# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 182/1843 data_auba4 # 1. SUBMISSION DETAILS _publ_contact_author ; Heinrich N\"oth Institut f\"ur anorganische Chemie Universit\"at M\"unchen Butenandtstr. 5-13 (Haus D) 81377 M\"unchen Bundesrepublik Deutschland ; _publ_contact_author_phone '089 2180 7454' _publ_contact_author_fax '089 2180 7865' _publ_contact_author_email H.Noeth@lrz.uni-muenchen.de _publ_requested_journal ? # 3. TITLE AND AUTHOR LIST _publ_section_title ; ? ; loop_ _publ_author_name _publ_author_address 'Heinrich N\"oth' ; Institut f\"ur anorganische Chemie Universit\"at M\"unchen Butenandtstr. 5-13 (Haus D) 81377 M\"unchen Bundesrepublik Deutschland ; 'Ch. Aubauer' ; Institut f\"ur anorganische Chemie Universit\"at M\"unchen Butenandtstr. 5-13 (Haus D) 81377 M\"unchen Bundesrepublik Deutschland ; 'T. M. Klap\"otke' ; Institut f\"ur anorganische Chemie Universit\"at M\"unchen Butenandtstr. 5-13 (Haus D) 81377 M\"unchen Bundesrepublik Deutschland ; 'M. Suter' ; ? ; _publ_manuscript_creation 'RTF-File by CIFRTF (H.Schwenk 1996)' _audit_creation_method 'SHELXL-CIF-file updated by CIFRTF' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H10 N20 P2' _chemical_formula_weight 496.34 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.3415(15) _cell_length_b 8.5508(18) _cell_length_c 17.879(4) _cell_angle_alpha 88.527(3) _cell_angle_beta 85.499(4) _cell_angle_gamma 67.684(3) _cell_volume 1035.1(4) _cell_formula_units_Z 2 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 323 _cell_measurement_theta_min 20.00 _cell_measurement_theta_max 1.00 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.592 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 0.262 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min 0.6491 _exptl_absorpt_correction_T_max 0.9828 _exptl_absorpt_process_details ? _exptl_special_details ; Diffractometer operator M. Suter scanspeed_seconds/frame 5 1200 frames measured in phi (0-360) with chi=0 and om=2th=25 65 frames measured in om (15-35) with chi=280, 2th=29 and phi=0 Crystal mounted in perfluorpolyetheroil ; _diffrn_ambient_temperature 193(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 'Siemens SMART Area-detector' _diffrn_measurement_method Hemisphere _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% ? _diffrn_reflns_number 5983 _diffrn_reflns_av_R_equivalents 0.0408 _diffrn_reflns_av_sigmaI/netI 0.0818 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.14 _diffrn_reflns_theta_max 28.56 _reflns_number_total 3153 _reflns_number_gt 1830 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (V4.C50)' _computing_cell_refinement 'SMART (V4.C50)' _computing_data_reduction 'SAINT (V4.D50)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (SHELXTL-Ver.5)' _computing_publication_material 