Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Dietrich Gudat' _publ_contact_author_address ; Institut fur Anorganische Chemie Universitat Stuttgart Pfaffenwaldring 55 Stuttgart 70569 GERMANY ; _publ_contact_author_email GUDAT@IAC.UNI-STUTTGART.DE _publ_section_title ; Structures, Dynamic Behaviour, and Reactivity of P-cyclopentadienyl-substituted 1,3,2-Diazaphospholenes ; loop_ _publ_author_name 'Dietrich Gudat' 'Sebastian Burck' 'Martin Nieger' 'Jurgen J. Tirree' data_gudat94 _database_code_depnum_ccdc_archive 'CCDC 631300' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-Cyclopentadienyl-1,3-bis-(2,6-diisopropyl-phenyl)-1,3,2-diazaphospholene ; _chemical_name_common ;2-Cyclopentadienyl-1,3-bis-(2,6-diisopropyl-phenyl)-1,3,2- diazaphospholene ; _chemical_melting_point ? _chemical_formula_moiety 'C31 H41 N2 P - thf' _chemical_formula_sum 'C35 H49 N2 O P' _chemical_formula_weight 544.73 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' O O 0.0106 0.0060 '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 monoclinic _symmetry_space_group_name_H-M 'P2(1)/n ' #(No.14) 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 9.9003(2) _cell_length_b 18.4544(4) _cell_length_c 17.5559(4) _cell_angle_alpha 90.00 _cell_angle_beta 98.506(1) _cell_angle_gamma 90.00 _cell_volume 3172.25(12) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 5906 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description blocks _exptl_crystal_colour yellow _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.141 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1184 _exptl_absorpt_coefficient_mu 0.115 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; dx = 40 mm, 30 sec./deg., 2 deg., 2 sets, 119 frames, mos. = 0.629(2) deg. ; _diffrn_ambient_temperature 123(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 'Nonius KappaCCD' _diffrn_measurement_method 'rotation in phi and omega, 2 deg.' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17886 _diffrn_reflns_av_R_equivalents 0.0280 _diffrn_reflns_av_sigmaI/netI 0.0421 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 27.48 _reflns_number_total 7035 _reflns_number_gt 5364 _reflns_threshold_expression >2sigma(I) _computing_data_collection Collect _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL-NT _computing_publication_material 'SHELXL-97 (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^)+(0.1071P)^2^+0.8501P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7035 _refine_ls_number_parameters 352 _refine_ls_number_restraints 36 _refine_ls_R_factor_all 0.0736 _refine_ls_R_factor_gt 0.0562 _refine_ls_wR_factor_ref 0.1798 _refine_ls_wR_factor_gt 0.1680 _refine_ls_goodness_of_fit_ref 1.095 _refine_ls_restrained_S_all 1.181 _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 0.28645(5) 0.58690(3) 0.32319(3) 0.01837(16) Uani 1 1 d . . . N2 N 0.33878(16) 0.52304(8) 0.39226(9) 0.0191(3) Uani 1 1 d . . . C3 C 0.37597(18) 0.55476(10) 0.46563(11) 0.0191(4) Uani 1 1 d . . . H3 H 0.3898 0.5280 0.5124 0.023 Uiso 1 1 calc R . . C4 C 0.38952(19) 0.62640(10) 0.46189(11) 0.0196(4) Uani 1 1 d . . . H4 H 0.4153 0.6565 0.5055 0.024 Uiso 1 1 calc R . . N5 N 0.36117(16) 0.65256(8) 0.38547(9) 0.0198(4) Uani 1 1 d . . . C6 C 0.34218(19) 0.44638(10) 0.37954(11) 0.0189(4) Uani 1 1 d . . . C7 C 0.2572(2) 0.40015(10) 0.41517(12) 0.0208(4) Uani 1 1 d . . . C8 C 0.2652(2) 0.32605(11) 0.40284(13) 0.0264(5) Uani 1 1 d . . . H8 H 0.2104 0.2942 0.4278 0.032 Uiso 1 1 calc R . . C9 C 0.3513(2) 0.29753(12) 0.35507(14) 0.0307(5) Uani 1 1 d . . . H9 H 0.3529 0.2468 0.3460 0.037 Uiso 1 1 calc R . . C10 C 0.4345(2) 0.34331(11) 0.32081(13) 0.0274(5) Uani 1 1 d . . . H10 H 0.4934 0.3234 0.2881 0.033 Uiso 1 1 calc R . . C11 C 0.4346(2) 0.41792(10) 0.33289(12) 0.0221(4) Uani 1 1 d . . . C12 C 0.5346(2) 0.46493(12) 0.29721(13) 0.0261(5) Uani 1 1 d . . . H12 H 0.5331 0.5144 0.3203 0.031 Uiso 1 1 calc R . . C13 C 0.6813(2) 0.43595(14) 0.31533(16) 0.0377(6) Uani 1 1 d . . . H13A H 0.7428 0.4675 0.2915 0.057 Uiso 1 1 calc R . . H13B H 0.6851 0.3867 0.2948 0.057 Uiso 1 1 calc R . . H13C H 0.7094 0.4351 0.3712 0.057 Uiso 1 1 calc R . . C14 C 0.4930(3) 0.47251(14) 0.21037(14) 0.0368(6) Uani 1 1 d . . . H14A H 0.5594 0.5031 0.1893 0.055 Uiso 1 1 calc R . . H14B H 0.4023 0.4948 0.1997 0.055 Uiso 1 1 calc R . . H14C H 0.4906 0.4245 0.1863 0.055 Uiso 1 1 calc R . . C15 C 0.1595(2) 0.42746(11) 0.46824(12) 0.0231(4) Uani 1 1 d . . . H15 H 0.1545 0.4815 0.4639 0.028 Uiso 1 1 calc R . . C16 C 0.0146(2) 0.39708(12) 0.44637(14) 0.0294(5) Uani 1 1 d . . . H16A H -0.0445 0.4161 0.4818 0.044 Uiso 1 1 calc R . . H16B H 0.0173 0.3441 0.4497 0.044 Uiso 1 1 calc R . . H16C H -0.0216 0.4116 0.3936 0.044 Uiso 1 1 calc R . . C17 C 0.2140(3) 0.40809(12) 0.55211(13) 0.0322(5) Uani 1 1 d . . . H17A H 0.1506 0.4260 0.5857 0.048 Uiso 1 1 calc R . . H17B H 0.3037 0.4305 0.5670 0.048 Uiso 1 1 calc R . . H17C H 0.2225 0.3553 0.5573 0.048 Uiso 1 1 calc R . . C18 C 0.36530(19) 0.72773(10) 0.36572(12) 0.0208(4) Uani 1 1 d . . . C19 C 0.2872(2) 0.77890(11) 0.40031(12) 0.0239(4) Uani 1 1 d . . . C20 C 0.2925(2) 0.85108(11) 0.37795(13) 0.0296(5) Uani 1 1 d . . . H20 H 0.2436 0.8865 0.4022 0.036 Uiso 1 1 calc R . . C21 C 0.3676(2) 0.87261(12) 0.32108(15) 0.0342(5) Uani 1 1 d . . . H21 H 0.3667 0.9218 0.3051 0.041 Uiso 1 1 calc R . . C22 C 0.4436(2) 0.82205(12) 0.28788(14) 0.0321(5) Uani 1 1 d . . . H22 H 0.4951 0.8371 0.2491 0.039 Uiso 1 1 calc R . . C23 C 0.4464(2) 0.74924(11) 0.31006(13) 0.0258(5) Uani 1 1 d . . . C24 C 0.5395(2) 0.69727(12) 0.27514(15) 0.0339(5) Uani 1 1 d . . . H24 H 0.5388 0.6500 0.3029 0.041 Uiso 1 1 calc R . . C25 C 0.4884(3) 0.68339(15) 0.18972(16) 0.0461(7) Uani 1 1 d . . . H25A H 0.5506 0.6499 0.1691 0.069 Uiso 1 1 calc R . . H25B H 0.4852 0.7293 0.1614 0.069 Uiso 1 1 calc R . . H25C H 0.3967 0.6622 0.1840 0.069 Uiso 1 1 calc R . . C26 C 0.6869(3) 0.72520(16) 0.2863(2) 0.0536(8) Uani 1 1 d . . . H26A H 0.7449 0.6906 0.2638 0.080 Uiso 1 1 calc R . . H26B H 0.7200 0.7305 0.3415 0.080 Uiso 1 1 calc R . . H26C H 0.6900 0.7723 0.2608 0.080 Uiso 1 1 calc R . . C27 C 0.2002(2) 0.75983(11) 0.46207(12) 0.0267(5) Uani 1 1 d . . . H27 H 0.1914 0.7059 0.4636 0.032 Uiso 1 1 calc R . . C28 C 0.0558(2) 0.79215(13) 0.44560(15) 0.0369(6) Uani 1 1 d . . . H28A H 0.0037 0.7779 0.4865 0.055 Uiso 1 1 calc R . . H28B H 0.0096 0.7741 0.3960 0.055 Uiso 1 1 calc R . . H28C H 0.0619 0.8451 0.4438 0.055 Uiso 1 1 calc R . . C29 C 0.2698(3) 0.78534(14) 0.54158(14) 0.0378(6) Uani 1 1 d . . . H29A H 0.2128 0.7723 0.5806 0.057 Uiso 1 1 calc R . . H29B H 0.2818 0.8380 0.5410 0.057 Uiso 1 1 calc R . . H29C H 0.3592 0.7619 0.5538 0.057 Uiso 1 1 calc R . . C30 C 0.0946(2) 0.59872(11) 0.33404(12) 0.0226(4) Uani 1 1 d . . . H30 H 0.0746 0.6043 0.3879 0.027 Uiso 1 1 calc R . . C31 C 0.0546(2) 0.66002(12) 0.28195(13) 0.0262(4) Uani 1 1 d . . . H31 H 0.0718 0.7097 0.2937 0.031 Uiso 1 1 calc R . . C32 C -0.0108(2) 0.63368(13) 0.21429(14) 