# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Charles L. B. Macdonald' 'Andreas Decken' 'C. Adam Dyker' 'Bobby D. Ellis' _publ_contact_author_name 'Prof Charles L. B. Macdonald' _publ_contact_author_address ; Chemistry and Biochemistry University of Windsor 401 Sunset Avenue Windsor Ontario N9B 3P4 CANADA ; _publ_contact_author_email CMACD@UWINDSOR.CA _publ_requested_journal 'Chemical Communications' _publ_section_title ; The synthesis, characterisation and electronic structure of N-heterocyclic carbene adducts of P(I) ; data_nb _database_code_depnum_ccdc_archive 'CCDC 261141' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '[NHC2P][Cl]' _chemical_melting_point ? _chemical_formula_moiety '[C22 H40 N4 P][Cl][C7 H8]' _chemical_formula_sum 'C29 H48 Cl N4 P' _chemical_formula_weight 519.13 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.134(3) _cell_length_b 12.243(3) _cell_length_c 13.037(3) _cell_angle_alpha 103.358(4) _cell_angle_beta 99.906(5) _cell_angle_gamma 100.772(4) _cell_volume 1506.3(7) _cell_formula_units_Z 2 _cell_measurement_temperature 198(2) _cell_measurement_reflns_used 3516 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 26.35 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.525 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.075 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.145 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 564 _exptl_absorpt_coefficient_mu 0.203 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 198(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10360 _diffrn_reflns_av_R_equivalents 0.0180 _diffrn_reflns_av_sigmaI/netI 0.0353 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 27.49 _reflns_number_total 6428 _reflns_number_gt 4752 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0835P)^2^+0.4101P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6428 _refine_ls_number_parameters 477 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0754 _refine_ls_R_factor_gt 0.0524 _refine_ls_wR_factor_ref 0.1560 _refine_ls_wR_factor_gt 0.1425 _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_restrained_S_all 1.094 _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 P P 0.54162(6) 0.34262(5) 0.37010(4) 0.03191(16) Uani 1 1 d . . . Cl Cl 0.13958(6) 0.74033(5) 0.13532(5) 0.04694(18) Uani 1 1 d . . . N1 N 0.74149(17) 0.37282(15) 0.24163(13) 0.0300(4) Uani 1 1 d . . . N2 N 0.77067(17) 0.52181(14) 0.37908(13) 0.0299(4) Uani 1 1 d . . . C1 C 0.6885(2) 0.41487(17) 0.32739(15) 0.0284(4) Uani 1 1 d . . . C3 C 0.8554(2) 0.45431(18) 0.23780(16) 0.0317(4) Uani 1 1 d . . . C4 C 0.8742(2) 0.54696(18) 0.32409(17) 0.0323(4) Uani 1 1 d . . . C5 C 0.6879(2) 0.25365(19) 0.16997(17) 0.0354(5) Uani 1 1 d . . . C6 C 0.6105(3) 0.2526(2) 0.05849(19) 0.0438(6) Uani 1 1 d . . . C7 C 0.7996(3) 0.1867(3) 0.1658(3) 0.0506(6) Uani 1 1 d . . . C8 C 0.9409(3) 0.4394(2) 0.1555(2) 0.0395(5) Uani 1 1 d . . . C9 C 0.9843(3) 0.6559(2) 0.3577(2) 0.0455(6) Uani 1 1 d . . . C10 C 0.7481(2) 0.59760(19) 0.47817(16) 0.0340(5) Uani 1 1 d . . . C11 C 0.8577(3) 0.6053(3) 0.5767(2) 0.0499(6) Uani 1 1 d . . . C12 C 0.7338(3) 0.7160(2) 0.4655(2) 0.0428(5) Uani 1 1 d . . . N21 N 0.31732(18) 0.22277(15) 0.19191(14) 0.0329(4) Uani 1 1 d . . . N22 N 0.37915(17) 0.40514(15) 0.19954(13) 0.0307(4) Uani 1 1 d . . . C21 C 0.4113(2) 0.32369(17) 0.24804(16) 0.0296(4) Uani 1 1 d . . . C22 C 0.2278(2) 0.24213(19) 0.10734(17) 0.0356(5) Uani 1 1 d . . . C23 C 0.2676(2) 0.35501(19) 0.11085(17) 0.0334(5) Uani 1 1 d . . . C25 C 0.3182(3) 0.11057(19) 0.2170(2) 0.0395(5) Uani 1 1 d . . . C26 C 0.1899(3) 0.0655(2) 0.2550(2) 0.0511(6) Uani 1 1 d . . . C27 C 0.3405(4) 0.0213(2) 0.1230(3) 0.0556(7) Uani 1 1 d . . . C28 C 0.1112(3) 0.1525(3) 0.0289(2) 0.0500(6) Uani 1 1 d . . . C29 C 0.2120(3) 0.4177(2) 0.0336(2) 0.0414(5) Uani 1 1 d . . . C30 C 0.4486(2) 0.52936(18) 0.24273(18) 0.0349(5) Uani 1 1 d . . . C31 C 0.5233(4) 0.5720(3) 0.1636(3) 0.0549(7) Uani 1 1 d . . . C32 C 0.3536(3) 0.6017(2) 0.2852(3) 0.0493(6) Uani 1 1 d . . . C41 C 0.6136(6) 0.9624(4) 0.3254(4) 0.1056(15) Uani 1 1 d . . . H41 H 0.5245 0.9719 0.3326 0.127 Uiso 1 1 calc R . . C42 C 0.6208(9) 0.8867(4) 0.2358(4) 0.132(2) Uani 1 1 d . . . H42 H 0.5392 0.8445 0.1832 0.158 Uiso 1 1 calc R . . C43 C 0.7394(10) 0.8714(6) 0.2215(7) 0.165(4) Uani 1 1 d . . . H43 H 0.7425 0.8181 0.1567 0.198 Uiso 1 1 calc R . . C44 C 0.8649(8) 0.9294(8) 0.2963(10) 0.196(5) Uani 1 1 d . . . H44 H 0.9517 0.9169 0.2852 0.236 Uiso 1 1 calc R . . C45 C 0.8483(8) 1.0140(6) 0.3968(9) 0.195(4) Uani 1 1 d . . . H45 H 0.9268 1.0575 0.4520 0.234 Uiso 1 1 calc R . . C46 C 0.7205(6) 1.0265(4) 0.4065(4) 0.1103(16) Uani 1 1 d . . . C47 C 0.6984(8) 1.1130(5) 0.5052(5) 0.162(3) Uani 1 1 d . . . H47A H 0.7009 1.1879 0.4898 0.243 Uiso 1 1 calc R . . H47B H 0.7716 1.1221 0.5685 0.243 Uiso 1 1 calc R . . H47C H 0.6087 1.0838 0.5199 0.243 Uiso 1 1 calc R . . H5 H 0.621(2) 0.219(2) 0.2061(18) 0.034(6) Uiso 1 1 d . . . H6A H 0.669(3) 0.282(2) 0.021(2) 0.048(7) Uiso 1 1 d . . . H6B H 0.565(3) 0.176(3) 0.021(2) 0.060(8) Uiso 1 1 d . . . H6C H 0.538(3) 0.301(2) 0.0661(19) 0.040(6) Uiso 1 1 d . . . H7A H 0.848(3) 0.198(3) 0.237(3) 0.061(8) Uiso 1 1 d . . . H7B H 