# Copyright The Royal Society of Chemistry, 1998 # TITLE AND AUTHOR LIST data_rm18 _publ_section_title ; Hydrazo-keto and azo-enol tautomerism in organometallic palladacycles ; loop_ _publ_author_name _publ_author_footnote _publ_author_address 'Joan Albert' . ; Departament Qu\'imica Inorg\`anica Universitat de Barcelona Mart\'i i Franque\'es 1-9. E-08028 Barcelona Spain ; 'Asensio Gonz\'alez' . ; Departament Qu\'imica Org\'anica Facultat de Farm\NLcia Universitat de Barcelona Pius XII s/n. E-08028 Barcelona Spain ; 'Jaume Granell' . ; Departament Qu\'imica Inorg\`anica Universitat de Barcelona Mart\'i i Franque\'es 1-9. E-08028 Barcelona Spain ; 'Rosa Moragas' . ; Departament Qu\'imica Inorg\`anica Universitat de Barcelona Mart\'i i Franque\'es 1-9. E-08028 Barcelona Spain ; 'Xavier Solans' . ; Departament de Cristalografia, Mineralogia i Dip\`osits Minerals Universitat de Barcelona Marti i Franqu\'es s/n E-08028 Barcelona Spain ; 'Merc\'e Font-Bard\'ia' . ; Departament de Cristalografia, Mineralogia i Dip\`osits Minerals Universitat de Barcelona Marti i Franqu\'es s/n E-08028 Barcelona Spain ; _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C27 H23 Cl N3 O3 P Pd' _chemical_formula_weight 610.30 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 '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' 'Pd' 'Pd' -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.475(3) _cell_length_b 10.4872(10) _cell_length_c 13.3010(15) _cell_angle_alpha 77.012(7) _cell_angle_beta 83.563(15) _cell_angle_gamma 87.239(13) _cell_volume 1279.4(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.584 _exptl_crystal_density_method ? _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.927 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _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 ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7545 _diffrn_reflns_av_R_equivalents 0.1389 _diffrn_reflns_av_sigmaI/netI 0.0301 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -4 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 29.96 _reflns_number_total 7444 _reflns_number_observed 6190 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 50 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^)+(0.0965P)^2^+0.3375P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0008(10) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 7394 _refine_ls_number_parameters 418 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0652 _refine_ls_R_factor_obs 0.0467 _refine_ls_wR_factor_all 0.1538 _refine_ls_wR_factor_obs 0.1260 _refine_ls_goodness_of_fit_all 