'SHELXL (Sheldrick 1997)' _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^)+(0.0724P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary 'direct methods' _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geometrically _refine_ls_hydrogen_treatment 'mixed ' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3153 _refine_ls_number_parameters 307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0920 _refine_ls_R_factor_gt 0.0488 _refine_ls_wR_factor_ref 0.1273 _refine_ls_wR_factor_gt 0.1148 _refine_ls_goodness_of_fit_ref 0.879 _refine_ls_restrained_S_all 0.879 _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 0.41336(16) 1.11644(12) 0.95088(6) 0.0289(3) Uani 1 1 d . . . P2 P 0.89860(16) 0.61733(12) 0.55001(6) 0.0289(3) Uani 1 1 d . . . N1 N 0.2794(5) 1.0454(4) 0.89694(19) 0.0358(9) Uani 1 1 d . . . N2 N 0.1200(5) 1.1449(4) 0.87376(19) 0.0319(9) Uani 1 1 d . . . N3 N -0.0231(6) 1.2162(5) 0.8487(2) 0.0472(11) Uani 1 1 d . . . N4 N 0.5873(5) 1.1714(4) 0.8999(2) 0.0368(10) Uani 1 1 d . . . N5 N 0.5401(5) 1.3053(4) 0.86269(19) 0.0318(9) Uani 1 1 d . . . N6 N 0.5199(5) 1.4180(4) 0.8263(2) 0.0407(10) Uani 1 1 d . . . N7 N 0.2250(5) 1.3267(4) 0.95331(18) 0.0292(9) Uani 1 1 d . . . N8 N 0.2571(5) 1.4419(4) 0.98338(19) 0.0326(9) Uani 1 1 d . . . N9 N 0.2732(6) 1.5544(4) 1.0096(2) 0.0477(11) Uani 1 1 d . . . N10 N 0.4066(5) 1.0912(4) 1.04231(19) 0.0253(9) Uani 1 1 d . . . N11 N 0.7564(6) 0.5430(4) 0.6083(2) 0.0342(10) Uani 1 1 d . . . N12 N 0.5925(8) 0.6411(5) 0.6377(3) 0.0359(12) Uani 1 1 d . . . N13 N 0.4466(8) 0.7082(6) 0.6693(3) 0.0524(13) Uani 1 1 d . . . N14 N 1.0575(5) 0.6775(4) 0.5956(2) 0.0353(9) Uani 1 1 d . . . N15 N 0.9990(5) 0.8125(4) 0.6325(2) 0.0341(9) Uani 1 1 d . . . N16 N 0.9656(5) 0.9277(4) 0.6678(2) 0.0406(10) Uani 1 1 d . . . N17 N 0.7068(5) 0.8249(4) 0.54956(18) 0.0309(9) Uani 1 1 d . . . N18 N 0.7448(5) 0.9400(4) 0.51751(19) 0.0326(9) Uani 1 1 d . . . N19 N 0.7684(6) 1.0529(4) 0.4907(2) 0.0470(11) Uani 1 1 d . . . N20 N 0.9145(5) 0.5884(4) 0.45866(17) 0.0270(9) Uani 1 1 d . . . C1 C 0.2583(6) 1.1844(5) 1.0983(2) 0.0272(12) Uani 1 1 d . . . C2 C 0.0708(7) 1.1794(5) 1.1021(3) 0.0373(13) Uani 1 1 d . . . H2A H 0.0423 1.1100 1.0679 0.045 Uiso 1 1 calc R . . C3 C -0.0737(8) 1.2731(6) 1.1545(3) 0.0442(14) Uani 1 1 d . . . H3A H -0.2013 1.2687 1.1561 0.053 Uiso 1 1 calc R . . C4 C -0.0345(7) 1.3745(5) 1.2053(3) 0.0435(12) Uani 1 1 d . . . H4A H -0.1352 1.4406 1.2411 0.052 Uiso 1 1 calc R . . C5 C 0.1516(8) 1.3782(6) 1.2033(3) 0.0415(13) Uani 1 1 d . . . H5A H 0.1796 1.4466 1.2382 0.050 Uiso 1 1 calc R . . C6 C 0.2994(7) 1.2824(5) 1.1505(3) 0.0344(12) Uani 1 1 d . . . H6A H 0.4282 1.2840 1.1500 0.041 Uiso 1 1 calc R . . C7 C 0.7823(6) 0.6815(4) 0.4038(2) 0.0292(10) Uani 1 1 d . . . C8 C 0.5997(6) 0.6695(5) 0.4004(2) 