0.0324(5) Uani 1 1 d . . . H32 H -0.0427 0.6618 0.1699 0.039 Uiso 1 1 calc R . . C33 C -0.0241(2) 0.55639(13) 0.22050(14) 0.0330(5) Uani 1 1 d . . . H33 H -0.0664 0.5252 0.1809 0.040 Uiso 1 1 calc R . . C34 C 0.0329(2) 0.53530(12) 0.29142(13) 0.0268(5) Uani 1 1 d . . . H34 H 0.0332 0.4872 0.3108 0.032 Uiso 1 1 calc R . . O1T O 0.2671(6) 1.0957(3) 0.5702(4) 0.1812(19) Uani 1 1 d DU . . C1T C 0.3266(8) 1.1294(3) 0.5029(4) 0.149(2) Uani 1 1 d DU . . H1T1 H 0.2606 1.1627 0.4729 0.178 Uiso 1 1 calc R . . H1T2 H 0.4123 1.1559 0.5208 0.178 Uiso 1 1 calc R . . C2T C 0.3509(9) 1.0674(4) 0.4592(5) 0.184(3) Uani 1 1 d DU . . H2T1 H 0.4501 1.0574 0.4648 0.220 Uiso 1 1 calc R . . H2T2 H 0.3169 1.0758 0.4040 0.220 Uiso 1 1 calc R . . C3T C 0.2815(8) 1.0071(3) 0.4865(4) 0.157(2) Uani 1 1 d DU . . H3T1 H 0.2277 0.9817 0.4425 0.189 Uiso 1 1 calc R . . H3T2 H 0.3489 0.9726 0.5133 0.189 Uiso 1 1 calc R . . C4T C 0.2012(7) 1.0294(3) 0.5333(4) 0.136(2) Uani 1 1 d DU . . H4T1 H 0.1914 0.9919 0.5725 0.163 Uiso 1 1 calc R . . H4T2 H 0.1096 1.0408 0.5050 0.163 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 0.0179(3) 0.0201(3) 0.0176(3) 0.00113(19) 0.00422(19) 0.00090(18) N2 0.0204(8) 0.0181(8) 0.0186(8) -0.0004(6) 0.0026(6) 0.0029(6) C3 0.0172(9) 0.0213(10) 0.0183(9) 0.0009(7) 0.0012(7) 0.0023(7) C4 0.0186(9) 0.0196(9) 0.0200(10) -0.0005(8) 0.0012(7) 0.0016(7) N5 0.0194(8) 0.0199(8) 0.0200(8) 0.0022(6) 0.0028(6) -0.0011(6) C6 0.0171(9) 0.0183(9) 0.0204(10) -0.0004(7) -0.0002(7) 0.0028(7) C7 0.0178(9) 0.0225(10) 0.0216(10) 0.0004(8) 0.0009(8) 0.0022(7) C8 0.0253(10) 0.0206(10) 0.0332(12) 0.0001(9) 0.0038(9) -0.0003(8) C9 0.0304(11) 0.0206(10) 0.0413(13) -0.0062(9) 0.0057(10) 0.0009(9) C10 0.0249(10) 0.0250(11) 0.0330(12) -0.0087(9) 0.0065(9) 0.0025(8) C11 0.0173(9) 0.0244(10) 0.0245(10) -0.0042(8) 0.0022(8) 0.0011(8) C12 0.0211(10) 0.0270(10) 0.0314(11) -0.0073(9) 0.0080(9) -0.0014(8) C13 0.0231(11) 0.0408(13) 0.0510(15) -0.0114(12) 0.0117(11) 0.0005(10) C14 0.0395(13) 0.0416(13) 0.0321(13) -0.0037(10) 0.0143(11) -0.0043(11) C15 0.0238(10) 0.0216(10) 0.0250(10) 0.0024(8) 0.0074(8) 0.0003(8) C16 0.0234(11) 0.0326(12) 0.0335(12) 0.0032(9) 0.0083(9) 0.0002(9) C17 0.0360(12) 0.0359(12) 0.0256(12) 0.0017(9) 0.0071(10) -0.0042(10) C18 0.0190(9) 0.0184(9) 0.0239(10) 0.0029(8) 0.0001(8) -0.0021(7) C19 0.0236(10) 0.0225(10) 0.0244(10) 0.0004(8) -0.0007(8) -0.0010(8) C20 0.0324(12) 0.0209(10) 0.0344(12) -0.0004(9) 0.0014(10) 0.0003(9) C21 0.0367(13) 0.0210(11) 0.0437(14) 0.0087(10) 0.0019(11) -0.0019(9) C22 0.0299(11) 0.0314(12) 0.0355(13) 0.0124(10) 0.0062(10) -0.0035(9) C23 0.0198(10) 0.0270(11) 0.0307(11) 0.0071(9) 0.0039(8) 0.0007(8) C24 0.0276(11) 0.0324(12) 0.0453(14) 0.0137(10) 0.0173(10) 0.0054(9) C25 0.0548(17) 0.0444(15) 0.0450(15) 0.0088(12) 0.0270(13) 0.0118(12) C26 0.0271(13) 0.0573(17) 0.080(2) 0.0298(16) 0.0190(14) 0.0064(12) C27 0.0289(11) 0.0241(10) 0.0277(11) -0.0005(9) 0.0066(9) 0.0045(8) C28 0.0338(13) 0.0375(13) 0.0414(14) 0.0014(11) 0.0121(11) 0.0078(10) C29 0.0469(15) 0.0364(13) 0.0299(12) -0.0060(10) 0.0050(11) 0.0083(11) C30 0.0180(9) 0.0271(10) 0.0230(10) 0.0021(8) 0.0043(8) 0.0012(8) C31 0.0203(10) 0.0255(10) 0.0321(12) 0.0031(9) 0.0018(9) 0.0038(8) C32 0.0267(11) 0.0374(13) 0.0307(12) 0.0090(10) -0.0037(9) 0.0009(9) C33 0.0274(11) 0.0382(13) 0.0313(12) -0.0009(10) -0.0026(9) -0.0072(10) C34 0.0226(10) 0.0270(11) 0.0303(11) 0.0034(9) 0.0024(9) -0.0058(8) O1T 0.166(4) 0.152(4) 0.227(5) -0.018(4) 0.033(4) 0.003(3) C1T 0.165(5) 0.129(5) 0.146(5) 0.056(4) 0.005(4) -0.019(4) C2T 0.212(6) 0.205(6) 0.162(5) 0.025(5) 0.122(5) 0.010(5) C3T 0.243(6) 0.083(3) 0.170(5) -0.047(3) 0.109(4) -0.015(4) C4T 0.155(5) 0.104(4) 0.161(5) -0.023(4) 0.063(4) -0.040(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 1.7152(16) . ? P1 N5 1.7239(17) . ? P1 C30 1.949(2) . ? N2 C3 1.413(2) . ? N2 C6 1.433(2) . ? C3 C4 1.332(3) . ? C3 H3 0.9500 . ? C4 N5 1.414(2) . ? C4 H4 0.9500 . ? N5 C18 1.432(2) . ? C6 C7 1.408(3) . ? C6 C11 1.416(3) . ? C7 C8 1.389(3) . ? C7 C15 1.525(3) . ? C8 C9 1.385(3) . ? C8 H8 0.9500 . ? C9 C10 1.379(3) . ? C9 H9 0.9500 . ? C10 C11 1.393(3) . ? C10 H10 0.9500 . ? C11 C12 1.519(3) . ? C12 C14 1.526(3) . ? C12 C13 1.536(3) . ? C12 H12 1.0000 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C17 1.534(3) . ? C15 C16 1.535(3) . ? C15 H15 1.0000 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C23 1.410(3) . ? C18 C19 1.413(3) . ? C19 C20 1.392(3) . ? C19 C27 1.523(3) . ? C20 C21 1.388(3) . ? C20 H20 0.9500 . ? C21 C22 1.381(3) . ? C21 H21 0.9500 . ? C22 C23 1.398(3) . ? C22 H22 0.9500 . ? C23 C24 1.521(3) . ? C24 C25 1.532(4) . ? C24 C26 1.533(3) . ? C24 H24 1.0000 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 C28 1.536(3) . ? C27 C29 1.536(3) . ? C27 H27 1.0000 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 C31 1.472(3) . ? C30 C34 1.472(3) . ? C30 H30 1.0000 . ? C31 C32 1.356(3) . ? C31 H31 0.9500 . ? C32 C33 1.438(3) . ? C32 H32 0.9500 . ? C33 C34 1.346(3) . ? C33 H33 0.9500 . ? C34 H34 0.9500 . ? O1T C4T 1.490(6) . ? O1T C1T 1.529(7) . ? C1T C2T 1.417(7) . ? C1T H1T1 0.9900 . ? C1T H1T2 0.9900 . ? C2T C3T 1.427(6) . ? C2T H2T1 0.9900 . ? C2T H2T2 0.9900 . ? C3T C4T 1.291(6) . ? C3T H3T1 0.9900 . ? C3T H3T2 0.9900 . ? C4T H4T1 0.9900 . ? C4T H4T2 0.9900 . ? 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 N5 88.75(8) . . ? N2 P1 C30 101.80(8) . . ? N5 P1 C30 101.09(8) . . ? C3 N2 C6 122.81(16) . . ? C3 N2 P1 111.74(12) . . ? C6 N2 P1 125.43(13) . . ? C4 C3 N2 112.39(17) . . ? C4 C3 H3 123.8 . . ? N2 C3 H3 123.8 . . ? C3 C4 N5 112.24(17) . . ? C3 C4 H4 123.9 . . ? N5 C4 H4 123.9 . . ? C4 N5 C18 123.48(16) . . ? C4 N5 P1 111.60(12) . . ? C18 N5 P1 123.52(13) . . ? C7 C6 C11 120.79(17) . . ? C7 C6 N2 119.96(16) . . ? C11 C6 N2 119.22(16) . . ? C8 C7 C6 118.41(17) . . ? C8 C7 C15 118.48(17) . . ? C6 C7 C15 123.10(17) . . ? C9 C8 C7 121.54(19) . . ? C9 C8 H8 119.2 . . ? C7 C8 H8 119.2 . . ? C10 C9 C8 119.50(19) . . ? C10 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? C9 C10 C11 121.74(19) . . ? C9 C10 H10 119.1 . . ? C11 C10 H10 119.1 . . ? C10 C11 C6 117.94(18) . . ? C10 C11 C12 119.17(17) . . ? C6 C11 C12 122.88(17) . . ? C11 C12 C14 111.60(18) . . ? C11 C12 C13 111.68(19) . . ? C14 C12 C13 110.26(18) . . ? C11 C12 H12 107.7 . . ? C14 C12 H12 107.7 . . ? C13 C12 H12 107.7 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C7 C15 C17 110.17(17) . . ? C7 C15 C16 112.36(17) . . ? C17 C15 C16 109.75(17) . . ? C7 C15 H15 108.1 . . ? C17 C15 H15 108.1 . . ? C16 C15 H15 108.1 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C23 C18 C19 120.88(18) . . ? C23 C18 N5 118.69(17) . . ? C19 C18 N5 120.42(17) . . ? C20 C19 C18 118.18(18) . . ? C20 C19 C27 118.11(18) . . ? C18 C19 C27 123.69(18) . . ? C21 C20 C19 121.6(2) . . ? C21 C20 H20 119.2 . . ? C19 C20 H20 119.2 . . ? C22 C21 C20 119.6(2) . . ? C22 C21 H21 120.2 . . ? C20 C21 H21 120.2 . . ? C21 C22 C23 121.4(2) . . ? C21 C22 H22 119.3 . . ? C23 C22 H22 119.3 . . ? C22 C23 C18 118.27(19) . . ? C22 C23 C24 118.82(18) . . ? C18 C23 C24 122.88(18) . . ? C23 C24 C25 111.6(2) . . ? C23 C24 C26 111.0(2) . . ? C25 C24 C26 110.6(2) . . ? C23 C24 H24 107.8 . . ? C25 C24 H24 107.8 . . ? C26 C24 H24 107.8 . . ? 