0.853(3) 0.208(3) 0.117(2) 0.061(9) Uiso 1 1 d . . . H7C H 0.759(3) 0.110(3) 0.138(3) 0.068(9) Uiso 1 1 d . . . H8A H 0.990(2) 0.513(2) 0.1542(19) 0.037(6) Uiso 1 1 d . . . H8B H 1.009(3) 0.397(3) 0.176(3) 0.071(9) Uiso 1 1 d . . . H8C H 0.890(3) 0.400(2) 0.088(2) 0.039(6) Uiso 1 1 d . . . H9A H 0.951(3) 0.720(3) 0.362(3) 0.070(10) Uiso 1 1 d . . . H9B H 1.040(4) 0.664(3) 0.433(3) 0.092(11) Uiso 1 1 d . . . H9C H 1.041(3) 0.656(3) 0.310(3) 0.066(9) Uiso 1 1 d . . . H10 H 0.661(2) 0.5577(19) 0.4883(17) 0.028(5) Uiso 1 1 d . . . H11A H 0.828(3) 0.646(3) 0.642(2) 0.061(8) Uiso 1 1 d . . . H11B H 0.942(3) 0.650(3) 0.573(2) 0.067(9) Uiso 1 1 d . . . H11C H 0.862(3) 0.527(3) 0.581(2) 0.053(8) Uiso 1 1 d . . . H12A H 0.826(3) 0.773(2) 0.482(2) 0.053(7) Uiso 1 1 d . . . H12B H 0.691(3) 0.714(2) 0.395(2) 0.059(8) Uiso 1 1 d . . . H12C H 0.681(3) 0.748(2) 0.519(2) 0.053(7) Uiso 1 1 d . . . H25 H 0.394(3) 0.129(2) 0.277(2) 0.044(7) Uiso 1 1 d . . . H26A H 0.177(3) 0.126(3) 0.311(3) 0.072(9) Uiso 1 1 d . . . H26B H 0.198(4) -0.002(3) 0.279(3) 0.087(11) Uiso 1 1 d . . . H26C H 0.111(4) 0.036(3) 0.197(3) 0.078(10) Uiso 1 1 d . . . H27A H 0.343(3) -0.045(3) 0.150(2) 0.068(9) Uiso 1 1 d . . . H27B H 0.414(4) 0.047(3) 0.107(3) 0.080(11) Uiso 1 1 d . . . H27C H 0.268(4) 0.008(3) 0.060(3) 0.085(11) Uiso 1 1 d . . . H28A H 0.142(3) 0.103(3) -0.017(3) 0.064(9) Uiso 1 1 d . . . H28B H 0.059(4) 0.108(3) 0.066(3) 0.077(10) Uiso 1 1 d . . . H28C H 0.057(3) 0.189(3) -0.016(3) 0.068(9) Uiso 1 1 d . . . H29A H 0.274(3) 0.428(2) -0.016(2) 0.059(8) Uiso 1 1 d . . . H29B H 0.199(3) 0.496(3) 0.075(2) 0.052(7) Uiso 1 1 d . . . H29C H 0.130(3) 0.373(2) -0.009(2) 0.048(7) Uiso 1 1 d . . . H30 H 0.520(2) 0.5324(19) 0.3055(18) 0.029(5) Uiso 1 1 d . . . H31A H 0.583(3) 0.643(3) 0.201(3) 0.072(10) Uiso 1 1 d . . . H31B H 0.587(4) 0.521(3) 0.141(3) 0.085(11) Uiso 1 1 d . . . H31C H 0.463(3) 0.581(3) 0.114(3) 0.059(9) Uiso 1 1 d . . . H32A H 0.405(3) 0.677(3) 0.324(2) 0.059(8) Uiso 1 1 d . . . H32B H 0.289(3) 0.606(3) 0.232(3) 0.070(10) Uiso 1 1 d . . . H32C H 0.310(3) 0.571(3) 0.332(3) 0.069(10) Uiso 1 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 0.0347(3) 0.0299(3) 0.0304(3) 0.0078(2) 0.0110(2) 0.0032(2) Cl 0.0501(4) 0.0396(3) 0.0466(3) 0.0129(3) 0.0058(3) 0.0029(3) N1 0.0295(9) 0.0291(9) 0.0309(8) 0.0053(7) 0.0099(7) 0.0066(7) N2 0.0307(9) 0.0280(9) 0.0302(8) 0.0053(7) 0.0099(7) 0.0057(7) C1 0.0300(10) 0.0266(10) 0.0285(9) 0.0073(8) 0.0072(8) 0.0059(8) C3 0.0302(10) 0.0335(11) 0.0326(10) 0.0094(8) 0.0102(8) 0.0070(9) C4 0.0292(10) 0.0330(11) 0.0361(10) 0.0098(9) 0.0104(8) 0.0072(8) C5 