 110.9(5) . 10_556 ? C10- C8 C10- 110.4(8) . 10_556 ? N3 C8 C9 105.8(7) . . ? C10- C8 C9 109.3(5) . . ? C10- C8 C9 109.3(5) 10_556 . ? C4 N2 P1 132.1(4) . . ? C4 N2 P2 131.4(4) . . ? P1 N2 P2 96.0(3) . . ? C8 N3 P2 144.0(6) . . ? N1 P1 N2 126.2(3) . . ? N1 P1 N2 126.2(3) . 10_556 ? N2 P1 N2 83.8(4) . 10_556 ? N1 P1 Se1 104.2(3) . . ? N2 P1 Se1 107.05(19) . . ? N2 P1 Se1 107.05(19) 10_556 . ? N1 P1 P2 139.0(3) . . ? N2 P1 P2 42.01(19) . . ? N2 P1 P2 42.01(19) 10_556 . ? Se1 P1 P2 116.74(11) . . ? N3 P2 N2 118.6(3) . 10_556 ? N3 P2 N2 118.6(3) . . ? N2 P2 N2 83.7(4) 10_556 . ? N3 P2 Se2 111.1(3) . . ? N2 P2 Se2 111.1(2) 10_556 . ? N2 P2 Se2 111.1(2) . . ? N3 P2 P1 126.4(3) . . ? N2 P2 P1 41.99(19) 10_556 . ? N2 P2 P1 41.99(19) . . ? Se2 P2 P1 122.42(11) . . ? P1 Se1 Se2 97.79(7) . 3_665 ? P2 Se2 Se1 98.63(7) . 2_655 ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.925 _refine_diff_density_min -0.700 _refine_diff_density_rms 0.115 #===END data_compound3 _database_code_depnum_ccdc_archive 'CCDC 867163' #TrackingRef 'final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H36 N4 P2 Se4' _chemical_formula_sum 'C16 H36 N4 P2 Se4' _chemical_formula_weight 662.27 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' P P 0.1023 0.0942 '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 'P 21/a ' _symmetry_space_group_name_Hall '-P 2yab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 11.2800(5) _cell_length_b 14.7500(5) _cell_length_c 15.5840(7) _cell_angle_alpha 90.00 _cell_angle_beta 95.3030(17) _cell_angle_gamma 90.00 _cell_volume 2581.77(18) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9486 _cell_measurement_theta_min 1.9 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.704 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1304 _exptl_absorpt_coefficient_mu 5.817 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.3358 _exptl_absorpt_correction_T_max 0.5185 _exptl_absorpt_process_details 'SADABS (SHELXTL-NT v5.1, Bruker)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7279 _diffrn_reflns_av_R_equivalents 0.0867 _diffrn_reflns_av_sigmaI/netI 0.1000 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.35 _diffrn_reflns_theta_max 24.50 _reflns_number_total 4181 _reflns_number_gt 2888 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^+46.4628P] 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 4181 _refine_ls_number_parameters 247 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1259 _refine_ls_R_factor_gt 0.0798 _refine_ls_wR_factor_ref 0.1728 _refine_ls_wR_factor_gt 0.1465 _refine_ls_goodness_of_fit_ref 1.151 _refine_ls_restrained_S_all 1.151 