# Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 1999 # CCDC Number: 186/1590 data_lus2 _audit_creation_method SHELXL _chemical_name_systematic ; tris(dimethylamino)phosphane-borane ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C6 H21 B N3 P' _chemical_formula_weight 177.04 _chemical_melting_point 292 _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'B' 'B' 0.0013 0.0007 '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 Monoclinic _symmetry_space_group_name_H-M Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 12.996(2) _cell_length_b 11.174(1) _cell_length_c 7.679(1) _cell_angle_alpha 90.00 _cell_angle_beta 96.29(1) _cell_angle_gamma 90.00 _cell_volume 1108.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 158(2) _cell_measurement_reflns_used 80 _cell_measurement_theta_min 22 _cell_measurement_theta_max 25 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.061 _exptl_crystal_density_method ? _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 0.201 _exptl_absorpt_correction_type None _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 158(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 ? _diffrn_measurement_method ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% None _diffrn_reflns_number 4672 _diffrn_reflns_av_R_equivalents 0.0261 _diffrn_reflns_av_sigmaI/netI 0.0251 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.15 _diffrn_reflns_theta_max 27.05 _reflns_number_total 2399 _reflns_number_observed 2335 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'CAD4-Software' _computing_cell_refinement 'CAD4-Software' _computing_data_reduction 'CADSHEL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1993)' _computing_molecular_graphics 'SHELXTL-5.01' _computing_publication_material 'SHELXL-93' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 1 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0361P)^2^+0.0772P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0015(9) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.06(6) _refine_ls_number_reflns 2398 _refine_ls_number_parameters 185 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0219 _refine_ls_R_factor_obs 0.0207 _refine_ls_wR_factor_all 0.0556 _refine_ls_wR_factor_obs 0.0543 _refine_ls_goodness_of_fit_all 1.083 _refine_ls_goodness_of_fit_obs 1.088 _refine_ls_restrained_S_all 1.097 _refine_ls_restrained_S_obs 1.087 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group P1 P 0.13216(3) 0.76043(2) 0.95610(4) 0.02042(8) Uani 1 d . . B1 B 0.11910(11) 0.79390(13) 1.1970(2) 0.0316(3) Uani 1 d . . N1 N 0.13427(7) 0.61419(8) 0.90498(11) 0.0251(2) Uani 1 d . . N2 N 0.03383(8) 0.81191(10) 0.82300(14) 0.0323(2) Uani 1 d . . N3 N 0.24606(7) 0.80345(9) 