0.0385(12) 0.0284(11) 0.0354(10) 0.0008(9) 0.0127(9) 0.0043(9) C6 0.0428(14) 0.0458(15) 0.0344(11) 0.0002(11) 0.0099(10) 0.0027(12) C7 0.0559(17) 0.0371(15) 0.0576(16) 0.0043(12) 0.0156(14) 0.0164(12) C8 0.0389(13) 0.0437(14) 0.0376(12) 0.0091(11) 0.0178(10) 0.0081(11) C9 0.0410(14) 0.0373(14) 0.0534(15) 0.0051(11) 0.0204(12) -0.0020(11) C10 0.0370(12) 0.0308(11) 0.0312(10) 0.0029(8) 0.0118(9) 0.0042(9) C11 0.0569(17) 0.0537(17) 0.0347(12) 0.0087(12) 0.0065(11) 0.0102(14) C12 0.0514(15) 0.0316(12) 0.0443(13) 0.0037(10) 0.0172(12) 0.0096(11) N21 0.0325(9) 0.0262(9) 0.0368(9) 0.0030(7) 0.0108(7) 0.0035(7) N22 0.0292(9) 0.0288(9) 0.0331(8) 0.0062(7) 0.0112(7) 0.0036(7) C21 0.0287(10) 0.0269(10) 0.0328(10) 0.0049(8) 0.0125(8) 0.0045(8) C22 0.0296(11) 0.0358(12) 0.0382(11) 0.0040(9) 0.0101(9) 0.0048(9) C23 0.0286(10) 0.0355(11) 0.0349(10) 0.0066(9) 0.0107(8) 0.0049(9) C25 0.0446(13) 0.0248(11) 0.0448(12) 0.0062(9) 0.0093(11) 0.0027(9) C26 0.0640(18) 0.0349(14) 0.0517(15) 0.0077(12) 0.0249(14) -0.0002(12) C27 0.0626(19) 0.0337(14) 0.073(2) 0.0062(13) 0.0320(17) 0.0123(13) C28 0.0401(14) 0.0438(15) 0.0532(15) 0.0022(13) 0.0017(12) 0.0004(12) C29 0.0341(12) 0.0499(15) 0.0391(12) 0.0138(11) 0.0079(10) 0.0053(11) C30 0.0354(11) 0.0262(11) 0.0412(11) 0.0084(9) 0.0088(9) 0.0036(9) C31 0.0597(18) 0.0424(16) 0.0603(17) 0.0164(14) 0.0227(15) -0.0047(14) C32 0.0508(16) 0.0380(14) 0.0575(16) 0.0055(13) 0.0132(14) 0.0154(12) C41 0.147(4) 0.062(2) 0.095(3) 0.031(2) -0.007(3) 0.013(3) C42 0.231(7) 0.067(3) 0.108(4) 0.039(3) 0.032(4) 0.048(4) C43 0.212(8) 0.130(5) 0.265(9) 0.148(6) 0.168(8) 0.087(6) C44 0.124(5) 0.169(7) 0.419(15) 0.229(10) 0.153(8) 0.063(5) C45 0.120(5) 0.111(5) 0.377(14) 0.149(8) 0.039(7) -0.005(4) C46 0.130(4) 0.067(3) 0.118(4) 0.047(3) -0.011(3) -0.005(3) C47 0.224(7) 0.098(4) 0.121(4) 0.021(4) -0.032(5) 0.010(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P C21 1.823(2) . ? P C1 1.824(2) . ? N1 C1 1.359(2) . ? N1 C3 1.394(3) . ? N1 C5 1.482(3) . ? N2 C1 1.361(3) . ? N2 C4 1.396(3) . ? N2 C10 1.486(3) . ? C3 C4 1.358(3) . ? C3 C8 1.491(3) . ? C4 C9 1.491(3) . ? C5 C7 1.518(3) . ? C5 C6 1.524(3) . ? C5 H5 0.97(2) . ? C6 H6A 0.91(3) . ? C6 H6B 0.94(3) . ? C6 H6C 1.03(3) . ? C7 H7A 0.94(3) . ? C7 H7B 0.95(3) . ? C7 H7C 0.91(3) . ? C8 H8A 0.95(3) . ? C8 H8B 0.98(3) . ? C8 H8C 0.91(3) . ? C9 H9A 0.91(3) . ? C9 H9B 1.02(4) . ? C9 H9C 0.92(3) . ? C10 C11 1.519(3) . ? C10 C12 1.527(3) . ? C10 H10 0.97(2) . ? C11 H11A 1.01(3) . ? C11 H11B 0.93(3) . ? C11 H11C 0.98(3) . ? C12 H12A 1.02(3) . ? C12 H12B 0.94(3) . ? C12 H12C 1.00(3) . ? N21 C21 1.368(3) . ? N21 