0.0357(11) Uani 1 1 d . . . H8A H 0.5615 0.5981 0.4343 0.043 Uiso 1 1 calc R . . C9 C 0.4737(7) 0.7615(5) 0.3477(3) 0.0429(12) Uani 1 1 d . . . H9A H 0.3494 0.7522 0.3452 0.051 Uiso 1 1 calc R . . C10 C 0.5264(7) 0.8660(5) 0.2990(2) 0.0426(12) Uani 1 1 d . . . H10A H 0.4384 0.9302 0.2634 0.051 Uiso 1 1 calc R . . C11 C 0.7069(7) 0.8775(5) 0.3021(2) 0.0389(12) Uani 1 1 d . . . H11A H 0.7429 0.9504 0.2684 0.047 Uiso 1 1 calc R . . C12 C 0.8386(6) 0.7839(5) 0.3538(2) 0.0321(11) Uani 1 1 d . . . H12A H 0.9647 0.7904 0.3547 0.038 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 0.0252(7) 0.0248(6) 0.0364(7) -0.0005(5) -0.0047(6) -0.0086(5) P2 0.0251(7) 0.0248(5) 0.0353(7) -0.0023(5) -0.0017(6) -0.0078(5) N1 0.027(2) 0.0305(18) 0.050(2) -0.0001(17) -0.016(2) -0.0084(17) N2 0.029(2) 0.0326(19) 0.035(2) -0.0038(17) -0.002(2) -0.0130(18) N3 0.034(3) 0.050(2) 0.056(3) 0.000(2) -0.014(2) -0.012(2) N4 0.026(2) 0.0261(18) 0.054(2) 0.0071(17) -0.002(2) -0.0060(16) N5 0.022(2) 0.033(2) 0.041(2) -0.0053(18) 0.002(2) -0.0110(17) N6 0.030(2) 0.036(2) 0.055(3) 0.007(2) -0.001(2) -0.0118(18) N7 0.025(2) 0.0244(17) 0.038(2) -0.0005(16) -0.0036(19) -0.0085(16) N8 0.023(2) 0.0304(19) 0.040(2) 0.0041(17) -0.0025(19) -0.0054(17) N9 0.049(3) 0.032(2) 0.062(3) -0.006(2) -0.009(2) -0.014(2) N10 0.019(2) 0.0180(17) 0.033(2) -0.0054(16) 0.0040(19) -0.0006(16) N11 0.028(3) 0.0269(19) 0.042(3) -0.0046(18) 0.005(2) -0.0056(18) N12 0.039(3) 0.036(3) 0.038(3) -0.002(2) 0.000(3) -0.020(2) N13 0.036(3) 0.058(3) 0.060(4) 0.000(2) 0.010(3) -0.017(3) N14 0.031(2) 0.0257(18) 0.047(2) -0.0089(17) -0.007(2) -0.0071(17) N15 0.030(2) 0.031(2) 0.042(2) 0.0019(19) -0.008(2) -0.0110(19) N16 0.042(3) 0.028(2) 0.052(3) -0.0076(19) -0.009(2) -0.0119(19) N17 0.030(2) 0.0242(17) 0.035(2) -0.0043(16) -0.0009(19) -0.0070(17) N18 0.023(2) 0.0292(19) 0.037(2) -0.0068(17) -0.0021(19) 0.0003(17) N19 0.047(3) 0.032(2) 0.057(3) 0.002(2) 0.001(2) -0.011(2) N20 0.028(2) 0.0224(16) 0.027(2) -0.0025(15) 0.0023(19) -0.0054(16) C1 0.020(3) 0.023(2) 0.034(3) 0.001(2) 0.002(3) -0.003(2) C2 0.032(3) 0.023(2) 0.054(3) 0.001(2) -0.008(3) -0.007(2) C3 0.030(3) 0.035(3) 0.062(4) 0.005(3) 0.000(3) -0.006(2) C4 0.040(3) 0.040(3) 0.037(3) -0.002(2) 0.010(3) -0.002(2) C5 0.049(4) 0.039(3) 0.033(3) 0.002(2) -0.009(3) -0.011(3) C6 0.032(3) 0.031(2) 0.038(3) -0.002(2) -0.007(3) -0.008(2) C7 0.027(3) 0.023(2) 0.034(2) -0.0078(19) -0.004(2) -0.0040(19) C8 0.032(3) 0.030(2) 0.041(3) -0.008(2) 0.005(2) -0.010(2) C9 0.031(3) 0.042(3) 0.052(3) -0.008(2) -0.014(3) -0.007(2) C10 0.043(3) 0.039(3) 0.036(3) -0.003(2) -0.007(3) -0.002(2) C11 0.049(3) 0.030(2) 0.031(3) 0.002(2) 0.002(2) -0.009(2) C12 0.028(3) 0.029(2) 0.033(3) -0.005(2) 0.001(2) -0.004(2) _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 N10 1.643(4) . ? P1 N1 