# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_g80_mn _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-(1,3-bis(2,6-diisopropylphenyl)-1,3,2-diazaborolen-2-yl)- N,N,N',N'-tetramethylphosphanediamine ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H48 B N4 P' _chemical_formula_sum 'C30 H48 B N4 P' _chemical_formula_weight 506.50 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 17.9692(13) _cell_length_b 10.7572(9) _cell_length_c 17.2353(14) _cell_angle_alpha 90.00 _cell_angle_beta 114.004(2) _cell_angle_gamma 90.00 _cell_volume 3043.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.65 _exptl_crystal_size_mid 0.52 _exptl_crystal_size_min 0.45 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.105 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 0.114 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7128 _exptl_absorpt_correction_T_max 0.7461 _exptl_absorpt_process_details 'Blessing, 1995' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator triumph _diffrn_measurement_device_type 'Bruker Kappa APEXII duo' _diffrn_measurement_method 'omega and phi scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 34170 _diffrn_reflns_av_R_equivalents 0.0453 _diffrn_reflns_av_sigmaI/netI 0.0521 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 30.51 _reflns_number_total 9276 _reflns_number_gt 6369 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEXII suite, 2008' _computing_cell_refinement 'Bruker APEXII suite, 2008' _computing_data_reduction 'Bruker APEXII suite, 2008' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'XP (Sheldrick, 2008)' _computing_publication_material SHELXL-97 _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^)+(0.0505P)^2^+0.9980P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9276 _refine_ls_number_parameters 329 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0812 _refine_ls_R_factor_gt 0.0457 _refine_ls_wR_factor_ref 0.1180 _refine_ls_wR_factor_gt 0.1019 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group B1 B 0.76048(8) 0.61215(14) 0.51403(9) 0.0145(3) Uani 1 1 d . . . N2 N 0.79634(6) 0.73461(10) 0.52533(7) 0.0135(2) Uani 1 1 d . . . C3 C 0.82557(8) 0.75389(12) 0.46237(8) 0.0160(3) Uani 1 1 d . . . H3 H 0.8511 0.8277 0.4551 0.019 Uiso 1 1 calc R . . C4 C 0.81177(7) 0.65152(12) 0.41374(8) 0.0155(2) Uani 1 1 d . . . H4 H 0.8261 0.6418 0.3668 0.019 Uiso 1 1 calc R . . N5 N 0.77291(6) 0.56137(10) 0.44290(7) 0.0137(2) Uani 1 1 d . . . C6 C 0.74324(8) 0.44885(12) 0.39511(8) 0.0159(2) Uani 1 1 d . . . C7 C 0.79672(8) 0.34857(13) 0.40636(9) 0.0186(3) Uani 1 1 d . . . C8 C 0.76598(10) 0.24214(14) 0.35748(10) 0.0275(3) Uani 1 1 d . . . H8 H 0.8010 0.1731 0.3639 0.033 Uiso 1 1 calc R . . C9 C 0.68555(11) 0.23500(15) 0.29982(10) 0.0322(4) Uani 1 1 d . . . H9 H 0.6657 0.1614 0.2675 0.039 Uiso 1 1 calc R . . C10 C 0.63422(10) 0.33485(15) 0.28929(10) 0.0286(3) Uani 1 1 d . . . H10 H 0.5791 0.3292 0.2494 0.034 Uiso 1 1 calc R . . C11 C 0.66149(8) 0.44431(13) 0.33609(9) 0.0204(3) Uani 1 1 d . . . C12 C 0.60364(8) 0.55375(16) 0.31936(10) 0.0272(3) Uani 1 1 d . . . H12 H 0.6335 0.6225 0.3588 0.033 Uiso 1 1 calc R . . C13 C 0.57727(9) 0.60102(16) 0.22813(11) 0.0304(3) Uani 1 1 d . . . H13A H 0.5395 0.6709 0.2184 0.046 Uiso 1 1 calc R . . H13B H 0.5501 0.5338 0.1882 0.046 Uiso 1 1 calc R . . H13C H 0.6253 0.6286 0.2194 0.046 Uiso 1 1 calc R . . C14 C 0.52881(10) 0.5212(2) 0.33648(11) 0.0431(5) Uani 1 1 d . . . H14A H 0.4929 0.5938 0.3246 0.065 Uiso 1 1 calc R . . H14B H 0.5462 0.4969 0.3961 0.065 Uiso 1 1 calc R . . H14C H 0.4994 0.4521 0.2997 0.065 Uiso 1 1 calc R . . C15 C 0.88626(9) 0.35504(14) 0.46742(9) 0.0216(3) Uani 1 1 d . . . H15 H 0.8921 0.4211 0.5103 0.026 Uiso 1 1 calc R . . C16 C 0.93844(9) 0.39289(15) 0.41921(10) 0.0260(3) Uani 1 1 d . . . H16A H 0.9959 0.3968 0.4589 0.039 Uiso 1 1 calc R . . H16B H 0.9209 0.4747 0.3931 0.039 Uiso 1 1 calc R . . H16C H 0.9318 0.3314 0.3749 0.039 Uiso 1 1 calc R . . C17 C 0.91858(11) 0.23297(15) 0.51542(10) 0.0312(4) Uani 1 1 d . . . H17A H 0.8855 0.2095 0.5464 0.047 Uiso 1 1 calc R . . H17B H 0.9753 0.2442 0.5557 0.047 Uiso 1 1 calc R . . H17C H 0.9156 0.1673 0.4748 0.047 Uiso 1 1 calc R . . C18 C 0.79200(8) 0.83393(12) 0.57915(8) 0.0148(2) Uani 1 1 d . . . C19 C 0.71648(8) 0.89252(12) 0.55976(9) 0.0176(3) Uani 1 1 d . . . C20 C 0.71156(9) 0.98271(13) 0.61557(10) 0.0223(3) Uani 1 1 d . . . H20 H 0.6607 1.0216 0.6042 0.027 Uiso 1 1 calc R . . C21 C 0.77929(10) 1.01665(14) 0.68721(10) 0.0246(3) Uani 1 1 d . . . H21 H 0.7744 1.0761 0.7256 0.029 Uiso 1 1 calc R . . C22 C 0.85400(9) 0.96355(13) 0.70251(9) 0.0227(3) Uani 1 1 d . . . H22 H 0.9008 0.9899 0.7503 0.027 Uiso 1 1 calc R . . C23 C 0.86213(8) 0.87191(12) 0.64903(8) 0.0175(3) Uani 1 1 d . . . C24 C 0.94630(8) 0.82330(13) 0.66430(9) 0.0204(3) Uani 1 1 d . . . H24 H 0.9395 0.7460 0.6299 0.025 Uiso 1 1 calc R . . C25 C 0.99867(9) 0.79168(16) 0.75734(10) 0.0302(3) Uani 1 1 d . . . H25A H 1.0519 0.7611 0.7627 0.045 Uiso 1 1 calc R . . H25B H 0.9715 0.7273 0.7766 0.045 Uiso 1 1 calc R . . H25C H 1.0061 0.8664 0.7923 0.045 Uiso 1 1 calc R . . C26 C 0.99064(9) 0.92019(15) 0.63313(10) 0.0273(3) Uani 1 1 d . . . H26A H 1.0453 0.8898 0.6436 0.041 Uiso 1 1 calc R . . H26B H 0.9950 0.9985 0.6638 0.041 Uiso 1 1 calc R . . H26C H 0.9599 0.9341 0.5721 0.041 Uiso 1 1 calc R . . C27 C 0.64400(8) 0.86696(14) 0.47659(10) 0.0232(3) Uani 1 1 d . . . H27 H 0.6533 0.7848 0.4549 0.028 Uiso 1 1 calc R . . C28 C 0.64130(11) 0.96609(19) 0.41179(11) 0.0411(4) Uani 1 1 d . . . H28A H 0.6941 0.9693 0.4077 0.062 Uiso 1 1 calc R . . H28B H 0.6295 1.0473 0.4300 0.062 Uiso 1 1 calc R . . H28C H 0.5986 0.9452 0.3562 0.062 Uiso 1 1 calc R . . C29 C 0.56330(9) 0.85967(19) 0.48560(13) 0.0403(4) Uani 1 1 d . . . H29A H 0.5666 0.7951 0.5270 0.061 Uiso 1 1 calc R . . H29B H 0.5196 0.8392 0.4305 0.061 Uiso 1 1 calc R . . H29C H 0.5518 0.9400 0.5052 0.061 Uiso 1 1 calc R . . P1 P 0.68726(2) 0.55583(3) 0.56326(2) 0.01549(8) Uani 1 1 d . . . N30 N 0.73730(7) 0.60174(12) 0.66567(7) 0.0208(2) Uani 1 1 d . . . C31 C 0.68930(11) 0.61996(16) 0.71516(10) 0.0310(4) Uani 1 1 d . . . H31A H 0.6333 0.6415 0.6771 0.046 Uiso 1 1 calc R . . H31B H 0.7130 0.6875 0.7560 0.046 Uiso 1 1 calc R . . H31C H 0.6892 0.5432 0.7458 0.046 Uiso 1 1 calc R . . C32 C 0.82119(9) 0.57172(16) 0.71799(10) 0.0305(4) Uani 1 1 d . . . H32A H 0.8525 0.5707 0.6829 0.046 Uiso 1 1 calc R . . H32B H 0.8240 0.4897 0.7438 0.046 Uiso 1 1 calc R . . H32C H 0.8439 0.6343 0.7628 0.046 Uiso 1 1 calc R . . N33 N 0.68730(7) 0.39943(11) 0.55239(8) 0.0228(3) Uani 1 1 d . . . C34 C 0.75991(10) 0.32318(14) 0.58393(11) 0.0293(3) Uani 1 1 d . . . H34A H 0.8058 0.3710 0.5827 0.044 Uiso 1 1 calc R . . H34B H 0.7511 0.2492 0.5480 0.044 Uiso 1 1 calc R . . H34C H 0.7720 0.2977 0.6424 0.044 Uiso 1 1 calc R . . C35 C 0.61524(10) 0.33032(15) 0.54675(11) 0.0300(3) Uani 1 1 d . . . H35A H 0.5684 0.3866 0.5292 0.045 Uiso 1 1 calc R . . H35B H 0.6250 0.2946 0.6024 0.045 Uiso 1 1 calc R . . H35C H 0.6040 0.2634 0.5049 0.045 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 B1 0.0126(6) 0.0154(7) 0.0129(6) 0.0009(5) 0.0026(5) 0.0026(5) N2 0.0123(5) 0.0152(5) 0.0116(5) -0.0015(4) 0.0035(4) 0.0013(4) C3 0.0152(6) 0.0170(6) 0.0154(6) -0.0002(5) 0.0058(5) -0.0018(5) C4 0.0134(6) 0.0189(6) 0.0140(6) 0.0000(5) 0.0052(5) 0.0000(5) N5 0.0131(5) 0.0138(5) 0.0124(5) -0.0013(4) 0.0033(4) -0.0007(4) C6 0.0187(6) 0.0150(6) 0.0134(6) -0.0023(5) 0.0058(5) -0.0025(5) C7 0.0247(7) 0.0166(6) 0.0141(6) 0.0005(5) 0.0072(5) 0.0014(5) C8 0.0416(9) 0.0161(7) 0.0220(7) -0.0012(6) 0.0101(7) 0.0023(6) C9 0.0459(10) 0.0195(7) 0.0254(8) -0.0073(6) 0.0085(7) -0.0104(7) C10 0.0275(8) 0.0288(8) 0.0229(7) -0.0060(6) 0.0033(6) -0.0118(6) C11 0.0185(6) 0.0232(7) 0.0177(6) -0.0040(6) 0.0055(5) -0.0040(5) C12 0.0146(6) 0.0360(9) 0.0241(7) -0.0091(7) 0.0006(6) 0.0008(6) C13 0.0238(7) 0.0291(8) 0.0359(9) 0.0022(7) 0.0096(7) 0.0020(6) C14 0.0206(8) 0.0827(15) 0.0232(8) 0.0056(9) 0.0060(7) 0.0096(8) C15 0.0247(7) 0.0230(7) 0.0150(6) 0.0014(5) 0.0059(5) 0.0088(6) C16 0.0252(7) 0.0297(8) 0.0216(7) 0.0020(6) 0.0079(6) 0.0081(6) C17 0.0409(9) 0.0316(8) 0.0215(7) 0.0067(6) 0.0130(7) 0.0176(7) C18 0.0178(6) 0.0134(6) 0.0132(6) 0.0001(5) 0.0064(5) 0.0003(5) C19 0.0178(6) 0.0162(6) 0.0186(6) 0.0024(5) 0.0072(5) 0.0018(5) C20 0.0273(7) 0.0186(7) 0.0253(7) 0.0020(6) 0.0150(6) 0.0058(5) C21 0.0376(8) 0.0191(7) 0.0212(7) -0.0034(6) 0.0163(7) 0.0017(6) C22 0.0288(7) 0.0208(7) 0.0156(6) -0.0049(5) 0.0062(6) -0.0020(6) C23 0.0197(6) 0.0164(6) 0.0148(6) -0.0009(5) 0.0055(5) -0.0012(5) C24 0.0159(6) 0.0209(7) 0.0186(7) -0.0051(5) 0.0011(5) -0.0001(5) C25 0.0218(7) 0.0346(9) 0.0232(8) -0.0003(7) -0.0021(6) -0.0002(6) C26 0.0229(7) 0.0306(8) 0.0269(8) -0.0066(6) 0.0086(6) -0.0053(6) C27 0.0170(6) 0.0224(7) 0.0251(7) -0.0015(6) 0.0032(6) 0.0052(5) C28 0.0327(9) 0.0563(12) 0.0241(8) 0.0102(8) 0.0012(7) 0.0004(8) C29 0.0175(7) 0.0493(11) 0.0488(11) 0.0046(9) 0.0079(7) 0.0034(7) P1 0.01507(15) 0.01640(16) 0.01484(16) 0.00032(13) 0.00592(12) -0.00018(13) N30 0.0219(6) 0.0257(6) 0.0154(6) -0.0010(5) 0.0082(5) -0.0019(5) C31 0.0432(9) 0.0320(9) 0.0260(8) -0.0066(7) 0.0226(7) -0.0044(7) C32 0.0271(8) 0.0401(9) 0.0175(7) 0.0029(7) 0.0022(6) -0.0031(7) N33 0.0268(6) 0.0177(6) 0.0283(7) -0.0014(5) 0.0157(5) -0.0037(5) C34 0.0391(9) 0.0189(7) 0.0376(9) 0.0055(6) 0.0236(8) 0.0042(6) C35 0.0348(8) 0.0266(8) 0.0329(9) -0.0046(7) 0.0182(7) -0.0129(7) _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 B1 N5 1.4401(18) . ? B1 N2 1.4445(18) . ? B1 P1 1.9303(15) . ? N2 C3 1.4001(16) . ? N2 C18 1.4377(16) . ? C3 C4 1.3444(18) . ? C3 H3 0.9500 . ? C4 N5 1.4022(16) . ? C4 H4 0.9500 . ? N5 C6 1.4390(16) . ? C6 C7 1.4046(19) . ? C6 C11 1.4068(18) . ? C7 C8 1.395(2) . ? C7 C15 1.524(2) . ? C8 C9 1.383(2) . ? C8 H8 0.9500 . ? C9 C10 1.379(2) . ? C9 H9 0.9500 . ? C10 C11 1.399(2) . ? C10 H10 0.9500 . ? C11 C12 1.519(2) . ? C12 C14 1.530(2) . ? C12 C13 1.533(2) . ? C12 H12 1.0000 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C17 1.535(2) . ? C15 C16 1.539(2) . ? C15 H15 1.0000 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C23 1.4038(18) . ? C18 C19 1.4077(18) . ? C19 C20 1.3941(19) . ? C19 C27 1.5191(19) . ? C20 C21 1.384(2) . ? C20 H20 0.9500 . ? C21 C22 1.382(2) . ? C21 H21 0.9500 . ? C22 C23 1.3972(19) . ? C22 H22 0.9500 . ? C23 C24 1.5187(19) . ? C24 C25 1.531(2) . ? C24 C26 1.536(2) . ? C24 H24 1.0000 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 C29 1.522(2) . ? C27 C28 1.531(2) . ? C27 H27 1.0000 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? P1 N33 1.6928(13) . ? P1 N30 1.6960(12) . ? N30 C32 1.4435(19) . ? N30 C31 1.4521(18) . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? N33 C34 1.447(2) . ? N33 C35 1.4617(18) . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N5 B1 N2 104.21(11) . . ? N5 B1 P1 128.66(10) . . ? N2 B1 P1 124.99(10) . . ? C3 N2 C18 121.73(11) . . ? C3 N2 B1 108.54(11) . . ? C18 N2 B1 128.78(11) . . ? C4 C3 N2 109.25(11) . . ? C4 C3 H3 125.4 . . ? N2 C3 H3 125.4 . . ? C3 C4 N5 109.60(11) . . ? C3 C4 H4 125.2 . . ? N5 C4 H4 125.2 . . ? C4 N5 C6 119.94(10) . . ? C4 N5 B1 108.37(11) . . ? C6 N5 B1 131.05(11) . . ? C7 C6 C11 121.85(12) . . ? C7 C6 N5 119.58(11) . . ? C11 C6 N5 118.54(12) . . ? C8 C7 C6 117.79(13) . . ? C8 C7 C15 120.12(13) . . ? C6 C7 C15 122.07(12) . . ? C9 C8 C7 121.37(14) . . ? C9 C8 H8 119.3 . . ? C7 C8 H8 119.3 . . ? C10 C9 C8 119.92(14) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C9 C10 C11 121.42(14) . . ? C9 C10 H10 119.3 . . ? C11 C10 H10 119.3 . . ? C10 C11 C6 117.65(13) . . ? C10 C11 C12 119.41(13) . . ? C6 C11 C12 122.91(12) . . ? C11 C12 C14 111.94(15) . . ? C11 C12 C13 110.74(13) . . ? C14 C12 C13 110.16(12) . . ? C11 C12 H12 108.0 . . ? C14 C12 H12 108.0 . . ? C13 C12 H12 108.0 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C7 C15 C17 113.26(13) . . ? C7 C15 C16 110.06(11) . . ? C17 C15 C16 109.71(12) . . ? C7 C15 H15 107.9 . . ? C17 C15 H15 107.9 . . ? C16 C15 H15 107.9 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C23 C18 C19 121.04(12) . . ? C23 C18 N2 120.29(11) . . ? C19 C18 N2 118.66(11) . . ? C20 C19 C18 118.25(13) . . ? C20 C19 C27 120.43(12) . . ? C18 C19 C27 121.11(12) . . ? C21 C20 C19 121.29(13) . . ? C21 C20 H20 119.4 . . ? C19 C20 H20 119.4 . . ? C22 C21 C20 119.64(13) . . ? C22 C21 H21 120.2 . . ? C20 C21 H21 120.2 . . ? C21 C22 C23 121.32(14) . . ? C21 C22 H22 119.3 . . ? C23 C22 H22 119.3 . . ? C22 C23 C18 118.23(13) . . ? C22 C23 C24 119.51(12) . . ? C18 C23 C24 122.12(12) . . ? C23 C24 C25 113.73(12) . . ? C23 C24 C26 109.11(12) . . ? C25 C24 C26 109.38(12) . . ? C23 C24 H24 108.2 . . ? C25 C24 H24 108.2 . . ? C26 C24 H24 108.2 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C24 C26 H26A 109.5 . . ? C24 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C24 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C19 C27 C29 113.56(13) . . ? C19 C27 C28 108.84(13) . . ? C29 C27 C28 111.20(13) . . ? C19 C27 H27 107.7 . . ? C29 C27 H27 107.7 . . ? C28 C27 H27 107.7 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C27 C29 H29A 109.5 . . ? C27 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C27 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? N33 P1 N30 112.37(6) . . ? N33 P1 B1 103.43(6) . . ? N30 P1 B1 101.45(6) . . ? C32 N30 C31 112.47(12) . . ? C32 N30 P1 124.18(10) . . ? C31 N30 P1 117.42(10) . . ? N30 C31 H31A 109.5 . . ? N30 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? N30 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? N30 C32 H32A 109.5 . . ? N30 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? N30 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C34 N33 C35 112.07(12) . . ? C34 N33 P1 124.24(10) . . ? C35 N33 P1 118.21(10) . . ? N33 C34 H34A 109.5 . . ? N33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? N33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? N33 C35 H35A 109.5 . . ? N33 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? N33 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N5 B1 N2 C3 1.61(13) . . . . ? P1 B1 N2 C3 -162.93(10) . . . . ? N5 B1 N2 C18 170.49(11) . . . . ? P1 B1 N2 C18 5.96(19) . . . . ? C18 N2 C3 C4 -170.91(11) . . . . ? B1 N2 C3 C4 -1.09(14) . . . . ? N2 C3 C4 N5 0.07(15) . . . . ? C3 C4 N5 C6 172.79(11) . . . . ? C3 C4 N5 B1 0.97(14) . . . . ? N2 B1 N5 C4 -1.56(13) . . . . ? P1 B1 N5 C4 162.19(10) . . . . ? N2 B1 N5 C6 -172.14(12) . . . . ? P1 B1 N5 C6 -8.4(2) . . . . ? C4 N5 C6 C7 84.04(15) . . . . ? B1 N5 C6 C7 -106.28(16) . . . . ? C4 N5 C6 C11 -93.93(14) . . . . ? B1 N5 C6 C11 75.75(18) . . . . ? C11 C6 C7 C8 -0.8(2) . . . . ? N5 C6 C7 C8 -178.65(12) . . . . ? C11 C6 C7 C15 177.31(13) . . . . ? N5 C6 C7 C15 -0.59(19) . . . . ? C6 C7 C8 C9 -0.1(2) . . . . ? C15 C7 C8 C9 -178.16(14) . . . . ? C7 C8 C9 C10 0.6(2) . . . . ? C8 C9 C10 C11 -0.2(2) . . . . ? C9 C10 C11 C6 -0.5(2) . . . . ? C9 C10 C11 C12 177.28(15) . . . . ? C7 C6 C11 C10 1.0(2) . . . . ? N5 C6 C11 C10 178.97(12) . . . . ? C7 C6 C11 C12 -176.68(13) . . . . ? N5 C6 C11 C12 1.2(2) . . . . ? C10 C11 C12 C14 60.82(19) . . . . ? C6 C11 C12 C14 -121.48(15) . . . . ? C10 C11 C12 C13 -62.52(18) . . . . ? C6 C11 C12 C13 115.17(15) . . . . ? C8 C7 C15 C17 -40.46(18) . . . . ? C6 C7 C15 C17 141.52(13) . . . . ? C8 C7 C15 C16 82.76(16) . . . . ? C6 C7 C15 C16 -95.26(15) . . . . ? C3 N2 C18 C23 -79.62(16) . . . . ? B1 N2 C18 C23 112.79(15) . . . . ? C3 N2 C18 C19 99.77(14) . . . . ? B1 N2 C18 C19 -67.82(17) . . . . ? C23 C18 C19 C20 -5.0(2) . . . . ? N2 C18 C19 C20 175.58(12) . . . . ? C23 C18 C19 C27 169.64(13) . . . . ? N2 C18 C19 C27 -9.74(19) . . . . ? C18 C19 C20 C21 1.6(2) . . . . ? C27 C19 C20 C21 -173.10(13) . . . . ? C19 C20 C21 C22 2.3(2) . . . . ? C20 C21 C22 C23 -2.8(2) . . . . ? C21 C22 C23 C18 -0.5(2) . . . . ? C21 C22 C23 C24 175.30(13) . . . . ? C19 C18 C23 C22 4.5(2) . . . . ? N2 C18 C23 C22 -176.14(12) . . . . ? C19 C18 C23 C24 -171.19(12) . . . . ? N2 C18 C23 C24 8.18(19) . . . . ? C22 C23 C24 C25 46.56(18) . . . . ? C18 C23 C24 C25 -137.82(14) . . . . ? C22 C23 C24 C26 -75.85(16) . . . . ? C18 C23 C24 C26 99.77(15) . . . . ? C20 C19 C27 C29 -44.11(19) . . . . ? C18 C19 C27 C29 141.32(14) . . . . ? C20 C19 C27 C28 80.34(17) . . . . ? C18 C19 C27 C28 -94.23(16) . . . . ? N5 B1 P1 N33 34.84(13) . . . . ? N2 B1 P1 N33 -164.50(11) . . . . ? N5 B1 P1 N30 151.43(12) . . . . ? N2 B1 P1 N30 -47.90(12) . . . . ? N33 P1 N30 C32 57.21(13) . . . . ? B1 P1 N30 C32 -52.65(13) . . . . ? N33 P1 N30 C31 -93.56(12) . . . . ? B1 P1 N30 C31 156.58(11) . . . . ? N30 P1 N33 C34 -53.44(13) . . . . ? B1 P1 N33 C34 55.16(13) . . . . ? N30 P1 N33 C35 98.30(12) . . . . ? B1 P1 N33 C35 -153.09(11) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.51 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.401 _refine_diff_density_min -0.291 _refine_diff_density_rms 0.053 _database_code_depnum_ccdc_archive 'CCDC 957947' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_gud86 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-(1,3-bis(2,6-diisopropylphenyl)-1,3,2-diazaborolen-2-yl)- 1,3-di-tert-butyl-1,3,2-diazaphospholene ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H56 B N4 P' _chemical_formula_sum 'C36 H56 B N4 P' _chemical_formula_weight 586.63 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.7029(8) _cell_length_b 12.3599(8) _cell_length_c 24.3641(18) _cell_angle_alpha 90.00 _cell_angle_beta 96.785(3) _cell_angle_gamma 90.00 _cell_volume 3499.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5564 _cell_measurement_theta_min 1.68 _cell_measurement_theta_max 26.47 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.113 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1280 _exptl_absorpt_coefficient_mu 0.108 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6370 _exptl_absorpt_correction_T_max 0.7454 _exptl_absorpt_process_details 'Blessing, 1995' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator Triumph _diffrn_measurement_device_type 'Bruker Kappa APEXII Duo' _diffrn_measurement_method 'Omega + Phi Scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 48124 _diffrn_reflns_av_R_equivalents 0.0534 _diffrn_reflns_av_sigmaI/netI 0.0386 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 26.47 _reflns_number_total 7217 _reflns_number_gt 5564 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEXII Software Suite, 2008' _computing_cell_refinement 'Bruker APEXII Software Suite, 2008' _computing_data_reduction 'Bruker APEXII Software Suite, 2008' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXS-plus, XP (Sheldrick, 1991)' _computing_publication_material SHELXL-97 _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^)+(0.0857P)^2^+1.4554P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7217 _refine_ls_number_parameters 393 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0736 _refine_ls_R_factor_gt 0.0528 _refine_ls_wR_factor_ref 0.1498 _refine_ls_wR_factor_gt 0.1395 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.12746(4) 0.12756(4) 0.10991(2) 0.01528(14) Uani 1 1 d . . . N1 N 0.04556(13) 0.08190(12) 0.16030(7) 0.0183(4) Uani 1 1 d . . . C1 C -0.00100(16) 0.26436(16) 0.14825(8) 0.0203(4) Uani 1 1 d . . . H1 H -0.0339 0.3313 0.1574 0.024 Uiso 1 1 calc R . . B1 B 0.26270(17) 0.17767(15) 0.15768(8) 0.0125(4) Uani 1 1 d . . . N2 N 0.05725(13) 0.25204(12) 0.10035(7) 0.0178(3) Uani 1 1 d . . . C2 C -0.00648(16) 0.17626(15) 0.17944(8) 0.0200(4) Uani 1 1 d . . . H2 H -0.0428 0.1766 0.2123 0.024 Uiso 1 1 calc R . . N3 N 0.32954(12) 0.11970(11) 0.20138(6) 0.0129(3) Uani 1 1 d . . . C3 C -0.02319(16) -0.02080(15) 0.15787(9) 0.0198(4) Uani 1 1 d . . . N4 N 0.33031(12) 0.27288(11) 0.15021(6) 0.0132(3) Uani 1 1 d . . . C4 C 0.0395(2) -0.10617(17) 0.12793(10) 0.0319(5) Uani 1 1 d . . . H4A H 0.0431 -0.0833 0.0897 0.048 Uiso 1 1 calc R . . H4B H -0.0020 -0.1750 0.1282 0.048 Uiso 1 1 calc R . . H4C H 0.1177 -0.1153 0.1467 0.048 Uiso 1 1 calc R . . C5 C -0.0288(2) -0.05867(19) 0.21703(10) 0.0348(5) Uani 1 1 d . . . H5A H 0.0494 -0.0695 0.2355 0.052 Uiso 1 1 calc R . . H5B H -0.0714 -0.1270 0.2166 0.052 Uiso 1 1 calc R . . H5C H -0.0680 -0.0039 0.2370 0.052 Uiso 1 1 calc R . . C6 C -0.14480(19) -0.00594(18) 0.12828(11) 0.0356(6) Uani 1 1 d . . . H6A H -0.1831 0.0531 0.1457 0.053 Uiso 1 1 calc R . . H6B H -0.1886 -0.0730 0.1308 0.053 Uiso 1 1 calc R . . H6C H -0.1407 0.0116 0.0893 0.053 Uiso 1 1 calc R . . C7 C -0.00658(16) 0.28204(15) 0.04551(8) 0.0210(4) Uani 1 1 d . . . C8 C 0.07721(19) 0.28225(19) 0.00265(9) 0.0292(5) Uani 1 1 d . . . H8A H 0.1401 0.3329 0.0139 0.044 Uiso 1 1 calc R . . H8B H 0.0371 0.3047 -0.0331 0.044 Uiso 1 1 calc R . . H8C H 0.1086 0.2093 -0.0006 0.044 Uiso 1 1 calc R . . C9 C -0.10619(18) 0.20502(18) 0.02813(9) 0.0286(5) Uani 1 1 d . . . H9A H -0.0760 0.1322 0.0229 0.043 Uiso 1 1 calc R . . H9B H -0.1485 0.2302 -0.0066 0.043 Uiso 1 1 calc R . . H9C H -0.1580 0.2031 0.0569 0.043 Uiso 1 1 calc R . . C10 C -0.0542(2) 0.39661(18) 0.05039(10) 0.0355(6) Uani 1 1 d . . . H10A H -0.1134 0.3961 0.0757 0.053 Uiso 1 1 calc R . . H10B H -0.0880 0.4217 0.0139 0.053 Uiso 1 1 calc R . . H10C H 