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.3580(3) 0.5260(2) 0.2002(2) 0.0239(7) Uani 1 1 d . . . P2 P 0.1729(3) 0.4706(2) 0.25982(19) 0.0248(7) Uani 1 1 d . . . Se1 Se 0.34395(12) 0.61929(9) 0.08304(9) 0.0370(4) Uani 1 1 d . . . Se2 Se -0.00825(11) 0.51460(9) 0.19742(9) 0.0350(4) Uani 1 1 d . . . Se3 Se 0.15222(13) 0.59204(10) 0.01798(9) 0.0412(4) Uani 1 1 d . . . Se4 Se 0.03057(13) 0.64455(9) 0.11954(10) 0.0446(4) Uani 1 1 d . . . N1 N 0.2578(8) 0.4408(6) 0.1810(6) 0.024(2) Uani 1 1 d . . . N2 N 0.2618(9) 0.5632(6) 0.2691(6) 0.029(2) Uani 1 1 d . . . N3 N 0.4844(9) 0.5103(6) 0.2366(6) 0.029(2) Uani 1 1 d . . . N4 N 0.1652(8) 0.4038(7) 0.3313(6) 0.028(2) Uani 1 1 d . . . C1 C 0.2700(11) 0.3512(8) 0.1377(7) 0.026(3) Uani 1 1 d . . . C2 C 0.3312(12) 0.3675(8) 0.0545(8) 0.039(3) Uani 1 1 d . . . H2A H 0.2794 0.4022 0.0147 0.059 Uiso 1 1 calc R . . H2B H 0.3483 0.3103 0.0289 0.059 Uiso 1 1 calc R . . H2C H 0.4041 0.4002 0.0681 0.059 Uiso 1 1 calc R . . C3 C 0.3451(11) 0.2884(8) 0.1981(8) 0.034(3) Uani 1 1 d . . . H3A H 0.4214 0.3157 0.2134 0.050 Uiso 1 1 calc R . . H3B H 0.3557 0.2316 0.1698 0.050 Uiso 1 1 calc R . . H3C H 0.3056 0.2783 0.2492 0.050 Uiso 1 1 calc R . . C4 C 0.1472(12) 0.3132(9) 0.1159(9) 0.043(4) Uani 1 1 d . . . H4A H 0.1121 0.2990 0.1681 0.064 Uiso 1 1 calc R . . H4B H 0.1522 0.2592 0.0821 0.064 Uiso 1 1 calc R . . H4C H 0.0989 0.3573 0.0836 0.064 Uiso 1 1 calc R . . C5 C 0.2812(11) 0.6302(9) 0.3409(9) 0.039(4) Uani 1 1 d . . . C6 C 0.3582(12) 0.5858(10) 0.4167(8) 0.047(4) Uani 1 1 d . . . H6A H 0.4352 0.5712 0.3989 0.071 Uiso 1 1 calc R . . H6B H 0.3201 0.5314 0.4339 0.071 Uiso 1 1 calc R . . H6C H 0.3671 0.6272 0.4644 0.071 Uiso 1 1 calc R . . C7 C 0.1630(13) 0.6593(9) 0.3669(9) 0.047(4) Uani 1 1 d . . . H7A H 0.1741 0.7062 0.4095 0.071 Uiso 1 1 calc R . . H7B H 0.1239 0.6084 0.3905 0.071 Uiso 1 1 calc R . . H7C H 0.1150 0.6818 0.3174 0.071 Uiso 1 1 calc R . . C8 C 0.3425(13) 0.7111(9) 0.3068(11) 0.054(4) Uani 1 1 d . . . H8A H 0.2966 0.7337 0.2564 0.081 Uiso 1 1 calc R . . H8B H 0.4202 0.6938 0.2922 0.081 Uiso 1 1 calc R . . H8C H 0.3501 0.7576 0.3501 0.081 Uiso 1 1 calc R . . C9 C 0.6111(10) 0.5211(8) 0.2279(8) 0.028(3) Uani 1 1 d . . . C10 C 0.6547(14) 0.4350(11) 0.1866(12) 0.072(6) Uani 1 1 d . . . H10A H 0.6377 0.3835 0.2210 0.107 Uiso 1 1 calc R . . H10B H 0.7391 0.4391 0.1829 0.107 Uiso 1 1 calc R . . H10C H 0.6150 0.4283 0.1298 0.107 Uiso 1 1 calc R . . C11 C 0.6355(13) 0.6004(11) 0.1716(10) 0.062(5) Uani 1 1 d . . . H11A H 0.5927 0.5928 0.1159 0.093 Uiso 1 1 calc R . . H11B H 0.7193 0.6037 0.1655 0.093 Uiso 1 1 calc R . . H11C H 0.6100 0.6552 0.1975 0.093 Uiso 1 1 calc R . . C12 C 0.6763(13) 0.5314(14) 