1.034 _refine_ls_goodness_of_fit_obs 1.047 _refine_ls_restrained_S_all 1.163 _refine_ls_restrained_S_obs 1.047 _refine_ls_shift/esd_max 0.106 _refine_ls_shift/esd_mean 0.006 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 Pd Pd 0.25688(2) 0.24097(2) 0.12117(2) 0.03214(9) Uani 1 d . . P P 0.34031(8) 0.15320(7) 0.27396(6) 0.0314(2) Uani 1 d . . Cl Cl 0.19413(12) 0.03353(8) 0.10025(7) 0.0495(2) Uani 1 d . . O1 O 0.0420(4) 0.4866(3) -0.1906(2) 0.0626(8) Uani 1 d . . N1 N 0.1926(4) 0.4710(3) -0.0335(2) 0.0458(7) Uani 1 d . . N2 N 0.1656(3) 0.3427(3) -0.0118(2) 0.0378(5) Uani 1 d . . C1 C 0.3266(3) 0.4214(3) 0.1131(2) 0.0357(6) Uani 1 d . . C2 C 0.4188(4) 0.4664(3) 0.1691(3) 0.0413(7) Uani 1 d . . C3 C 0.4573(4) 0.5980(4) 0.1450(3) 0.0442(7) Uani 1 d . . C4 C 0.4043(5) 0.6882(4) 0.0649(3) 0.0546(10) Uani 1 d . . C5 C 0.3158(5) 0.6454(4) 0.0060(3) 0.0553(10) Uani 1 d . . C6 C 0.2783(4) 0.5138(3) 0.0290(2) 0.0389(6) Uani 1 d . . C7 C 0.0894(4) 0.2935(3) -0.0690(3) 0.0419(7) Uani 1 d . . C8 C 0.0280(4) 0.3684(4) -0.1619(3) 0.0462(7) Uani 1 d . . C9 C -0.0472(7) 0.2911(6) -0.2186(4) 0.0665(13) Uani 1 d . . C10 C 0.2753(3) -0.0081(3) 0.3407(2) 0.0341(6) Uani 1 d . . C11 C 0.1313(4) -0.0175(4) 0.3762(3) 0.0455(7) Uani 1 d . . C12 C 0.0776(5) -0.1337(4) 0.4355(3) 0.0530(9) Uani 1 d . . C13 C 0.1671(5) -0.2418(4) 0.4602(3) 0.0513(9) Uani 1 d . . C14 C 0.3074(5) -0.2353(4) 0.4237(4) 0.0536(9) Uani 1 d . . C15 C 0.3631(4) -0.1183(4) 0.3636(3) 0.0466(8) Uani 1 d . . C16 C 0.2924(3) 0.2424(3) 0.3761(2) 0.0347(6) Uani 1 d . . C17 C 0.3399(4) 0.1982(4) 0.4738(3) 0.0467(8) Uani 1 d . . C18 C 0.3016(4) 0.2657(4) 0.5521(3) 0.0505(9) Uani 1 d . . C19 C 0.2144(4) 0.3760(4) 0.5333(3) 0.0495(9) Uani 1 d . . C20 C 0.1613(4) 0.4160(3) 0.4394(3) 0.0437(7) Uani 1 d . . C21 C 0.1992(4) 0.3495(3) 0.3604(3) 0.0385(6) Uani 1 d . . C22 C 0.5322(3) 0.1345(3) 0.2563(2) 0.0352(6) Uani 1 d . . C23 C 0.5878(4) 0.0605(3) 0.1847(3) 0.0412(7) Uani 1 d . . C24 C 0.7317(4) 0.0424(4) 0.1656(3) 0.0508(9) Uani 1 d . . C25 C 0.8234(4) 0.0987(5) 0.2134(4) 0.0630(12) Uani 1 d . . C26 C 0.7709(5) 0.1749(7) 0.2832(4) 0.0710(14) Uani 1 d . . C27 C 0.6259(4) 0.1922(5) 0.3053(3) 0.0541(9) Uani 1 d . . N3 N 0.5559(4) 0.6394(4) 0.2065(3) 0.0577(9) Uani 1 d . . O2 O 0.5917(5) 0.7517(4) 0.1865(3) 0.0811(11) Uani 1 d . . O3 O 0.6023(6) 0.5578(4) 0.2770(4) 0.106(2) Uani 1 d . . H1N H 0.1668(53) 0.5124(50) -0.0864(39) 0.058(14) Uiso 1 d . . H2 H 0.4660(58) 0.4114(51) 0.2249(42) 0.068(15) Uiso 1 d . . H4 H 0.4299(61) 0.7704(57) 0.0514(44) 0.076(17) Uiso 1 d . . H5 H 0.2913(65) 0.7023(58) -0.0573(47) 