0.0083 0.4454 0.0647 0.053 Uiso 1 1 calc R . . C11 C 0.43009(15) 0.17806(14) 0.21826(8) 0.0154(4) Uani 1 1 d . . . H11 H 0.4882 0.1573 0.2469 0.018 Uiso 1 1 calc R . . C12 C 0.43104(15) 0.26818(14) 0.18745(8) 0.0163(4) Uani 1 1 d . . . H12 H 0.4908 0.3206 0.1905 0.020 Uiso 1 1 calc R . . C13 C 0.31301(14) 0.01649(13) 0.22630(8) 0.0138(4) Uani 1 1 d . . . C14 C 0.28351(15) 0.01256(14) 0.28016(8) 0.0163(4) Uani 1 1 d . . . C15 C 0.26784(16) -0.08910(16) 0.30363(9) 0.0212(4) Uani 1 1 d . . . H15 H 0.2473 -0.0936 0.3401 0.025 Uiso 1 1 calc R . . C16 C 0.28199(16) -0.18297(15) 0.27420(9) 0.0218(4) Uani 1 1 d . . . H16 H 0.2681 -0.2513 0.2900 0.026 Uiso 1 1 calc R . . C17 C 0.31628(16) -0.17733(15) 0.22183(9) 0.0205(4) Uani 1 1 d . . . H17 H 0.3280 -0.2424 0.2025 0.025 Uiso 1 1 calc R . . C18 C 0.33410(15) -0.07817(14) 0.19673(8) 0.0166(4) Uani 1 1 d . . . C19 C 0.27085(18) 0.11423(15) 0.31404(8) 0.0221(4) Uani 1 1 d . . . H19 H 0.2792 0.1780 0.2896 0.027 Uiso 1 1 calc R . . C20 C 0.3663(2) 0.1201(2) 0.36213(10) 0.0375(6) Uani 1 1 d . . . H20A H 0.3588 0.0594 0.3873 0.056 Uiso 1 1 calc R . . H20B H 0.3603 0.1884 0.3820 0.056 Uiso 1 1 calc R . . H20C H 0.4412 0.1164 0.3480 0.056 Uiso 1 1 calc R . . C21 C 0.1529(2) 0.12126(19) 0.33444(11) 0.0363(6) Uani 1 1 d . . . H21A H 0.0931 0.1226 0.3027 0.054 Uiso 1 1 calc R . . H21B H 0.1483 0.1875 0.3562 0.054 Uiso 1 1 calc R . . H21C H 0.1414 0.0582 0.3576 0.054 Uiso 1 1 calc R . . C22 C 0.38051(17) -0.07221(15) 0.14120(8) 0.0207(4) Uani 1 1 d . . . H22 H 0.3457 -0.0071 0.1214 0.025 Uiso 1 1 calc R . . C23 C 0.35096(19) -0.17031(17) 0.10392(9) 0.0278(5) Uani 1 1 d . . . H23A H 0.3756 -0.1568 0.0675 0.042 Uiso 1 1 calc R . . H23B H 0.2677 -0.1826 0.1000 0.042 Uiso 1 1 calc R . . H23C H 0.3907 -0.2343 0.1204 0.042 Uiso 1 1 calc R . . C24 C 0.51086(18) -0.05583(18) 0.14961(9) 0.0278(5) Uani 1 1 d . . . H24A H 0.5475 -0.1186 0.1690 0.042 Uiso 1 1 calc R . . H24B H 0.5292 0.0096 0.1716 0.042 Uiso 1 1 calc R . . H24C H 0.5394 -0.0480 0.1136 0.042 Uiso 1 1 calc R . . C25 C 0.32947(15) 0.34718(14) 0.10470(8) 0.0139(4) Uani 1 1 d . . . C26 C 0.28110(15) 0.45078(14) 0.10813(8) 0.0152(4) Uani 1 1 d . . . C27 C 0.28908(16) 0.52103(15) 0.06401(8) 0.0197(4) Uani 1 1 d . . . H27 H 0.2568 0.5914 0.0650 0.024 Uiso 1 1 calc R . . C28 C 0.34278(17) 0.49089(16) 0.01874(9) 0.0236(4) Uani 1 1 d . . . H28 H 0.3465 0.5401 -0.0109 0.028 Uiso 1 1 calc R . . C29 C 0.39110(17) 0.38899(16) 0.01670(9) 0.0218(4) Uani 1 1 d . . . H29 H 0.4285 0.3689 -0.0143 0.026 Uiso 1 1 calc R . . C30 C 0.38549(16) 0.31550(15) 0.05970(8) 0.0180(4) Uani 1 1 d . . . C31 C 0.22622(16) 0.48528(14) 0.15872(8) 0.0176(4) Uani 1 1 d . . . H31 H 0.1798 0.4231 0.1703 0.021 Uiso 1 1 calc R . . C32 C 0.14601(17) 0.58273(16) 0.14833(9) 0.0244(5) Uani 1 1 d . . . H32A H 0.1910 0.6466 0.1406 0.037 Uiso 1 1 calc R . . H32B H 0.1071 0.5961 0.1811 0.037 Uiso 1 1 calc R . . H32C H 0.0886 0.5679 0.1166 0.037 Uiso 1 1 calc R . . C33 C 0.31760(19) 0.51270(16) 0.20682(9) 0.0274(5) Uani 1 1 d . . . H33A H 0.3609 0.4472 0.2187 0.041 Uiso 1 1 calc R . . H33B H 0.2802 0.5412 0.2377 0.041 Uiso 1 1 calc R . . H33C H 0.3703 0.5672 0.1949 0.041 Uiso 1 1 calc R . . C34 C 0.44195(17) 0.20489(16) 0.05673(9) 0.0220(4) Uani 1 1 d . . . H34 H 0.4282 0.1639 0.0907 0.026 Uiso 1 1 calc R . . C35 C 0.57216(18) 0.21591(18) 0.05682(10) 0.0304(5) Uani 1 1 d . . . H35A H 0.5884 0.2548 0.0236 0.046 Uiso 1 1 calc R . . H35B H 0.6071 0.1438 0.0573 0.046 Uiso 1 1 calc R . . H35C H 0.6044 0.2562 0.0897 0.046 Uiso 1 1 calc R . . C36 C 0.3885(2) 0.13985(18) 0.00676(10) 0.0334(5) Uani 1 1 d . . . H36A H 0.3059 0.1308 0.0088 0.050 Uiso 1 1 calc R . . H36B H 0.4253 0.0686 0.0068 0.050 Uiso 1 1 calc R . . H36C H 0.4001 0.1785 -0.0273 0.050 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0164(2) 0.0109(2) 0.0185(3) -0.00025(18) 0.00192(18) -0.00088(17) N1 0.0191(8) 0.0127(8) 0.0235(9) -0.0002(6) 0.0043(7) -0.0027(6) C1 0.0180(9) 0.0184(10) 0.0239(11) -0.0041(8) 0.0002(8) 0.0028(7) B1 0.0148(9) 0.0072(9) 0.0160(10) -0.0008(7) 0.0034(8) -0.0005(7) N2 0.0198(8) 0.0128(8) 0.0202(9) 0.0007(6) -0.0006(7) 0.0016(6) C2 0.0182(9) 0.0203(10) 0.0219(10) -0.0034(8) 0.0037(8) 0.0010(7) N3 0.0151(7) 0.0077(7) 0.0162(8) 0.0009(6) 0.0030(6) -0.0007(6) C3 0.0187(9) 0.0134(9) 0.0272(11) 0.0011(8) 0.0031(8) -0.0065(7) N4 0.0154(7) 0.0088(7) 0.0154(8) 0.0031(6) 0.0017(6) -0.0012(6) C4 0.0364(12) 0.0166(10) 0.0438(14) -0.0069(9) 0.0096(11) -0.0089(9) C5 0.0433(13) 0.0281(12) 0.0341(13) 0.0050(10) 0.0089(11) -0.0137(10) C6 0.0243(11) 0.0254(11) 0.0546(16) 0.0072(11) -0.0055(11) -0.0087(9) C7 0.0213(10) 0.0168(10) 0.0228(10) 0.0020(8) -0.0059(8) -0.0015(8) C8 0.0305(11) 0.0327(12) 0.0232(11) 0.0058(9) -0.0012(9) -0.0032(9) C9 0.0258(11) 0.0284(11) 0.0297(12) 0.0011(9) -0.0053(9) -0.0053(9) C10 0.0455(14) 0.0218(11) 0.0354(13) 0.0019(9) -0.0107(11) 0.0075(10) C11 0.0149(9) 0.0119(9) 0.0187(10) 0.0004(7) -0.0007(7) -0.0006(7) C12 0.0146(9) 0.0115(9) 0.0224(10) 0.0005(7) 0.0010(7) -0.0020(7) C13 0.0125(8) 0.0077(8) 0.0207(10) 0.0033(7) 0.0006(7) 0.0005(6) C14 0.0149(9) 0.0129(9) 0.0209(10) 0.0028(7) 0.0019(7) -0.0001(7) C15 0.0205(10) 0.0199(10) 0.0232(11) 0.0078(8) 0.0031(8) -0.0007(7) C16 0.0191(9) 0.0120(9) 0.0329(12) 0.0084(8) -0.0023(8) -0.0025(7) C17 0.0208(9) 0.0089(9) 0.0304(11) 0.0005(8) -0.0029(8) 0.0002(7) C18 0.0157(9) 0.0107(9) 0.0223(10) -0.0004(7) -0.0019(7) 0.0008(7) C19 0.0327(11) 0.0155(9) 0.0199(10) 0.0016(8) 0.0102(9) 0.0012(8) C20 0.0460(14) 0.0349(13) 0.0307(13) -0.0107(10) 0.0013(11) -0.0016(11) C21 0.0389(13) 0.0286(12) 0.0446(15) -0.0018(10) 0.0185(11) 0.0055(10) C22 0.0274(11) 0.0126(9) 0.0222(11) -0.0022(7) 0.0029(8) 0.0032(7) C23 0.0320(11) 0.0227(11) 0.0283(12) -0.0090(9) 0.0021(9) 0.0001(9) C24 0.0284(11) 0.0264(11) 0.0298(12) -0.0065(9) 0.0085(9) -0.0027(9) C25 0.0147(8) 0.0084(8) 0.0186(9) 0.0041(7) 0.0015(7) -0.0031(6) C26 0.0141(9) 0.0116(8) 0.0193(10) 0.0001(7) -0.0005(7) -0.0034(7) C27 0.0221(10) 0.0095(9) 0.0268(11) 0.0041(7) 0.0004(8) -0.0015(7) C28 0.0264(10) 0.0204(10) 0.0236(11) 0.0114(8) 0.0013(9) -0.0026(8) C29 0.0223(10) 0.0218(10) 0.0223(10) 0.0045(8) 0.0073(8) -0.0004(8) C30 0.0169(9) 0.0143(9) 0.0231(10) 0.0022(7) 0.0037(8) -0.0013(7) C31 0.0214(9) 0.0089(8) 0.0227(10) -0.0011(7) 0.0034(8) -0.0016(7) C32 0.0224(10) 0.0188(10) 0.0316(12) -0.0048(8) 0.0021(9) 0.0018(8) C33 0.0375(12) 0.0166(10) 0.0262(12) -0.0058(8) -0.0043(9) 0.0076(9) C34 0.0244(10) 0.0177(10) 0.0253(11) 0.0031(8) 0.0083(8) 0.0034(8) C35 0.0274(11) 0.0278(11) 0.0370(13) -0.0006(10) 0.0081(10) 0.0084(9) C36 0.0332(12) 0.0241(11) 0.0435(14) -0.0096(10) 0.0073(10) 0.0045(9) _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 N1 1.7386(16) . ? P1 N2 1.7468(16) . ? P1 B1 1.951(2) . ? N1 C2 1.420(2) . ? N1 C3 1.500(2) . ? C1 C2 1.334(3) . ? C1 N2 1.428(2) . ? C1 H1 0.9500 . ? B1 N3 1.436(2) . ? B1 N4 1.442(2) . ? N2 C7 1.498(2) . ? C2 H2 0.9500 . ? N3 C11 1.400(2) . ? N3 C13 1.436(2) . ? C3 C4 1.520(3) . ? C3 C5 1.524(3) . ? C3 C6 1.529(3) . ? N4 C12 1.401(2) . ? N4 C25 1.439(2) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.515(3) . ? C7 C9 1.526(3) . ? C7 C10 1.531(3) . ? 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 C12 1.344(2) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.397(3) . ? C13 C18 1.411(2) . ? C14 C15 1.402(3) . ? C14 C19 1.520(3) . ? C15 C16 1.384(3) . ? C15 H15 0.9500 . ? C16 C17 1.384(3) . ? C16 H16 0.9500 . ? C17 C18 1.396(3) . ? C17 H17 0.9500 . ? C18 C22 1.518(3) . ? C19 C20 1.522(3) . ? C19 C21 1.524(3) . ? C19 H19 1.0000 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 C24 1.528(3) . ? C22 C23 1.530(3) . ? C22 H22 1.0000 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 C30 1.398(3) . ? C25 C26 1.406(2) . ? C26 C27 1.394(3) . ? C26 C31 1.517(3) . ? C27 C28 1.384(3) . ? C27 H27 0.9500 . ? C28 C29 1.384(3) . ? C28 H28 0.9500 . ? C29 C30 1.394(3) . ? C29 H29 0.9500 . ? C30 C34 1.524(3) . ? C31 C33 1.528(3) . ? C31 C32 1.530(3) . ? C31 H31 1.0000 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C34 C36 1.530(3) . ? C34 C35 1.530(3) . ? C34 H34 1.0000 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 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 N1 P1 N2 95.18(8) . . ? N1 P1 B1 99.08(8) . . ? N2 P1 B1 97.79(8) . . ? C2 N1 C3 117.33(15) . . ? C2 N1 P1 105.01(12) . . ? C3 N1 P1 125.78(13) . . ? C2 C1 N2 116.00(17) . . ? C2 C1 H1 122.0 . . ? N2 C1 H1 122.0 . . ? N3 B1 N4 104.00(15) . . ? N3 B1 P1 128.05(13) . . ? N4 B1 P1 127.03(14) . . ? C1 N2 C7 117.81(15) . . ? C1 N2 P1 104.33(12) . . ? C7 N2 P1 120.93(12) . . ? C1 C2 N1 115.60(17) . . ? C1 C2 H2 122.2 . . ? N1 C2 H2 122.2 . . ? C11 N3 C13 118.96(15) . . ? C11 N3 B1 109.03(14) . . ? C13 N3 B1 131.92(15) . . ? N1 C3 C4 108.63(15) . . ? N1 C3 C5 107.78(16) . . ? C4 C3 C5 108.53(18) . . ? N1 C3 C6 112.46(16) . . ? C4 C3 C6 109.40(18) . . ? C5 C3 C6 109.95(18) . . ? C12 N4 C25 117.01(14) . . ? C12 N4 B1 108.46(14) . . ? C25 N4 B1 131.64(15) . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C3 C6 H6A 109.5 . . ? C3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N2 C7 C8 108.66(16) . . ? N2 C7 C9 112.16(16) . . ? C8 C7 C9 110.21(17) . . ? N2 C7 C10 107.89(16) . . ? C8 C7 C10 108.84(18) . . ? C9 C7 C10 109.00(17) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 N3 108.97(16) . . ? C12 C11 H11 125.5 . . ? N3 C11 H11 125.5 . . ? C11 C12 N4 109.53(15) . . ? C11 C12 H12 125.2 . . ? N4 C12 H12 125.2 . . ? C14 C13 C18 121.90(16) . . ? C14 C13 N3 119.26(15) . . ? C18 C13 N3 118.72(16) . . ? C13 C14 C15 118.26(17) . . ? C13 C14 C19 122.15(16) . . ? C15 C14 C19 119.57(17) . . ? C16 C15 C14 120.70(19) . . ? C16 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? C17 C16 C15 120.06(17) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C16 C17 C18 121.51(18) . . ? C16 C17 H17 119.2 . . ? C18 C17 H17 119.2 . . ? C17 C18 C13 117.39(18) . . ? C17 C18 C22 121.37(16) . . ? C13 C18 C22 121.16(16) . . ? C14 C19 C20 110.35(17) . . ? C14 C19 C21 111.98(17) . . ? C20 C19 C21 110.92(19) . . ? C14 C19 H19 107.8 . . ? C20 C19 H19 107.8 . . ? C21 C19 H19 107.8 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C19 C21 H21A 109.5 . . ? C19 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C19 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C18 C22 C24 110.09(16) . . ? C18 C22 C23 114.27(16) . . ? C24 C22 C23 109.67(17) . . ? C18 C22 H22 107.5 . . ? C24 C22 H22 107.5 . . ? C23 C22 H22 107.5 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C22 C24 H24A 109.5 . . ? C22 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C22 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C30 C25 C26 122.07(16) . . ? C30 C25 N4 117.67(15) . . ? C26 C25 N4 120.09(16) . . ? C27 C26 C25 117.21(17) . . ? C27 C26 C31 121.67(16) . . ? C25 C26 C31 121.09(16) . . ? C28 C27 C26 121.69(17) . . ? C28 C27 H27 119.2 . . ? C26 C27 H27 119.2 . . ? C27 C28 C29 119.99(18) . . ? C27 C28 H28 120.0 . . ? C29 C28 H28 120.0 . . ? C28 C29 C30 120.68(19) . . ? C28 C29 H29 119.7 . . ? C30 C29 H29 119.7 . . ? C29 C30 C25 118.35(17) . . ? C29 C30 C34 119.32(17) . . ? C25 C30 C34 122.32(17) . . ? C26 C31 C33 111.12(16) . . ? C26 C31 C32 113.41(16) . . ? C33 C31 C32 108.20(15) . . ? C26 C31 H31 108.0 . . ? C33 C31 H31 108.0 . . ? C32 C31 H31 108.0 . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C31 C33 H33A 109.5 . . ? C31 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C31 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C30 C34 C36 111.75(17) . . ? C30 C34 C35 110.94(16) . . ? C36 C34 C35 111.19(18) . . ? C30 C34 H34 107.6 . . ? C36 C34 H34 107.6 . . ? C35 C34 H34 107.6 . . ? C34 C35 H35A 109.5 . . ? C34 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C34 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C34 C36 H36A 109.5 . . ? C34 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C34 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 P1 N1 C2 -17.71(13) . . . . ? B1 P1 N1 C2 81.05(13) . . . . ? N2 P1 N1 C3 123.47(15) . . . . ? B1 P1 N1 C3 -137.77(15) . . . . ? N1 P1 B1 N3 51.39(18) . . . . ? N2 P1 B1 N3 147.94(17) . . . . ? N1 P1 B1 N4 -141.37(16) . . . . ? N2 P1 B1 N4 -44.82(17) . . . . ? C2 C1 N2 C7 124.75(18) . . . . ? C2 C1 N2 P1 -12.5(2) . . . . ? N1 P1 N2 C1 17.29(12) . . . . ? B1 P1 N2 C1 -82.63(12) . . . . ? N1 P1 N2 C7 -118.32(14) . . . . ? B1 P1 N2 C7 141.76(14) . . . . ? N2 C1 C2 N1 -0.6(3) . . . . ? C3 N1 C2 C1 -131.57(18) . . . . ? P1 N1 C2 C1 13.5(2) . . . . ? N4 B1 N3 C11 0.03(19) . . . . ? P1 B1 N3 C11 169.56(14) . . . . ? N4 B1 N3 C13 -176.39(17) . . . . ? P1 B1 N3 C13 -6.9(3) . . . . ? C2 N1 C3 C4 170.97(18) . . . . ? P1 N1 C3 C4 33.9(2) . . . . ? C2 N1 C3 C5 -71.6(2) . . . . ? P1 N1 C3 C5 151.34(15) . . . . ? C2 N1 C3 C6 49.7(2) . . . . ? P1 N1 C3 C6 -87.3(2) . . . . ? N3 B1 N4 C12 0.66(19) . . . . ? P1 B1 N4 C12 -169.02(14) . . . . ? N3 B1 N4 C25 160.28(17) . . . . ? P1 B1 N4 C25 -9.4(3) . . . . ? C1 N2 C7 C8 169.81(16) . . . . ? P1 N2 C7 C8 -60.22(19) . . . . ? C1 N2 C7 C9 -68.1(2) . . . . ? P1 N2 C7 C9 61.9(2) . . . . ? C1 N2 C7 C10 52.0(2) . . . . ? P1 N2 C7 C10 -178.07(14) . . . . ? C13 N3 C11 C12 176.22(16) . . . . ? B1 N3 C11 C12 -0.7(2) . . . . ? N3 C11 C12 N4 1.2(2) . . . . ? C25 N4 C12 C11 -164.17(16) . . . . ? B1 N4 C12 C11 -1.1(2) . . . . ? C11 N3 C13 C14 74.6(2) . . . . ? B1 N3 C13 C14 -109.2(2) . . . . ? C11 N3 C13 C18 -101.5(2) . . . . ? B1 N3 C13 C18 74.6(2) . . . . ? C18 C13 C14 C15 -4.0(3) . . . . ? N3 C13 C14 C15 -179.99(16) . . . . ? C18 C13 C14 C19 174.58(17) . . . . ? N3 C13 C14 C19 -1.4(3) . . . . ? C13 C14 C15 C16 0.4(3) . . . . ? C19 C14 C15 C16 -178.21(18) . . . . ? C14 C15 C16 C17 2.5(3) . . . . ? C15 C16 C17 C18 -1.9(3) . . . . ? C16 C17 C18 C13 -1.5(3) . . . . ? C16 C17 C18 C22 175.22(17) . . . . ? C14 C13 C18 C17 4.5(3) . . . . ? N3 C13 C18 C17 -179.44(16) . . . . ? C14 C13 C18 C22 -172.24(17) . . . . ? N3 C13 C18 C22 3.8(3) . . . . ? C13 C14 C19 C20 -111.9(2) . . . . ? C15 C14 C19 C20 66.6(2) . . . . ? C13 C14 C19 C21 124.0(2) . . . . ? C15 C14 C19 C21 -57.4(2) . . . . ? C17 C18 C22 C24 -95.5(2) . . . . ? C13 C18 C22 C24 81.1(2) . . . . ? C17 C18 C22 C23 28.4(3) . . . . ? C13 C18 C22 C23 -154.95(17) . . . . ? C12 N4 C25 C30 79.0(2) . . . . ? B1 N4 C25 C30 -79.3(2) . . . . ? C12 N4 C25 C26 -96.3(2) . . . . ? B1 N4 C25 C26 105.4(2) . . . . ? C30 C25 C26 C27 1.2(3) . . . . ? N4 C25 C26 C27 176.32(16) . . . . ? C30 C25 C26 C31 -176.79(17) . . . . ? N4 C25 C26 C31 -1.7(2) . . . . ? C25 C26 C27 C28 -0.4(3) . . . . ? C31 C26 C27 C28 177.65(17) . . . . ? C26 C27 C28 C29 -0.5(3) . . . . ? C27 C28 C29 C30 0.6(3) . . . . ? C28 C29 C30 C25 0.3(3) . . . . ? C28 C29 C30 C34 -178.63(18) . . . . ? C26 C25 C30 C29 -1.2(3) . . . . ? N4 C25 C30 C29 -176.41(16) . . . . ? C26 C25 C30 C34 177.67(17) . . . . ? N4 C25 C30 C34 2.5(3) . . . . ? C27 C26 C31 C33 -101.6(2) . . . . ? C25 C26 C31 C33 76.3(2) . . . . ? C27 C26 C31 C32 20.6(2) . . . . ? C25 C26 C31 C32 -161.50(16) . . . . ? C29 C30 C34 C36 -61.5(2) . . . . ? C25 C30 C34 C36 119.6(2) . . . . ? C29 C30 C34 C35 63.2(2) . . . . ? C25 C30 C34 C35 -115.7(2) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.47 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.695 _refine_diff_density_min -0.485 _refine_diff_density_rms 0.063 _database_code_depnum_ccdc_archive 'CCDC 957948' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_gud125 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-(1,3-bis(2,6-diisopropylphenyl)-1,3,2-diazaborolen-2-yl)- 1,3-bis(2,6-dimethylphenyl)-1,3,2-diazaphospholene ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C44 H56 B N4 P' _chemical_formula_sum 'C44 H56 B N4 P' _chemical_formula_weight 682.71 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 triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.4257(4) _cell_length_b 12.4802(5) _cell_length_c 13.2635(5) _cell_angle_alpha 97.682(2) _cell_angle_beta 98.396(2) _cell_angle_gamma 103.761(2) _cell_volume 1945.80(12) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.41 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.165 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7223 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_process_details 'Blessing, 1995' _exptl_special_details ; the su^s of cell-angle are correct. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator triumph _diffrn_measurement_device_type 'Bruker Kappa ApexII Duo' _diffrn_measurement_method 'omega and phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 31455 _diffrn_reflns_av_R_equivalents 0.0370 _diffrn_reflns_av_sigmaI/netI 0.0347 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 25.35 _reflns_number_total 7097 _reflns_number_gt 5587 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker ApexII Software-Suite, 2008' _computing_cell_refinement 'Bruker ApexII Software-Suite, 2008' _computing_data_reduction 'Bruker ApexII Software-Suite, 2008' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXS-plus, XP (Sheldrick, 1991)' _computing_publication_material SHELXL-97 _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^)+(0.0399P)^2^+1.0420P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7097 _refine_ls_number_parameters 455 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0565 _refine_ls_R_factor_gt 0.0389 _refine_ls_wR_factor_ref 0.0979 _refine_ls_wR_factor_gt 0.0895 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.60785(3) 0.23101(4) 0.67775(3) 0.01316(11) Uani 1 1 d . . . N2 N 0.51352(11) 0.27930(11) 0.74667(10) 0.0155(3) Uani 1 1 d . . . C3 C 0.50800(13) 0.38301(14) 0.71561(13) 0.0171(4) Uani 1 1 d . . . H3 H 0.4791 0.4361 0.7540 0.021 Uiso 1 1 calc R . . C4 C 0.54624(13) 0.40024(14) 0.62904(13) 0.0169(4) Uani 1 1 d . . . H4 H 0.5462 0.4659 0.6002 0.020 Uiso 1 1 calc R . . N5 N 0.58736(11) 0.31168(11) 0.58326(10) 0.0150(3) Uani 1 1 d . . . C6 C 0.55316(13) 0.26962(14) 0.47373(12) 0.0164(4) Uani 1 1 d . . . C7 C 0.47052(13) 0.16836(15) 0.43427(13) 0.0188(4) Uani 1 1 d . . . C8 C 0.44542(15) 0.13200(16) 0.32798(14) 0.0249(4) Uani 1 1 d . . . H8 H 0.3916 0.0624 0.3004 0.030 Uiso 1 1 calc R . . C9 C 0.49654(16) 0.19429(17) 0.26109(14) 0.0281(4) Uani 1 1 d . . . H9 H 0.4777 0.1680 0.1885 0.034 Uiso 1 1 calc R . . C10 C 0.57509(15) 0.29484(17) 0.30081(14) 0.0254(4) Uani 1 1 d . . . H10 H 0.6090 0.3387 0.2548 0.030 Uiso 1 1 calc R . . C11 C 0.60576(14) 0.33342(15) 0.40678(13) 0.0203(4) Uani 1 1 d . . . C12 C 0.69522(15) 0.44175(15) 0.44676(14) 0.0251(4) Uani 1 1 d . . . H12A H 0.7426 0.4576 0.3948 0.038 Uiso 1 1 calc R . . H12B H 0.7420 0.4354 0.5108 0.038 Uiso 1 1 calc R . . H12C H 0.6594 0.5028 0.4608 0.038 Uiso 1 1 calc R . . C13 C 0.40514(14) 0.09886(15) 0.50044(14) 0.0227(4) Uani 1 1 d . . . H13A H 0.3400 0.0436 0.4564 0.034 Uiso 1 1 calc R . . H13B H 0.3790 0.1476 0.5502 0.034 Uiso 1 1 calc R . . H13C H 0.4537 0.0601 0.5378 0.034 Uiso 1 1 calc R . . C14 C 0.41577(13) 0.20298(14) 0.76761(12) 0.0154(3) Uani 1 1 d . . . C15 C 0.43606(14) 0.12146(14) 0.82623(12) 0.0176(4) Uani 1 1 d . . . C16 C 0.34533(15) 0.04226(15) 0.84598(13) 0.0228(4) Uani 1 1 d . . . H16 H 0.3591 -0.0143 0.8836 0.027 Uiso 1 1 calc R . . C17 C 0.23612(15) 0.04487(16) 0.81178(14) 0.0242(4) Uani 1 1 d . . . H17 H 0.1748 -0.0091 0.8261 0.029 Uiso 1 1 calc R . . C18 C 0.21656(14) 0.12631(16) 0.75672(13) 0.0233(4) Uani 1 1 d . . . H18 H 0.1410 0.1285 0.7345 0.028 Uiso 1 1 calc R . . C19 C 0.30359(14) 0.20546(15) 0.73249(13) 0.0189(4) Uani 1 1 d . . . C20 C 0.26831(14) 0.28602(17) 0.66618(15) 0.0265(4) Uani 1 1 d . . . H20A H 0.1875 0.2588 0.6374 0.040 Uiso 1 1 calc R . . H20B H 0.3109 0.2908 0.6096 0.040 Uiso 1 1 calc R . . H20C H 0.2838 0.3604 0.7088 0.040 Uiso 1 1 calc R . . C21 C 0.55355(14) 0.11533(15) 0.86756(14) 0.0213(4) Uani 1 1 d . . . H21A H 0.5519 0.0745 0.9257 0.032 Uiso 1 1 calc R . . H21B H 0.6028 0.1913 0.8912 0.032 Uiso 1 1 calc R . . H21C H 0.5824 0.0762 0.8127 0.032 Uiso 1 1 calc R . . B22 B 0.75342(14) 0.32259(15) 0.75654(14) 0.0126(4) Uani 1 1 d . . . N23 N 0.85059(11) 0.27964(11) 0.75229(10) 0.0137(3) Uani 1 1 d . . . C24 C 0.94437(13) 0.35665(14) 0.81626(13) 0.0173(4) Uani 1 1 d . . . H24 H 1.0191 0.3486 0.8268 0.021 Uiso 1 1 calc R . . C25 C 0.91171(13) 0.44307(14) 0.85999(13) 0.0167(4) Uani 1 1 d . . . H25 H 0.9598 0.5059 0.9074 0.020 Uiso 1 1 calc R . . N26 N 0.79616(11) 0.42789(11) 0.82589(10) 0.0135(3) Uani 1 1 d . . . C27 C 0.75138(13) 0.51675(14) 0.86868(12) 0.0149(3) Uani 1 1 d . . . C28 C 0.75779(13) 0.61092(14) 0.82026(13) 0.0172(4) Uani 1 1 d . . . C29 C 0.72869(14) 0.70199(15) 0.87112(14) 0.0220(4) Uani 1 1 d . . . H29 H 0.7304 0.7660 0.8392 0.026 Uiso 1 1 calc R . . C30 C 0.69758(15) 0.70143(15) 0.96632(15) 0.0256(4) Uani 1 1 d . . . H30 H 0.6805 0.7655 1.0005 0.031 Uiso 1 1 calc R . . C31 C 0.69122(15) 0.60804(15) 1.01214(14) 0.0241(4) Uani 1 1 d . . . H31 H 0.6688 0.6082 1.0776 0.029 Uiso 1 1 calc R . . C32 C 0.71702(13) 0.51334(15) 0.96439(13) 0.0183(4) Uani 1 1 d . . . C33 C 0.70539(14) 0.41074(15) 1.01581(13) 0.0206(4) Uani 1 1 d . . . H33 H 0.7252 0.3513 0.9693 0.025 Uiso 1 1 calc R . . C34 C 0.58322(14) 0.36581(16) 1.02877(14) 0.0244(4) Uani 1 1 d . . . H34A H 0.5769 0.2995 1.0618 