0.3135(10) 0.073(6) Uani 1 1 d . . . H12A H 0.6420 0.5801 0.3438 0.110 Uiso 1 1 calc R . . H12B H 0.7583 0.5448 0.3071 0.110 Uiso 1 1 calc R . . H12C H 0.6711 0.4761 0.3454 0.110 Uiso 1 1 calc R . . C13 C 0.0908(12) 0.3630(9) 0.3935(9) 0.043(4) Uani 1 1 d . . . C14 C 0.1376(15) 0.3899(14) 0.4840(8) 0.071(5) Uani 1 1 d . . . H14A H 0.1329 0.4546 0.4899 0.107 Uiso 1 1 calc R . . H14B H 0.2190 0.3709 0.4948 0.107 Uiso 1 1 calc R . . H14C H 0.0906 0.3614 0.5246 0.107 Uiso 1 1 calc R . . C15 C 0.1011(13) 0.2603(10) 0.3854(8) 0.048(4) Uani 1 1 d . . . H15A H 0.0868 0.2432 0.3259 0.072 Uiso 1 1 calc R . . H15B H 0.0433 0.2317 0.4179 0.072 Uiso 1 1 calc R . . H15C H 0.1795 0.2414 0.4072 0.072 Uiso 1 1 calc R . . C16 C -0.0413(11) 0.3898(12) 0.3754(10) 0.056(4) Uani 1 1 d . . . H16A H -0.0720 0.3662 0.3204 0.084 Uiso 1 1 calc R . . H16B H -0.0482 0.4546 0.3751 0.084 Uiso 1 1 calc R . . H16C H -0.0858 0.3651 0.4195 0.084 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 P1 0.0244(17) 0.0221(16) 0.0252(17) -0.0005(14) 0.0026(13) -0.0005(13) P2 0.0232(17) 0.0280(17) 0.0230(17) -0.0024(14) 0.0014(13) -0.0004(13) Se1 0.0383(8) 0.0341(8) 0.0373(8) 0.0124(6) -0.0027(6) -0.0079(6) Se2 0.0226(7) 0.0389(8) 0.0424(8) 0.0034(6) -0.0023(6) 0.0019(6) Se3 0.0428(9) 0.0418(8) 0.0365(8) 0.0125(7) -0.0094(6) -0.0041(7) Se4 0.0417(9) 0.0348(8) 0.0553(10) 0.0090(7) -0.0067(7) 0.0059(6) N1 0.028(6) 0.019(5) 0.022(5) 0.002(4) -0.002(4) 0.003(4) N2 0.039(6) 0.020(5) 0.028(6) -0.006(4) 0.000(5) 0.002(5) N3 0.029(6) 0.029(6) 0.028(6) 0.000(5) -0.004(4) -0.006(5) N4 0.023(6) 0.040(6) 0.022(5) 0.001(5) 0.004(4) 0.003(5) C1 0.034(7) 0.032(7) 0.013(6) -0.006(5) 0.005(5) -0.012(6) C2 0.055(9) 0.030(7) 0.034(8) -0.016(6) 0.012(7) 0.001(6) C3 0.040(8) 0.020(6) 0.038(7) -0.003(6) -0.008(6) 0.011(6) C4 0.040(8) 0.039(8) 0.047(9) -0.011(7) -0.008(7) 0.012(6) C5 0.020(7) 0.050(8) 0.050(9) -0.029(7) 0.016(6) -0.011(6) C6 0.038(8) 0.067(10) 0.033(8) -0.022(7) -0.014(6) 0.004(7) C7 0.070(11) 0.041(8) 0.031(8) -0.012(7) 0.008(7) -0.003(7) C8 0.040(9) 0.033(8) 0.089(12) -0.020(8) 0.008(8) 0.004(7) C9 0.021(7) 0.020(6) 0.042(8) -0.002(6) 0.006(6) -0.004(5) C10 0.044(10) 0.061(11) 0.113(15) -0.043(11) 0.024(10) -0.012(8) C11 0.040(9) 0.076(12) 0.072(11) 0.028(10) 0.014(8) -0.007(8) C12 0.030(9) 0.131(17) 0.054(11) -0.002(11) -0.018(8) -0.003(10) C13 0.043(9) 0.041(8) 0.044(9) 0.004(7) -0.003(7) -0.003(7) C14 0.066(12) 0.126(16) 0.020(8) 0.011(9) -0.001(7) -0.016(11) C15 0.042(9) 0.069(10) 0.031(8) 0.018(7) -0.008(6) -0.015(8) C16 0.025(8) 0.096(13) 0.050(9) 0.015(9) 0.017(7) 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 P1 N3 1.503(10) . ? P1 N2 