0.084(18) Uiso 1 d . . H7 H 0.0726(46) 0.1995(44) -0.0457(33) 0.047(11) Uiso 1 d . . H9 H -0.1144(88) 0.3342(80) -0.2737(65) 0.130(27) Uiso 1 d . . H9A H -0.1110(94) 0.2355(86) -0.1826(67) 0.130(30) Uiso 1 d . . H9B H 0.0178(87) 0.2464(76) -0.2686(62) 0.133(29) Uiso 1 d . . H11 H 0.0701(63) 0.0622(59) 0.3517(45) 0.087(18) Uiso 1 d . . H12 H -0.0134(60) -0.1448(51) 0.4536(41) 0.068(15) Uiso 1 d . . H13 H 0.1249(73) -0.3205(66) 0.4901(51) 0.103(21) Uiso 1 d . . H14 H 0.3666(81) -0.3035(74) 0.4366(57) 0.121(26) Uiso 1 d . . H15 H 0.4528(58) -0.1100(49) 0.3434(39) 0.067(15) Uiso 1 d . . H17 H 0.3942(48) 0.1163(45) 0.4858(34) 0.052(12) Uiso 1 d . . H18 H 0.3249(37) 0.2337(33) 0.6209(27) 0.028(8) Uiso 1 d . . H19 H 0.1930(55) 0.4148(49) 0.5717(39) 0.062(14) Uiso 1 d . . H20 H 0.1014(46) 0.4941(43) 0.4296(33) 0.046(11) Uiso 1 d . . H21 H 0.1681(36) 0.3840(33) 0.2988(27) 0.026(8) Uiso 1 d . . H23 H 0.5296(46) 0.0207(42) 0.1503(33) 0.045(11) Uiso 1 d . . H24 H 0.7588(50) -0.0112(46) 0.1231(37) 0.054(12) Uiso 1 d . . H25 H 0.9260(66) 0.0835(55) 0.2011(43) 0.081(17) Uiso 1 d . . H26 H 0.8284(76) 0.2079(68) 0.3075(54) 0.102(23) Uiso 1 d . . H27 H 0.5923(47) 0.2447(43) 0.3451(35) 0.049(11) 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 Pd 0.03879(14) 0.02996(13) 0.02919(12) -0.00746(8) -0.00945(8) 0.00238(8) P 0.0346(4) 0.0317(3) 0.0299(3) -0.0098(3) -0.0088(3) 0.0068(3) Cl 0.0745(6) 0.0349(4) 0.0432(4) -0.0117(3) -0.0172(4) -0.0028(4) O1 0.082(2) 0.051(2) 0.054(2) 0.0029(13) -0.0321(15) -0.0046(15) N1 0.064(2) 0.0354(14) 0.0366(14) 0.0001(11) -0.0162(13) -0.0033(13) N2 0.0465(15) 0.0357(13) 0.0315(12) -0.0054(10) -0.0109(10) 0.0009(11) C1 0.042(2) 0.0346(14) 0.0312(13) -0.0081(11) -0.0047(11) -0.0010(12) C2 0.047(2) 0.039(2) 0.039(2) -0.0103(13) -0.0061(13) -0.0042(13) C3 0.045(2) 0.046(2) 0.045(2) -0.0202(14) 0.0018(14) -0.0103(14) C4 0.072(3) 0.038(2) 0.053(2) -0.010(2) 0.006(2) -0.017(2) C5 0.080(3) 0.037(2) 0.047(2) -0.0032(15) -0.006(2) -0.011(2) C6 0.047(2) 0.0361(15) 0.0338(14) -0.0064(12) -0.0065(12) -0.0053(13) C7 0.053(2) 0.040(2) 0.0343(15) -0.0067(12) -0.0144(13) -0.0004(14) C8 0.052(2) 0.052(2) 0.0350(15) -0.0051(13) -0.0141(13) -0.0011(15) C9 0.086(3) 0.071(3) 0.046(2) -0.006(2) -0.030(2) -0.020(3) C10 0.0376(14) 0.0354(14) 0.0317(13) -0.0109(11) -0.0089(11) 0.0048(11) C11 0.040(2) 0.046(2) 0.054(2) -0.0175(15) -0.0075(14) 0.0038(14) C12 0.046(2) 0.054(2) 0.061(2) -0.020(2) 0.003(2) -0.009(2) C13 0.066(2) 0.042(2) 0.046(2) -0.0100(15) -0.004(2) -0.014(2) C14 0.059(2) 0.035(2) 0.063(2) 0.000(2) -0.012(2) 0.003(2) C15 0.043(2) 0.039(2) 