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 . . ? C19 C27 C28 112.64(18) . . ? C19 C27 C29 110.56(18) . . ? C28 C27 C29 109.38(18) . . ? C19 C27 H27 108.0 . . ? C28 C27 H27 108.0 . . ? C29 C27 H27 108.0 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C27 C29 H29A 109.5 . . ? C27 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C27 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C31 C30 C34 104.00(18) . . ? C31 C30 P1 101.64(13) . . ? C34 C30 P1 101.47(13) . . ? C31 C30 H30 115.9 . . ? C34 C30 H30 115.9 . . ? P1 C30 H30 115.9 . . ? C32 C31 C30 108.57(19) . . ? C32 C31 H31 125.7 . . ? C30 C31 H31 125.7 . . ? C31 C32 C33 109.1(2) . . ? C31 C32 H32 125.5 . . ? C33 C32 H32 125.5 . . ? C34 C33 C32 109.0(2) . . ? C34 C33 H33 125.5 . . ? C32 C33 H33 125.5 . . ? C33 C34 C30 109.02(19) . . ? C33 C34 H34 125.5 . . ? C30 C34 H34 125.5 . . ? C4T O1T C1T 101.0(6) . . ? C2T C1T O1T 101.9(5) . . ? C2T C1T H1T1 111.4 . . ? O1T C1T H1T1 111.4 . . ? C2T C1T H1T2 111.4 . . ? O1T C1T H1T2 111.4 . . ? H1T1 C1T H1T2 109.3 . . ? C1T C2T C3T 108.5(5) . . ? C1T C2T H2T1 110.0 . . ? C3T C2T H2T1 110.0 . . ? C1T C2T H2T2 110.0 . . ? C3T C2T H2T2 110.0 . . ? H2T1 C2T H2T2 108.4 . . ? C4T C3T C2T 109.8(5) . . ? C4T C3T H3T1 109.7 . . ? C2T C3T H3T1 109.7 . . ? C4T C3T H3T2 109.7 . . ? C2T C3T H3T2 109.7 . . ? H3T1 C3T H3T2 108.2 . . ? C3T C4T O1T 105.4(5) . . ? C3T C4T H4T1 110.7 . . ? O1T C4T H4T1 110.7 . . ? C3T C4T H4T2 110.7 . . ? O1T C4T H4T2 110.7 . . ? H4T1 C4T H4T2 108.8 . . ? 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 N5 P1 N2 C3 16.43(13) . . . . ? C30 P1 N2 C3 -84.64(14) . . . . ? N5 P1 N2 C6 -165.14(15) . . . . ? C30 P1 N2 C6 93.79(15) . . . . ? C6 N2 C3 C4 168.34(16) . . . . ? P1 N2 C3 C4 -13.18(19) . . . . ? N2 C3 C4 N5 0.9(2) . . . . ? C3 C4 N5 C18 178.56(16) . . . . ? C3 C4 N5 P1 11.7(2) . . . . ? N2 P1 N5 C4 -15.92(13) . . . . ? C30 P1 N5 C4 85.86(14) . . . . ? N2 P1 N5 C18 177.20(15) . . . . ? C30 P1 N5 C18 -81.02(15) . . . . ? C3 N2 C6 C7 62.8(2) . . . . ? P1 N2 C6 C7 -115.42(18) . . . . ? C3 N2 C6 C11 -115.2(2) . . . . ? P1 N2 C6 C11 66.5(2) . . . . ? C11 C6 C7 C8 -0.7(3) . . . . ? N2 C6 C7 C8 -178.69(18) . . . . ? C11 C6 C7 C15 177.76(19) . . . . ? N2 C6 C7 C15 -0.3(3) . . . . ? C6 C7 C8 C9 -1.8(3) . . . . ? C15 C7 C8 C9 179.7(2) . . . . ? C7 C8 C9 C10 2.2(4) . . . . ? C8 C9 C10 C11 0.0(4) . . . . ? C9 C10 C11 C6 -2.4(3) . . . . ? C9 C10 C11 C12 176.5(2) . . . . ? C7 C6 C11 C10 2.7(3) . . . . ? N2 C6 C11 C10 -179.26(18) . . . . ? C7 C6 C11 C12 -176.11(19) . . . . ? N2 C6 C11 C12 1.9(3) . . . . ? C10 C11 C12 C14 73.2(3) . . . . ? C6 C11 C12 C14 -108.0(2) . . . . ? C10 C11 C12 C13 -50.8(3) . . . . ? C6 C11 C12 C13 128.0(2) . . . . ? C8 C7 C15 C17 71.3(2) . . . . ? C6 C7 C15 C17 -107.1(2) . . . . ? C8 C7 C15 C16 -51.4(3) . . . . ? C6 C7 C15 C16 130.2(2) . . . . ? C4 N5 C18 C23 126.5(2) . . . . ? P1 N5 C18 C23 -68.2(2) . . . . ? C4 N5 C18 C19 -54.8(3) . . . . ? P1 N5 C18 C19 110.51(19) . . . . ? C23 C18 C19 C20 0.0(3) . . . . ? N5 C18 C19 C20 -178.67(19) . . . . ? C23 C18 C19 C27 -178.5(2) . . . . ? N5 C18 C19 C27 2.8(3) . . . . ? C18 C19 C20 C21 2.6(3) . . . . ? C27 C19 C20 C21 -178.8(2) . . . . ? C19 C20 C21 C22 -2.8(4) . . . . ? C20 C21 C22 C23 0.3(4) . . . . ? C21 C22 C23 C18 2.2(3) . . . . ? C21 C22 C23 C24 -176.0(2) . . . . ? C19 C18 C23 C22 -2.3(3) . . . . ? N5 C18 C23 C22 176.35(19) . . . . ? C19 C18 C23 C24 175.8(2) . . . . ? N5 C18 C23 C24 -5.5(3) . . . . ? C22 C23 C24 C25 -69.9(3) . . . . ? C18 C23 C24 C25 112.0(2) . . . . ? C22 C23 C24 C26 53.9(3) . . . . ? C18 C23 C24 C26 -124.1(2) . . . . ? C20 C19 C27 C28 49.1(3) . . . . ? C18 C19 C27 C28 -132.4(2) . . . . ? C20 C19 C27 C29 -73.6(2) . . . . ? C18 C19 C27 C29 104.9(2) . . . . ? N2 P1 C30 C31 173.02(13) . . . . ? N5 P1 C30 C31 81.97(15) . . . . ? N2 P1 C30 C34 -79.90(15) . . . . ? N5 P1 C30 C34 -170.94(13) . . . . ? C34 C30 C31 C32 -5.4(2) . . . . ? P1 C30 C31 C32 99.68(17) . . . . ? C30 C31 C32 C33 3.6(2) . . . . ? C31 C32 C33 C34 -0.1(3) . . . . ? C32 C33 C34 C30 -3.4(2) . . . . ? C31 C30 C34 C33 5.4(2) . . . . ? P1 C30 C34 C33 -99.84(18) . . . . ? C4T O1T C1T C2T -29.1(7) . . . . ? O1T C1T C2T C3T 13.5(9) . . . . ? C1T C2T C3T C4T 10.2(11) . . . . ? C2T C3T C4T O1T -30.0(10) . . . . ? C1T O1T C4T C3T 36.8(8) . . . . ? _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.660 _refine_diff_density_min -0.680 _refine_diff_density_rms 0.061 #============================================================================== data_gudat81 _database_code_depnum_ccdc_archive 'CCDC 631301' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-pentamethylcyclopentadienyl-1,3-bis-mesityl-1,3,2-diazaphospholene ; _chemical_name_common ;2-pentamethylcyclopentadienyl-1,3-bis-mesityl-1,3,2- diazaphospholene ; _chemical_melting_point ? _chemical_formula_moiety 'C30 H39 N2 P' _chemical_formula_sum 'C30 H39 N2 P' _chemical_formula_weight 458.60 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 #(No.2) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.9703(2) _cell_length_b 10.6255(3) _cell_length_c 13.7990(4) _cell_angle_alpha 75.585(1) _cell_angle_beta 85.812(1) _cell_angle_gamma 69.263(1) _cell_volume 1323.93(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3097 _cell_measurement_theta_min 1 _cell_measurement_theta_max 25 _exptl_crystal_description blocks _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.150 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.124 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; dx 0 40 mm, 180 sec./deg., 1 deg., 12 sets, 868 frames, mos.= 0.556(2) deg. ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'rotation in phi and omega, 1 deg.' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 6707 _diffrn_reflns_av_R_equivalents 0.0225 _diffrn_reflns_av_sigmaI/netI 0.0585 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 25.03 _reflns_number_total 4456 _reflns_number_gt 3057 _reflns_threshold_expression >2sigma(I) _computing_data_collection Collect _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL-NT _computing_publication_material 'SHELXL-97 (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^)+(0.0696P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4456 _refine_ls_number_parameters 308 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0714 _refine_ls_R_factor_gt 0.0440 _refine_ls_wR_factor_ref 0.1220 _refine_ls_wR_factor_gt 0.1118 _refine_ls_goodness_of_fit_ref 0.976 _refine_ls_restrained_S_all 0.976 _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 0.55646(5) 0.10664(5) 0.29576(4) 0.03742(18) Uani 1 1 d . . . N2 N 0.54613(17) 0.23492(15) 0.18710(11) 0.0402(4) Uani 1 1 d . . . C3 C 0.6408(2) 0.1811(2) 0.11485(15) 0.0462(5) Uani 1 1 d . . . H3 H 0.6441 0.2324 0.0500 0.055 Uiso 1 1 calc R . . C4 C 0.7245(2) 0.0510(2) 0.14775(15) 0.0457(5) Uani 1 1 d . . . H4 H 0.7935 0.0024 0.1087 0.055 Uiso 1 1 calc R . . N5 N 0.69909(16) -0.00756(15) 0.24840(11) 0.0388(4) Uani 1 1 d . . . C6 C 0.4484(2) 0.37574(19) 0.16801(15) 0.0399(5) Uani 1 1 d . . . C7 C 0.3590(2) 0.4331(2) 0.08188(15) 0.0428(5) Uani 1 1 d . . . C8 C 0.2592(2) 0.5670(2) 0.07120(16) 0.0483(6) Uani 1 1 d . . . H8 H 0.1994 0.6052 0.0148 0.058 Uiso 1 1 calc R . . C9 C 0.2448(2) 0.6450(2) 0.13949(17) 0.0485(6) Uani 1 1 d . . . C10 C 0.3385(2) 0.5877(2) 0.22087(16) 0.0498(6) Uani 1 1 d . . . H10 H 0.3320 0.6393 0.2676 0.060 Uiso 1 1 calc R . . C11 C 0.4421(2) 0.4561(2) 0.23546(15) 0.0436(5) Uani 1 1 d . . . C12 C 0.5484(3) 0.4093(2) 0.32103(18) 0.0629(7) Uani 1 1 d . . . H12A H 0.5327 0.3346 0.3703 0.094 Uiso 1 1 calc R . . H12B H 0.5359 0.4853 0.3508 0.094 Uiso 1 1 calc R . . H12C H 0.6441 0.3784 0.2964 0.094 Uiso 1 1 calc R . . C13 C 0.1321(3) 0.7888(2) 0.12695(19) 0.0668(7) Uani 1 1 d . . . H13A H 0.1459 0.8303 0.1780 0.100 Uiso 1 1 calc R . . H13B H 0.0383 0.7818 0.1326 0.100 Uiso 1 1 calc R . . H13C H 0.1410 0.8450 0.0623 0.100 Uiso 1 1 calc R . . C14 C 0.3665(3) 0.3607(2) -0.00014(16) 0.0594(6) Uani 1 1 d . . . H14A H 0.2757 0.3980 -0.0349 0.089 Uiso 1 1 calc R . . H14B H 0.3887 0.2634 0.0283 0.089 Uiso 1 1 calc R . . H14C H 0.4398 0.3746 -0.0462 0.089 Uiso 1 1 calc R . . C15 C 0.8229(2) -0.10279(19) 0.30920(14) 0.0392(5) Uani 1 1 d . . . C16 C 0.9107(2) -0.0530(2) 0.35159(15) 0.0452(5) Uani 1 1 d . . . C17 C 1.0295(2) -0.1468(2) 0.40776(16) 0.0521(6) Uani 1 1 d . . . H17 H 1.0868 -0.1136 0.4372 0.063 Uiso 1 1 calc R . . C18 C 1.0661(2) -0.2887(2) 0.42162(16) 0.0511(6) Uani 1 1 d . . . C19 C 0.9811(2) -0.3350(2) 0.37652(16) 0.0518(6) Uani 1 1 d . . . H19 H 1.0052 -0.4299 0.3843 0.062 Uiso 1 1 calc R . . C20 C 0.8594(2) -0.2453(2) 0.31927(15) 0.0453(5) Uani 1 1 d . . . C21 C 0.7759(3) -0.3028(2) 0.2669(2) 0.0657(7) Uani 1 1 d . . . H21A H 0.6839 -0.2909 0.2972 0.099 Uiso 1 1 calc R . . H21B H 0.8274 -0.3997 0.2723 0.099 Uiso 1 1 calc R . . H21C H 0.7630 -0.2546 0.1975 0.099 Uiso 1 1 calc R . . C22 C 1.1967(3) -0.3884(2) 0.48437(19) 0.0716(8) Uani 1 1 d . . . H22A H 1.2141 -0.4807 0.4779 0.107 Uiso 1 1 calc R . . H22B H 1.1799 -0.3852 0.5533 0.107 Uiso 1 1 calc R . . H22C H 1.2786 -0.3624 0.4617 0.107 Uiso 1 1 calc R . . C23 C 0.8790(3) 0.0999(2) 0.3371(2) 0.0647(7) Uani 1 1 d . . . H23A H 0.8507 0.1464 0.2687 0.097 Uiso 1 1 calc R . . H23B H 0.9634 0.1151 0.3529 0.097 Uiso 1 1 calc R . . H23C H 0.8028 0.1359 0.3804 0.097 Uiso 1 1 calc R . . C24 C 0.3926(2) 0.05430(19) 0.28917(15) 0.0416(5) Uani 1 1 d . . . C25 C 0.3488(2) 0.0458(2) 0.19020(16) 0.0439(5) Uani 1 1 d . . . C26 C 0.2224(2) 0.1479(2) 0.16141(17) 0.0497(6) Uani 1 1 d . . . C27 C 0.1757(2) 0.2291(2) 0.23652(18) 0.0509(6) Uani 1 1 d . . . C28 C 0.2699(2) 0.1746(2) 0.31324(16) 0.0473(6) Uani 1 1 d . . . C29 C 0.4214(3) -0.0812(2) 0.37102(18) 0.0628(7) Uani 1 1 d . . . H29A H 0.4491 -0.0690 0.4323 0.094 Uiso 1 1 calc R . . H29B H 0.4971 -0.1546 0.3504 0.094 Uiso 1 1 calc R . . H29C H 0.3358 -0.1043 0.3814 0.094 Uiso 1 1 calc R . . C30 C 0.4322(2) -0.0643(2) 0.13746(18) 0.0614(7) Uani 1 1 d . . . H30A H 0.3828 -0.0510 0.0765 0.092 Uiso 1 1 calc R . . H30B H 0.4414 -0.1537 0.1798 0.092 Uiso 1 1 calc R . . H30C H 0.5257 -0.0588 0.1222 0.092 Uiso 1 1 calc R . . C31 C 0.1340(3) 0.1744(3) 0.0696(2) 0.0798(8) Uani 1 1 d . . . H31A H 0.1906 0.1209 0.0248 0.120 Uiso 1 1 calc R . . H31B H 0.1036 0.2712 0.0367 0.120 Uiso 1 1 calc R . . H31C H 0.0513 0.1482 0.0889 0.120 Uiso 1 1 calc R . . C32 C 0.0428(3) 0.3569(2) 0.2246(2) 0.0759(8) Uani 1 1 d . . . H32A H 0.0186 0.3801 0.2881 0.114 Uiso 1 1 calc R . . H32B H -0.0352 0.3394 0.2004 0.114 Uiso 1 1 calc R . . H32C H 0.0604 0.4326 0.1776 0.114 Uiso 1 1 calc R . . C33 C 0.2609(3) 0.2207(3) 0.40773(19) 0.0727(8) Uani 1 1 d . . . H33A H 0.3200 0.2763 0.4031 0.109 Uiso 1 1 calc R . . H33B H 0.2936 0.1412 0.4629 0.109 Uiso 1 1 calc R . . H33C H 0.1633 0.2746 0.4181 0.109 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 0.0345(3) 0.0390(3) 0.0352(3) -0.0079(2) -0.0003(2) -0.0088(2) N2 0.0396(10) 0.0362(9) 0.0387(9) -0.0077(7) 0.0035(8) -0.0073(8) C3 0.0465(13) 0.0483(13) 0.0363(11) -0.0055(10) 0.0057(10) -0.0115(11) C4 0.0437(13) 0.0463(12) 0.0395(12) -0.0118(10) 0.0078(10) -0.0070(11) N5 0.0356(10) 0.0378(9) 0.0356(9) -0.0058(7) -0.0001(7) -0.0057(8) C6 0.0368(12) 0.0345(11) 0.0421(12) -0.0035(9) 0.0021(9) -0.0091(10) C7 0.0426(12) 0.0419(12) 0.0409(12) -0.0044(10) 0.0012(9) -0.0149(10) C8 0.0422(13) 0.0457(13) 0.0461(13) 0.0020(11) -0.0045(10) -0.0101(11) C9 0.0405(13) 0.0418(12) 0.0516(13) -0.0037(11) 0.0070(10) -0.0066(10) C10 0.0505(14) 0.0426(12) 0.0504(13) -0.0111(10) 0.0022(11) -0.0094(11) C11 0.0425(13) 0.0376(12) 0.0466(12) -0.0081(10) -0.0025(10) -0.0097(10) C12 0.0649(16) 0.0518(13) 0.0696(16) -0.0205(12) -0.0197(13) -0.0094(12) C13 0.0584(15) 0.0509(14) 0.0686(16) -0.0049(12) 0.0016(12) 0.0015(12) C14 0.0669(16) 0.0565(14) 0.0484(13) -0.0056(11) -0.0101(11) -0.0165(13) C15 0.0310(11) 0.0424(12) 0.0384(11) -0.0074(9) 0.0027(9) -0.0078(10) C16 0.0367(12) 0.0475(12) 0.0468(12) -0.0089(10) 0.0030(10) -0.0114(10) C17 0.0381(13) 0.0637(15) 0.0534(13) -0.0158(11) -0.0023(10) -0.0145(11) C18 0.0377(13) 0.0610(15) 0.0434(12) -0.0085(11) 0.0001(10) -0.0063(11) C19 0.0468(14) 0.0411(12) 0.0546(14) -0.0077(11) -0.0021(11) -0.0016(11) C20 0.0405(13) 0.0413(12) 0.0472(12) -0.0088(10) -0.0006(10) -0.0066(10) C21 0.0602(16) 0.0453(13) 0.0860(18) -0.0176(13) -0.0189(13) -0.0063(12) C22 0.0491(15) 0.0780(17) 0.0653(16) -0.0015(14) -0.0161(12) -0.0027(13) C23 0.0540(15) 0.0584(15) 0.0867(18) -0.0161(13) -0.0106(13) -0.0243(13) C24 0.0351(12) 0.0427(11) 0.0430(12) -0.0069(10) 0.0026(9) -0.0113(10) C25 0.0395(12) 0.0431(12) 0.0511(13) -0.0128(10) -0.0006(10) -0.0153(10) C26 0.0419(13) 0.0482(13) 0.0571(14) -0.0081(11) -0.0087(11) -0.0145(11) C27 0.0348(12) 0.0448(12) 0.0669(15) -0.0111(12) 0.0040(11) -0.0088(10) C28 0.0360(12) 0.0527(13) 0.0537(14) -0.0174(11) 0.0137(10) -0.0153(11) C29 0.0584(15) 0.0592(15) 0.0644(15) 0.0028(12) 0.0017(12) -0.0247(12) C30 0.0540(15) 0.0630(15) 0.0720(16) -0.0313(13) -0.0030(12) -0.0151(13) C31 0.0664(18) 0.0851(19) 0.0825(19) -0.0147(16) -0.0281(14) -0.0178(15) C32 0.0480(15) 0.0545(15) 0.110(2) -0.0153(15) 0.0031(14) -0.0028(12) C33 0.0602(17) 0.0956(19) 0.0676(16) -0.0383(15) 0.0213(13) -0.0246(15) _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 N5 1.7202(16) . ? P1 N2 1.7384(15) . ? P1 C24 1.917(2) . ? N2 C3 1.406(3) . ? N2 C6 1.437(2) . ? C3 C4 1.319(3) . ? C3 H3 0.9300 . ? C4 N5 1.418(2) . ? C4 H4 0.9300 . ? N5 C15 1.448(2) . ? C6 C11 1.396(3) . ? C6 C7 1.410(3) . ? C7 C8 1.396(3) . ? C7 C14 1.503(3) . ? C8 C9 1.372(3) . ? C8 H8 0.9300 . ? C9 C10 1.384(3) . ? C9 C13 1.519(3) . ? C10 C11 1.389(3) . ? C10 H10 0.9300 . ? C11 C12 1.511(3) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C16 1.394(3) . ? C15 C20 1.399(3) . ? C16 C17 1.383(3) . ? C16 C23 1.505(3) . ? C17 C18 1.386(3) . ? C17 H17 0.9300 . ? C18 C19 1.369(3) . ? C18 C22 1.516(3) . ? C19 C20 1.397(3) . ? C19 H19 0.9300 . ? C20 C21 1.503(3) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? 