# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Rory Waterman' 'Samantha N. MacMillan' 'Joseph M. Tanski' _publ_contact_author_name 'Rory Waterman' _publ_contact_author_address ; Department of Chemistry University of Vermont Cook Physical Science Building 82 University Place Burlington Vermont 05405 UNITED STATES OF AMERICA ; _publ_contact_author_email RORY.WATERMAN@UVM.EDU _publ_requested_journal 'Chemical Communications' _publ_section_title ; Insertion of Benzylisocyanide into a Zr-P bond and Rearrangement. Atom-Economical Synthesis of a Phosphaalkene ; data_rw431zr _database_code_depnum_ccdc_archive 'CCDC 651742' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H52 N5 P Si3 Zr' _chemical_formula_weight 677.22 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' Si Si 0.0817 0.0704 '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' Zr Zr -2.9673 0.5597 '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 16.5616(8) _cell_length_b 10.9871(5) _cell_length_c 21.1696(10) _cell_angle_alpha 90.00 _cell_angle_beta 110.8890(10) _cell_angle_gamma 90.00 _cell_volume 3598.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 125(2) _cell_measurement_reflns_used 9805 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 30.16 _exptl_crystal_description Bulk _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.250 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1432 _exptl_absorpt_coefficient_mu 0.475 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8905 _exptl_absorpt_correction_T_max 0.9152 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 125(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 49757 _diffrn_reflns_av_R_equivalents 0.0351 _diffrn_reflns_av_sigmaI/netI 0.0293 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.35 _diffrn_reflns_theta_max 30.45 _reflns_number_total 10366 _reflns_number_gt 8613 _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. EXTI refined to 0 H on C16 located and refined ; _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^)+(0.0326P)^2^+1.2334P] 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 10366 _refine_ls_number_parameters 365 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0394 _refine_ls_R_factor_gt 0.0289 _refine_ls_wR_factor_ref 0.0724 _refine_ls_wR_factor_gt 0.0678 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.006 _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 Zr Zr 0.914033(8) 0.052214(11) 0.170618(7) 0.01429(4) Uani 1 1 d . . . N1 N 0.89136(8) -0.01128(11) 0.25452(6) 0.0187(2) Uani 1 1 d . . . N2 