0.037 Uiso 1 1 calc R . . H34B H 0.5337 0.3455 0.9607 0.037 Uiso 1 1 calc R . . H34C H 0.5608 0.4237 1.0721 0.037 Uiso 1 1 calc R . . C35 C 0.78469(15) 0.43399(17) 1.12047(15) 0.0296(4) Uani 1 1 d . . . H35A H 0.7743 0.3655 1.1506 0.044 Uiso 1 1 calc R . . H35B H 0.7677 0.4930 1.1671 0.044 Uiso 1 1 calc R . . H35C H 0.8629 0.4584 1.1108 0.044 Uiso 1 1 calc R . . C36 C 0.79943(15) 0.61711(15) 0.71852(14) 0.0223(4) Uani 1 1 d . . . H36 H 0.7846 0.5388 0.6804 0.027 Uiso 1 1 calc R . . C37 C 0.73903(17) 0.68131(16) 0.64941(15) 0.0288(4) Uani 1 1 d . . . H37A H 0.7686 0.6823 0.5849 0.043 Uiso 1 1 calc R . . H37B H 0.7516 0.7584 0.6853 0.043 Uiso 1 1 calc R . . H37C H 0.6580 0.6445 0.6336 0.043 Uiso 1 1 calc R . . C38 C 0.92682(16) 0.67045(18) 0.73697(16) 0.0322(5) Uani 1 1 d . . . H38A H 0.9514 0.6735 0.6703 0.048 Uiso 1 1 calc R . . H38B H 0.9665 0.6254 0.7759 0.048 Uiso 1 1 calc R . . H38C H 0.9440 0.7465 0.7766 0.048 Uiso 1 1 calc R . . C39 C 0.86422(12) 0.17325(13) 0.70711(12) 0.0130(3) Uani 1 1 d . . . C40 C 0.87997(12) 0.09727(14) 0.77318(13) 0.0148(3) Uani 1 1 d . . . C41 C 0.90234(13) -0.00183(14) 0.73108(14) 0.0190(4) Uani 1 1 d . . . H41 H 0.9139 -0.0546 0.7742 0.023 Uiso 1 1 calc R . . C42 C 0.90787(14) -0.02428(15) 0.62749(14) 0.0224(4) Uani 1 1 d . . . H42 H 0.9236 -0.0920 0.6001 0.027 Uiso 1 1 calc R . . C43 C 0.89073(13) 0.05090(15) 0.56356(14) 0.0199(4) Uani 1 1 d . . . H43 H 0.8940 0.0337 0.4923 0.024 Uiso 1 1 calc R . . C44 C 0.86877(13) 0.15148(14) 0.60148(13) 0.0155(3) Uani 1 1 d . . . C45 C 0.85335(14) 0.23565(15) 0.53158(13) 0.0197(4) Uani 1 1 d . . . H45 H 0.7945 0.2709 0.5540 0.024 Uiso 1 1 calc R . . C46 C 0.81280(17) 0.18344(18) 0.41747(14) 0.0312(5) Uani 1 1 d . . . H46A H 0.8046 0.2421 0.3770 0.047 Uiso 1 1 calc R . . H46B H 0.7399 0.1282 0.4088 0.047 Uiso 1 1 calc R . . H46C H 0.8679 0.1464 0.3933 0.047 Uiso 1 1 calc R . . C47 C 0.96214(16) 0.32922(17) 0.54525(15) 0.0298(4) Uani 1 1 d . . . H47A H 0.9505 0.3826 0.4996 0.045 Uiso 1 1 calc R . . H47B H 1.0230 0.2969 0.5276 0.045 Uiso 1 1 calc R . . H47C H 0.9826 0.3680 0.6173 0.045 Uiso 1 1 calc R . . C48 C 0.87525(14) 0.12013(15) 0.88750(13) 0.0189(4) Uani 1 1 d . . . H48 H 0.8422 0.1853 0.9001 0.023 Uiso 1 1 calc R . . C49 C 0.80099(15) 0.02026(16) 0.92165(14) 0.0244(4) Uani 1 1 d . . . H49A H 0.8003 0.0385 0.9957 0.037 Uiso 1 1 calc R . . H49B H 0.8311 -0.0451 0.9088 0.037 Uiso 1 1 calc R . . H49C H 0.7240 0.0033 0.8823 0.037 Uiso 1 1 calc R . . C50 C 0.99387(15) 0.15136(17) 0.95384(15) 0.0291(4) Uani 1 1 d . . . H50A H 0.9887 0.1656 1.0272 0.044 Uiso 1 1 calc R . . H50B H 1.0398 0.2189 0.9357 0.044 Uiso 1 1 calc R . . H50C H 1.0289 0.0895 0.9410 0.044 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0113(2) 0.0140(2) 0.0132(2) 0.00080(17) 0.00164(16) 0.00283(16) N2 0.0126(7) 0.0164(8) 0.0179(7) 0.0026(6) 0.0046(5) 0.0038(6) C3 0.0149(8) 0.0154(9) 0.0205(9) 0.0007(7) 0.0019(7) 0.0048(7) C4 0.0147(8) 0.0152(9) 0.0188(9) 0.0012(7) -0.0006(7) 0.0034(7) N5 0.0161(7) 0.0144(7) 0.0137(7) 0.0019(6) 0.0008(5) 0.0042(6) C6 0.0154(8) 0.0206(9) 0.0135(8) 0.0017(7) 0.0007(6) 0.0071(7) C7 0.0143(8) 0.0225(10) 0.0194(9) 0.0011(7) 0.0004(7) 0.0074(7) C8 0.0213(9) 0.0267(10) 0.0222(10) -0.0051(8) -0.0011(7) 0.0063(8) C9 0.0310(10) 0.0382(12) 0.0131(9) -0.0008(8) 0.0005(8) 0.0102(9) C10 0.0276(10) 0.0330(11) 0.0178(9) 0.0075(8) 0.0050(7) 0.0099(8) C11 0.0194(9) 0.0234(10) 0.0186(9) 0.0040(7) 0.0019(7) 0.0073(7) C12 0.0286(10) 0.0238(10) 0.0229(10) 0.0090(8) 0.0057(8) 0.0037(8) C13 0.0175(9) 0.0233(10) 0.0218(9) -0.0020(8) 0.0013(7) -0.0006(7) C14 0.0155(8) 0.0173(9) 0.0120(8) -0.0011(7) 0.0045(6) 0.0026(7) C15 0.0189(8) 0.0192(9) 0.0133(8) -0.0010(7) 0.0038(7) 0.0039(7) C16 0.0276(10) 0.0220(10) 0.0183(9) 0.0046(8) 0.0076(7) 0.0028(8) C17 0.0209(9) 0.0257(10) 0.0216(9) 0.0019(8) 0.0085(7) -0.0037(8) C18 0.0158(8) 0.0316(11) 0.0197(9) -0.0009(8) 0.0052(7) 0.0029(8) C19 0.0166(8) 0.0245(10) 0.0145(9) -0.0007(7) 0.0037(7) 0.0048(7) C20 0.0156(9) 0.0352(11) 0.0298(10) 0.0099(9) 0.0004(7) 0.0088(8) C21 0.0232(9) 0.0221(10) 0.0204(9) 0.0057(8) 0.0033(7) 0.0085(8) B22 0.0120(8) 0.0153(10) 0.0108(9) 0.0043(7) 0.0035(7) 0.0023(7) N23 0.0133(7) 0.0132(7) 0.0139(7) 0.0010(6) 0.0020(5) 0.0030(5) C24 0.0099(8) 0.0179(9) 0.0217(9) 0.0010(7) 0.0004(6) 0.0017(7) C25 0.0128(8) 0.0157(9) 0.0182(9) -0.0003(7) -0.0004(6) 0.0011(7) N26 0.0136(7) 0.0138(7) 0.0138(7) 0.0017(6) 0.0034(5) 0.0050(5) C27 0.0103(7) 0.0140(9) 0.0175(8) -0.0033(7) 0.0004(6) 0.0026(6) C28 0.0134(8) 0.0153(9) 0.0201(9) 0.0002(7) -0.0003(7) 0.0018(7) C29 0.0204(9) 0.0142(9) 0.0298(10) 0.0011(8) 0.0017(7) 0.0048(7) C30 0.0241(9) 0.0175(10) 0.0331(11) -0.0074(8) 0.0069(8) 0.0070(8) C31 0.0234(9) 0.0249(10) 0.0229(10) -0.0031(8) 0.0093(7) 0.0054(8) C32 0.0146(8) 0.0190(9) 0.0185(9) -0.0014(7) 0.0031(7) 0.0017(7) C33 0.0219(9) 0.0209(10) 0.0184(9) 0.0005(7) 0.0077(7) 0.0037(7) C34 0.0211(9) 0.0302(11) 0.0191(9) 0.0028(8) 0.0054(7) 0.0015(8) C35 0.0217(9) 0.0339(12) 0.0304(11) 0.0072(9) 0.0008(8) 0.0035(8) C36 0.0313(10) 0.0148(9) 0.0210(9) 0.0023(7) 0.0048(8) 0.0068(8) C37 0.0387(11) 0.0173(10) 0.0260(10) 0.0059(8) -0.0014(8) 0.0023(8) C38 0.0331(11) 0.0383(12) 0.0325(11) 0.0156(9) 0.0146(9) 0.0129(9) C39 0.0072(7) 0.0130(8) 0.0175(8) -0.0003(7) 0.0016(6) 0.0023(6) C40 0.0079(7) 0.0149(9) 0.0201(9) 0.0020(7) 0.0009(6) 0.0021(6) C41 0.0148(8) 0.0142(9) 0.0297(10) 0.0062(7) 0.0054(7) 0.0050(7) C42 0.0173(8) 0.0141(9) 0.0353(11) -0.0032(8) 0.0098(8) 0.0040(7) C43 0.0160(8) 0.0206(9) 0.0214(9) -0.0026(7) 0.0080(7) 0.0021(7) C44 0.0092(7) 0.0176(9) 0.0181(9) 0.0003(7) 0.0026(6) 0.0020(6) C45 0.0189(9) 0.0280(10) 0.0158(9) 0.0048(7) 0.0066(7) 0.0103(7) C46 0.0331(11) 0.0465(13) 0.0177(10) 0.0050(9) 0.0060(8) 0.0168(10) C47 0.0294(10) 0.0334(12) 0.0298(11) 0.0153(9) 0.0090(8) 0.0068(9) C48 0.0203(9) 0.0194(9) 0.0179(9) 0.0051(7) 0.0009(7) 0.0077(7) C49 0.0243(9) 0.0282(11) 0.0232(10) 0.0114(8) 0.0037(7) 0.0080(8) C50 0.0274(10) 0.0301(11) 0.0242(10) 0.0057(8) -0.0056(8) 0.0027(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 N5 1.7365(14) . ? P1 N2 1.7534(14) . ? P1 B22 1.9533(18) . ? N2 C3 1.423(2) . ? N2 C14 1.442(2) . ? C3 C4 1.329(2) . ? C3 H3 0.9500 . ? C4 N5 1.425(2) . ? C4 H4 0.9500 . ? N5 C6 1.441(2) . ? C6 C11 1.400(2) . ? C6 C7 1.405(2) . ? C7 C8 1.387(2) . ? C7 C13 1.503(2) . ? C8 C9 1.382(3) . ? C8 H8 0.9500 . ? C9 C10 1.377(3) . ? C9 H9 0.9500 . ? C10 C11 1.389(2) . ? C10 H10 0.9500 . ? C11 C12 1.505(2) . ? 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 C15 1.407(2) . ? C14 C19 1.413(2) . ? C15 C16 1.394(2) . ? C15 C21 1.506(2) . ? C16 C17 1.376(3) . ? C16 H16 0.9500 . ? C17 C18 1.375(3) . ? C17 H17 0.9500 . ? C18 C19 1.388(2) . ? C18 H18 0.9500 . ? C19 C20 1.520(2) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? B22 N26 1.434(2) . ? B22 N23 1.438(2) . ? N23 C24 1.401(2) . ? N23 C39 1.440(2) . ? C24 C25 1.332(2) . ? C24 H24 0.9500 . ? C25 N26 1.400(2) . ? C25 H25 0.9500 . ? N26 C27 1.442(2) . ? C27 C32 1.400(2) . ? C27 C28 1.404(2) . ? C28 C29 1.393(2) . ? C28 C36 1.519(2) . ? C29 C30 1.374(3) . ? C29 H29 0.9500 . ? C30 C31 1.376(3) . ? C30 H30 0.9500 . ? C31 C32 1.393(2) . ? C31 H31 0.9500 . ? C32 C33 1.517(2) . ? C33 C35 1.529(2) . ? C33 C34 1.531(2) . ? C33 H33 1.0000 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C36 C37 1.525(2) . ? C36 C38 1.533(3) . ? C36 H36 1.0000 . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 0.9800 . ? C39 C40 1.402(2) . ? C39 C44 1.403(2) . ? C40 C41 1.394(2) . ? C40 C48 1.517(2) . ? C41 C42 1.380(3) . ? C41 H41 0.9500 . ? C42 C43 1.378(3) . ? C42 H42 0.9500 . ? C43 C44 1.392(2) . ? C43 H43 0.9500 . ? C44 C45 1.518(2) . ? C45 C46 1.525(2) . ? C45 C47 1.531(3) . ? C45 H45 1.0000 . ? C46 H46A 0.9800 . ? C46 H46B 0.9800 . ? C46 H46C 0.9800 . ? C47 H47A 0.9800 . ? C47 H47B 0.9800 . ? C47 H47C 0.9800 . ? C48 C49 1.528(2) . ? C48 C50 1.535(2) . ? C48 H48 1.0000 . ? C49 H49A 0.9800 . ? C49 H49B 0.9800 . ? C49 H49C 0.9800 . ? C50 H50A 0.9800 . ? C50 H50B 0.9800 . ? C50 H50C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N5 P1 N2 92.37(7) . . ? N5 P1 B22 99.55(7) . . ? N2 P1 B22 101.85(7) . . ? C3 N2 C14 121.63(13) . . ? C3 N2 P1 105.53(10) . . ? C14 N2 P1 121.37(11) . . ? C4 C3 N2 115.12(15) . . ? C4 C3 H3 122.4 . . ? N2 C3 H3 122.4 . . ? C3 C4 N5 114.21(15) . . ? C3 C4 H4 122.9 . . ? N5 C4 H4 122.9 . . ? C4 N5 C6 119.48(13) . . ? C4 N5 P1 106.51(11) . . ? C6 N5 P1 125.31(11) . . ? C11 C6 C7 120.52(15) . . ? C11 C6 N5 117.52(15) . . ? C7 C6 N5 121.96(15) . . ? C8 C7 C6 118.23(16) . . ? C8 C7 C13 118.03(16) . . ? C6 C7 C13 123.71(15) . . ? C9 C8 C7 121.77(17) . . ? C9 C8 H8 119.1 . . ? C7 C8 H8 119.1 . . ? C10 C9 C8 119.26(17) . . ? C10 C9 H9 120.4 . . ? C8 C9 H9 120.4 . . ? C9 C10 C11 121.25(17) . . ? C9 C10 H10 119.4 . . ? C11 C10 H10 119.4 . . ? C10 C11 C6 118.91(16) . . ? C10 C11 C12 119.34(16) . . ? C6 C11 C12 121.74(15) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C7 C13 H13A 109.5 . . ? C7 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C7 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C15 C14 C19 119.40(15) . . ? C15 C14 N2 116.54(14) . . ? C19 C14 N2 124.06(15) . . ? C16 C15 C14 119.59(15) . . ? C16 C15 C21 118.28(16) . . ? C14 C15 C21 122.12(15) . . ? C17 C16 C15 120.90(17) . . ? C17 C16 H16 119.6 . . ? C15 C16 H16 119.6 . . ? C18 C17 C16 119.39(16) . . ? C18 C17 H17 120.3 . . ? C16 C17 H17 120.3 . . ? C17 C18 C19 122.15(16) . . ? C17 C18 H18 118.9 . . ? C19 C18 H18 118.9 . . ? C18 C19 C14 118.53(16) . . ? C18 C19 C20 115.97(15) . . ? C14 C19 C20 125.47(15) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C15 C21 H21A 109.5 . . ? C15 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C15 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N26 B22 N23 104.22(13) . . ? N26 B22 P1 137.51(13) . . ? N23 B22 P1 118.24(12) . . ? C24 N23 B22 108.66(13) . . ? C24 N23 C39 118.07(13) . . ? B22 N23 C39 132.78(13) . . ? C25 C24 N23 108.90(14) . . ? C25 C24 H24 125.5 . . ? N23 C24 H24 125.5 . . ? C24 C25 N26 110.10(14) . . ? C24 C25 H25 124.9 . . ? N26 C25 H25 124.9 . . ? C25 N26 B22 108.10(13) . . ? C25 N26 C27 114.89(13) . . ? B22 N26 C27 136.99(13) . . ? C32 C27 C28 121.84(15) . . ? C32 C27 N26 118.76(15) . . ? C28 C27 N26 118.83(14) . . ? C29 C28 C27 117.50(16) . . ? C29 C28 C36 120.29(16) . . ? C27 C28 C36 122.16(15) . . ? C30 C29 C28 121.54(17) . . ? C30 C29 H29 119.2 . . ? C28 C29 H29 119.2 . . ? C29 C30 C31 119.99(17) . . ? C29 C30 H30 120.0 . . ? C31 C30 H30 120.0 . . ? C30 C31 C32 121.29(17) . . ? C30 C31 H31 119.4 . . ? C32 C31 H31 119.4 . . ? C31 C32 C27 117.79(16) . . ? C31 C32 C33 119.69(15) . . ? C27 C32 C33 122.51(15) . . ? C32 C33 C35 112.43(15) . . ? C32 C33 C34 110.36(14) . . ? C35 C33 C34 110.06(14) . . ? C32 C33 H33 107.9 . . ? C35 C33 H33 107.9 . . ? C34 C33 H33 107.9 . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C33 C35 H35A 109.5 . . ? C33 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C33 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C28 C36 C37 112.89(15) . . ? C28 C36 C38 111.15(14) . . ? C37 C36 C38 109.17(15) . . ? C28 C36 H36 107.8 . . ? C37 C36 H36 107.8 . . ? C38 C36 H36 107.8 . . ? C36 C37 H37A 109.5 . . ? C36 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C36 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C36 C38 H38A 109.5 . . ? C36 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C36 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C40 C39 C44 122.15(15) . . ? C40 C39 N23 117.81(14) . . ? C44 C39 N23 119.91(14) . . ? C41 C40 C39 117.84(15) . . ? C41 C40 C48 119.65(15) . . ? C39 C40 C48 122.50(15) . . ? C42 C41 C40 120.80(16) . . ? C42 C41 H41 119.6 . . ? C40 C41 H41 119.6 . . ? C43 C42 C41 120.46(16) . . ? C43 C42 H42 119.8 . . ? C41 C42 H42 119.8 . . ? C42 C43 C44 121.24(16) . . ? C42 C43 H43 119.4 . . ? C44 C43 H43 119.4 . . ? C43 C44 C39 117.51(15) . . ? C43 C44 C45 121.12(15) . . ? C39 C44 C45 121.35(15) . . ? C44 C45 C46 113.76(15) . . ? C44 C45 C47 110.72(14) . . ? C46 C45 C47 110.10(15) . . ? C44 C45 H45 107.3 . . ? C46 C45 H45 107.3 . . ? C47 C45 H45 107.3 . . ? C45 C46 H46A 109.5 . . ? C45 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? C45 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? C45 C47 H47A 109.5 . . ? C45 C47 H47B 109.5 . . ? H47A C47 H47B 109.5 . . ? C45 C47 H47C 109.5 . . ? H47A C47 H47C 109.5 . . ? H47B C47 H47C 109.5 . . ? C40 C48 C49 112.14(14) . . ? C40 C48 C50 110.96(14) . . ? C49 C48 C50 109.44(14) . . ? C40 C48 H48 108.1 . . ? C49 C48 H48 108.1 . . ? C50 C48 H48 108.1 . . ? C48 C49 H49A 109.5 . . ? C48 C49 H49B 109.5 . . ? H49A C49 H49B 109.5 . . ? C48 C49 H49C 109.5 . . ? H49A C49 H49C 109.5 . . ? H49B C49 H49C 109.5 . . ? C48 C50 H50A 109.5 . . ? C48 C50 H50B 109.5 . . ? H50A C50 H50B 109.5 . . ? C48 C50 H50C 109.5 . . ? H50A C50 H50C 109.5 . . ? H50B C50 H50C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N5 P1 N2 C3 -22.18(11) . . . . ? B22 P1 N2 C3 78.09(11) . . . . ? N5 P1 N2 C14 121.62(12) . . . . ? B22 P1 N2 C14 -138.11(12) . . . . ? C14 N2 C3 C4 -126.63(16) . . . . ? P1 N2 C3 C4 17.05(16) . . . . ? N2 C3 C4 N5 -0.7(2) . . . . ? C3 C4 N5 C6 133.07(15) . . . . ? C3 C4 N5 P1 -16.27(16) . . . . ? N2 P1 N5 C4 22.03(11) . . . . ? B22 P1 N5 C4 -80.41(11) . . . . ? N2 P1 N5 C6 -125.01(13) . . . . ? B22 P1 N5 C6 132.55(13) . . . . ? C4 N5 C6 C11 77.72(19) . . . . ? P1 N5 C6 C11 -139.09(14) . . . . ? C4 N5 C6 C7 -102.50(19) . . . . ? P1 N5 C6 C7 40.7(2) . . . . ? C11 C6 C7 C8 2.0(2) . . . . ? N5 C6 C7 C8 -177.77(15) . . . . ? C11 C6 C7 C13 -176.03(16) . . . . ? N5 C6 C7 C13 4.2(3) . . . . ? C6 C7 C8 C9 -2.2(3) . . . . ? C13 C7 C8 C9 175.98(17) . . . . ? C7 C8 C9 C10 0.4(3) . . . . ? C8 C9 C10 C11 1.6(3) . . . . ? C9 C10 C11 C6 -1.7(3) . . . . ? C9 C10 C11 C12 177.70(17) . . . . ? C7 C6 C11 C10 -0.1(3) . . . . ? N5 C6 C11 C10 179.65(15) . . . . ? C7 C6 C11 C12 -179.50(16) . . . . ? N5 C6 C11 C12 0.3(2) . . . . ? C3 N2 C14 C15 -161.53(15) . . . . ? P1 N2 C14 C15 60.41(18) . . . . ? C3 N2 C14 C19 18.9(2) . . . . ? P1 N2 C14 C19 -119.13(16) . . . . ? C19 C14 C15 C16 2.0(2) . . . . ? N2 C14 C15 C16 -177.54(14) . . . . ? C19 C14 C15 C21 -178.96(15) . . . . ? N2 C14 C15 C21 1.5(2) . . . . ? C14 C15 C16 C17 -2.1(3) . . . . ? C21 C15 C16 C17 178.84(16) . . . . ? C15 C16 C17 C18 0.5(3) . . . . ? C16 C17 C18 C19 1.2(3) . . . . ? C17 C18 C19 C14 -1.3(3) . . . . ? C17 C18 C19 C20 176.75(17) . . . . ? C15 C14 C19 C18 -0.4(2) . . . . ? N2 C14 C19 C18 179.15(15) . . . . ? C15 C14 C19 C20 -178.19(16) . . . . ? N2 C14 C19 C20 1.3(3) . . . . ? N5 P1 B22 N26 71.74(19) . . . . ? N2 P1 B22 N26 -22.7(2) . . . . ? N5 P1 B22 N23 -110.66(13) . . . . ? N2 P1 B22 N23 154.86(12) . . . . ? N26 B22 N23 C24 0.07(17) . . . . ? P1 B22 N23 C24 -178.26(12) . . . . ? N26 B22 N23 C39 171.71(15) . . . . ? P1 B22 N23 C39 -6.6(2) . . . . ? B22 N23 C24 C25 0.50(19) . . . . ? C39 N23 C24 C25 -172.55(14) . . . . ? N23 C24 C25 N26 -0.9(2) . . . . ? C24 C25 N26 B22 0.94(19) . . . . ? C24 C25 N26 C27 179.87(14) . . . . ? N23 B22 N26 C25 -0.59(17) . . . . ? P1 B22 N26 C25 177.23(15) . . . . ? N23 B22 N26 C27 -179.16(17) . . . . ? P1 B22 N26 C27 -1.3(3) . . . . ? C25 N26 C27 C32 -85.72(18) . . . . ? B22 N26 C27 C32 92.8(2) . . . . ? C25 N26 C27 C28 85.78(18) . . . . ? B22 N26 C27 C28 -95.7(2) . . . . ? C32 C27 C28 C29 0.1(2) . . . . ? N26 C27 C28 C29 -171.14(14) . . . . ? C32 C27 C28 C36 177.51(15) . . . . ? N26 C27 C28 C36 6.3(2) . . . . ? C27 C28 C29 C30 1.6(2) . . . . ? C36 C28 C29 C30 -175.84(16) . . . . ? C28 C29 C30 C31 -2.1(3) . . . . ? C29 C30 C31 C32 0.7(3) . . . . ? C30 C31 C32 C27 0.9(3) . . . . ? C30 C31 C32 C33 -178.05(16) . . . . ? C28 C27 C32 C31 -1.3(2) . . . . ? N26 C27 C32 C31 169.90(14) . . . . ? C28 C27 C32 C33 177.63(15) . . . . ? N26 C27 C32 C33 -11.1(2) . . . . ? C31 C32 C33 C35 -62.7(2) . . . . ? C27 C32 C33 C35 118.33(18) . . . . ? C31 C32 C33 C34 60.6(2) . . . . ? C27 C32 C33 C34 -118.36(17) . . . . ? C29 C28 C36 C37 -37.3(2) . . . . ? C27 C28 C36 C37 145.37(16) . . . . ? C29 C28 C36 C38 85.77(19) . . . . ? C27 C28 C36 C38 -91.59(19) . . . . ? C24 N23 C39 C40 69.73(19) . . . . ? B22 N23 C39 C40 -101.30(19) . . . . ? C24 N23 C39 C44 -106.16(17) . . . . ? B22 N23 C39 C44 82.8(2) . . . . ? C44 C39 C40 C41 0.9(2) . . . . ? N23 C39 C40 C41 -174.87(13) . . . . ? C44 C39 C40 C48 179.97(14) . . . . ? N23 C39 C40 C48 4.2(2) . . . . ? C39 C40 C41 C42 -0.5(2) . . . . ? C48 C40 C41 C42 -179.54(15) . . . . ? C40 C41 C42 C43 -0.3(2) . . . . ? C41 C42 C43 C44 0.7(2) . . . . ? C42 C43 C44 C39 -0.3(2) . . . . ? C42 C43 C44 C45 178.17(15) . . . . ? C40 C39 C44 C43 -0.6(2) . . . . ? N23 C39 C44 C43 175.15(13) . . . . ? C40 C39 C44 C45 -179.01(14) . . . . ? N23 C39 C44 C45 -3.3(2) . . . . ? C43 C44 C45 C46 25.5(2) . . . . ? C39 C44 C45 C46 -156.07(15) . . . . ? C43 C44 C45 C47 -99.09(18) . . . . ? C39 C44 C45 C47 79.31(19) . . . . ? C41 C40 C48 C49 -48.8(2) . . . . ? C39 C40 C48 C49 132.12(16) . . . . ? C41 C40 C48 C50 73.89(19) . . . . ? C39 C40 C48 C50 -105.15(17) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.316 _refine_diff_density_min -0.369 _refine_diff_density_rms 0.045 _database_code_depnum_ccdc_archive 'CCDC 957949' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_gud140 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,3-bis(2,6-diisopropylphenyl)-2-(phenylphosphanyl)-1,3,2-diazaborolene ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C32 H42 B N2 P' _chemical_formula_sum 'C32 H42 B N2 P' _chemical_formula_weight 496.46 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 orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 12.0947(13) _cell_length_b 13.6131(12) _cell_length_c 17.9876(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2961.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.113 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 0.115 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7129 _exptl_absorpt_correction_T_max 0.7451 _exptl_absorpt_process_details 'Blessing, 1995' _exptl_special_details ; Disorder of an isopropylgroup, (CH3)28-(CH)27-(CH3)29. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator triumph _diffrn_measurement_device_type 'Bruker Kappa ApexII Duo' _diffrn_measurement_method 'omega and phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20575 _diffrn_reflns_av_R_equivalents 0.0604 _diffrn_reflns_av_sigmaI/netI 0.0736 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 25.35 _reflns_number_total 5423 _reflns_number_gt 4111 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker ApexII Software-Suite, 2008' _computing_cell_refinement 'Bruker ApexII Software-Suite, 2008' _computing_data_reduction 'Bruker ApexII Software-Suite, 2008' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXS-plus, XP (Sheldrick, 1991)' _computing_publication_material SHELXL-97 _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^)+(0.0361P)^2^+0.3887P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.06(11) _refine_ls_number_reflns 5423 _refine_ls_number_parameters 327 _refine_ls_number_restraints 13 _refine_ls_R_factor_all 0.0770 _refine_ls_R_factor_gt 0.0462 _refine_ls_wR_factor_ref 0.0910 _refine_ls_wR_factor_gt 0.0815 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.72885(6) 0.72160(5) 0.63585(4) 0.02445(18) Uani 1 1 d . . . H1 H 0.680(2) 0.7813(19) 0.6849(13) 0.037 Uiso 1 1 d . . . B1 B 0.8134(3) 0.6522(2) 0.71023(15) 0.0171(7) Uani 1 1 d . . . N2 N 0.77869(18) 0.63066(13) 0.78423(10) 0.0163(5) Uani 1 1 d . . . C3 C 0.8570(2) 0.56821(18) 0.81628(14) 0.0196(6) Uani 1 1 d . . . H3 H 0.8538 0.5428 0.8654 0.024 Uiso 1 1 calc R . . C4 C 0.9370(2) 0.54979(19) 0.76712(13) 0.0206(6) Uani 1 1 d . . . H4 H 0.9997 0.5094 0.7758 0.025 Uiso 1 1 calc R . . N5 N 0.91367(18) 0.59963(14) 0.70057(10) 0.0161(5) Uani 1 1 d . . . C6 C 0.9764(2) 0.58610(17) 0.63396(14) 0.0181(6) Uani 1 1 d . . . C7 C 1.0741(2) 0.63831(17) 0.62340(14) 0.0206(6) Uani 1 1 d . . . C8 C 1.1291(2) 0.6271(2) 0.55599(14) 0.0266(7) Uani 1 1 d . . . H8 H 1.1959 0.6620 0.5474 0.032 Uiso 1 1 calc R . . C9 C 1.0877(2) 0.56598(19) 0.50162(15) 0.0274(7) Uani 1 1 d . . . H9 H 1.1253 0.5604 0.4554 0.033 Uiso 1 1 calc R . . C10 C 0.9932(2) 0.51333(19) 0.51349(14) 0.0248(7) Uani 1 1 d . . . H10 H 0.9669 0.4706 0.4757 0.030 Uiso 1 1 calc R . . C11 C 0.9346(2) 0.52107(18) 0.58005(14) 0.0188(6) Uani 1 1 d . . . C12 C 0.8340(2) 0.45796(19) 0.59384(14) 0.0253(7) Uani 1 1 d . . . H12 H 0.7942 0.4855 0.6379 0.030 Uiso 1 1 calc R . . C13 C 0.7536(3) 0.4577(2) 0.52855(16) 0.0394(8) Uani 1 1 d . . . H13A H 0.6897 0.4163 0.5406 0.059 Uiso 1 1 calc R . . H13B H 0.7907 0.4316 0.4843 0.059 Uiso 1 1 calc R . . H13C H 0.7286 0.5249 0.5187 0.059 Uiso 1 1 calc R . . C14 C 0.8693(3) 0.3528(2) 0.61312(17) 0.0416(8) Uani 1 1 d . . . H14A H 0.8035 0.3125 0.6222 0.062 Uiso 1 1 calc R . . H14B H 0.9155 0.3536 0.6579 0.062 Uiso 1 1 calc R . . H14C H 0.9115 0.3250 0.5716 0.062 Uiso 1 1 calc R . . C15 C 1.1211(2) 0.70588(19) 0.68320(15) 0.0267(7) Uani 1 1 d . . . H15 H 1.0629 0.7153 0.7220 0.032 Uiso 1 1 calc R . . C16 C 1.1523(3) 0.8067(2) 0.65316(18) 0.0440(9) Uani 1 1 d . . . H16A H 1.1807 0.8475 0.6938 0.066 Uiso 1 1 