0.89987(13) 0.0287(2) Uani 1 d . . C11 C 0.03555(13) 0.5508(2) 0.9082(2) 0.0396(4) Uani 1 d . . C12 C 0.22001(13) 0.54337(15) 0.9907(2) 0.0374(3) Uani 1 d . . C21 C -0.04763(11) 0.8860(2) 0.8811(2) 0.0411(3) Uani 1 d . . C22 C 0.02615(13) 0.7957(2) 0.6334(2) 0.0449(3) Uani 1 d . . C31 C 0.28656(12) 0.91752(13) 0.9696(2) 0.0385(3) Uani 1 d . . C32 C 0.28283(13) 0.77184(14) 0.7336(2) 0.0434(3) Uani 1 d . . H1A H 0.0439(16) 0.7420(15) 1.2237(27) 0.040(5) Uiso 1 d . . H1B H 0.1180(15) 0.8913(18) 1.2187(28) 0.050(5) Uiso 1 d . . H1C H 0.1906(19) 0.7563(19) 1.2758(33) 0.051(7) Uiso 1 d . . H11A H 0.0459(16) 0.4693(21) 0.8595(29) 0.055(5) Uiso 1 d . . H11B H 0.0180(19) 0.5392(24) 1.0074(37) 0.074(7) Uiso 1 d . . H11C H -0.0150(15) 0.5948(16) 0.8433(27) 0.036(4) Uiso 1 d . . H12A H 0.2795(15) 0.5813(16) 0.9809(24) 0.035(4) Uiso 1 d . . H12B H 0.2206(13) 0.4701(18) 0.9357(25) 0.040(4) Uiso 1 d . . H12C H 0.2154(15) 0.5236(19) 1.1059(30) 0.048(5) Uiso 1 d . . H21A H -0.0367(16) 0.8902(17) 0.9926(29) 0.045(5) Uiso 1 d . . H21B H -0.1089(18) 0.8536(20) 0.8469(29) 0.055(5) Uiso 1 d . . H21C H -0.0499(15) 0.9608(18) 0.8244(29) 0.051(5) Uiso 1 d . . H22A H 0.0408(20) 0.8701(28) 0.5746(37) 0.077(7) Uiso 1 d . . H22B H -0.0492(22) 0.7783(23) 0.5853(38) 0.072(7) Uiso 1 d . . H22C H 0.0656(24) 0.7339(27) 0.6105(41) 0.074(9) Uiso 1 d . . H31A H 0.2602(13) 0.9789(18) 0.8847(27) 0.046(5) Uiso 1 d . . H31B H 0.2612(19) 0.9388(22) 1.0841(34) 0.068(7) Uiso 1 d . . H31C H 0.3617(16) 0.9140(19) 0.9784(26) 0.052(5) Uiso 1 d . . H32A H 0.2546(16) 0.6914(18) 0.6918(29) 0.051(5) Uiso 1 d . . H32B H 0.3627(21) 0.7738(22) 0.7592(38) 0.073(7) Uiso 1 d . . H32C H 0.2610(15) 0.8288(18) 0.6469(28) 0.051(5) Uiso 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.02072(11) 0.02124(11) 0.01968(12) -0.00145(13) 0.00394(8) -0.00148(13) B1 0.0376(7) 0.0362(7) 0.0217(6) -0.0056(5) 0.0064(5) 0.0009(5) N1 0.0302(4) 0.0215(4) 0.0240(5) -0.0010(3) 0.0047(4) -0.0033(4) N2 0.0301(5) 0.0387(6) 0.0274(5) -0.0019(4) 0.0008(4) 0.0100(4) N3 0.0271(5) 0.0287(5) 0.0315(5) -0.0024(4) 0.0096(4) -0.0069(3) C11 0.0479(8) 0.0358(8) 0.0362(8) -0.0048(6) 0.0096(7) -0.0215(7) C12 0.0512(8) 0.0282(7) 0.0325(8) 0.0023(6) 0.0032(6) 0.0093(6) C21 0.0299(6) 0.0478(8) 0.0450(9) -0.0043(7) 0.0017(6) 0.0140(6) C22 0.0510(8) 0.0528(8) 0.0286(7) -0.0032(6) -0.0057(6) 0.0136(7) C31 0.0372(7) 0.0327(7) 0.0454(8) -0.0029(6) 0.0033(6) -0.0143(5) C32 0.0447(8) 0.0474(8) 0.0423(8) -0.0049(6) 0.0238(7) -0.0109(6) _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 1.6499(11) . ? P1 N3 1.6579(10) . ? P1 N1 1.6815(9) . ? P1 B1 1.9133(14) . ? B1 H1A 1.17(2) . ? B1 H1B 1.10(2) . ? B1 H1C 1.13(2) . ? N1 C12 1.463(2) . ? N1 C11 1.468(2) . ? N2 C21 