N 1.03679(8) 0.00078(12) 0.17491(6) 0.0208(2) Uani 1 1 d . . . N3 N 0.81567(8) 0.01226(11) 0.08014(6) 0.0172(2) Uani 1 1 d . . . N4 N 0.90863(8) -0.17435(11) 0.16038(6) 0.0201(2) Uani 1 1 d . . . N5 N 0.89808(8) 0.24999(11) 0.16661(6) 0.0177(2) Uani 1 1 d . . . Si1 Si 0.94990(3) 0.02915(4) 0.33770(2) 0.02235(9) Uani 1 1 d . . . Si2 Si 1.11177(3) 0.07327(4) 0.14817(2) 0.02082(9) Uani 1 1 d . . . Si3 Si 0.70993(3) 0.06393(4) 0.05545(2) 0.01938(8) Uani 1 1 d . . . P P 0.83936(3) 0.45977(3) 0.09367(2) 0.02251(8) Uani 1 1 d . . . C1 C 0.83871(10) -0.12398(14) 0.24139(8) 0.0222(3) Uani 1 1 d . . . H1A H 0.7815 -0.1090 0.2059 0.027 Uiso 1 1 calc R . . H1B H 0.8296 -0.1503 0.2831 0.027 Uiso 1 1 calc R . . C2 C 1.06115(10) -0.12156(14) 0.20631(8) 0.0253(3) Uani 1 1 d . . . H2A H 1.0613 -0.1207 0.2531 0.030 Uiso 1 1 calc R . . H2B H 1.1198 -0.1436 0.2079 0.030 Uiso 1 1 calc R . . C3 C 0.83166(10) -0.09831(13) 0.04653(7) 0.0218(3) Uani 1 1 d . . . H3A H 0.8849 -0.0882 0.0360 0.026 Uiso 1 1 calc R . . H3B H 0.7827 -0.1127 0.0037 0.026 Uiso 1 1 calc R . . C4 C 0.88680(10) -0.22230(13) 0.21829(7) 0.0231(3) Uani 1 1 d . . . H4A H 0.9403 -0.2450 0.2560 0.028 Uiso 1 1 calc R . . H4B H 0.8501 -0.2958 0.2041 0.028 Uiso 1 1 calc R . . C5 C 0.99580(10) -0.21361(14) 0.16412(8) 0.0259(3) Uani 1 1 d . . . H5B H 0.9982 -0.2182 0.1181 0.031 Uiso 1 1 calc R . . H5C H 1.0090 -0.2952 0.1851 0.031 Uiso 1 1 calc R . . C6 C 0.84148(11) -0.20556(13) 0.09427(7) 0.0241(3) Uani 1 1 d . . . H6A H 0.7858 -0.2223 0.1001 0.029 Uiso 1 1 calc R . . H6B H 0.8588 -0.2793 0.0754 0.029 Uiso 1 1 calc R . . C7 C 0.88096(14) 0.11215(18) 0.37675(9) 0.0389(4) Uani 1 1 d . . . H7A H 0.8347 0.0583 0.3786 0.058 Uiso 1 1 calc R . . H7B H 0.8556 0.1841 0.3495 0.058 Uiso 1 1 calc R . . H7C H 0.9164 0.1376 0.4227 0.058 Uiso 1 1 calc R . . C8 C 0.99591(12) -0.10654(16) 0.39241(9) 0.0343(4) Uani 1 1 d . . . H8A H 0.9487 -0.1577 0.3950 0.051 Uiso 1 1 calc R . . H8B H 1.0315 -0.0792 0.4379 0.051 Uiso 1 1 calc R . . H8C H 1.0316 -0.1536 0.3730 0.051 Uiso 1 1 calc R . . C9 C 1.04284(11) 0.12531(15) 0.33698(8) 0.0297(4) Uani 1 1 d . . . H9A H 1.0211 0.2036 0.3154 0.045 Uiso 1 1 calc R . . H9B H 1.0739 0.0834 0.3117 0.045 Uiso 1 1 calc R . . H9C H 1.0821 0.1393 0.3835 0.045 Uiso 1 1 calc R . . C10 C 1.16994(11) -0.04062(16) 0.11399(9) 0.0321(4) Uani 1 1 d . . . H10A H 1.1277 -0.0890 0.0786 0.048 Uiso 1 1 calc R . . H10B H 1.2045 -0.0944 0.1506 0.048 Uiso 1 1 calc R . . H10C H 1.2080 0.0021 0.0950 0.048 Uiso 1 1 calc R . . C11 C 1.05478(10) 0.18337(15) 0.07941(8) 