0.053(2) -0.0027(14) -0.0048(15) 0.0049(14) C16 0.0385(14) 0.0343(14) 0.0333(14) -0.0122(11) -0.0060(11) 0.0053(11) C17 0.053(2) 0.053(2) 0.037(2) -0.0165(14) -0.0153(14) 0.020(2) C18 0.051(2) 0.067(2) 0.037(2) -0.020(2) -0.0120(14) 0.016(2) C19 0.055(2) 0.053(2) 0.045(2) -0.026(2) 0.003(2) 0.005(2) C20 0.051(2) 0.0347(15) 0.047(2) -0.0145(13) -0.0001(14) 0.0067(13) C21 0.044(2) 0.0331(14) 0.0369(15) -0.0073(12) -0.0032(12) 0.0067(12) C22 0.0357(14) 0.0366(14) 0.0336(13) -0.0086(11) -0.0060(11) 0.0058(11) C23 0.050(2) 0.0329(14) 0.039(2) -0.0083(12) -0.0001(13) 0.0044(13) C24 0.051(2) 0.048(2) 0.049(2) -0.011(2) 0.007(2) 0.012(2) C25 0.037(2) 0.089(3) 0.058(2) -0.011(2) -0.004(2) 0.012(2) C26 0.040(2) 0.115(4) 0.069(3) -0.042(3) -0.016(2) 0.009(2) C27 0.043(2) 0.076(3) 0.054(2) -0.033(2) -0.012(2) 0.008(2) N3 0.060(2) 0.060(2) 0.062(2) -0.030(2) -0.001(2) -0.015(2) O2 0.099(3) 0.064(2) 0.089(3) -0.030(2) -0.007(2) -0.037(2) O3 0.138(4) 0.079(3) 0.121(4) -0.024(3) -0.080(3) -0.024(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 Pd C1 2.010(3) . ? Pd N2 2.103(3) . ? Pd P 2.2475(8) . ? Pd Cl 2.3659(9) . ? P C22 1.814(3) . ? P C16 1.822(3) . ? P C10 1.825(3) . ? O1 C8 1.222(5) . ? N1 N2 1.342(4) . ? N1 C6 1.380(4) . ? N1 H1N 0.80(5) . ? N2 C7 1.304(4) . ? C1 C2 1.373(5) . ? C1 C6 1.409(4) . ? C2 C3 1.401(5) . ? C2 H2 0.97(5) . ? C3 C4 1.380(6) . ? C3 N3 1.449(5) . ? C4 C5 1.363(6) . ? C4 H4 0.88(6) . ? C5 C6 1.399(5) . ? C5 H5 0.96(6) . ? C7 C8 1.470(5) . ? C7 H7 0.98(4) . ? C8 C9 1.479(6) . ? C9 H9 1.04(9) . ? C9 H9A 0.88(9) . ? C9 H9B 1.03(8) . ? C10 C15 1.389(4) . ? C10 C11 1.393(5) . ? C11 C12 1.380(6) . ? C11 H11 1.01(6) . ? C12 C13 1.384(6) . ? C12 H12 0.87(6) . ? C13 C14 1.362(6) . ? C13 H13 0.92(7) . ? C14 C15 1.396(5) . ? C14 H14 0.89(7) . ? C15 H15 0.86(5) . ? C16 C21 1.388(4) . ? C16 C17 1.394(4) . ? C17 C18 1.393(5) . ? C17 H17 0.97(5) . ? C18 C19 1.381(5) . ? C18 H18 0.95(3) . ? C19 C20 1.370(6) . ? C19 H19 0.73(5) . ? C20 C21 1.393(4) . ? C20 H20 0.97(4) . ? C21 H21 0.89(3) . ? C22 C27 1.392(5) . ? C22 C23 1.402(4) . ? C23 C24 1.371(5) . ? C23 H23 0.92(5) . ? C24 C25 1.360(7) . ? C24 H24 0.89(5) . ? C25 C26 1.392(7) . ? C25 H25 0.98(6) . ? C26 C27 1.384(6) . ? C26 H26 0.79(7) . ? C27 H27 0.87(4) . ? N3 O2 1.204(5) . ? N3 O3 1.226(6) . ? 