1.452(2) . ? N2 C22 1.459(2) . ? N3 C32 1.455(2) . ? N3 C31 1.458(2) . ? C11 H11A 1.00(2) . ? C11 H11B 0.83(3) . ? C11 H11C 0.92(2) . ? C12 H12A 0.89(2) . ? C12 H12B 0.92(2) . ? C12 H12C 0.92(2) . ? C21 H21A 0.85(2) . ? C21 H21B 0.89(2) . ? C21 H21C 0.94(2) . ? C22 H22A 0.97(3) . ? C22 H22B 1.03(3) . ? C22 H22C 0.89(3) . ? C31 H31A 0.98(2) . ? C31 H31B 1.00(3) . ? C31 H31C 0.97(2) . ? C32 H32A 1.01(2) . ? C32 H32B 1.04(3) . ? C32 H32C 0.94(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 P1 N3 112.99(6) . . ? N2 P1 N1 103.03(6) . . ? N3 P1 N1 100.55(5) . . ? N2 P1 B1 112.72(6) . . ? N3 P1 B1 111.81(6) . . ? N1 P1 B1 114.90(6) . . ? P1 B1 H1A 103.6(10) . . ? P1 B1 H1B 110.1(11) . . ? H1A B1 H1B 116.0(14) . . ? P1 B1 H1C 106.8(13) . . ? H1A B1 H1C 111.9(15) . . ? H1B B1 H1C 108.0(16) . . ? C12 N1 C11 110.82(11) . . ? C12 N1 P1 116.86(9) . . ? C11 N1 P1 115.36(10) . . ? C21 N2 C22 113.87(12) . . ? C21 N2 P1 123.34(10) . . ? C22 N2 P1 122.58(9) . . ? C32 N3 C31 113.23(11) . . ? C32 N3 P1 123.14(9) . . ? C31 N3 P1 117.02(9) . . ? N1 C11 H11A 106.2(12) . . ? N1 C11 H11B 114.8(18) . . ? H11A C11 H11B 105.2(22) . . ? N1 C11 H11C 107.8(11) . . ? H11A C11 H11C 113.6(17) . . ? H11B C11 H11C 109.3(21) . . ? N1 C12 H12A 109.2(11) . . ? N1 C12 H12B 108.6(12) . . ? H12A C12 H12B 109.4(15) . . ? N1 C12 H12C 115.9(12) . . ? H12A C12 H12C 110.1(17) . . ? H12B C12 H12C 103.4(17) . . ? N2 C21 H21A 107.1(13) . . ? N2 C21 H21B 109.7(14) . . ? H21A C21 H21B 111.4(19) . . ? N2 C21 H21C 110.6(12) . . ? H21A C21 H21C 114.0(19) . . ? H21B C21 H21C 104.1(18) . . ? N2 C22 H22A 111.2(17) . . ? N2 C22 H22B 110.0(15) . . ? H22A C22 H22B 102.8(21) . . ? N2 C22 H22C 108.4(20) . . ? H22A C22 H22C 115.1(24) . . ? H22B C22 H22C 109.2(25) . . ? N3 C31 H31A 106.3(11) . . ? N3 C31 H31B 113.0(14) . . ? H31A C31 H31B 107.0(18) . . ? N3 C31 H31C 108.0(13) . . ? H31A C31 H31C 110.4(16) . . ? H31B C31 H31C 111.9(19) . . ? N3 C32 H32A 110.6(12) . . ? N3 C32 H32B 104.3(16) . . ? H32A C32 H32B 113.6(18) . . ? N3 C32 H32C 110.7(12) . . ? H32A C32 H32C 107.8(18) . . ? H32B C32 H32C 109.8(19) . . ? 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 N2 P1 N1 C12 174.67(10) . . . . ? N3 P1 N1 C12 57.87(10) . . . . ? B1 P1 N1 C12 -62.34(11) . . . . ? N2 P1 N1 C11 -52.42(11) . . . . ? N3 P1 N1 C11 -169.22(10) . . . . ? B1 P1 N1 C11 70.57(11) . . . . ? N3 P1 N2 C21 -121.52(12) . . . . ? N1 P1 N2 C21 130.88(12) . . . . ? B1 P1 N2 C21 6.44(14) . . . . ? N3 P1 N2 C22 52.82(13) . . . . ? N1 P1 N2 C22 -54.77(13) . . . . ? B1 P1 N2 C22 -179.21(12) . . . . ? N2 P1 N3 C32 -61.66(12) . . . . ? N1 P1 N3 C32 47.50(12) . . . . ? B1 P1 N3 C32 169.90(12) . . . . ? N2 P1 N3 C31 87.84(11) . . . . ? N1 P1 N3 C31 -162.99(10) . . . . ? B1 P1 