0.0261(3) Uani 1 1 d . . . H11A H 1.0093 0.1408 0.0433 0.039 Uiso 1 1 calc R . . H11B H 1.0962 0.2187 0.0612 0.039 Uiso 1 1 calc R . . H11C H 1.0290 0.2483 0.0977 0.039 Uiso 1 1 calc R . . C12 C 1.19221(10) 0.16084(15) 0.21858(8) 0.0284(3) Uani 1 1 d . . . H12A H 1.1626 0.2266 0.2329 0.043 Uiso 1 1 calc R . . H12B H 1.2362 0.1955 0.2028 0.043 Uiso 1 1 calc R . . H12C H 1.2199 0.1063 0.2568 0.043 Uiso 1 1 calc R . . C13 C 0.67652(11) 0.16080(15) -0.02198(8) 0.0302(4) Uani 1 1 d . . . H13A H 0.6808 0.1136 -0.0599 0.045 Uiso 1 1 calc R . . H13B H 0.7145 0.2320 -0.0140 0.045 Uiso 1 1 calc R . . H13C H 0.6167 0.1877 -0.0326 0.045 Uiso 1 1 calc R . . C14 C 0.63325(11) -0.06836(15) 0.03877(9) 0.0287(3) Uani 1 1 d . . . H14A H 0.6405 -0.1200 0.0034 0.043 Uiso 1 1 calc R . . H14B H 0.5737 -0.0381 0.0239 0.043 Uiso 1 1 calc R . . H14C H 0.6456 -0.1159 0.0803 0.043 Uiso 1 1 calc R . . C15 C 0.69717(10) 0.15589(15) 0.12579(8) 0.0254(3) Uani 1 1 d . . . H15A H 0.7267 0.1148 0.1690 0.038 Uiso 1 1 calc R . . H15B H 0.6356 0.1643 0.1186 0.038 Uiso 1 1 calc R . . H15C H 0.7225 0.2367 0.1266 0.038 Uiso 1 1 calc R . . C16 C 0.87590(9) 0.31250(13) 0.10731(7) 0.0182(3) Uani 1 1 d . . . H16 H 0.8805(10) 0.2663(15) 0.0705(8) 0.018(4) Uiso 1 1 d . . . C17 C 0.88825(9) 0.31926(13) 0.22255(7) 0.0191(3) Uani 1 1 d . . . H17A H 0.8837 0.2608 0.2567 0.023 Uiso 1 1 calc R . . H17B H 0.8330 0.3645 0.2050 0.023 Uiso 1 1 calc R . . C21 C 0.82553(10) 0.48118(13) 0.00465(8) 0.0219(3) Uani 1 1 d . . . C22 C 0.88429(13) 0.44206(15) -0.02461(9) 0.0332(4) Uani 1 1 d . . . H22A H 0.9325 0.3941 0.0013 0.040 Uiso 1 1 calc R . . C23 C 0.87374(15) 0.47183(17) -0.09076(10) 0.0420(5) Uani 1 1 d . . . H23A H 0.9139 0.4427 -0.1100 0.050 Uiso 1 1 calc R . . C24 C 0.80509(14) 0.54371(16) -0.12883(9) 0.0379(4) Uani 1 1 d . . . H24A H 0.7984 0.5651 -0.1739 0.045 Uiso 1 1 calc R . . C25 C 0.74657(12) 0.58406(16) -0.10089(9) 0.0364(4) Uani 1 1 d . . . H25A H 0.6992 0.6332 -0.1269 0.044 Uiso 1 1 calc R . . C26 C 0.75628(11) 0.55352(15) -0.03492(9) 0.0288(3) Uani 1 1 d . . . H26A H 0.7154 0.5821 -0.0163 0.035 Uiso 1 1 calc R . . C31 C 0.95983(9) 0.40925(12) 0.25776(7) 0.0182(3) Uani 1 1 d . . . C32 C 1.03149(10) 0.42640(13) 0.23959(8) 0.0223(3) Uani 1 1 d . . . H32A H 1.0365 0.3825 0.2025 0.027 Uiso 1 1 calc R . . C33 C 1.09647(10) 0.50765(15) 0.27539(8) 0.0266(3) Uani 1 1 d . . . H33A H 1.1454 0.5188 0.2626 0.032 Uiso 1 1 calc R . . C34 C 1.08976(11) 0.57231(14) 0.32978(8) 0.0276(3) Uani 1 1 d . . . H34A H 1.1340 0.6276 0.3542 0.033 Uiso 1 1 calc R . . C35 C 1.01846(11) 0.55563(14) 0.34817(8) 0.0266(3) Uani 1 1 d . . . H35A H 1.0137 0.5993 0.3854 0.032 Uiso 1 1 calc R . . C36 C 0.95367(10) 0.47493(14) 0.31224(8) 0.0230(3) Uani 1 1 d . . . H36A H 0.9046 0.4644 0.3250 0.028 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 Zr 0.01620(7) 0.01113(6) 0.01598(7) 0.00078(5) 0.00627(5) 0.00018(5) N1 0.0213(6) 0.0162(6) 0.0191(6) 0.0006(5) 0.0078(5) -0.0017(5) N2 0.0200(6) 0.0183(6) 0.0248(6) 0.0039(5) 0.0089(5) 0.0032(5) N3 0.0213(6) 0.0124(5) 0.0178(6) 0.0001(4) 0.0067(5) 0.0015(4) N4 0.0250(6) 0.0141(6) 0.0197(6) 0.0021(4) 0.0059(5) 0.0013(5) N5 0.0201(6) 0.0134(5) 0.0206(6) -0.0001(4) 0.0087(5) -0.0006(4) Si1 0.0292(2) 0.0203(2) 0.01691(19) -0.00048(15) 0.00752(17) -0.00357(16) Si2 0.01743(19) 0.0227(2) 0.0233(2) 0.00326(16) 0.00853(16) 0.00292(15) Si3 0.01908(19) 0.01717(19) 0.0195(2) 0.00101(15) 0.00402(15) 0.00103(15) P 0.0303(2) 0.01337(17) 0.0244(2) 0.00192(14) 0.01043(16) 0.00349(14) C1 0.0243(7) 0.0221(7) 0.0197(7) 0.0018(6) 0.0074(6) -0.0064(6) C2 0.0224(7) 0.0240(8) 0.0292(8) 0.0079(6) 0.0090(6) 0.0083(6) C3 0.0301(8) 0.0163(7) 0.0177(7) -0.0011(5) 0.0071(6) 0.0030(6) C4 0.0298(8) 0.0149(7) 0.0218(7) 0.0049(5) 0.0060(6) -0.0032(6) C5 0.0317(8) 0.0159(7) 0.0312(8) 0.0037(6) 0.0125(7) 0.0079(6) C6 0.0339(8) 0.0129(6) 0.0214(7) -0.0023(5) 0.0048(6) -0.0002(6) C7 0.0538(12) 0.0391(10) 0.0314(9) -0.0057(8) 0.0246(9) -0.0016(9) C8 0.0414(10) 0.0301(9) 0.0233(8) 0.0061(7) 0.0017(7) -0.0071(8) C9 0.0312(9) 0.0251(8) 0.0282(8) -0.0011(6) 0.0051(7) -0.0068(7) C10 0.0303(9) 0.0359(9) 0.0354(9) 0.0015(7) 0.0180(7) 0.0069(7) C11 0.0242(8) 0.0303(8) 0.0249(8) 0.0050(6) 0.0100(6) 0.0026(6) C12 0.0230(8) 0.0274(8) 0.0316(9) 0.0038(7) 0.0059(7) -0.0004(6) C13 0.0293(8) 0.0276(8) 0.0277(8) 0.0065(7) 0.0028(7) 0.0041(7) C14 0.0241(8) 0.0277(8) 0.0294(8) -0.0022(6) 0.0037(6) -0.0045(6) C15 0.0220(7) 0.0247(8) 0.0316(8) -0.0030(6) 0.0120(6) 0.0008(6) C16 0.0190(7) 0.0149(6) 0.0217(7) -0.0003(5) 0.0083(6) -0.0011(5) C17 0.0215(7) 0.0165(7) 0.0220(7) -0.0011(5) 0.0110(6) -0.0012(5) C21 0.0265(8) 0.0142(6) 0.0225(7) 0.0013(5) 0.0056(6) -0.0032(5) C22 0.0427(10) 0.0257(8) 0.0339(9) 0.0085(7) 0.0170(8) 0.0092(7) C23 0.0679(14) 0.0298(9) 0.0380(10) 0.0054(8) 0.0308(10) 0.0066(9) C24 0.0625(13) 0.0250(9) 0.0222(8) 0.0000(7) 0.0103(8) -0.0072(8) C25 0.0374(10) 0.0284(9) 0.0302(9) 0.0055(7) -0.0040(8) -0.0037(7) C26 0.0264(8) 0.0252(8) 0.0305(9) 0.0024(6) 0.0050(7) -0.0004(6) C31 0.0212(7) 0.0127(6) 0.0198(7) 0.0024(5) 0.0063(6) 0.0021(5) C32 0.0228(7) 0.0206(7) 