C22 1.397(3) . ? N21 C25 1.485(3) . ? N22 C21 1.357(3) . ? N22 C23 1.398(3) . ? N22 C30 1.481(3) . ? C22 C23 1.353(3) . ? C22 C28 1.492(3) . ? C23 C29 1.498(3) . ? C25 C27 1.522(4) . ? C25 C26 1.524(4) . ? C25 H25 0.95(3) . ? C26 H26A 0.96(3) . ? C26 H26B 0.96(4) . ? C26 H26C 0.95(4) . ? C27 H27A 0.96(3) . ? C27 H27B 0.83(4) . ? C27 H27C 0.96(4) . ? C28 H28A 0.89(3) . ? C28 H28B 0.96(4) . ? C28 H28C 0.97(3) . ? C29 H29A 0.99(3) . ? C29 H29B 1.03(3) . ? C29 H29C 0.91(3) . ? C30 C31 1.510(3) . ? C30 C32 1.515(3) . ? C30 H30 0.99(2) . ? C31 H31A 0.93(4) . ? C31 H31B 1.01(4) . ? C31 H31C 0.85(3) . ? C32 H32A 0.94(3) . ? C32 H32B 0.89(3) . ? C32 H32C 0.93(3) . ? C41 C42 1.335(7) . ? C41 C46 1.346(6) . ? C41 H41 0.9500 . ? C42 C43 1.288(9) . ? C42 H42 0.9500 . ? C43 C44 1.410(12) . ? C43 H43 0.9500 . ? C44 C45 1.527(13) . ? C44 H44 0.9500 . ? C45 C46 1.355(9) . ? C45 H45 0.9500 . ? C46 C47 1.545(8) . ? C47 H47A 0.9800 . ? C47 H47B 0.9800 . ? C47 H47C 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 C21 P C1 97.35(9) . . ? C1 N1 C3 110.12(17) . . ? C1 N1 C5 122.83(17) . . ? C3 N1 C5 126.91(17) . . ? C1 N2 C4 109.65(16) . . ? C1 N2 C10 123.34(17) . . ? C4 N2 C10 127.01(17) . . ? N1 C1 N2 106.15(17) . . ? N1 C1 P 127.83(15) . . ? N2 C1 P 125.97(14) . . ? C4 C3 N1 106.79(18) . . ? C4 C3 C8 127.4(2) . . ? N1 C3 C8 125.79(19) . . ? C3 C4 N2 107.27(18) . . ? C3 C4 C9 127.8(2) . . ? N2 C4 C9 124.89(19) . . ? N1 C5 C7 111.9(2) . . ? N1 C5 C6 111.66(19) . . ? C7 C5 C6 113.3(2) . . ? N1 C5 H5 102.9(13) . . ? C7 C5 H5 108.4(13) . . ? C6 C5 H5 108.0(13) . . ? C5 C6 H6A 111.2(17) . . ? C5 C6 H6B 108.2(18) . . ? H6A C6 H6B 110(2) . . ? C5 C6 H6C 110.0(13) . . ? H6A C6 H6C 109(2) . . ? H6B C6 H6C 109(2) . . ? C5 C7 H7A 107.7(18) . . ? C5 C7 H7B 109.4(18) . . ? H7A C7 H7B 116(3) . . ? C5 C7 H7C 109(2) . . ? H7A C7 H7C 107(3) . . ? H7B C7 H7C 107(3) . . ? C3 C8 H8A 109.5(14) . . ? C3 C8 H8B 109.1(18) . . ? H8A C8 H8B 107(2) . . ? C3 C8 H8C 112.8(16) . . ? H8A C8 H8C 109(2) . . ? H8B C8 H8C 109(2) . . ? C4 C9 H9A 113(2) . . ? C4 C9 H9B 109(2) . . ? H9A C9 H9B 107(3) . . ? C4 C9 H9C 111.4(19) . . ? H9A C9 H9C 107(3) . . ? H9B C9 H9C 110(3) . . ? N2 C10 C11 110.87(19) . . ? N2 C10 C12 112.82(18) . . ? C11 C10 C12 112.8(2) . . ? N2 C10 H10 104.9(13) . . ? C11 C10 H10 106.8(13) . . ? C12 C10 H10 108.2(13) . . ? C10 C11 H11A 106.5(16) . . ? C10 C11 H11B 109.3(19) . . ? H11A C11 H11B 109(3) . . ? C10 C11 H11C 109.3(16) . . ? H11A C11 H11C 110(2) . . ? H11B C11 H11C 113(3) . . ? C10 C12 H12A 112.8(16) . . ? C10 C12 H12B 113.1(18) . . ? H12A C12 H12B 105(2) . . ? C10 C12 H12C 