1.686(10) . ? P1 N1 1.698(9) . ? P1 Se1 2.280(3) . ? P1 P2 2.500(4) . ? P2 N4 1.494(10) . ? P2 N1 1.685(9) . ? P2 N2 1.694(10) . ? P2 Se2 2.275(3) . ? Se1 Se3 2.3371(19) . ? Se2 Se4 2.3317(19) . ? Se3 Se4 2.321(2) . ? N1 C1 1.496(14) . ? N2 C5 1.494(15) . ? N3 C9 1.457(14) . ? N4 C13 1.468(16) . ? C1 C4 1.504(16) . ? C1 C3 1.520(16) . ? C1 C2 1.545(16) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 C7 1.491(17) . ? C5 C8 1.501(19) . ? C5 C6 1.546(19) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C12 1.471(18) . ? C9 C11 1.503(18) . ? C9 C10 1.525(18) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.513(19) . ? C13 C15 1.525(19) . ? C13 C16 1.542(18) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? 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 N3 P1 N2 117.0(5) . . ? N3 P1 N1 123.0(5) . . ? N2 P1 N1 84.1(5) . . ? N3 P1 Se1 112.8(4) . . ? N2 P1 Se1 108.2(4) . . ? N1 P1 Se1 108.0(3) . . ? N3 P1 P2 127.3(4) . . ? N2 P1 P2 42.4(3) . . ? N1 P1 P2 42.1(3) . . ? Se1 P1 P2 119.77(15) . . ? N4 P2 N1 116.6(5) . . ? N4 P2 N2 122.9(5) . . ? N1 P2 N2 84.2(5) . . ? N4 P2 Se2 113.3(4) . . ? N1 P2 Se2 108.2(3) . . ? N2 P2 Se2 107.9(4) . . ? N4 P2 P1 126.9(4) . . ? N1 P2 P1 42.6(3) . . ? N2 P2 P1 42.2(3) . . ? Se2 P2 P1 119.71(15) . . ? P1 Se1 Se3 103.68(10) . . ? P2 Se2 Se4 104.65(10) . . ? Se4 Se3 Se1 103.20(7) . . ? Se3 Se4 Se2 103.41(7) . . ? C1 N1 P2 129.9(7) . . ? C1 N1 P1 130.3(8) . . ? P2 N1 P1 95.3(5) . . ? C5 N2 P1 129.3(8) . . ? C5 N2 P2 129.9(8) . . ? P1 N2 P2 95.4(5) . . ? C9 N3 P1 148.5(9) . . ? C13 N4 P2 146.9(9) . . ? N1 C1 C4 108.0(10) . . ? N1 C1 C3 109.2(9) . . ? C4 C1 C3 111.2(10) . . ? N1 C1 C2 107.9(9) . . ? C4 C1 C2 110.0(10) . . ? C3 C1 C2 110.4(10) . . ? 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 . . ? C1 C4 H4A 109.5 . . ? C1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C7 C5 N2 108.7(10) . . ? C7 C5 C8 108.7(12) . . ? N2 C5 C8 107.5(11) . . ? C7 C5 C6 111.5(11) . . ? N2 C5 C6 109.0(10) . . ? C8 C5 C6 111.2(11) . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C7 H7A 109.5 . . ? C5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C5 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C5 C8 H8A 109.5 . . ? C5 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C5 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N3 C9 C12 109.8(11) . . ? N3 C9 C11 111.9(10) . . ? C12 C9 C11 110.2(12) . . ? N3 C9 C10 107.8(10) . . ? C12 C9 C10 108.4(13) . . ? C11 C9 C10 108.5(12) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N4 C13 C14 109.7(11) . . ? N4 C13 C15 107.5(11) . . ? C14 C13 C15 108.4(12) . . ? N4 C13 C16 112.1(11) . . ? C14 C13 C16 110.5(13) . . ? C15 C13 C16 108.5(12) . . ? 