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 1.497(3) . ? C24 C28 1.512(3) . ? C24 C29 1.541(3) . ? C25 C26 1.346(3) . ? C25 C30 1.495(3) . ? C26 C27 1.458(3) . ? C26 C31 1.507(3) . ? C27 C28 1.339(3) . ? C27 C32 1.508(3) . ? C28 C33 1.490(3) . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 H33A 0.9600 . ? C33 H33B 0.9600 . ? C33 H33C 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 N5 P1 N2 90.18(7) . . ? N5 P1 C24 107.29(9) . . ? N2 P1 C24 105.05(8) . . ? C3 N2 C6 122.85(15) . . ? C3 N2 P1 110.96(12) . . ? C6 N2 P1 126.06(13) . . ? C4 C3 N2 113.63(17) . . ? C4 C3 H3 123.2 . . ? N2 C3 H3 123.2 . . ? C3 C4 N5 113.58(18) . . ? C3 C4 H4 123.2 . . ? N5 C4 H4 123.2 . . ? C4 N5 C15 117.00(15) . . ? C4 N5 P1 111.12(12) . . ? C15 N5 P1 122.40(12) . . ? C11 C6 C7 119.82(18) . . ? C11 C6 N2 119.62(18) . . ? C7 C6 N2 120.56(19) . . ? C8 C7 C6 117.8(2) . . ? C8 C7 C14 117.96(19) . . ? C6 C7 C14 124.21(19) . . ? C9 C8 C7 123.4(2) . . ? C9 C8 H8 118.3 . . ? C7 C8 H8 118.3 . . ? C8 C9 C10 117.12(19) . . ? C8 C9 C13 122.0(2) . . ? C10 C9 C13 120.9(2) . . ? C9 C10 C11 122.6(2) . . ? C9 C10 H10 118.7 . . ? C11 C10 H10 118.7 . . ? C10 C11 C6 119.00(19) . . ? C10 C11 C12 118.1(2) . . ? C6 C11 C12 122.78(18) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C9 C13 H13A 109.5 . . ? C9 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C9 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C7 C14 H14A 109.5 . . ? C7 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C7 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 C20 120.15(18) . . ? C16 C15 N5 120.45(17) . . ? C20 C15 N5 119.25(19) . . ? C17 C16 C15 119.0(2) . . ? C17 C16 C23 119.6(2) . . ? C15 C16 C23 121.45(18) . . ? C16 C17 C18 122.2(2) . . ? C16 C17 H17 118.9 . . ? C18 C17 H17 118.9 . . ? C19 C18 C17 117.8(2) . . ? C19 C18 C22 121.5(2) . . ? C17 C18 C22 120.7(2) . . ? C18 C19 C20 122.6(2) . . ? C18 C19 H19 118.7 . . ? C20 C19 H19 118.7 . . ? C19 C20 C15 118.2(2) . . ? C19 C20 C21 119.73(19) . . ? C15 C20 C21 121.99(18) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C18 C22 H22A 109.5 . . ? C18 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C18 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C16 C23 H23A 109.5 . . ? C16 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C16 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C25 C24 C28 103.37(16) . . ? C25 C24 C29 113.65(18) . . ? C28 C24 C29 113.14(17) . . ? C25 C24 P1 118.80(14) . . ? C28 C24 P1 103.02(14) . . ? C29 C24 P1 104.61(14) . . ? C26 C25 C30 127.4(2) . . ? C26 C25 C24 108.71(19) . . ? C30 C25 C24 123.80(18) . . ? C25 C26 C27 109.6(2) . . ? C25 C26 C31 127.3(2) . . ? C27 C26 C31 123.0(2) . . ? C28 C27 C26 109.61(19) . . ? C28 C27 C32 127.0(2) . . ? C26 C27 C32 123.4(2) . . ? C27 C28 C33 127.6(2) . . ? C27 C28 C24 108.6(2) . . ? C33 C28 C24 123.8(2) . . ? C24 C29 H29A 109.5 . . ? C24 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C24 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C25 C30 H30A 109.5 . . ? C25 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C25 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C26 C31 H31A 109.5 . . ? C26 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C26 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C27 C32 H32A 109.5 . . ? C27 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C27 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C28 C33 H33A 109.5 . . ? C28 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C28 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 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 N5 P1 N2 C3 6.72(15) . . . . ? C24 P1 N2 C3 -101.26(15) . . . . ? N5 P1 N2 C6 -177.41(17) . . . . ? C24 P1 N2 C6 74.61(18) . . . . ? C6 N2 C3 C4 178.18(18) . . . . ? P1 N2 C3 C4 -5.8(2) . . . . ? N2 C3 C4 N5 1.1(3) . . . . ? C3 C4 N5 C15 -143.22(19) . . . . ? C3 C4 N5 P1 4.1(2) . . . . ? N2 P1 N5 C4 -6.10(14) . . . . ? C24 P1 N5 C4 99.74(14) . . . . ? N2 P1 N5 C15 139.13(15) . . . . ? C24 P1 N5 C15 -115.04(15) . . . . ? C3 N2 C6 C11 -130.3(2) . . . . ? P1 N2 C6 C11 54.3(2) . . . . ? C3 N2 C6 C7 49.8(3) . . . . ? P1 N2 C6 C7 -125.64(18) . . . . ? C11 C6 C7 C8 -4.4(3) . . . . ? N2 C6 C7 C8 175.48(17) . . . . ? C11 C6 C7 C14 174.10(19) . . . . ? N2 C6 C7 C14 -6.0(3) . . . . ? C6 C7 C8 C9 0.5(3) . . . . ? C14 C7 C8 C9 -178.2(2) . . . . ? C7 C8 C9 C10 2.3(3) . . . . ? C7 C8 C9 C13 -178.22(19) . . . . ? C8 C9 C10 C11 -1.1(3) . . . . ? C13 C9 C10 C11 179.40(19) . . . . ? C9 C10 C11 C6 -2.8(3) . . . . ? C9 C10 C11 C12 174.0(2) . . . . ? C7 C6 C11 C10 5.6(3) . . . . ? N2 C6 C11 C10 -174.34(17) . . . . ? C7 C6 C11 C12 -171.04(19) . . . . ? N2 C6 C11 C12 9.0(3) . . . . ? C4 N5 C15 C16 80.0(2) . . . . ? P1 N5 C15 C16 -63.3(2) . . . . ? C4 N5 C15 C20 -95.5(2) . . . . ? P1 N5 C15 C20 121.14(18) . . . . ? C20 C15 C16 C17 -3.3(3) . . . . ? N5 C15 C16 C17 -178.83(17) . . . . ? C20 C15 C16 C23 176.4(2) . . . . ? N5 C15 C16 C23 0.9(3) . . . . ? C15 C16 C17 C18 1.4(3) . . . . ? C23 C16 C17 C18 -178.3(2) . . . . ? C16 C17 C18 C19 0.8(3) . . . . ? C16 C17 C18 C22 -179.5(2) . . . . ? C17 C18 C19 C20 -1.0(3) . . . . ? C22 C18 C19 C20 179.3(2) . . . . ? C18 C19 C20 C15 -0.9(3) . . . . ? C18 C19 C20 C21 176.4(2) . . . . ? C16 C15 C20 C19 3.1(3) . . . . ? N5 C15 C20 C19 178.62(17) . . . . ? C16 C15 C20 C21 -174.1(2) . . . . ? N5 C15 C20 C21 1.4(3) . . . . ? N5 P1 C24 C25 -56.22(17) . . . . ? N2 P1 C24 C25 38.78(17) . . . . ? N5 P1 C24 C28 -169.67(12) . . . . ? N2 P1 C24 C28 -74.67(14) . . . . ? N5 P1 C24 C29 71.83(15) . . . . ? N2 P1 C24 C29 166.84(13) . . . . ? C28 C24 C25 C26 1.4(2) . . . . ? C29 C24 C25 C26 124.37(19) . . . . ? P1 C24 C25 C26 -111.91(18) . . . . ? C28 C24 C25 C30 -175.95(18) . . . . ? C29 C24 C25 C30 -52.9(3) . . . . ? P1 C24 C25 C30 70.8(2) . . . . ? C30 C25 C26 C27 177.6(2) . . . . ? C24 C25 C26 C27 0.4(2) . . . . ? C30 C25 C26 C31 0.8(4) . . . . ? C24 C25 C26 C31 -176.4(2) . . . . ? C25 C26 C27 C28 -2.3(3) . . . . ? C31 C26 C27 C28 174.7(2) . . . . ? C25 C26 C27 C32 176.02(19) . . . . ? C31 C26 C27 C32 -7.0(3) . . . . ? C26 C27 C28 C33 -177.1(2) . . . . ? C32 C27 C28 C33 4.7(4) . . . . ? C26 C27 C28 C24 3.1(2) . . . . ? C32 C27 C28 C24 -175.1(2) . . . . ? C25 C24 C28 C27 -2.7(2) . . . . ? C29 C24 C28 C27 -126.1(2) . . . . ? P1 C24 C28 C27 121.53(16) . . . . ? C25 C24 C28 C33 177.4(2) . . . . ? C29 C24 C28 C33 54.1(3) . . . . ? P1 C24 C28 C33 -58.3(2) . . . . ? _diffrn_measured_fraction_theta_max 0.954 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.954 _refine_diff_density_max 0.199 _refine_diff_density_min -0.217 _refine_diff_density_rms 