0.0239(7) -0.0013(6) 0.0087(6) -0.0005(6) C33 0.0218(8) 0.0268(8) 0.0305(8) -0.0009(6) 0.0083(6) -0.0031(6) C34 0.0258(8) 0.0211(8) 0.0277(8) -0.0025(6) -0.0004(6) -0.0009(6) C35 0.0308(8) 0.0226(8) 0.0223(7) -0.0041(6) 0.0045(6) 0.0041(6) C36 0.0259(8) 0.0215(7) 0.0230(7) -0.0006(6) 0.0105(6) 0.0027(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 Zr N1 2.0636(12) . ? Zr N3 2.0713(12) . ? Zr N2 2.0807(12) . ? Zr N5 2.1870(12) . ? Zr N4 2.4975(12) . ? N1 C1 1.4826(18) . ? N1 Si1 1.7380(13) . ? N2 C2 1.4901(19) . ? N2 Si2 1.7315(13) . ? N3 C3 1.4787(18) . ? N3 Si3 1.7347(13) . ? N4 C5 1.482(2) . ? N4 C6 1.4843(19) . ? N4 C4 1.4925(18) . ? N5 C16 1.3615(18) . ? N5 C17 1.4648(18) . ? Si1 C7 1.8687(19) . ? Si1 C9 1.8714(17) . ? Si1 C8 1.8749(17) . ? Si2 C11 1.8690(16) . ? Si2 C12 1.8724(17) . ? Si2 C10 1.8747(17) . ? Si3 C13 1.8652(16) . ? Si3 C15 1.8727(16) . ? Si3 C14 1.8789(16) . ? P C16 1.7156(15) . ? P C21 1.8307(16) . ? C1 C4 1.523(2) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C5 1.517(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C6 1.523(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 H5B 0.9900 . ? C5 H5C 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? 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 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16 0.955(16) . ? C17 C31 1.519(2) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C21 C22 1.395(2) . ? C21 C26 1.401(2) . ? C22 C23 1.387(2) . ? C22 H22A 0.9500 . ? C23 C24 1.383(3) . ? C23 H23A 0.9500 . ? C24 C25 1.376(3) . ? C24 H24A 0.9500 . ? C25 C26 1.389(2) . ? C25 H25A 0.9500 . ? C26 H26A 0.9500 . ? C31 C32 1.385(2) . ? C31 C36 1.395(2) . ? C32 C33 1.396(2) . ? C32 H32A 0.9500 . ? C33 C34 1.391(2) . ? C33 H33A 0.9500 . ? C34 C35 1.381(2) . ? C34 H34A 0.9500 . ? C35 C36 1.391(2) . ? C35 H35A 0.9500 . ? C36 H36A 0.9500 . ? 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 N1 Zr N3 113.57(5) . . ? N1 Zr N2 110.21(5) . . ? N3 Zr N2 114.64(5) . . ? N1 Zr N5 108.23(5) . . ? N3 Zr N5 97.49(4) . . ? N2 Zr N5 111.97(5) . . ? N1 Zr N4 74.09(4) . . ? N3 Zr N4 73.53(4) . . ? N2 Zr N4 74.77(5) . . ? N5 Zr N4 170.70(4) . . ? C1 N1 Si1 118.80(9) . . ? C1 N1 Zr 113.35(9) . . ? Si1 N1 Zr 125.36(7) . . ? C2 N2 Si2 116.69(10) . . ? C2 N2 Zr 111.68(9) . . ? Si2 N2 Zr 131.63(7) . . ? C3 N3 Si3 117.30(10) . . ? C3 N3 Zr 113.72(9) . . ? Si3 N3 Zr 125.86(6) . . ? C5 N4 C6 111.80(12) . . ? C5 N4 C4 111.72(11) . . ? C6 N4 C4 111.93(12) . . ? C5 N4 Zr 106.35(9) . . ? C6 N4 Zr 107.68(8) . . ? C4 N4 Zr 106.99(8) . . ? C16 N5 C17 