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 . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 24.50 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.787 _refine_diff_density_min -0.676 _refine_diff_density_rms 0.189 data_shelxl _database_code_depnum_ccdc_archive 'CCDC 876357' #TrackingRef 'CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C48 H108 N12 P6 S6, C6 H6' _chemical_formula_sum 'C54 H114 N12 P6 S6' _chemical_formula_weight 1309.75 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M 'P 63/m ' _symmetry_space_group_name_Hall '-P 6c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y, x-y, z' '-x+y, -x, z' 'x-y, x, z+1/2' 'y, -x+y, z+1/2' '-x, -y, -z' 'x, y, -z-1/2' 'y, -x+y, -z' 'x-y, x, -z' '-x+y, -x, -z-1/2' '-y, x-y, -z-1/2' _cell_length_a 16.5400(7) _cell_length_b 16.5400(7) _cell_length_c 15.5330(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 3680.1(2) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 8741 _cell_measurement_theta_min 1.9 _cell_measurement_theta_max 27.4 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.182 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1416 _exptl_absorpt_coefficient_mu 0.358 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.9159 _exptl_absorpt_correction_T_max 0.9483 _exptl_absorpt_process_details 'SADABS (SHELXTL-NT v5.1, Bruker)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enraf Nonius FR590D, fine-focus sealed tube' _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_device_type 'KappaCCD (Nonius, FR540C)' _diffrn_measurement_method 'phi\omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7147 _diffrn_reflns_av_R_equivalents 0.0678 _diffrn_reflns_av_sigmaI/netI 0.0493 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 25.04 _reflns_number_total 2249 _reflns_number_gt 1706 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0842P)^2^+9.9906P] 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 2249 _refine_ls_number_parameters 133 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1082 _refine_ls_R_factor_gt 0.0807 _refine_ls_wR_factor_ref 0.2134 _refine_ls_wR_factor_gt 0.1912 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.20502(12) 0.42454(12) 0.2500 0.0399(5) Uani 1 2 d S . . P2 P 0.55784(12) 0.62037(12) 0.2500 0.0436(5) Uani 1 2 d S . . S1 S 0.33483(11) 0.55184(11) 0.2500 0.0487(6) Uani 1 2 d S . . S2 S 0.42569(12) 0.49605(12) 0.2500 0.0652(8) Uani 1 2 d S . . N1 N 0.1371(3) 0.4383(3) 0.1780(3) 0.0451(10) Uani 1 1 d . . . N2 N 0.2276(4) 0.3472(4) 0.2500 0.0475(15) Uani 1 2 d S . . N3 N 0.6343(4) 0.5966(4) 0.2500 0.0481(15) Uani 1 2 d S . . C1 C 0.1329(4) 