calc R . . H16B H 1.0868 0.8380 0.6315 0.066 Uiso 1 1 calc R . . H16C H 1.2093 0.7995 0.6149 0.066 Uiso 1 1 calc R . . C17 C 1.2211(3) 0.6586(2) 0.72042(17) 0.0425(8) Uani 1 1 d . . . H17A H 1.2491 0.7022 0.7594 0.064 Uiso 1 1 calc R . . H17B H 1.2790 0.6475 0.6833 0.064 Uiso 1 1 calc R . . H17C H 1.1993 0.5957 0.7425 0.064 Uiso 1 1 calc R . . C18 C 0.6768(2) 0.65636(18) 0.81951(13) 0.0168(6) Uani 1 1 d . . . C19 C 0.6721(2) 0.73960(17) 0.86480(14) 0.0197(6) Uani 1 1 d D A . C20 C 0.5702(3) 0.7660(2) 0.89421(13) 0.0265(7) Uani 1 1 d . . . H20 H 0.5650 0.8224 0.9251 0.032 Uiso 1 1 calc R . . C21 C 0.4766(2) 0.7119(2) 0.87941(14) 0.0277(7) Uani 1 1 d . . . H21 H 0.4071 0.7325 0.8986 0.033 Uiso 1 1 calc R . . C22 C 0.4833(2) 0.6280(2) 0.83674(14) 0.0258(7) Uani 1 1 d . . . H22 H 0.4184 0.5905 0.8276 0.031 Uiso 1 1 calc R . . C23 C 0.5834(2) 0.59737(18) 0.80689(13) 0.0198(6) Uani 1 1 d . . . C24 C 0.5893(2) 0.50292(18) 0.76177(14) 0.0246(7) Uani 1 1 d . . . H24 H 0.6690 0.4901 0.7508 0.029 Uiso 1 1 calc R . . C25 C 0.5457(3) 0.41493(19) 0.80470(16) 0.0386(8) Uani 1 1 d . . . H25A H 0.5521 0.3558 0.7739 0.058 Uiso 1 1 calc R . . H25B H 0.4679 0.4258 0.8175 0.058 Uiso 1 1 calc R . . H25C H 0.5889 0.4064 0.8503 0.058 Uiso 1 1 calc R . . C26 C 0.5299(3) 0.5132(2) 0.68772(16) 0.0413(8) Uani 1 1 d . . . H26A H 0.5359 0.4516 0.6599 0.062 Uiso 1 1 calc R . . H26B H 0.5638 0.5665 0.6590 0.062 Uiso 1 1 calc R . . H26C H 0.4518 0.5283 0.6965 0.062 Uiso 1 1 calc R . . C27 C 0.7744(3) 0.79923(18) 0.88173(14) 0.0304(7) Uani 1 1 d D . . H27 H 0.8339 0.7688 0.8507 0.037 Uiso 0.470(11) 1 calc PR A 1 H27' H 0.8391 0.7539 0.8772 0.037 Uiso 0.530(11) 1 calc PR A 2 C28 C 0.7621(6) 0.9069(4) 0.8504(4) 0.0264(18) Uiso 0.470(11) 1 d PD A 1 H28A H 0.7521 0.9043 0.7964 0.040 Uiso 0.470(11) 1 calc PR A 1 H28B H 0.8287 0.9447 0.8622 0.040 Uiso 0.470(11) 1 calc PR A 1 H28C H 0.6976 0.9384 0.8732 0.040 Uiso 0.470(11) 1 calc PR A 1 C29 C 0.8185(7) 0.7982(6) 0.9574(3) 0.038(2) Uiso 0.470(11) 1 d PD A 1 H29A H 0.8861 0.8378 0.9594 0.058 Uiso 0.470(11) 1 calc PR A 1 H29B H 0.8354 0.7305 0.9719 0.058 Uiso 0.470(11) 1 calc PR A 1 H29C H 0.7636 0.8257 0.9916 0.058 Uiso 0.470(11) 1 calc PR A 1 C28' C 0.7945(6) 0.8811(5) 0.8319(3) 0.0358(19) Uiso 0.530(11) 1 d PD A 2 H28D H 0.8623 0.9152 0.8469 0.054 Uiso 0.530(11) 1 calc PR A 2 H28E H 0.7320 0.9268 0.8341 0.054 Uiso 0.530(11) 1 calc PR A 2 H28F H 0.8027 0.8566 0.7810 0.054 Uiso 0.530(11) 1 calc PR A 2 C29' C 0.7687(7) 0.8333(5) 0.9657(2) 0.0320(19) Uiso 0.530(11) 1 d PD A 2 H29D H 0.7541 0.7763 0.9975 0.048 Uiso 0.530(11) 1 calc PR A 2 H29E H 0.7092 0.8815 0.9717 0.048 Uiso 0.530(11) 1 calc PR A 2 H29F H 0.8393 0.8632 0.9799 0.048 Uiso 0.530(11) 1 calc PR A 2 C30 C 0.8245(2) 0.81061(19) 0.59402(14) 0.0239(7) Uani 1 1 d . . . C31 C 0.8299(2) 0.9080(2) 0.61701(15) 0.0304(7) Uani 1 1 d . . . H31 H 0.7894 0.9283 0.6596 0.037 Uiso 1 1 calc R . . C32 C 0.8938(3) 0.9759(2) 0.57853(18) 0.0429(9) Uani 1 1 d . . . H32 H 0.8952 1.0426 0.5939 0.051 Uiso 1 1 calc R . . C33 C 0.9549(3) 0.9463(3) 0.51817(19) 0.0478(10) Uani 1 1 d . . . H33 H 0.9988 0.9926 0.4919 0.057 Uiso 1 1 calc R . . C34 C 0.9525(3) 0.8493(3) 0.49553(18) 0.0446(9) Uani 1 1 d . . . H34 H 0.9959 0.8287 0.4543 0.054 Uiso 1 1 calc R . . C35 C 0.8873(2) 0.7824(2) 0.53274(14) 0.0319(7) Uani 1 1 d . . . H35 H 0.8851 0.7161 0.5163 0.038 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0180(4) 0.0296(4) 0.0258(4) 0.0065(3) -0.0018(3) 0.0004(3) B1 0.0158(18) 0.0145(15) 0.0211(16) -0.0037(13) -0.0016(13) -0.0014(13) N2 0.0154(12) 0.0169(11) 0.0167(10) 0.0013(9) -0.0007(10) 0.0012(10) C3 0.0219(16) 0.0166(13) 0.0203(14) 0.0047(11) -0.0012(12) 0.0007(12) C4 0.0196(17) 0.0220(14) 0.0203(14) 0.0011(11) -0.0039(13) 0.0035(12) N5 0.0151(13) 0.0188(11) 0.0145(11) -0.0001(9) 0.0010(9) -0.0002(10) C6 0.0162(15) 0.0180(13) 0.0202(13) 0.0007(11) 0.0023(13) 0.0046(11) C7 0.0154(15) 0.0157(13) 0.0306(15) 0.0015(12) 0.0004(13) 0.0029(12) C8 0.0198(17) 0.0246(15) 0.0355(16) 0.0034(13) 0.0080(14) 0.0013(13) C9 0.0276(19) 0.0300(16) 0.0245(15) 0.0055(13) 0.0095(14) 0.0064(14) C10 0.0269(18) 0.0273(15) 0.0202(14) -0.0051(12) 0.0021(13) 0.0054(15) C11 0.0174(16) 0.0188(13) 0.0202(14) 0.0003(11) 0.0007(12) 0.0048(12) C12 0.0259(17) 0.0279(15) 0.0223(14) -0.0084(12) 0.0015(13) -0.0037(14) C13 0.027(2) 0.0452(19) 0.0458(18) -0.0064(14) -0.0060(15) -0.0030(16) C14 0.041(2) 0.0351(17) 0.049(2) 0.0059(15) -0.0068(16) -0.0143(17) C15 0.0208(17) 0.0221(15) 0.0371(16) -0.0061(13) 0.0005(14) -0.0017(13) C16 0.047(2) 0.0227(16) 0.062(2) 0.0008(15) -0.0137(18) -0.0064(15) C17 0.044(2) 0.0292(16) 0.0540(19) -0.0049(14) -0.0193(18) 0.0014(17) C18 0.0188(15) 0.0170(13) 0.0145(13) 0.0058(11) 0.0027(12) 0.0037(12) C19 0.0211(16) 0.0175(13) 0.0205(13) 0.0022(11) 0.0006(13) 0.0035(12) C20 0.036(2) 0.0230(14) 0.0202(14) -0.0005(12) 0.0025(13) 0.0093(15) C21 0.0209(16) 0.0314(16) 0.0308(16) 0.0122(14) 0.0090(13) 0.0105(15) C22 0.0189(17) 0.0274(15) 0.0310(15) 0.0091(12) -0.0007(13) -0.0011(14) C23 0.0199(16) 0.0211(14) 0.0184(13) 0.0063(11) 0.0002(12) 0.0010(13) C24 0.0195(17) 0.0296(15) 0.0245(15) -0.0018(12) 0.0002(12) -0.0061(14) C25 0.047(2) 0.0260(16) 0.0426(18) -0.0012(14) 0.0081(16) -0.0043(15) C26 0.048(2) 0.0379(18) 0.0385(18) -0.0028(15) -0.0085(17) -0.0123(17) C27 0.0255(16) 0.0233(15) 0.0425(17) -0.0115(12) -0.0030(15) 0.0024(14) C30 0.0203(17) 0.0287(16) 0.0227(15) 0.0105(12) -0.0066(13) -0.0001(13) C31 0.0298(18) 0.0363(17) 0.0252(15) 0.0085(13) -0.0105(13) -0.0023(15) C32 0.041(2) 0.0363(18) 0.051(2) 0.0166(17) -0.0202(18) -0.0097(17) C33 0.027(2) 0.061(2) 0.055(2) 0.0349(19) -0.0060(18) -0.0084(18) C34 0.032(2) 0.062(2) 0.0393(19) 0.0248(18) 0.0064(16) 0.0089(18) C35 0.0260(18) 0.0404(17) 0.0294(16) 0.0142(14) -0.0004(14) 0.0082(16) _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 C30 1.836(3) . ? P1 B1 1.931(3) . ? P1 H1 1.34(3) . ? B1 N5 1.418(4) . ? B1 N2 1.426(3) . ? N2 C3 1.397(3) . ? N2 C18 1.430(3) . ? C3 C4 1.334(4) . ? C3 H3 0.9500 . ? C4 N5 1.405(3) . ? C4 H4 0.9500 . ? N5 C6 1.430(3) . ? C6 C7 1.392(3) . ? C6 C11 1.407(3) . ? C7 C8 1.391(4) . ? C7 C15 1.526(4) . ? C8 C9 1.378(4) . ? C8 H8 0.9500 . ? C9 C10 1.365(4) . ? C9 H9 0.9500 . ? C10 C11 1.395(4) . ? C10 H10 0.9500 . ? C11 C12 1.511(4) . ? C12 C13 1.525(4) . ? C12 C14 1.534(4) . ? C12 H12 1.0000 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.523(4) . ? C15 C17 1.524(4) . ? C15 H15 1.0000 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C19 1.397(3) . ? C18 C23 1.404(4) . ? C19 C20 1.389(4) . ? C19 C27 1.511(4) . ? C20 C21 1.377(4) . ? C20 H20 0.9500 . ? C21 C22 1.379(4) . ? C21 H21 0.9500 . ? C22 C23 1.388(4) . ? C22 H22 0.9500 . ? C23 C24 1.522(4) . ? C24 C26 1.519(4) . ? C24 C25 1.520(4) . ? C24 H24 1.0000 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 C28' 1.451(5) . ? C27 C29 1.462(5) . ? C27 C28 1.577(5) . ? C27 C29' 1.582(5) . ? C27 H27 1.0000 . ? C27 H27' 1.0000 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C28' H28D 0.9800 . ? C28' H28E 0.9800 . ? C28' H28F 0.9800 . ? C29' H29D 0.9800 . ? C29' H29E 0.9800 . ? C29' H29F 0.9800 . ? C30 C31 1.390(4) . ? C30 C35 1.392(4) . ? C31 C32 1.390(4) . ? C31 H31 0.9500 . ? C32 C33 1.374(5) . ? C32 H32 0.9500 . ? C33 C34 1.382(5) . ? C33 H33 0.9500 . ? C34 C35 1.378(4) . ? C34 H34 0.9500 . ? C35 H35 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 C30 P1 B1 105.84(12) . . ? C30 P1 H1 98.6(11) . . ? B1 P1 H1 94.4(11) . . ? N5 B1 N2 105.2(2) . . ? N5 B1 P1 127.9(2) . . ? N2 B1 P1 126.2(2) . . ? C3 N2 B1 108.1(2) . . ? C3 N2 C18 123.4(2) . . ? B1 N2 C18 128.2(2) . . ? C4 C3 N2 109.4(2) . . ? C4 C3 H3 125.3 . . ? N2 C3 H3 125.3 . . ? C3 C4 N5 109.2(2) . . ? C3 C4 H4 125.4 . . ? N5 C4 H4 125.4 . . ? C4 N5 B1 108.1(2) . . ? C4 N5 C6 123.1(2) . . ? B1 N5 C6 128.4(2) . . ? C7 C6 C11 122.1(2) . . ? C7 C6 N5 119.9(2) . . ? C11 C6 N5 117.9(2) . . ? C8 C7 C6 118.0(2) . . ? C8 C7 C15 120.1(2) . . ? C6 C7 C15 121.9(2) . . ? C9 C8 C7 120.7(3) . . ? C9 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? C10 C9 C8 120.6(3) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C9 C10 C11 121.3(3) . . ? C9 C10 H10 119.3 . . ? C11 C10 H10 119.3 . . ? C10 C11 C6 117.2(2) . . ? C10 C11 C12 120.5(2) . . ? C6 C11 C12 122.3(2) . . ? C11 C12 C13 112.9(2) . . ? C11 C12 C14 110.1(2) . . ? C13 C12 C14 110.4(2) . . ? C11 C12 H12 107.7 . . ? C13 C12 H12 107.7 . . ? C14 C12 H12 107.7 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 C17 109.9(2) . . ? C16 C15 C7 112.7(2) . . ? C17 C15 C7 110.5(2) . . ? C16 C15 H15 107.8 . . ? C17 C15 H15 107.8 . . ? C7 C15 H15 107.8 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C19 C18 C23 121.7(2) . . ? C19 C18 N2 119.5(2) . . ? C23 C18 N2 118.8(2) . . ? C20 C19 C18 117.9(2) . . ? C20 C19 C27 120.8(2) . . ? C18 C19 C27 121.3(2) . . ? C21 C20 C19 121.2(2) . . ? C21 C20 H20 119.4 . . ? C19 C20 H20 119.4 . . ? C20 C21 C22 120.1(3) . . ? C20 C21 H21 119.9 . . ? C22 C21 H21 119.9 . . ? C21 C22 C23 121.0(3) . . ? C21 C22 H22 119.5 . . ? C23 C22 H22 119.5 . . ? C22 C23 C18 117.9(2) . . ? C22 C23 C24 120.0(2) . . ? C18 C23 C24 122.1(2) . . ? C26 C24 C25 110.7(2) . . ? C26 C24 C23 111.6(2) . . ? C25 C24 C23 112.3(2) . . ? C26 C24 H24 107.3 . . ? C25 C24 H24 107.3 . . ? C23 C24 H24 107.3 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C24 C26 H26A 109.5 . . ? C24 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C24 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C28' C27 C29 121.5(4) . . ? C28' C27 C19 115.2(3) . . ? C29 C27 C19 118.8(3) . . ? C28' C27 C28 23.3(3) . . ? C29 C27 C28 112.1(4) . . ? C19 C27 C28 110.5(3) . . ? C28' C27 C29' 111.8(4) . . ? C29 C27 C29' 29.5(3) . . ? C19 C27 C29' 108.3(3) . . ? C28 C27 C29' 93.7(3) . . ? C28' C27 H27 81.5 . . ? C29 C27 H27 104.7 . . ? C19 C27 H27 104.7 . . ? C28 C27 H27 104.7 . . ? C29' C27 H27 133.3 . . ? C28' C27 H27' 107.0 . . ? C29 C27 H27' 77.5 . . ? C19 C27 H27' 107.0 . . ? C28 C27 H27' 128.2 . . ? C29' C27 H27' 107.0 . . ? H27 C27 H27' 30.3 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C27 C29 H29A 109.5 . . ? C27 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C27 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C27 C28' H28D 109.5 . . ? C27 C28' H28E 109.5 . . ? H28D C28' H28E 109.5 . . ? C27 C28' H28F 109.5 . . ? H28D C28' H28F 109.5 . . ? H28E C28' H28F 109.5 . . ? C27 C29' H29D 109.5 . . ? C27 C29' H29E 109.5 . . ? H29D C29' H29E 109.5 . . ? C27 C29' H29F 109.5 . . ? H29D C29' H29F 109.5 . . ? H29E C29' H29F 109.5 . . ? C31 C30 C35 118.2(3) . . ? C31 C30 P1 122.5(2) . . ? C35 C30 P1 119.1(2) . . ? C32 C31 C30 120.8(3) . . ? C32 C31 H31 119.6 . . ? C30 C31 H31 119.6 . . ? C33 C32 C31 119.8(3) . . ? C33 C32 H32 120.1 . . ? C31 C32 H32 120.1 . . ? C32 C33 C34 120.1(3) . . ? C32 C33 H33 119.9 . . ? C34 C33 H33 119.9 . . ? C35 C34 C33 120.0(3) . . ? C35 C34 H34 120.0 . . ? C33 C34 H34 120.0 . . ? C34 C35 C30 121.0(3) . . ? C34 C35 H35 119.5 . . ? C30 C35 H35 119.