1.703(3) . ? P1 N4 1.713(4) . ? P1 N10 1.774(3) 2_677 ? P1 N7 1.804(3) . ? P1 P1 2.6298(19) 2_677 ? P2 N20 1.646(3) . ? P2 N11 1.696(4) . ? P2 N14 1.708(3) . ? P2 N20 1.775(3) 2_766 ? P2 N17 1.799(3) . ? P2 P2 2.634(2) 2_766 ? N1 N2 1.252(4) . ? N2 N3 1.118(4) . ? N4 N5 1.253(4) . ? N5 N6 1.118(4) . ? N7 N8 1.240(4) . ? N8 N9 1.130(4) . ? N10 C1 1.426(5) . ? N10 P1 1.774(3) 2_677 ? N11 N12 1.259(6) . ? N12 N13 1.118(5) . ? N14 N15 1.253(5) . ? N15 N16 1.119(4) . ? N17 N18 1.236(4) . ? N18 N19 1.132(4) . ? N20 C7 1.435(4) . ? N20 P2 1.775(3) 2_766 ? C1 C2 1.389(6) . ? C1 C6 1.393(5) . ? C2 C3 1.372(6) . ? C3 C4 1.389(6) . ? C4 C5 1.377(6) . ? C5 C6 1.395(6) . ? C7 C12 1.384(5) . ? C7 C8 1.389(5) . ? C8 C9 1.382(5) . ? C9 C10 1.369(6) . ? C10 C11 1.371(6) . ? C11 C12 1.395(5) . ? 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 N10 P1 N1 121.17(16) . . ? N10 P1 N4 124.05(16) . . ? N1 P1 N4 113.36(18) . . ? N10 P1 N10 79.4(2) . 2_677 ? N1 P1 N10 90.90(15) . 2_677 ? N4 P1 N10 88.53(16) . 2_677 ? N10 P1 N7 95.25(17) . . ? N1 P1 N7 91.32(15) . . ? N4 P1 N7 95.09(15) . . ? N10 P1 N7 174.62(18) 2_677 . ? N10 P1 P1 41.53(12) . 2_677 ? N1 P1 P1 109.50(12) . 2_677 ? N4 P1 P1 109.42(12) . 2_677 ? N10 P1 P1 37.88(12) 2_677 2_677 ? N7 P1 P1 136.78(14) . 2_677 ? N20 P2 N11 120.86(16) . . ? N20 P2 N14 124.15(17) . . ? N11 P2 N14 113.42(17) . . ? N20 P2 N20 79.37(15) . 2_766 ? N11 P2 N20 90.55(18) . 2_766 ? N14 P2 N20 88.26(16) . 2_766 ? N20 P2 N17 95.29(15) . . ? N11 P2 N17 91.83(18) . . ? N14 P2 N17 95.19(16) . . ? N20 P2 N17 174.64(16) 2_766 . ? N20 P2 P2 41.47(11) . 2_766 ? N11 P2 P2 109.09(14) . 2_766 ? N14 P2 P2 109.29(14) . 2_766 ? N20 P2 P2 37.91(10) 2_766 2_766 ? N17 P2 P2 136.76(12) . 2_766 ? N2 N1 P1 120.8(3) . . ? N3 N2 N1 171.1(4) . . ? N5 N4 P1 121.4(3) . . ? N6 N5 N4 172.0(4) . . ? N8 N7 P1 118.9(2) . . ? N9 N8 N7 175.1(4) . . ? C1 N10 P1 129.1(2) . . ? C1 N10 P1 127.7(2) . 2_677 ? P1 N10 P1 100.6(2) . 2_677 ? N12 N11 P2 121.0(3) . . ? N13 N12 N11 170.0(4) . . ? N15 N14 P2 121.7(3) . . ? N16 N15 N14 172.9(4) . . ? N18 N17 P2 118.4(3) . . ? N19 N18 N17 175.3(4) . . ? C7 N20 P2 129.6(3) . . ? C7 N20 P2 128.1(3) . 2_766 ? P2 N20 P2 100.63(15) . 2_766 ? C2 C1 C6 118.7(5) . . ? C2 C1 N10 121.0(4) . . ? C6 C1 N10 120.3(4) . . ? C3 C2 C1 121.0(4) . . ? C2 C3 C4 120.4(4) . . ? C5 C4 C3 119.4(5) . . ? C4 C5 C6 120.5(4) . . ? C1 C6 C5 120.0(4) . . ? C12 C7 C8 119.9(4) . . ? C12 C7 N20 119.3(4) . . ? C8 C7 N20 120.8(4) . . ? C9 C8 C7 119.9(4) . . ? C10 C9 C8 120.6(4) . . ? C9 C10 C11 119.6(4) . . ? C10 C11 C12 121.1(4) . . ? C7 C12 C11 118.9(4) . . ? _diffrn_measured_fraction_theta_max 0.597 _diffrn_reflns_theta_full 28.56 _diffrn_measured_fraction_theta_full 0.597 _refine_diff_density_max 0.311 _refine_diff_density_min -0.337 _refine_diff_density_rms 0.064