0.4331(4) 0.0819(4) 0.0585(15) Uani 1 1 d . . . C2 C 0.2252(9) 0.4636(9) 0.0509(9) 0.071(3) Uiso 0.52 1 d P A 1 C2A C 0.1943(10) 0.3888(10) 0.0434(9) 0.073(4) Uiso 0.48 1 d P A 2 C3 C 0.0570(8) 0.3259(8) 0.0678(8) 0.070(3) Uiso 0.57 1 d P A 1 C3A C 0.0402(11) 0.3873(11) 0.0388(10) 0.072(4) Uiso 0.43 1 d P A 2 C4 C 0.0879(8) 0.4906(8) 0.0541(7) 0.066(3) Uiso 0.55 1 d P A 1 C4A C 0.1942(10) 0.5387(11) 0.0440(10) 0.071(4) Uiso 0.45 1 d P A 2 C5 C 0.1898(5) 0.2470(5) 0.2500 0.054(2) Uani 1 2 d S . . C6 C 0.2274(6) 0.2218(5) 0.1704(5) 0.086(2) Uani 1 1 d . . . H6A H 0.2040 0.2357 0.1193 0.129 Uiso 1 1 calc R . . H6B H 0.2074 0.1564 0.1715 0.129 Uiso 1 1 calc R . . H6C H 0.2944 0.2574 0.1704 0.129 Uiso 1 1 calc R . . C7 C 0.0846(6) 0.1933(6) 0.2500 0.087(3) Uani 1 2 d S . . H7A H 0.0629 0.1276 0.2475 0.131 Uiso 1 2 calc SR . . H7B H 0.0618 0.2111 0.2008 0.131 Uiso 0.50 1 calc PR . . H7C H 0.0619 0.2070 0.3017 0.131 Uiso 0.50 1 calc PR . . C8 C 0.6552(5) 0.5203(5) 0.2500 0.0480(18) Uani 1 2 d S . . C9 C 0.7619(6) 0.5668(6) 0.2500 0.080(3) Uani 1 2 d S . . H9A H 0.7860 0.5992 0.1966 0.121 Uiso 0.50 1 calc PR . . H9B H 0.7795 0.5200 0.2565 0.121 Uiso 0.50 1 calc PR . . H9C H 0.7869 0.6103 0.2969 0.121 Uiso 0.50 1 calc PR . . C10 C 0.6163(4) 0.4597(4) 0.1707(4) 0.0625(16) Uani 1 1 d . . . H10A H 0.5494 0.4301 0.1711 0.094 Uiso 1 1 calc R . . H10B H 0.6345 0.4130 0.1707 0.094 Uiso 1 1 calc R . . H10C H 0.6403 0.4978 0.1201 0.094 Uiso 1 1 calc R . . C11 C 0.053(4) 0.053(5) 0.939(4) 0.21(3) Uiso 0.30 1 d P . 1 C11A C 0.056(2) 0.0920(15) 0.994(2) 0.182(9) Uiso 0.70 1 d P . 2 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 P1 0.0310(9) 0.0374(10) 0.0512(11) 0.000 0.000 0.0172(8) P2 0.0322(9) 0.0332(9) 0.0666(13) 0.000 0.000 0.0173(8) S1 0.0230(8) 0.0280(9) 0.0961(15) 0.000 0.000 0.0135(7) S2 0.0214(8) 0.0283(9) 0.145(2) 0.000 0.000 0.0114(7) N1 0.035(2) 0.046(2) 0.052(2) 0.009(2) 0.0046(19) 0.0182(19) N2 0.041(3) 0.040(3) 0.064(4) 0.000 0.000 0.022(3) N3 0.034(3) 0.035(3) 0.075(4) 0.000 0.000 0.017(3) C1 0.059(3) 0.056(3) 0.063(4) -0.010(3) -0.012(3) 0.031(3) C5 0.051(4) 0.032(4) 0.083(6) 0.000 0.000 0.023(3) C6 0.121(6) 0.074(4) 0.085(5) -0.005(4) 0.014(5) 0.066(5) C7 0.058(6) 0.050(5) 0.131(9) 0.000 0.000 0.011(5) C8 0.043(4) 0.036(4) 0.073(5) 0.000 0.000 0.026(3) C9 0.043(5) 0.055(5) 0.152(10) 0.000 0.000 0.031(4) C10 0.074(4) 0.055(3) 0.064(4) -0.008(3) 0.006(3) 0.036(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 P1 N2 1.500(6) . ? P1 N1 1.680(4) . ? P1 N1 1.680(4) 8_556 ? P1 S1 2.127(2) . ? P1 P2 2.515(2) 4_565 ? P2 N3 1.501(6) . ? P2 N1 1.690(4) 3_665 ? P2 N1 1.690(4) 12_666 ? P2 S2 2.124(3) . ? P2 P1 