N3 C31 -40.59(12) . . . . ? _refine_diff_density_max 0.231 _refine_diff_density_min -0.170 _refine_diff_density_rms 0.030 #===END data_mit7 _audit_creation_method SHELXL _chemical_name_systematic ; Tris(dimethylamino)iminophosphorane ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C6 H19 N4 P' _chemical_formula_weight 178.22 _chemical_melting_point -19 _chemical_compound_source Fluka 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/n 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 8.2190(9) _cell_length_b 10.0901(3) _cell_length_c 12.1644(14) _cell_angle_alpha 90.00 _cell_angle_beta 97.512(6) _cell_angle_gamma 90.00 _cell_volume 1000.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 163(2) _cell_measurement_reflns_used 88 _cell_measurement_theta_min 20 _cell_measurement_theta_max 25 _exptl_crystal_description Column _exptl_crystal_colour Colourless _exptl_crystal_size_max 1.00 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.50 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.184 _exptl_crystal_density_method ? _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 0.228 _exptl_absorpt_correction_type None _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; Crystal grown in capillary ; _diffrn_ambient_temperature 163(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 ? _diffrn_measurement_method ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% None _diffrn_reflns_number 2863 _diffrn_reflns_av_R_equivalents 0.0134 _diffrn_reflns_av_sigmaI/netI 0.0145 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 3 _diffrn_reflns_theta_min 3.19 _diffrn_reflns_theta_max 27.03 _reflns_number_total 2177 _reflns_number_observed 1995 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'CAD4 Software' _computing_cell_refinement 'CAD4 Software' _computing_data_reduction 'CADSHEL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'SHELXTL' _computing_publication_material 'SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 1 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0714P)^2^+0.2105P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2176 _refine_ls_number_parameters 176 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0399 _refine_ls_R_factor_obs 0.0360 _refine_ls_wR_factor_all 0.1054 _refine_ls_wR_factor_obs 0.1006 _refine_ls_goodness_of_fit_all 1.075 _refine_ls_goodness_of_fit_obs 1.084 _refine_ls_restrained_S_all 1.084 _refine_ls_restrained_S_obs 1.084 _refine_ls_shift/esd_max -0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group P P 0.04761(4) 0.16135(3) 0.83076(3) 0.02356(14) Uani 1 d . . N1 N 0.19557(13) 0.22424(11) 0.92425(9) 0.0275(3) Uani 1 d . . N2 N 0.15077(14) 0.14743(10) 0.72281(10) 0.0292(3) Uani 1 d . . N3 N -0.09294(14) 0.27823(11) 0.80512(10) 0.0293(3) Uani 1 d . . N4 N -0.0441(2) 0.03262(12) 0.85743(11) 0.0348(3) Uani 1 d . . C11 C 0.3371(2) 0.1371(2) 0.9561(2) 0.0422(4) Uani 1 d . . C12 C 0.1416(2) 0.28887(14) 1.02118(12) 0.0332(3) Uani 1 d . . C21 C 0.0903(2) 0.05785(13) 0.63297(12) 0.0313(3) Uani 1 d . . C22 C 0.2748(2) 0.2389(2) 0.69325(14) 0.0373(3) Uani 1 d . . C31 C -0.2473(2) 0.2740(2) 0.8520(2) 0.0424(4) Uani 1 d . . C32 C -0.0526(2) 0.40972(15) 0.76813(14) 0.0403(4) Uani 1 d . . H1 H 0.0076(28) -0.0160(26) 0.8959(18) 0.062(7) Uiso 1 d . . H11A H 0.3074(26) 0.0629(23) 1.0097(18) 0.057(6) Uiso 1 d . . H11B H 0.4300(28) 0.1897(24) 0.9942(20) 0.066(6) Uiso 1 d . . H11C H 0.3793(24) 0.0996(21) 0.8885(16) 0.048(5) Uiso 1 d . . H12A H 0.1140(25) 0.2258(24) 1.0791(17) 0.058(6) Uiso 1 d . . H12B H 0.0513(24) 0.3497(19) 0.9997(16) 0.042(5) Uiso 1 d . . H12C H 0.2293(25) 0.3436(20) 1.0581(17) 0.051(6) Uiso 1 d . . H21A H 0.1813(21) 0.0041(20) 0.6132(14) 0.038(4) Uiso 1 d . . H21B H 0.0440(24) 0.1007(22) 0.5657(17) 0.051(5) Uiso 1 d . . H21C H 0.0097(22) 0.0059(18) 0.6542(13) 0.034(4) Uiso 1 d . . H22A H 0.3661(24) 0.1923(20) 0.6762(16) 0.044(5) Uiso 1 d . . H22B H 0.3068(23) 0.2980(21) 0.7513(17) 0.048(5) Uiso 1 d . . H22B H 0.2338(24) 0.2852(22) 0.6285(17) 0.048(5) Uiso 1 d . . H31A H -0.2754(26) 0.1828(24) 0.8712(18) 0.057(6) Uiso 1 d . . H31B H -0.3325(26) 0.3042(22) 0.8027(17) 0.052(5) Uiso 1 d . . H31C H -0.2442(24) 0.3302(20) 0.9175(18) 0.050(6) Uiso 1 d . . H32A H 0.0386(25) 0.4067(21) 0.7251(16) 0.049(5) Uiso 1 d . . H32B H -0.0295(28) 0.4730(23) 0.8298(19) 0.060(6) Uiso 1 d . . H32C H -0.1415(26) 0.4486(22) 0.7259(17) 0.051(5) Uiso 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P 0.0278(2) 0.0136(2) 0.0304(2) -0.00194(10) 0.00792(14) -0.00261(10) N1 0.0295(6) 0.0210(5) 0.0327(6) -0.0051(4) 0.0067(4) -0.0013(4) N2 0.0341(6) 0.0207(5) 0.0348(6) -0.0071(4) 0.0125(5) -0.0062(4) N3 0.0312(6) 0.0205(5) 0.0373(6) 0.0001(4) 0.0088(4) 0.0024(4) N4 0.0402(6) 0.0206(6) 0.0444(7) 0.0027(5) 0.0089(5) -0.0090(5) C11 0.0362(8) 0.0364(8) 0.0520(9) -0.0097(7) -0.0025(7) 0.0054(6) C12 0.0411(8) 0.0277(7) 0.0315(6) -0.0075(5) 0.0078(6) -0.0046(6) C21 0.0401(7) 0.0205(6) 0.0337(7) -0.0058(5) 0.0065(6) 0.0011(5) C22 0.0421(8) 0.0293(7) 0.0445(8) -0.0070(6) 0.0208(7) -0.0104(6) C31 0.0330(7) 0.0424(9) 0.0541(9) -0.0025(7) 0.0143(7) 0.0069(6) C32 0.0514(9) 0.0216(7) 0.0486(9) 0.0067(6) 0.0093(7) 0.0064(6) _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 P N4 1.5572(12) . ? P N3 1.6518(11) . ? P N2 1.6594(11) . ? P N1 1.6773(11) . ? N1 C12 1.466(2) . ? N1 C11 1.469(2) . ? N2 C21 1.455(2) . ? N2 C22 1.455(2) . ? N3 C32 1.453(2) . ? N3 C31 1.458(2) . ? N4 H1 0.77(2) . ? C11 