114.34(12) . . ? C16 N5 Zr 121.75(9) . . ? C17 N5 Zr 122.12(9) . . ? N1 Si1 C7 111.39(8) . . ? N1 Si1 C9 107.42(7) . . ? C7 Si1 C9 111.23(9) . . ? N1 Si1 C8 112.32(7) . . ? C7 Si1 C8 107.02(9) . . ? C9 Si1 C8 107.44(8) . . ? N2 Si2 C11 109.30(7) . . ? N2 Si2 C12 111.46(7) . . ? C11 Si2 C12 107.80(8) . . ? N2 Si2 C10 110.26(7) . . ? C11 Si2 C10 108.52(8) . . ? C12 Si2 C10 109.42(8) . . ? N3 Si3 C13 113.76(7) . . ? N3 Si3 C15 108.97(7) . . ? C13 Si3 C15 107.98(8) . . ? N3 Si3 C14 110.21(7) . . ? C13 Si3 C14 107.90(8) . . ? C15 Si3 C14 107.85(8) . . ? C16 P C21 101.63(7) . . ? N1 C1 C4 108.22(12) . . ? N1 C1 H1A 110.1 . . ? C4 C1 H1A 110.1 . . ? N1 C1 H1B 110.1 . . ? C4 C1 H1B 110.1 . . ? H1A C1 H1B 108.4 . . ? N2 C2 C5 108.41(12) . . ? N2 C2 H2A 110.0 . . ? C5 C2 H2A 110.0 . . ? N2 C2 H2B 110.0 . . ? C5 C2 H2B 110.0 . . ? H2A C2 H2B 108.4 . . ? N3 C3 C6 108.15(12) . . ? N3 C3 H3A 110.1 . . ? C6 C3 H3A 110.1 . . ? N3 C3 H3B 110.1 . . ? C6 C3 H3B 110.1 . . ? H3A C3 H3B 108.4 . . ? N4 C4 C1 108.72(11) . . ? N4 C4 H4A 109.9 . . ? C1 C4 H4A 109.9 . . ? N4 C4 H4B 109.9 . . ? C1 C4 H4B 109.9 . . ? H4A C4 H4B 108.3 . . ? N4 C5 C2 108.32(12) . . ? N4 C5 H5B 110.0 . . ? C2 C5 H5B 110.0 . . ? N4 C5 H5C 110.0 . . ? C2 C5 H5C 110.0 . . ? H5B C5 H5C 108.4 . . ? N4 C6 C3 108.29(12) . . ? N4 C6 H6A 110.0 . . ? C3 C6 H6A 110.0 . . ? N4 C6 H6B 110.0 . . ? C3 C6 H6B 110.0 . . ? H6A C6 H6B 108.4 . . ? Si1 C7 H7A 109.5 . . ? Si1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? Si1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? Si1 C8 H8A 109.5 . . ? Si1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? Si1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? Si1 C9 H9A 109.5 . . ? Si1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? Si1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? Si2 C10 H10A 109.5 . . ? Si2 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? Si2 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? Si2 C11 H11A 109.5 . . ? Si2 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? Si2 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? Si2 C12 H12A 109.5 . . ? Si2 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? Si2 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? Si3 C13 H13A 109.5 . . ? Si3 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? Si3 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? Si3 C14 H14A 109.5 . . ? Si3 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? Si3 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? Si3 C15 H15A 