107.7(16) . . ? H12A C12 H12C 107(2) . . ? H12B C12 H12C 111(2) . . ? C21 N21 C22 109.61(17) . . ? C21 N21 C25 123.54(18) . . ? C22 N21 C25 126.81(18) . . ? C21 N22 C23 110.02(17) . . ? C21 N22 C30 122.94(17) . . ? C23 N22 C30 126.89(18) . . ? N22 C21 N21 106.04(17) . . ? N22 C21 P 128.42(15) . . ? N21 C21 P 125.33(15) . . ? C23 C22 N21 107.24(18) . . ? C23 C22 C28 127.7(2) . . ? N21 C22 C28 125.1(2) . . ? C22 C23 N22 107.04(19) . . ? C22 C23 C29 128.5(2) . . ? N22 C23 C29 124.3(2) . . ? N21 C25 C27 111.9(2) . . ? N21 C25 C26 112.0(2) . . ? C27 C25 C26 111.9(2) . . ? N21 C25 H25 104.2(16) . . ? C27 C25 H25 109.9(16) . . ? C26 C25 H25 106.5(16) . . ? C25 C26 H26A 109(2) . . ? C25 C26 H26B 110(2) . . ? H26A C26 H26B 112(3) . . ? C25 C26 H26C 111(2) . . ? H26A C26 H26C 112(3) . . ? H26B C26 H26C 102(3) . . ? C25 C27 H27A 104.3(19) . . ? C25 C27 H27B 109(2) . . ? H27A C27 H27B 112(3) . . ? C25 C27 H27C 110(2) . . ? H27A C27 H27C 114(3) . . ? H27B C27 H27C 107(3) . . ? C22 C28 H28A 111(2) . . ? C22 C28 H28B 110(2) . . ? H28A C28 H28B 107(3) . . ? C22 C28 H28C 109.7(19) . . ? H28A C28 H28C 105(3) . . ? H28B C28 H28C 114(3) . . ? C23 C29 H29A 110.1(17) . . ? C23 C29 H29B 110.4(15) . . ? H29A C29 H29B 111(2) . . ? C23 C29 H29C 109.0(17) . . ? H29A C29 H29C 106(2) . . ? H29B C29 H29C 110(2) . . ? N22 C30 C31 111.2(2) . . ? N22 C30 C32 112.35(19) . . ? C31 C30 C32 115.0(2) . . ? N22 C30 H30 104.1(13) . . ? C31 C30 H30 106.3(13) . . ? C32 C30 H30 106.9(12) . . ? C30 C31 H31A 108(2) . . ? C30 C31 H31B 111(2) . . ? H31A C31 H31B 104(3) . . ? C30 C31 H31C 108(2) . . ? H31A C31 H31C 109(3) . . ? H31B C31 H31C 118(3) . . ? C30 C32 H32A 110.1(18) . . ? C30 C32 H32B 111(2) . . ? H32A C32 H32B 109(3) . . ? C30 C32 H32C 111(2) . . ? H32A C32 H32C 108(3) . . ? H32B C32 H32C 108(3) . . ? C42 C41 C46 126.3(7) . . ? C42 C41 H41 116.9 . . ? C46 C41 H41 116.9 . . ? C43 C42 C41 119.4(8) . . ? C43 C42 H42 120.3 . . ? C41 C42 H42 120.3 . . ? C42 C43 C44 123.8(8) . . ? C42 C43 H43 118.1 . . ? C44 C43 H43 118.1 . . ? C43 C44 C45 113.8(6) . . ? C43 C44 H44 123.1 . . ? C45 C44 H44 123.1 . . ? C46 C45 C44 119.4(8) . . ? C46 C45 H45 120.3 . . ? C44 C45 H45 120.3 . . ? C41 C46 C45 117.4(7) . . ? C41 C46 C47 121.2(6) . . ? C45 C46 C47 121.5(7) . . ? C46 C47 H47A 109.5 . . ? C46 C47 H47B 109.5 . . ? H47A C47 H47B 109.5 . . ? C46 C47 H47C 109.5 . . ? H47A C47 H47C 109.5 . . ? H47B C47 H47C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.930 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.930 _refine_diff_density_max 0.788 _refine_diff_density_min -0.509 _refine_diff_density_rms 0.055