H11A 1.04(2) . ? C11 H11B 0.99(2) . ? C11 H11C 1.01(2) . ? C12 H12A 1.00(2) . ? C12 H12B 0.97(2) . ? C12 H12C 0.97(2) . ? C21 H21A 0.98(2) . ? C21 H21B 0.96(2) . ? C21 H21C 0.91(2) . ? C22 H22A 0.93(2) . ? C22 H22B 0.94(2) . ? C22 H22B 0.94(2) . ? C31 H31A 0.98(2) . ? C31 H31B 0.91(2) . ? C31 H31C 0.97(2) . ? C32 H32A 0.97(2) . ? C32 H32B 0.98(2) . ? C32 H32C 0.92(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N4 P N3 106.80(7) . . ? N4 P N2 113.94(6) . . ? N3 P N2 109.15(6) . . ? N4 P N1 120.15(7) . . ? N3 P N1 106.56(6) . . ? N2 P N1 99.69(6) . . ? C12 N1 C11 111.51(12) . . ? C12 N1 P 116.42(9) . . ? C11 N1 P 115.55(9) . . ? C21 N2 C22 112.96(11) . . ? C21 N2 P 119.17(9) . . ? C22 N2 P 126.08(9) . . ? C32 N3 C31 113.17(12) . . ? C32 N3 P 121.86(10) . . ? C31 N3 P 121.87(10) . . ? P N4 H1 114.5(18) . . ? N1 C11 H11A 110.7(12) . . ? N1 C11 H11B 109.7(14) . . ? H11A C11 H11B 108.7(18) . . ? N1 C11 H11C 110.8(11) . . ? H11A C11 H11C 112.0(17) . . ? H11B C11 H11C 104.9(17) . . ? N1 C12 H12A 113.9(13) . . ? N1 C12 H12B 111.4(11) . . ? H12A C12 H12B 110.9(16) . . ? N1 C12 H12C 109.9(12) . . ? H12A C12 H12C 105.1(16) . . ? H12B C12 H12C 105.1(16) . . ? N2 C21 H21A 109.4(10) . . ? N2 C21 H21B 114.8(13) . . ? H21A C21 H21B 105.7(15) . . ? N2 C21 H21C 109.6(10) . . ? H21A C21 H21C 111.1(16) . . ? H21B C21 H21C 106.2(16) . . ? N2 C22 H22A 110.2(12) . . ? N2 C22 H22B 110.8(12) . . ? H22A C22 H22B 109.5(16) . . ? N2 C22 H22B 109.7(12) . . ? H22A C22 H22B 106.0(16) . . ? H22B C22 H22B 110.6(18) . . ? N3 C31 H31A 111.3(13) . . ? N3 C31 H31B 111.4(13) . . ? H31A C31 H31B 106.5(19) . . ? N3 C31 H31C 111.8(12) . . ? H31A C31 H31C 109.4(18) . . ? H31B C31 H31C 106.2(18) . . ? N3 C32 H32A 111.3(12) . . ? N3 C32 H32B 112.7(13) . . ? H32A C32 H32B 110.2(19) . . ? N3 C32 H32C 111.3(13) . . ? H32A C32 H32C 108.9(17) . . ? H32B C32 H32C 102.0(18) . . ? 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 N4 P N1 C12 -73.06(12) . . . . ? N3 P N1 C12 48.37(11) . . . . ? N2 P N1 C12 161.83(10) . . . . ? N4 P N1 C11 60.67(13) . . . . ? N3 P N1 C11 -177.90(11) . . . . ? N2 P N1 C11 -64.45(12) . . . . ? N4 P N2 C21 30.65(13) . . . . ? N3 P N2 C21 -88.62(11) . . . . ? N1 P N2 C21 159.94(11) . . . . ? N4 P N2 C22 -165.73(13) . . . . ? N3 P N2 C22 75.00(14) . . . . ? N1 P N2 C22 -36.44(14) . . . . ? N4 P N3 C32 -174.88(12) . . . . ? N2 P N3 C32 -51.28(13) . . . . ? N1 P N3 C32 55.54(13) . . . . ? N4 P N3 C31 26.38(14) . . . . ? N2 P N3 C31 149.99(12) . . . . ? N1 P N3 C31 -103.20(12) . . . . ? _refine_diff_density_max 0.529 _refine_diff_density_min -0.556 _refine_diff_density_rms 0.059 #===END data_mit6 _audit_creation_method SHELXL _chemical_name_systematic ; Tris(dimethylamino)oxophosphorane ; _chemical_name_common 'HMPA' _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C6 H18 N3 O P' _chemical_formula_weight 179.20 _chemical_melting_point 7 _chemical_compound_source 'Aldrich Chemicals' 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)/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 6.398(1) _cell_length_b 12.570(3) _cell_length_c 6.428(1) _cell_angle_alpha 90.00 _cell_angle_beta 104.19(3) _cell_angle_gamma 90.00 _cell_volume 501.2(2) _cell_formula_units_Z 2 _cell_measurement_temperature 163(2) _cell_measurement_reflns_used 100 _cell_measurement_theta_min 20 _cell_measurement_theta_max 27 _exptl_crystal_description Column _exptl_crystal_colour Colourless _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.187 _exptl_crystal_density_method ? _exptl_crystal_F_000 196 _exptl_absorpt_coefficient_mu 0.232 _exptl_absorpt_correction_type None _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; 'Crystal grown in situ in capillary, by slow tem. decrease' ; _diffrn_ambient_temperature 163(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 ? _diffrn_measurement_method ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% None _diffrn_reflns_number 3326 _diffrn_reflns_av_R_equivalents 0.0237 _diffrn_reflns_av_sigmaI/netI 0.0282 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.24 _diffrn_reflns_theta_max 31.09 _reflns_number_total 1671 _reflns_number_observed 1345 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'CAD4 Software' _computing_cell_refinement 'CAD4 Software' _computing_data_reduction 'CADSHEL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'SHELXTL' _computing_publication_material 'SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 1 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0809P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1670 _refine_ls_number_parameters 91 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0592 _refine_ls_R_factor_obs 0.0427 _refine_ls_wR_factor_all 0.1162 _refine_ls_wR_factor_obs 0.1063 _refine_ls_goodness_of_fit_all 1.045 _refine_ls_goodness_of_fit_obs 1.075 _refine_ls_restrained_S_all 1.047 _refine_ls_restrained_S_obs 1.075 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group P1 P 0.36754(6) 0.2500 0.51474(6) 0.02618(15) Uani 1 d S . N1 N 0.1022(2) 0.2500 0.4179(2) 0.0297(3) Uani 1 d S . O1 O 0.5070(2) 0.2500 0.3624(2) 0.0407(4) Uani 1 d S . N2 N 0.4071(2) 0.14044(10) 0.6603(2) 0.0348(3) Uani 1 d . . C2 C 0.2903(3) 0.11866(14) 0.8250(3) 0.0444(4) Uani 1 d . . C1 C 0.0030(2) 0.1532(2) 0.3098(3) 0.0448(4) Uani 1 d . . C3 C 0.6180(3) 0.0892(2) 0.7066(3) 0.0545(5) Uani 1 d . . H11 H -0.1422(36) 0.1548(18) 0.2938(32) 0.056(6) Uiso 1 d . . H12 H 0.0647(38) 0.0860(20) 