109.5 . . ? Si3 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? Si3 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N5 C16 P 126.44(11) . . ? N5 C16 H16 114.2(10) . . ? P C16 H16 119.3(10) . . ? N5 C17 C31 116.28(12) . . ? N5 C17 H17A 108.2 . . ? C31 C17 H17A 108.2 . . ? N5 C17 H17B 108.2 . . ? C31 C17 H17B 108.2 . . ? H17A C17 H17B 107.4 . . ? C22 C21 C26 117.47(15) . . ? C22 C21 P 124.51(12) . . ? C26 C21 P 117.61(12) . . ? C23 C22 C21 121.27(17) . . ? C23 C22 H22A 119.4 . . ? C21 C22 H22A 119.4 . . ? C24 C23 C22 120.29(19) . . ? C24 C23 H23A 119.9 . . ? C22 C23 H23A 119.9 . . ? C25 C24 C23 119.48(17) . . ? C25 C24 H24A 120.3 . . ? C23 C24 H24A 120.3 . . ? C24 C25 C26 120.50(17) . . ? C24 C25 H25A 119.8 . . ? C26 C25 H25A 119.8 . . ? C25 C26 C21 120.98(17) . . ? C25 C26 H26A 119.5 . . ? C21 C26 H26A 119.5 . . ? C32 C31 C36 118.81(14) . . ? C32 C31 C17 123.25(13) . . ? C36 C31 C17 117.92(13) . . ? C31 C32 C33 120.50(14) . . ? C31 C32 H32A 119.7 . . ? C33 C32 H32A 119.7 . . ? C34 C33 C32 120.16(15) . . ? C34 C33 H33A 119.9 . . ? C32 C33 H33A 119.9 . . ? C35 C34 C33 119.63(15) . . ? C35 C34 H34A 120.2 . . ? C33 C34 H34A 120.2 . . ? C34 C35 C36 120.07(15) . . ? C34 C35 H35A 120.0 . . ? C36 C35 H35A 120.0 . . ? C35 C36 C31 120.83(15) . . ? C35 C36 H36A 119.6 . . ? C31 C36 H36A 119.6 . . ? 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 N3 Zr N1 C1 30.52(11) . . . . ? N2 Zr N1 C1 -99.67(10) . . . . ? N5 Zr N1 C1 137.58(10) . . . . ? N4 Zr N1 C1 -32.99(9) . . . . ? N3 Zr N1 Si1 -167.72(7) . . . . ? N2 Zr N1 Si1 62.09(9) . . . . ? N5 Zr N1 Si1 -60.66(9) . . . . ? N4 Zr N1 Si1 128.77(9) . . . . ? N1 Zr N2 C2 35.13(11) . . . . ? N3 Zr N2 C2 -94.48(10) . . . . ? N5 Zr N2 C2 155.66(10) . . . . ? N4 Zr N2 C2 -31.10(10) . . . . ? N1 Zr N2 Si2 -145.67(9) . . . . ? N3 Zr N2 Si2 84.72(10) . . . . ? N5 Zr N2 Si2 -25.14(11) . . . . ? N4 Zr N2 Si2 148.10(10) . . . . ? N1 Zr N3 C3 -96.46(10) . . . . ? N2 Zr N3 C3 31.47(11) . . . . ? N5 Zr N3 C3 149.87(10) . . . . ? N4 Zr N3 C3 -32.61(9) . . . . ? N1 Zr N3 Si3 62.92(9) . . . . ? N2 Zr N3 Si3 -169.15(7) . . . . ? N5 Zr N3 Si3 -50.76(8) . . . . ? N4 Zr N3 Si3 126.76(9) . . . . ? N1 Zr N4 C5 -116.07(10) . . . . ? N3 Zr N4 C5 122.74(10) . . . . ? N2 Zr N4 C5 0.66(9) . . . . ? N5 Zr N4 C5 138.2(2) . . . . ? N1 Zr N4 C6 123.95(10) . . . . ? N3 Zr N4 C6 2.76(9) . . . . ? N2 Zr N4 C6 -119.31(10) . . . . ? N5 Zr N4 C6 18.2(3) . . . . ? N1 Zr N4 C4 3.46(9) . . . . ? N3 Zr N4 C4 -117.73(10) . . . . ? N2 Zr N4 C4 120.19(10) . . . . ? N5 Zr N4 C4 -102.3(3) . . . . ? N1 