0.042 #============================================================================== data_gudat93 _database_code_depnum_ccdc_archive 'CCDC 631302' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Dimethoxyethane-lithium-eta^5-2-(1,3-dimesityl-1,3,2-diazaphospholenyl)- cyclopentadienide ; _chemical_name_common ; Dimethoxyethane-lithium-eta$5-2-(1,3-dimesityl-1,3,2- diazaphospholenyl)-cyclopentadienide ; _chemical_melting_point ? _chemical_formula_moiety '(C25 H28 N2 P) Li (C4 H10 O2)' _chemical_formula_sum 'C29 H38 Li N2 O2 P' _chemical_formula_weight 484.52 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' Li Li -0.0003 0.0001 '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' O O 0.0106 0.0060 '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 monoclinic _symmetry_space_group_name_H-M P2(1)/n #(No.14) 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 8.5950(3) _cell_length_b 21.7213(8) _cell_length_c 14.6049(6) _cell_angle_alpha 90.00 _cell_angle_beta 92.711(2) _cell_angle_gamma 90.00 _cell_volume 2723.60(18) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 4755 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description plates _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.182 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1040 _exptl_absorpt_coefficient_mu 0.128 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; dx = 40 mm, 240 sec./deg., 1 deg., 2 sets, 222 frames, mos. = 0.823(3) deg. ; _diffrn_ambient_temperature 123(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 'Nonius KappaCCD' _diffrn_measurement_method 'rotation in phi and omega, 1 deg.' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12355 _diffrn_reflns_av_R_equivalents 0.0405 _diffrn_reflns_av_sigmaI/netI 0.0869 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.95 _diffrn_reflns_theta_max 25.03 _reflns_number_total 4776 _reflns_number_gt 2984 _reflns_threshold_expression >2sigma(I) _computing_data_collection Collect _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL-NT _computing_publication_material 'SHELXL-97 (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^)+(0.0610P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4776 _refine_ls_number_parameters 322 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0895 _refine_ls_R_factor_gt 0.0496 _refine_ls_wR_factor_ref 0.1243 _refine_ls_wR_factor_gt 0.1140 _refine_ls_goodness_of_fit_ref 0.967 _refine_ls_restrained_S_all 0.967 _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 P1 P 0.46548(7) 0.13386(3) 0.70773(5) 0.02653(19) Uani 1 1 d . . . N2 N 0.3692(2) 0.07879(8) 0.63881(13) 0.0264(5) Uani 1 1 d . . . C3 C 0.3120(3) 0.03044(11) 0.69115(18) 0.0296(6) Uani 1 1 d . . . H3 H 0.2404 0.0005 0.6673 0.036 Uiso 1 1 calc R . . C4 C 0.3682(3) 0.03072(11) 0.77760(18) 0.0309(6) Uani 1 1 d . . . H4 H 0.3404 0.0015 0.8224 0.037 Uiso 1 1 calc R . . N5 N 0.4739(2) 0.07955(9) 0.79475(14) 0.0290(5) Uani 1 1 d . . . C6 C 0.3419(3) 0.08392(10) 0.54211(17) 0.0251(6) Uani 1 1 d . . . C7 C 0.1904(3) 0.08540(10) 0.50286(18) 0.0288(6) Uani 1 1 d . . . C8 C 0.1702(3) 0.09095(11) 0.40739(18) 0.0338(7) Uani 1 1 d . . . H8 H 0.0675 0.0912 0.3803 0.041 Uiso 1 1 calc R . . C9 C 0.2951(3) 0.09603(11) 0.35117(18) 0.0330(6) Uani 1 1 d . . . C10 C 0.4428(3) 0.09364(11) 0.39162(17) 0.0312(6) Uani 1 1 d . . . H10 H 0.5295 0.0969 0.3539 0.037 Uiso 1 1 calc R . . C11 C 0.4700(3) 0.08663(10) 0.48584(17) 0.0264(6) Uani 1 1 d . . . C12 C 0.6348(3) 0.07816(11) 0.52394(18) 0.0340(6) Uani 1 1 d . . . H12A H 0.6619 0.1119 0.5664 0.051 Uiso 1 1 calc R . . H12B H 0.7062 0.0783 0.4736 0.051 Uiso 1 1 calc R . . H12C H 0.6433 0.0388 0.5566 0.051 Uiso 1 1 calc R . . C13 C 0.2720(4) 0.10409(14) 0.24797(18) 0.0518(8) Uani 1 1 d . . . H13A H 0.3468 0.1344 0.2268 0.078 Uiso 1 1 calc R . . H13B H 0.1658 0.1185 0.2331 0.078 Uiso 1 1 calc R . . H13C H 0.2887 0.0646 0.2176 0.078 Uiso 1 1 calc R . . C14 C 0.0502(3) 0.08241(12) 0.56047(19) 0.0396(7) Uani 1 1 d . . . H14A H 0.0263 0.0393 0.5738 0.059 Uiso 1 1 calc R . . H14B H -0.0391 0.1013 0.5271 0.059 Uiso 1 1 calc R . . H14C H 0.0719 0.1046 0.6180 0.059 Uiso 1 1 calc R . . C15 C 0.5833(3) 0.07989(10) 0.87224(17) 0.0268(6) Uani 1 1 d . . . C16 C 0.7434(3) 0.07501(10) 0.85825(18) 0.0296(6) Uani 1 1 d . . . C17 C 0.8471(3) 0.07629(10) 0.93455(18) 0.0314(6) Uani 1 1 d . . . H17 H 0.9556 0.0732 0.9255 0.038 Uiso 1 1 calc R . . C18 C 0.7978(3) 0.08197(10) 1.02339(18) 0.0318(6) Uani 1 1 d . . . C19 C 0.6380(3) 0.08571(10) 1.03454(17) 0.0308(6) Uani 1 1 d . . . H19 H 0.6019 0.0895 1.0948 0.037 Uiso 1 1 calc R . . C20 C 0.5293(3) 0.08409(10) 0.96092(17) 0.0275(6) Uani 1 1 d . . . C21 C 0.3575(3) 0.08565(11) 0.97870(17) 0.0309(6) Uani 1 1 d . . . H21A H 0.3010 0.1065 0.9278 0.046 Uiso 1 1 calc R . . H21B H 0.3417 0.1080 1.0358 0.046 Uiso 1 1 calc R . . H21C H 0.3185 0.0435 0.9840 0.046 Uiso 1 1 calc R . . C22 C 0.9120(3) 0.08254(12) 1.10449(18) 0.0418(7) Uani 1 1 d . . . H22A H 0.8933 0.1188 1.1424 0.063 Uiso 1 1 calc R . . H22B H 1.0183 0.0841 1.0831 0.063 Uiso 1 1 calc R . . H22C H 0.8990 0.0451 1.1409 0.063 Uiso 1 1 calc R . . C23 C 0.8054(3) 0.06775(12) 0.76356(18) 0.0355(7) Uani 1 1 d . . . H23A H 0.8088 0.1081 0.7336 0.053 Uiso 1 1 calc R . . H23B H 0.7370 0.0402 0.7270 0.053 Uiso 1 1 calc R . . H23C H 0.9106 0.0503 0.7687 0.053 Uiso 1 1 calc R . . C24 C 0.3182(3) 0.18710(10) 0.73839(16) 0.0255(6) Uani 1 1 d . . . C25 C 0.1683(3) 0.18075(12) 0.77598(17) 0.0343(7) Uani 1 1 d . . . H25 H 0.1213 0.1429 0.7920 0.041 Uiso 1 1 calc R . . C26 C 0.1027(3) 0.23832(13) 0.78534(18) 0.0406(7) Uani 1 1 d . . . H26 H 0.0032 0.2466 0.8084 0.049 Uiso 1 1 calc R . . C27 C 0.2077(3) 0.28253(13) 0.75511(18) 0.0422(7) Uani 1 1 d . . . H27 H 0.1925 0.3258 0.7545 0.051 Uiso 1 1 calc R . . C28 C 0.3383(3) 0.25146(11) 0.72625(17) 0.0323(6) Uani 1 1 d . . . H28 H 0.4272 0.2704 0.7021 0.039 Uiso 1 1 calc R . . Li1 Li 0.3301(5) 0.2345(2) 0.8775(3) 0.0372(11) Uani 1 1 d . . . C1D C 0.1088(3) 0.23378(14) 1.0310(2) 0.0551(8) Uani 1 1 d . . . H1D1 H 0.0414 0.2122 0.9854 0.083 Uiso 1 1 calc R . . H1D2 H 0.0754 0.2768 1.0353 0.083 Uiso 1 1 calc R . . H1D3 H 0.1014 0.2138 1.0908 0.083 Uiso 1 1 calc R . . O1D O 0.2638(2) 0.23161(8) 1.00442(12) 0.0420(5) Uani 1 1 d . . . C2D C 0.3691(3) 0.26258(13) 1.0663(2) 0.0462(8) Uani 1 1 d . . . H2D1 H 0.3573 0.2473 1.1295 0.055 Uiso 1 1 calc R . . H2D2 H 0.3477 0.3074 1.0654 0.055 Uiso 1 1 calc R . . C3D C 0.5320(4) 0.25031(12) 1.0368(2) 0.0461(8) Uani 1 1 d . . . H3D1 H 0.6063 0.2794 1.0675 0.055 Uiso 1 1 calc R . . H3D2 H 0.5640 0.2078 1.0534 0.055 Uiso 1 1 calc R . . O2D O 0.5311(2) 0.25830(8) 0.93995(14) 0.0466(5) Uani 1 1 d . . . C4D C 0.6819(3) 0.24809(13) 0.9047(2) 0.0571(9) Uani 1 1 d . . . H4D1 H 0.6763 0.2539 0.8381 0.086 Uiso 1 1 calc R . . H4D2 H 0.7159 0.2060 0.9191 0.086 Uiso 1 1 calc R . . H4D3 H 0.7565 0.2774 0.9329 0.086 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 0.0241(4) 0.0313(4) 0.0243(4) 0.0005(3) 