2.515(2) 3_665 ? S1 S2 2.121(2) . ? N1 C1 1.494(7) . ? N1 P2 1.690(4) 4_565 ? N2 C5 1.451(9) . ? N3 C8 1.465(8) . ? C1 C2 1.431(14) . ? C1 C3A 1.487(16) . ? C1 C4 1.534(13) . ? C1 C3 1.594(13) . ? C1 C4A 1.629(16) . ? C1 C2A 1.635(15) . ? C5 C7 1.508(12) . ? C5 C6 1.533(8) . ? C5 C6 1.533(8) 8_556 ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 C10 1.512(7) . ? C8 C10 1.512(7) 8_556 ? C8 C9 1.532(10) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C11 1.52(8) 4 ? C11 C11 1.52(8) 3 ? C11A C11A 1.34(2) 10_557 ? C11A C11A 1.34(2) 9_557 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 P1 N1 125.7(2) . . ? N2 P1 N1 125.7(2) . 8_556 ? N1 P1 N1 83.5(3) . 8_556 ? N2 P1 S1 106.6(2) . . ? N1 P1 S1 106.15(15) . . ? N1 P1 S1 106.15(15) 8_556 . ? N2 P1 P2 138.2(3) . 4_565 ? N1 P1 P2 41.87(14) . 4_565 ? N1 P1 P2 41.87(14) 8_556 4_565 ? S1 P1 P2 115.21(9) . 4_565 ? N3 P2 N1 119.2(2) . 3_665 ? N3 P2 N1 119.2(2) . 12_666 ? N1 P2 N1 82.9(3) 3_665 12_666 ? N3 P2 S2 109.9(2) . . ? N1 P2 S2 111.62(16) 3_665 . ? N1 P2 S2 111.62(16) 12_666 . ? N3 P2 P1 127.4(2) . 3_665 ? N1 P2 P1 41.56(14) 3_665 3_665 ? N1 P2 P1 41.56(14) 12_666 3_665 ? S2 P2 P1 122.73(10) . 3_665 ? S2 S1 P1 98.83(9) . . ? S1 S2 P2 100.88(10) . . ? C1 N1 P1 132.3(4) . . ? C1 N1 P2 130.5(4) . 4_565 ? P1 N1 P2 96.6(2) . 4_565 ? C5 N2 P1 145.7(5) . . ? C8 N3 P2 144.9(5) . . ? C2 C1 C3A 132.4(9) . . ? C2 C1 N1 107.7(7) . . ? C3A C1 N1 119.1(8) . . ? C2 C1 C4 116.7(8) . . ? C3A C1 C4 59.5(8) . . ? N1 C1 C4 105.6(6) . . ? C2 C1 C3 117.0(8) . . ? C3A C1 C3 48.2(7) . . ? N1 C1 C3 101.0(6) . . ? C4 C1 C3 107.1(7) . . ? C2 C1 C4A 61.1(7) . . ? C3A C1 C4A 108.3(9) . . ? N1 C1 C4A 108.2(7) . . ? C4 C1 C4A 57.9(7) . . ? C3 C1 C4A 149.8(8) . . ? C2 C1 C2A 40.7(7) . . ? C3A C1 C2A 108.6(9) . . ? N1 C1 C2A 111.7(6) . . ? C4 C1 C2A 141.0(8) . . ? C3 C1 C2A 76.8(7) . . ? C4A C1 C2A 98.8(8) . . ? N2 C5 C7 112.5(7) . . ? N2 C5 C6 108.0(5) . . ? C7 C5 C6 110.2(5) . . ? N2 C5 C6 108.0(5) . 8_556 ? C7 C5 C6 110.2(5) . 8_556 ? C6 C5 C6 107.6(7) . 8_556 ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C7 H7A 109.5 . . ? C5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C5 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N3 C8 C10 111.4(4) . . ? N3 C8 C10 111.4(4) . 8_556 ? C10 C8 C10 109.0(6) . 8_556 ? N3 C8 C9 106.0(6) . . ? C10 C8 C9 109.5(4) . . ? C10 C8 C9 109.5(4) 8_556 . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C11 C11 C11 60.00(3) 4 3 ? C11A C11A C11A 117.8(15) 10_557 9_557 ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.04 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.561 _refine_diff_density_min -0.357 _refine_diff_density_rms 0.092