Zr N5 C16 -154.26(10) . . . . ? N3 Zr N5 C16 -36.36(11) . . . . ? N2 Zr N5 C16 84.07(11) . . . . ? N4 Zr N5 C16 -51.3(3) . . . . ? N1 Zr N5 C17 9.58(11) . . . . ? N3 Zr N5 C17 127.48(10) . . . . ? N2 Zr N5 C17 -112.09(10) . . . . ? N4 Zr N5 C17 112.6(3) . . . . ? C1 N1 Si1 C7 -83.21(13) . . . . ? Zr N1 Si1 C7 115.94(9) . . . . ? C1 N1 Si1 C9 154.75(11) . . . . ? Zr N1 Si1 C9 -6.10(11) . . . . ? C1 N1 Si1 C8 36.83(14) . . . . ? Zr N1 Si1 C8 -124.03(9) . . . . ? C2 N2 Si2 C11 154.98(11) . . . . ? Zr N2 Si2 C11 -24.19(12) . . . . ? C2 N2 Si2 C12 -85.97(12) . . . . ? Zr N2 Si2 C12 94.87(10) . . . . ? C2 N2 Si2 C10 35.76(13) . . . . ? Zr N2 Si2 C10 -143.40(10) . . . . ? C3 N3 Si3 C13 -83.58(12) . . . . ? Zr N3 Si3 C13 117.70(9) . . . . ? C3 N3 Si3 C15 155.90(10) . . . . ? Zr N3 Si3 C15 -2.82(10) . . . . ? C3 N3 Si3 C14 37.75(12) . . . . ? Zr N3 Si3 C14 -120.98(9) . . . . ? Si1 N1 C1 C4 -103.15(12) . . . . ? Zr N1 C1 C4 59.92(13) . . . . ? Si2 N2 C2 C5 -119.42(12) . . . . ? Zr N2 C2 C5 59.91(14) . . . . ? Si3 N3 C3 C6 -101.47(12) . . . . ? Zr N3 C3 C6 59.79(14) . . . . ? C5 N4 C4 C1 140.82(12) . . . . ? C6 N4 C4 C1 -92.93(14) . . . . ? Zr N4 C4 C1 24.80(13) . . . . ? N1 C1 C4 N4 -53.13(15) . . . . ? C6 N4 C5 C2 145.87(12) . . . . ? C4 N4 C5 C2 -87.81(14) . . . . ? Zr N4 C5 C2 28.60(13) . . . . ? N2 C2 C5 N4 -57.09(16) . . . . ? C5 N4 C6 C3 -91.02(14) . . . . ? C4 N4 C6 C3 142.77(13) . . . . ? Zr N4 C6 C3 25.44(14) . . . . ? N3 C3 C6 N4 -53.34(16) . . . . ? C17 N5 C16 P 0.26(18) . . . . ? Zr N5 C16 P 165.27(8) . . . . ? C21 P C16 N5 178.88(13) . . . . ? C16 N5 C17 C31 -79.32(16) . . . . ? Zr N5 C17 C31 115.74(11) . . . . ? C16 P C21 C22 -43.01(15) . . . . ? C16 P C21 C26 144.50(12) . . . . ? C26 C21 C22 C23 -1.1(3) . . . . ? P C21 C22 C23 -173.62(15) . . . . ? C21 C22 C23 C24 1.4(3) . . . . ? C22 C23 C24 C25 -0.9(3) . . . . ? C23 C24 C25 C26 0.3(3) . . . . ? C24 C25 C26 C21 0.0(3) . . . . ? C22 C21 C26 C25 0.4(2) . . . . ? P C21 C26 C25 173.48(13) . . . . ? N5 C17 C31 C32 -0.5(2) . . . . ? N5 C17 C31 C36 -178.60(13) . . . . ? C36 C31 C32 C33 0.2(2) . . . . ? C17 C31 C32 C33 -177.89(14) . . . . ? C31 C32 C33 C34 0.0(2) . . . . ? C32 C33 C34 C35 0.0(2) . . . . ? C33 C34 C35 C36 -0.2(2) . . . . ? C34 C35 C36 C31 0.5(2) . . . . ? C32 C31 C36 C35 -0.5(2) . . . . ? C17 C31 C36 C35 177.75(13) . . . . ? _diffrn_measured_fraction_theta_max 0.947 _diffrn_reflns_theta_full 30.45 _diffrn_measured_fraction_theta_full 0.947 _refine_diff_density_max 0.476 _refine_diff_density_min -0.352 _refine_diff_density_rms 0.061