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 C1 Pd N2 80.54(12) . . ? C1 Pd P 94.68(9) . . ? N2 Pd P 172.23(8) . . ? C1 Pd Cl 169.85(9) . . ? N2 Pd Cl 93.58(8) . . ? P Pd Cl 92.00(3) . . ? C22 P C16 108.74(15) . . ? C22 P C10 105.63(14) . . ? C16 P C10 99.61(14) . . ? C22 P Pd 110.17(10) . . ? C16 P Pd 115.47(10) . . ? C10 P Pd 116.32(10) . . ? N2 N1 C6 117.3(3) . . ? N2 N1 H1N 115.6(37) . . ? C6 N1 H1N 126.4(37) . . ? C7 N2 N1 121.2(3) . . ? C7 N2 Pd 126.8(2) . . ? N1 N2 Pd 111.9(2) . . ? C2 C1 C6 116.0(3) . . ? C2 C1 Pd 131.7(2) . . ? C6 C1 Pd 112.1(2) . . ? C1 C2 C3 121.2(3) . . ? C1 C2 H2 124.2(33) . . ? C3 C2 H2 114.5(33) . . ? C4 C3 C2 121.9(3) . . ? C4 C3 N3 119.5(3) . . ? C2 C3 N3 118.6(4) . . ? C5 C4 C3 118.2(4) . . ? C5 C4 H4 121.6(38) . . ? C3 C4 H4 120.2(38) . . ? C4 C5 C6 120.1(4) . . ? C4 C5 H5 119.5(37) . . ? C6 C5 H5 119.6(37) . . ? N1 C6 C5 119.4(3) . . ? N1 C6 C1 118.1(3) . . ? C5 C6 C1 122.5(3) . . ? N2 C7 C8 125.0(3) . . ? N2 C7 H7 115.4(26) . . ? C8 C7 H7 119.6(26) . . ? O1 C8 C7 121.3(3) . . ? O1 C8 C9 122.8(4) . . ? C7 C8 C9 115.8(4) . . ? C8 C9 H9 122.3(45) . . ? C8 C9 H9A 117.9(55) . . ? H9 C9 H9A 94.1(64) . . ? C8 C9 H9B 114.7(46) . . ? H9 C9 H9B 94.4(55) . . ? H9A C9 H9B 109.6(66) . . ? C15 C10 C11 119.0(3) . . ? C15 C10 P 123.4(3) . . ? C11 C10 P 117.5(2) . . ? C12 C11 C10 120.5(3) . . ? C12 C11 H11 123.2(34) . . ? C10 C11 H11 116.1(34) . . ? C11 C12 C13 119.9(4) . . ? C11 C12 H12 122.5(35) . . ? C13 C12 H12 117.4(35) . . ? C14 C13 C12 120.4(4) . . ? C14 C13 H13 121.6(42) . . ? C12 C13 H13 116.8(43) . . ? C13 C14 C15 120.3(4) . . ? C13 C14 H14 122.4(49) . . ? C15 C14 H14 117.4(50) . . ? C10 C15 C14 119.9(4) . . ? C10 C15 H15 117.8(34) . . ? C14 C15 H15 122.1(34) . . ? C21 C16 C17 118.9(3) . . ? C21 C16 P 120.3(2) . . ? C17 C16 P 120.5(2) . . ? C18 C17 C16 120.4(3) . . ? C18 C17 H17 122.0(26) . . ? C16 C17 H17 117.5(26) . . ? C19 C18 C17 119.7(3) . . ? C19 C18 H18 117.7(21) . . ? C17 C18 H18 122.3(21) . . ? C20 C19 C18 120.2(3) . . ? C20 C19 H19 116.5(41) . . ? C18 C19 H19 123.3(41) . . ? C19 C20 C21 120.5(3) . . ? C19 C20 H20 117.2(26) . . ? C21 C20 H20 122.2(26) . . ? C16 C21 C20 120.1(3) . . ? C16 C21 H21 122.8(22) . . ? C20 C21 H21 116.9(22) . . ? C27 C22 C23 118.7(3) . . ? C27 C22 P 124.7(3) . . ? C23 C22 P 116.5(3) . . ? C24 C23 C22 120.6(4) . . ? C24 C23 H23 117.7(26) . . ? C22 C23 H23 121.7(26) . . ? C25 C24 C23 120.7(4) . . ? C25 C24 H24 123.9(31) . . ? C23 C24 H24 115.3(31) . . ? C24 C25 C26 119.8(4) . . ? C24 C25 H25 120.5(33) . . ? C26 C25 H25 119.6(34) . . ? C27 C26 C25 120.4(5) . . ? C27 C26 H26 123.4(51) . . ? C25 C26 H26 116.2(51) . . ? C26 C27 C22 119.8(4) . . ? C26 C27 H27 120.8(30) . . ? C22 C27 H27 119.2(30) . . ? O2 N3 O3 121.7(4) . . ? O2 N3 C3 119.8(4) . . ? O3 N3 C3 118.5(4) . . ? _refine_diff_density_max 1.447 _refine_diff_density_min -1.253 _refine_diff_density_rms 0.114