0.0029(3) -0.0015(3) N2 0.0284(12) 0.0305(11) 0.0205(12) -0.0002(9) 0.0044(9) -0.0037(9) C3 0.0271(15) 0.0273(14) 0.0346(17) -0.0004(12) 0.0022(12) -0.0041(11) C4 0.0314(15) 0.0288(14) 0.0328(17) 0.0033(12) 0.0060(13) -0.0044(12) N5 0.0262(12) 0.0347(12) 0.0257(12) 0.0035(10) -0.0018(10) -0.0044(9) C6 0.0255(14) 0.0256(13) 0.0243(15) -0.0027(11) 0.0027(12) -0.0033(11) C7 0.0251(15) 0.0279(13) 0.0336(16) -0.0029(12) 0.0049(12) -0.0002(11) C8 0.0275(15) 0.0358(15) 0.0370(18) -0.0034(13) -0.0103(13) 0.0014(12) C9 0.0374(17) 0.0353(15) 0.0260(16) -0.0006(12) -0.0026(13) -0.0029(12) C10 0.0322(16) 0.0381(15) 0.0239(15) -0.0005(12) 0.0087(12) -0.0059(12) C11 0.0267(14) 0.0273(13) 0.0249(15) -0.0044(11) 0.0000(12) -0.0036(11) C12 0.0243(14) 0.0471(16) 0.0308(16) -0.0048(13) 0.0034(12) -0.0007(12) C13 0.059(2) 0.067(2) 0.0282(17) 0.0054(15) -0.0084(15) -0.0076(16) C14 0.0255(15) 0.0497(17) 0.0439(18) -0.0043(14) 0.0033(13) -0.0018(13) C15 0.0309(15) 0.0229(13) 0.0263(15) 0.0011(11) 0.0000(12) 0.0002(11) C16 0.0298(15) 0.0291(13) 0.0298(16) 0.0015(12) 0.0019(13) -0.0004(11) C17 0.0242(14) 0.0318(14) 0.0380(18) 0.0026(13) 0.0003(13) -0.0021(11) C18 0.0381(17) 0.0258(13) 0.0309(16) 0.0017(12) -0.0045(13) -0.0010(12) C19 0.0387(17) 0.0285(13) 0.0254(15) 0.0003(12) 0.0029(13) -0.0006(12) C20 0.0324(15) 0.0231(12) 0.0269(15) 0.0034(11) 0.0009(12) 0.0013(11) C21 0.0316(15) 0.0345(14) 0.0269(15) 0.0028(12) 0.0050(12) 0.0032(11) C22 0.0429(18) 0.0434(16) 0.0382(18) 0.0029(14) -0.0075(14) -0.0028(13) C23 0.0279(15) 0.0435(15) 0.0353(17) 0.0021(13) 0.0040(13) 0.0023(12) C24 0.0262(14) 0.0317(13) 0.0188(14) -0.0014(11) 0.0022(11) -0.0008(11) C25 0.0295(15) 0.0467(16) 0.0269(16) 0.0025(13) 0.0031(12) -0.0005(12) C26 0.0300(16) 0.0638(19) 0.0283(17) -0.0018(15) 0.0039(13) 0.0164(15) C27 0.0522(19) 0.0412(16) 0.0338(17) 0.0042(14) 0.0077(15) 0.0131(15) C28 0.0355(16) 0.0377(15) 0.0245(15) 0.0039(12) 0.0106(12) 0.0018(12) Li1 0.034(3) 0.048(3) 0.030(3) -0.002(2) 0.005(2) 0.001(2) C1D 0.049(2) 0.071(2) 0.047(2) -0.0102(17) 0.0246(16) -0.0045(16) O1D 0.0390(12) 0.0545(11) 0.0327(11) -0.0065(10) 0.0056(9) 0.0012(9) C2D 0.055(2) 0.0464(17) 0.0373(18) -0.0092(14) -0.0011(16) -0.0042(15) C3D 0.053(2) 0.0415(16) 0.042(2) -0.0098(14) -0.0116(16) 0.0064(14) O2D 0.0307(12) 0.0646(13) 0.0446(14) -0.0002(10) 0.0019(10) 0.0011(9) C4D 0.0309(18) 0.0603(19) 0.081(3) -0.0004(18) 0.0081(17) 0.0012(14) _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. Cp is the centroid of the (C24-C28) ring with the coordinates 0.22704 0.22803 0.75621 ; 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 N5 1.733(2) . ? P1 N2 1.7464(19) . ? P1 C24 1.787(2) . ? N2 C3 1.402(3) . ? N2 C6 1.425(3) . ? C3 C4 1.330(3) . ? C3 H3 0.9500 . ? C4 N5 1.412(3) . ? C4 H4 0.9500 . ? N5 C15 1.436(3) . ? C6 C7 1.398(3) . ? C6 C11 1.405(3) . ? C7 C8 1.402(3) . ? C7 C14 1.504(3) . ? C8 C9 1.386(4) . ? C8 H8 0.9500 . ? C9 C10 1.376(3) . ? C9 C13 1.521(3) . ? C10 C11 1.393(3) . ? C10 H10 0.9500 . ? C11 C12 1.509(3) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C20 1.399(3) . ? C15 C16 1.405(3) . ? C16 C17 1.394(3) . ? C16 C23 1.514(4) . ? C17 C18 1.390(4) . ? C17 H17 0.9500 . ? C18 C19 1.393(3) . ? C18 C22 1.502(3) . ? C19 C20 1.391(3) . ? C19 H19 0.9500 . ? C20 C21 1.512(3) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 C28 1.421(3) . ? C24 C25 1.432(3) . ? C24 Li1 2.275(5) . ? C25 C26 1.381(3) . ? C25 Li1 2.302(5) . ? C25 H25 0.9500 . ? C26 C27 1.404(4) . ? C26 Li1 2.321(5) . ? C26 H26 0.9500 . ? C27 C28 1.392(3) . ? C27 Li1 2.283(5) . ? C27 H27 0.9500 . ? C28 Li1 2.244(5) . ? C28 H28 0.9500 . ? Li1 Cp 1.947(5) . ? Li1 O1D 1.966(5) . ? Li1 O2D 1.984(5) . ? C1D O1D 1.406(3) . ? C1D H1D1 0.9800 . ? C1D H1D2 0.9800 . ? C1D H1D3 0.9800 . ? O1D C2D 1.418(3) . ? C2D C3D 1.508(4) . ? C2D H2D1 0.9900 . ? C2D H2D2 0.9900 . ? C3D O2D 1.425(3) . ? C3D H3D1 0.9900 . ? C3D H3D2 0.9900 . ? O2D C4D 1.434(3) . ? C4D H4D1 0.9800 . ? C4D H4D2 0.9800 . ? C4D H4D3 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 N5 P1 N2 87.64(9) . . ? N5 P1 C24 105.21(11) . . ? N2 P1 C24 105.42(10) . . ? C3 N2 C6 123.6(2) . . ? C3 N2 P1 111.58(16) . . ? C6 N2 P1 124.68(15) . . ? C4 C3 N2 113.2(2) . . ? C4 C3 H3 123.4 . . ? N2 C3 H3 123.4 . . ? C3 C4 N5 111.9(2) . . ? C3 C4 H4 124.0 . . ? N5 C4 H4 124.0 . . ? C4 N5 C15 122.37(19) . . ? C4 N5 P1 112.15(16) . . ? C15 N5 P1 125.27(15) . . ? C7 C6 C11 119.9(2) . . ? C7 C6 N2 121.0(2) . . ? C11 C6 N2 119.1(2) . . ? C6 C7 C8 118.6(2) . . ? C6 C7 C14 121.7(2) . . ? C8 C7 C14 119.7(2) . . ? C9 C8 C7 122.2(2) . . ? C9 C8 H8 118.9 . . ? C7 C8 H8 118.9 . . ? C10 C9 C8 117.8(2) . . ? C10 C9 C13 120.3(3) . . ? C8 C9 C13 121.9(2) . . ? C9 C10 C11 122.5(2) . . ? C9 C10 H10 118.8 . . ? C11 C10 H10 118.8 . . ? C10 C11 C6 118.9(2) . . ? C10 C11 C12 119.2(2) . . ? C6 C11 C12 121.8(2) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C9 C13 H13A 109.5 . . ? C9 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C9 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C7 C14 H14A 109.5 . . ? C7 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C7 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C20 C15 C16 120.6(2) . . ? C20 C15 N5 119.8(2) . . ? C16 C15 N5 119.6(2) . . ? C17 C16 C15 118.4(2) . . ? C17 C16 C23 119.5(2) . . ? C15 C16 C23 122.0(2) . . ? C18 C17 C16 122.4(2) . . ? C18 C17 H17 118.8 . . ? C16 C17 H17 118.8 . . ? C17 C18 C19 117.4(2) . . ? C17 C18 C22 121.3(2) . . ? C19 C18 C22 121.2(2) . . ? C20 C19 C18 122.5(2) . . ? C20 C19 H19 118.7 . . ? C18 C19 H19 118.7 . . ? C19 C20 C15 118.5(2) . . ? C19 C20 C21 119.5(2) . . ? C15 C20 C21 122.0(2) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C18 C22 H22A 109.5 . . ? C18 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C18 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C16 C23 H23A 109.5 . . ? C16 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C16 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C28 C24 C25 105.0(2) . . ? C28 C24 P1 120.94(19) . . ? C25 C24 P1 134.03(18) . . ? C28 C24 Li1 70.47(17) . . ? C25 C24 Li1 72.79(18) . . ? P1 C24 Li1 120.95(16) . . ? C26 C25 C24 109.3(2) . . ? C26 C25 Li1 73.40(19) . . ? C24 C25 Li1 70.76(18) . . ? C26 C25 H25 125.4 . . ? C24 C25 H25 125.4 . . ? Li1 C25 H25 122.1 . . ? C25 C26 C27 108.4(2) . . ? C25 C26 Li1 71.84(18) . . ? C27 C26 Li1 70.75(19) . . ? C25 C26 H26 125.8 . . ? C27 C26 H26 125.8 . . ? Li1 C26 H26 123.3 . . ? C28 C27 C26 107.7(2) . . ? C28 C27 Li1 70.57(19) . . ? C26 C27 Li1 73.76(19) . . ? C28 C27 H27 126.2 . . ? C26 C27 H27 126.2 . . ? Li1 C27 H27 121.3 . . ? C27 C28 C24 109.6(2) . . ? C27 C28 Li1 73.63(19) . . ? C24 C28 Li1 72.88(18) . . ? C27 C28 H28 125.2 . . ? C24 C28 H28 125.2 . . ? Li1 C28 H28 120.0 . . ? O1D Li1 Cp 135.7(2) . . ? O2D Li1 Cp 141.8(2) . . ? O1D Li1 O2D 81.93(19) . . ? O1D Li1 C28 163.2(2) . . ? O2D Li1 C28 110.0(2) . . ? O1D Li1 C24 145.6(2) . . ? O2D Li1 C24 122.0(2) . . ? C28 Li1 C24 36.64(11) . . ? O1D