0.3924(38) 0.066(6) Uiso 1 d . . H13 H 0.0248(36) 0.1443(17) 0.1651(37) 0.059(6) Uiso 1 d . . H21 H 0.1547(33) 0.1521(16) 0.7916(30) 0.046(5) Uiso 1 d . . H22 H 0.2756(37) 0.0408(18) 0.8417(35) 0.062(6) Uiso 1 d . . H23 H 0.3651(33) 0.1478(18) 0.9674(35) 0.055(6) Uiso 1 d . . H31 H 0.6080(42) 0.0122(24) 0.7288(38) 0.080(8) Uiso 1 d . . H32 H 0.6795(45) 0.1013(22) 0.5915(45) 0.084(8) Uiso 1 d . . H33 H 0.7141(37) 0.1128(17) 0.8406(36) 0.061(6) Uiso 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0143(2) 0.0424(3) 0.0226(2) 0.000 0.00607(13) 0.000 N1 0.0160(6) 0.0438(8) 0.0289(6) 0.000 0.0049(5) 0.000 O1 0.0216(6) 0.0740(10) 0.0294(6) 0.000 0.0119(5) 0.000 N2 0.0275(5) 0.0410(6) 0.0360(5) 0.0039(4) 0.0080(4) 0.0054(4) C2 0.0472(8) 0.0448(8) 0.0437(8) 0.0109(6) 0.0162(6) -0.0033(7) C1 0.0211(6) 0.0674(10) 0.0449(8) -0.0228(7) 0.0065(5) -0.0080(6) C3 0.0385(8) 0.0732(12) 0.0482(9) 0.0073(9) 0.0036(7) 0.0239(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 O1 1.4774(13) . ? P1 N2 1.6491(12) 4_565 ? P1 N2 1.6491(12) . ? P1 N1 1.6589(15) . ? N1 C1 1.466(2) . ? N1 C1 1.466(2) 4_565 ? N2 C3 1.459(2) . ? N2 C2 1.463(2) . ? C2 H21 0.94(2) . ? C2 H22 0.99(2) . ? C2 H23 0.99(2) . ? C1 H11 0.91(2) . ? C1 H12 1.02(3) . ? C1 H13 0.98(2) . ? C3 H31 0.98(3) . ? C3 H32 0.93(3) . ? C3 H33 0.97(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 P1 N2 110.03(5) . 4_565 ? O1 P1 N2 110.03(5) . . ? N2 P1 N2 113.25(9) 4_565 . ? O1 P1 N1 118.69(8) . . ? N2 P1 N1 102.32(5) 4_565 . ? N2 P1 N1 102.32(5) . . ? C1 N1 C1 112.2(2) . 4_565 ? C1 N1 P1 117.52(8) . . ? C1 N1 P1 117.52(8) 4_565 . ? C3 N2 C2 112.36(14) . . ? C3 N2 P1 119.34(12) . . ? C2 N2 P1 122.16(10) . . ? N2 C2 H21 111.0(12) . . ? N2 C2 H22 110.0(13) . . ? H21 C2 H22 111.0(19) . . ? N2 C2 H23 112.5(12) . . ? H21 C2 H23 104.7(17) . . ? H22 C2 H23 107.5(18) . . ? N1 C1 H11 110.3(14) . . ? N1 C1 H12 111.8(14) . . ? H11 C1 H12 109.3(18) . . ? N1 C1 H13 113.5(13) . . ? H11 C1 H13 105.9(17) . . ? H12 C1 H13 105.7(17) . . ? N2 C3 H31 112.0(16) . . ? N2 C3 H32 108.4(17) . . ? H31 C3 H32 109.3(23) . . ? N2 C3 H33 113.5(13) . . ? H31 C3 H33 102.7(19) . . ? H32 C3 H33 110.8(21) . . ? 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 O1 P1 N1 C1 69.33(12) . . . . ? N2 P1 N1 C1 -169.40(12) 4_565 . . . ? N2 P1 N1 C1 -51.93(14) . . . . ? O1 P1 N1 C1 -69.33(12) . . . 4_565 ? N2 P1 N1 C1 51.93(14) 4_565 . . 4_565 ? N2 P1 N1 C1 169.40(12) . . . 4_565 ? O1 P1 N2 C3 29.73(15) . . . . ? N2 P1 N2 C3 -93.86(14) 4_565 . . . ? N1 P1 N2 C3 156.78(13) . . . . ? O1 P1 N2 C2 -179.94(12) . . . . ? N2 P1 N2 C2 56.5(2) 4_565 . . . ? N1 P1 N2 C2 -52.89(13) . . . . ? _refine_diff_density_max 0.786 _refine_diff_density_min -0.430 _refine_diff_density_rms 0.073