Li1 C27 127.5(2) . . ? O2D Li1 C27 126.8(2) . . ? C28 Li1 C27 35.80(11) . . ? C24 Li1 C27 60.55(15) . . ? O1D Li1 C25 113.5(2) . . ? O2D Li1 C25 156.2(3) . . ? C28 Li1 C25 59.71(15) . . ? C24 Li1 C25 36.45(11) . . ? C27 Li1 C25 59.05(14) . . ? O1D Li1 C26 105.9(2) . . ? O2D Li1 C26 161.5(2) . . ? C28 Li1 C26 59.23(15) . . ? C24 Li1 C26 59.87(14) . . ? C27 Li1 C26 35.49(11) . . ? C25 Li1 C26 34.76(11) . . ? O1D C1D H1D1 109.5 . . ? O1D C1D H1D2 109.5 . . ? H1D1 C1D H1D2 109.5 . . ? O1D C1D H1D3 109.5 . . ? H1D1 C1D H1D3 109.5 . . ? H1D2 C1D H1D3 109.5 . . ? C1D O1D C2D 113.1(2) . . ? C1D O1D Li1 125.4(2) . . ? C2D O1D Li1 112.4(2) . . ? O1D C2D C3D 107.9(2) . . ? O1D C2D H2D1 110.1 . . ? C3D C2D H2D1 110.1 . . ? O1D C2D H2D2 110.1 . . ? C3D C2D H2D2 110.1 . . ? H2D1 C2D H2D2 108.4 . . ? O2D C3D C2D 107.5(2) . . ? O2D C3D H3D1 110.2 . . ? C2D C3D H3D1 110.2 . . ? O2D C3D H3D2 110.2 . . ? C2D C3D H3D2 110.2 . . ? H3D1 C3D H3D2 108.5 . . ? C3D O2D C4D 112.0(2) . . ? C3D O2D Li1 112.9(2) . . ? C4D O2D Li1 125.2(2) . . ? O2D C4D H4D1 109.5 . . ? O2D C4D H4D2 109.5 . . ? H4D1 C4D H4D2 109.5 . . ? O2D C4D H4D3 109.5 . . ? H4D1 C4D H4D3 109.5 . . ? H4D2 C4D H4D3 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 N5 P1 N2 C3 16.43(17) . . . . ? C24 P1 N2 C3 -88.71(17) . . . . ? N5 P1 N2 C6 -167.7(2) . . . . ? C24 P1 N2 C6 87.2(2) . . . . ? C6 N2 C3 C4 171.8(2) . . . . ? P1 N2 C3 C4 -12.2(3) . . . . ? N2 C3 C4 N5 -0.9(3) . . . . ? C3 C4 N5 C15 -161.4(2) . . . . ? C3 C4 N5 P1 13.7(3) . . . . ? N2 P1 N5 C4 -17.00(17) . . . . ? C24 P1 N5 C4 88.34(18) . . . . ? N2 P1 N5 C15 157.9(2) . . . . ? C24 P1 N5 C15 -96.7(2) . . . . ? C3 N2 C6 C7 57.1(3) . . . . ? P1 N2 C6 C7 -118.3(2) . . . . ? C3 N2 C6 C11 -122.0(2) . . . . ? P1 N2 C6 C11 62.6(3) . . . . ? C11 C6 C7 C8 -1.4(3) . . . . ? N2 C6 C7 C8 179.5(2) . . . . ? C11 C6 C7 C14 179.8(2) . . . . ? N2 C6 C7 C14 0.7(3) . . . . ? C6 C7 C8 C9 -1.1(4) . . . . ? C14 C7 C8 C9 177.7(2) . . . . ? C7 C8 C9 C10 1.9(4) . . . . ? C7 C8 C9 C13 -178.0(2) . . . . ? C8 C9 C10 C11 -0.3(4) . . . . ? C13 C9 C10 C11 179.7(2) . . . . ? C9 C10 C11 C6 -2.1(4) . . . . ? C9 C10 C11 C12 174.0(2) . . . . ? C7 C6 C11 C10 2.9(3) . . . . ? N2 C6 C11 C10 -177.9(2) . . . . ? C7 C6 C11 C12 -173.2(2) . . . . ? N2 C6 C11 C12 6.0(3) . . . . ? C4 N5 C15 C20 -66.6(3) . . . . ? P1 N5 C15 C20 119.0(2) . . . . ? C4 N5 C15 C16 112.4(3) . . . . ? P1 N5 C15 C16 -62.0(3) . . . . ? C20 C15 C16 C17 -1.9(3) . . . . ? N5 C15 C16 C17 179.1(2) . . . . ? C20 C15 C16 C23 177.4(2) . . . . ? N5 C15 C16 C23 -1.5(3) . . . . ? C15 C16 C17 C18 0.2(4) . . . . ? C23 C16 C17 C18 -179.1(2) . . . . ? C16 C17 C18 C19 0.7(4) . . . . ? C16 C17 C18 C22 179.3(2) . . . . ? C17 C18 C19 C20 -0.1(3) . . . . ? C22 C18 C19 C20 -178.7(2) . . . . ? C18 C19 C20 C15 -1.4(3) . . . . ? C18 C19 C20 C21 177.4(2) . . . . ? C16 C15 C20 C19 2.4(3) . . . . ? N5 C15 C20 C19 -178.58(19) . . . . ? C16 C15 C20 C21 -176.4(2) . . . . ? N5 C15 C20 C21 2.6(3) . . . . ? N5 P1 C24 C28 139.07(19) . . . . ? N2 P1 C24 C28 -129.17(19) . . . . ? N5 P1 C24 C25 -41.2(3) . . . . ? N2 P1 C24 C25 50.5(3) . . . . ? N5 P1 C24 Li1 54.5(2) . . . . ? N2 P1 C24 Li1 146.27(18) . . . . ? C28 C24 C25 C26 0.2(3) . . . . ? P1 C24 C25 C26 -179.6(2) . . . . ? Li1 C24 C25 C26 63.7(2) . . . . ? C28 C24 C25 Li1 -63.55(19) . . . . ? P1 C24 C25 Li1 116.7(3) . . . . ? C24 C25 C26 C27 -0.4(3) . . . . ? Li1 C25 C26 C27 61.6(2) . . . . ? C24 C25 C26 Li1 -62.1(2) . . . . ? C25 C26 C27 C28 0.5(3) . . . . ? Li1 C26 C27 C28 62.8(2) . . . . ? C25 C26 C27 Li1 -62.3(2) . . . . ? C26 C27 C28 C24 -0.4(3) . . . . ? Li1 C27 C28 C24 64.5(2) . . . . ? C26 C27 C28 Li1 -64.9(2) . . . . ? C25 C24 C28 C27 0.1(3) . . . . ? P1 C24 C28 C27 179.93(18) . . . . ? Li1 C24 C28 C27 -65.0(2) . . . . ? C25 C24 C28 Li1 65.1(2) . . . . ? P1 C24 C28 Li1 -115.1(2) . . . . ? C27 C28 Li1 O1D 7.9(9) . . . . ? C24 C28 Li1 O1D -109.2(9) . . . . ? C27 C28 Li1 O2D -125.8(2) . . . . ? C24 C28 Li1 O2D 117.0(2) . . . . ? C27 C28 Li1 C24 117.1(2) . . . . ? C24 C28 Li1 C27 -117.1(2) . . . . ? C27 C28 Li1 C25 77.99(18) . . . . ? C24 C28 Li1 C25 -39.14(14) . . . . ? C27 C28 Li1 C26 37.41(16) . . . . ? C24 C28 Li1 C26 -79.72(16) . . . . ? C28 C24 Li1 O1D 151.2(4) . . . . ? C25 C24 Li1 O1D 37.7(4) . . . . ? P1 C24 Li1 O1D -93.8(4) . . . . ? C28 C24 Li1 O2D -80.6(3) . . . . ? C25 C24 Li1 O2D 165.9(3) . . . . ? P1 C24 Li1 O2D 34.4(3) . . . . ? C25 C24 Li1 C28 -113.4(2) . . . . ? P1 C24 Li1 C28 115.0(2) . . . . ? C28 C24 Li1 C27 36.72(15) . . . . ? C25 C24 Li1 C27 -76.73(17) . . . . ? P1 C24 Li1 C27 151.77(18) . . . . ? C28 C24 Li1 C25 113.4(2) . . . . ? P1 C24 Li1 C25 -131.5(2) . . . . ? C28 C24 Li1 C26 77.83(17) . . . . ? C25 C24 Li1 C26 -35.61(15) . . . . ? P1 C24 Li1 C26 -167.12(18) . . . . ? C28 C27 Li1 O1D -177.1(3) . . . . ? C26 C27 Li1 O1D -61.2(3) . . . . ? C28 C27 Li1 O2D 72.1(3) . . . . ? C26 C27 Li1 O2D -171.9(3) . . . . ? C26 C27 Li1 C28 116.0(2) . . . . ? C28 C27 Li1 C24 -37.59(15) . . . . ? C26 C27 Li1 C24 78.39(18) . . . . ? C28 C27 Li1 C25 -79.98(18) . . . . ? C26 C27 Li1 C25 36.00(16) . . . . ? C28 C27 Li1 C26 -116.0(2) . . . . ? C26 C25 Li1 O1D 84.2(3) . . . . ? C24 C25 Li1 O1D -157.8(3) . . . . ? C26 C25 Li1 O2D -148.7(6) . . . . ? C24 C25 Li1 O2D -30.7(6) . . . . ? C26 C25 Li1 C28 -78.61(18) . . . . ? C24 C25 Li1 C28 39.35(14) . . . . ? C26 C25 Li1 C24 -118.0(2) . . . . ? C26 C25 Li1 C27 -36.77(17) . . . . ? C24 C25 Li1 C27 81.19(17) . . . . ? C24 C25 Li1 C26 118.0(2) . . . . ? C25 C26 Li1 O1D -108.4(2) . . . . ? C27 C26 Li1 O1D 133.8(2) . . . . ? C25 C26 Li1 O2D 138.6(8) . . . . ? C27 C26 Li1 O2D 20.8(8) . . . . ? C25 C26 Li1 C28 80.12(18) . . . . ? C27 C26 Li1 C28 -37.73(16) . . . . ? C25 C26 Li1 C24 37.35(15) . . . . ? C27 C26 Li1 C24 -80.50(19) . . . . ? C25 C26 Li1 C27 117.9(2) . . . . ? C27 C26 Li1 C25 -117.9(2) . . . . ? O2D Li1 O1D C1D 160.8(2) . . . . ? C28 Li1 O1D C1D 24.1(10) . . . . ? C24 Li1 O1D C1D -61.5(5) . . . . ? C27 Li1 O1D C1D 29.9(4) . . . . ? C25 Li1 O1D C1D -38.2(3) . . . . ? C26 Li1 O1D C1D -2.0(3) . . . . ? O2D Li1 O1D C2D 16.2(2) . . . . ? C28 Li1 O1D C2D -120.5(8) . . . . ? C24 Li1 O1D C2D 153.9(4) . . . . ? C27 Li1 O1D C2D -114.7(3) . . . . ? C25 Li1 O1D C2D 177.2(2) . . . . ? C26 Li1 O1D C2D -146.62(19) . . . . ? C1D O1D C2D C3D 173.1(2) . . . . ? Li1 O1D C2D C3D -37.8(3) . . . . ? O1D C2D C3D O2D 45.1(3) . . . . ? C2D C3D O2D C4D 179.5(2) . . . . ? C2D C3D O2D Li1 -32.7(3) . . . . ? O1D Li1 O2D C3D 10.4(2) . . . . ? C28 Li1 O2D C3D 178.3(2) . . . . ? C24 Li1 O2D C3D -142.9(2) . . . . ? C27 Li1 O2D C3D 141.9(3) . . . . ? C25 Li1 O2D C3D -122.0(6) . . . . ? C26 Li1 O2D C3D 127.1(8) . . . . ? O1D Li1 O2D C4D 153.1(2) . . . . ? C28 Li1 O2D C4D -39.0(3) . . . . ? C24 Li1 O2D C4D -0.2(4) . . . . ? C27 Li1 O2D C4D -75.3(4) . . . . ? C25 Li1 O2D C4D 20.7(7) . . . . ? C26 Li1 O2D C4D -90.2(8) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.632 _refine_diff_density_min -0.275 _refine_diff_density_rms 0.045