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C30 P1 B1 N5 -56.1(3) . . . . ? C30 P1 B1 N2 134.3(2) . . . . ? N5 B1 N2 C3 0.4(3) . . . . ? P1 B1 N2 C3 171.93(19) . . . . ? N5 B1 N2 C18 -172.6(2) . . . . ? P1 B1 N2 C18 -1.1(4) . . . . ? B1 N2 C3 C4 -0.2(3) . . . . ? C18 N2 C3 C4 173.3(2) . . . . ? N2 C3 C4 N5 -0.1(3) . . . . ? C3 C4 N5 B1 0.4(3) . . . . ? C3 C4 N5 C6 -172.5(2) . . . . ? N2 B1 N5 C4 -0.5(3) . . . . ? P1 B1 N5 C4 -171.8(2) . . . . ? N2 B1 N5 C6 171.9(2) . . . . ? P1 B1 N5 C6 0.6(4) . . . . ? C4 N5 C6 C7 -83.7(3) . . . . ? B1 N5 C6 C7 104.9(3) . . . . ? C4 N5 C6 C11 97.8(3) . . . . ? B1 N5 C6 C11 -73.6(3) . . . . ? C11 C6 C7 C8 2.1(4) . . . . ? N5 C6 C7 C8 -176.4(2) . . . . ? C11 C6 C7 C15 -177.7(2) . . . . ? N5 C6 C7 C15 3.8(4) . . . . ? C6 C7 C8 C9 -0.1(4) . . . . ? C15 C7 C8 C9 179.7(2) . . . . ? C7 C8 C9 C10 -1.6(4) . . . . ? C8 C9 C10 C11 1.3(4) . . . . ? C9 C10 C11 C6 0.6(4) . . . . ? C9 C10 C11 C12 -176.5(2) . . . . ? C7 C6 C11 C10 -2.3(4) . . . . ? N5 C6 C11 C10 176.1(2) . . . . ? C7 C6 C11 C12 174.8(2) . . . . ? N5 C6 C11 C12 -6.8(3) . . . . ? C10 C11 C12 C13 -47.7(3) . . . . ? C6 C11 C12 C13 135.3(3) . . . . ? C10 C11 C12 C14 76.3(3) . . . . ? C6 C11 C12 C14 -100.8(3) . . . . ? C8 C7 C15 C16 49.1(3) . . . . ? C6 C7 C15 C16 -131.1(3) . . . . ? C8 C7 C15 C17 -74.3(3) . . . . ? C6 C7 C15 C17 105.5(3) . . . . ? C3 N2 C18 C19 90.8(3) . . . . ? B1 N2 C18 C19 -97.2(3) . . . . ? C3 N2 C18 C23 -89.9(3) . . . . ? B1 N2 C18 C23 82.2(3) . . . . ? C23 C18 C19 C20 -3.5(4) . . . . ? N2 C18 C19 C20 175.8(2) . . . . ? C23 C18 C19 C27 176.3(2) . . . . ? N2 C18 C19 C27 -4.4(3) . . . . ? C18 C19 C20 C21 0.1(4) . . . . ? C27 C19 C20 C21 -179.7(2) . . . . ? C19 C20 C21 C22 2.2(4) . . . . ? C20 C21 C22 C23 -1.2(4) . . . . ? C21 C22 C23 C18 -2.1(4) . . . . ? C21 C22 C23 C24 178.3(2) . . . . ? C19 C18 C23 C22 4.4(3) . . . . ? N2 C18 C23 C22 -174.9(2) . . . . ? C19 C18 C23 C24 -175.9(2) . . . . ? N2 C18 C23 C24 4.7(3) . . . . ? C22 C23 C24 C26 69.3(3) . . . . ? C18 C23 C24 C26 -110.3(3) . . . . ? C22 C23 C24 C25 -55.6(3) . . . . ? C18 C23 C24 C25 124.7(3) . . . . ? C20 C19 C27 C28' -87.6(5) . . . . ? C18 C19 C27 C28' 92.6(5) . . . . ? C20 C19 C27 C29 68.6(5) . . . . ? C18 C19 C27 C29 -111.1(5) . . . . ? C20 C19 C27 C28 -62.9(5) . . . . ? C18 C19 C27 C28 117.3(4) . . . . ? C20 C19 C27 C29' 38.4(4) . . . . ? C18 C19 C27 C29' -141.4(4) . . . . ? B1 P1 C30 C31 -96.3(2) . . . . ? B1 P1 C30 C35 89.5(2) . . . . ? C35 C30 C31 C32 1.8(4) . . . . ? P1 C30 C31 C32 -172.5(2) . . . . ? C30 C31 C32 C33 -1.8(4) . . . . ? C31 C32 C33 C34 0.2(5) . . . . ? C32 C33 C34 C35 1.2(5) . . . . ? C33 C34 C35 C30 -1.1(5) . . . . ? C31 C30 C35 C34 -0.4(4) . . . . ? P1 C30 C35 C34 174.1(2) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.237 _refine_diff_density_min -0.222 _refine_diff_density_rms 0.043 _database_code_depnum_ccdc_archive 'CCDC 957950' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_gud154 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,3-bis(2,6-diisopropylphenyl)-2-phosphanyl-1,3,2-diazaborolene ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H38 B N2 P' _chemical_formula_sum 'C26 H38 B N2 P' _chemical_formula_weight 420.36 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 triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.5063(5) _cell_length_b 9.4119(6) _cell_length_c 18.3880(14) _cell_angle_alpha 77.441(3) _cell_angle_beta 86.774(4) _cell_angle_gamma 78.004(3) _cell_volume 1240.23(15) _cell_formula_units_Z 2 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description irregular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.126 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 456 _exptl_absorpt_coefficient_mu 0.126 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7086 _exptl_absorpt_correction_T_max 0.7461 _exptl_absorpt_process_details 'Blessing, 1995' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator triumph _diffrn_measurement_device_type 'Bruker Kappa ApexII Duo' _diffrn_measurement_method 'omega and phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23221 _diffrn_reflns_av_R_equivalents 0.0385 _diffrn_reflns_av_sigmaI/netI 0.0392 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 27.47 _reflns_number_total 5671 _reflns_number_gt 4365 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker ApexII Software-Suite, 2008' _computing_cell_refinement 'Bruker ApexII Software-Suite, 2008' _computing_data_reduction 'Bruker ApexII Software-Suite, 2008' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXS-plus, XP (Sheldrick, 1991)' _computing_publication_material SHELXL-97 _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^)+(0.0399P)^2^+1.1460P] 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 5671 _refine_ls_number_parameters 277 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0720 _refine_ls_R_factor_gt 0.0503 _refine_ls_wR_factor_ref 0.1245 _refine_ls_wR_factor_gt 0.1127 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.49651(7) 0.90747(6) 0.24455(4) 0.02965(15) Uani 1 1 d . . . H1 H 0.394(3) 0.824(3) 0.2707(14) 0.044 Uiso 1 1 d . . . H2 H 0.510(3) 0.940(3) 0.3036(14) 0.044 Uiso 1 1 d . . . B1 B 0.7143(3) 0.7556(2) 0.25385(11) 0.0151(4) Uani 1 1 d . . . N2 N 0.89176(19) 0.76915(15) 0.27169(8) 0.0138(3) Uani 1 1 d . . . C3 C 1.0150(2) 0.63883(19) 0.26382(10) 0.0167(3) Uani 1 1 d . . . H3 H 1.1423 0.6192 0.2723 0.020 Uiso 1 1 calc R . . C4 C 0.9247(2) 0.54678(19) 0.24246(10) 0.0178(4) Uani 1 1 d . . . H4 H 0.9780 0.4513 0.2335 0.021 Uiso 1 1 calc R . . N5 N 0.73935(19) 0.61270(16) 0.23521(8) 0.0161(3) Uani 1 1 d . . . C6 C 0.6112(2) 0.54315(18) 0.20794(10) 0.0156(3) Uani 1 1 d . . . C7 C 0.5438(2) 0.42821(19) 0.25634(10) 0.0160(3) Uani 1 1 d . . . C8 C 0.4212(2) 0.3620(2) 0.22782(10) 0.0189(4) Uani 1 1 d . . . H8 H 0.3752 0.2830 0.2592 0.023 Uiso 1 1 calc R . . C9 C 0.3655(3) 0.4096(2) 0.15459(10) 0.0216(4) Uani 1 1 d . . . H9 H 0.2805 0.3642 0.1363 0.026 Uiso 1 1 calc R . . C10 C 0.4333(3) 0.5234(2) 0.10776(10) 0.0206(4) Uani 1 1 d . . . H10 H 0.3932 0.5556 0.0577 0.025 Uiso 1 1 calc R . . C11 C 0.5592(2) 0.59121(19) 0.13292(10) 0.0179(4) Uani 1 1 d . . . C12 C 0.6460(3) 0.7063(2) 0.07950(10) 0.0238(4) Uani 1 1 d . . . H12 H 0.6697 0.7793 0.1081 0.029 Uiso 1 1 calc R . . C13 C 0.8298(3) 0.6319(3) 0.05080(12) 0.0333(5) Uani 1 1 d . . . H13A H 0.9070 0.5771 0.0932 0.050 Uiso 1 1 calc R . . H13B H 0.8899 0.7081 0.0204 0.050 Uiso 1 1 calc R . . H13C H 0.8102 0.5630 0.0204 0.050 Uiso 1 1 calc R . . C14 C 0.5259(3) 0.7925(2) 0.01393(11) 0.0296(5) Uani 1 1 d . . . H14A H 0.5896 0.8643 -0.0181 0.044 Uiso 1 1 calc R . . H14B H 0.4119 0.8454 0.0325 0.044 Uiso 1 1 calc R . . H14C H 0.4990 0.7233 -0.0148 0.044 Uiso 1 1 calc R . . C15 C 0.5979(2) 0.38098(19) 0.33785(10) 0.0184(4) Uani 1 1 d . . . H15 H 0.7262 0.3934 0.3410 0.022 Uiso 1 1 calc R . . C16 C 0.4773(3) 0.4836(2) 0.38305(10) 0.0249(4) Uani 1 1 d . . . H16A H 0.5129 0.4527 0.4355 0.037 Uiso 1 1 calc R . . H16B H 0.3496 0.4776 0.3788 0.037 Uiso 1 1 calc R . . H16C H 0.4921 0.5861 0.3638 0.037 Uiso 1 1 calc R . . C17 C 0.5915(3) 0.2188(2) 0.37189(11) 0.0236(4) Uani 1 1 d . . . H17A H 0.6275 0.1954 0.4242 0.035 Uiso 1 1 calc R . . H17B H 0.6755 0.1540 0.3445 0.035 Uiso 1 1 calc R . . H17C H 0.4675 0.2029 0.3687 0.035 Uiso 1 1 calc R . . C18 C 0.9526(2) 0.88773(18) 0.29410(9) 0.0131(3) Uani 1 1 d . . . C19 C 0.9950(2) 0.87177(19) 0.36918(9) 0.0158(3) Uani 1 1 d . . . C20 C 1.0623(2) 0.9854(2) 0.38912(10) 0.0186(4) Uani 1 1 d . . . H20 H 1.0933 0.9766 0.4395 0.022 Uiso 1 1 calc R . . C21 C 1.0844(2) 1.11055(19) 0.33670(10) 0.0197(4) Uani 1 1 d . . . H21 H 1.1307 1.1867 0.3512 0.024 Uiso 1 1 calc R . . C22 C 1.0392(2) 1.12492(19) 0.26328(10) 0.0180(4) Uani 1 1 d . . . H22 H 1.0544 1.2116 0.2278 0.022 Uiso 1 1 calc R . . C23 C 0.9717(2) 1.01493(18) 0.24017(9) 0.0146(3) Uani 1 1 d . . . C24 C 0.9263(2) 1.0306(2) 0.15888(10) 0.0190(4) Uani 1 1 d . . . H24 H 0.8222 0.9798 0.1578 0.023 Uiso 1 1 calc R . . C25 C 1.0862(3) 0.9527(2) 0.11768(11) 0.0312(5) Uani 1 1 d . . . H25A H 1.0537 0.9644 0.0655 0.047 Uiso 1 1 calc R . . H25B H 1.1150 0.8467 0.1411 0.047 Uiso 1 1 calc R . . H25C H 1.1926 0.9967 0.1199 0.047 Uiso 1 1 calc R . . C26 C 0.8664(3) 1.1924(2) 0.11840(11) 0.0296(5) Uani 1 1 d . . . H26A H 0.8388 1.1961 0.0665 0.044 Uiso 1 1 calc R . . H26B H 0.9645 1.2460 0.1198 0.044 Uiso 1 1 calc R . . H26C H 0.7574 1.2388 0.1430 0.044 Uiso 1 1 calc R . . C27 C 0.9597(3) 0.7390(2) 0.42753(10) 0.0215(4) Uani 1 1 d . . . H27 H 0.9684 0.6537 0.4023 0.026 Uiso 1 1 calc R . . C28 C 1.0966(3) 0.6910(2) 0.49075(11) 0.0301(5) Uani 1 1 d . . . H28A H 1.0670 0.6049 0.5262 0.045 Uiso 1 1 calc R . . H28B H 1.0913 0.7730 0.5163 0.045 Uiso 1 1 calc R . . H28C H 1.2195 0.6642 0.4704 0.045 Uiso 1 1 calc R . . C29 C 0.7660(3) 0.7737(3) 0.45861(12) 0.0345(5) Uani 1 1 d . . . H29A H 0.6794 0.8043 0.4175 0.052 Uiso 1 1 calc R . . H29B H 0.7554 0.8543 0.4855 0.052 Uiso 1 1 calc R . . H29C H 0.7392 0.6849 0.4927 0.052 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0164(2) 0.0267(3) 0.0492(4) -0.0181(2) -0.0011(2) -0.0010(2) B1 0.0167(9) 0.0166(9) 0.0136(9) -0.0050(7) 0.0015(7) -0.0054(7) N2 0.0147(7) 0.0139(7) 0.0139(7) -0.0047(5) 0.0003(5) -0.0035(5) C3 0.0139(8) 0.0168(8) 0.0187(9) -0.0052(7) -0.0010(7) 0.0001(6) C4 0.0176(8) 0.0148(8) 0.0207(9) -0.0056(7) 0.0018(7) -0.0016(7) N5 0.0149(7) 0.0173(7) 0.0188(7) -0.0074(6) 0.0014(6) -0.0062(6) C6 0.0151(8) 0.0161(8) 0.0189(9) -0.0094(7) 0.0022(7) -0.0050(6) C7 0.0150(8) 0.0176(8) 0.0175(9) -0.0074(7) 0.0034(7) -0.0049(6) C8 0.0180(9) 0.0213(9) 0.0207(9) -0.0073(7) 0.0044(7) -0.0094(7) C9 0.0202(9) 0.0280(10) 0.0231(10) -0.0122(8) 0.0016(7) -0.0126(8) C10 0.0241(9) 0.0264(9) 0.0146(8) -0.0085(7) -0.0001(7) -0.0084(8) C11 0.0209(9) 0.0177(8) 0.0171(9) -0.0077(7) 0.0039(7) -0.0056(7) C12 0.0352(11) 0.0245(9) 0.0168(9) -0.0074(7) 0.0042(8) -0.0154(8) C13 0.0269(11) 0.0488(13) 0.0239(11) -0.0006(9) 0.0044(9) -0.0153(10) C14 0.0417(12) 0.0217(10) 0.0239(10) -0.0046(8) 0.0059(9) -0.0045(9) C15 0.0186(9) 0.0210(9) 0.0173(9) -0.0047(7) 0.0002(7) -0.0073(7) C16 0.0339(11) 0.0252(10) 0.0154(9) -0.0057(8) 0.0012(8) -0.0041(8) C17 0.0238(10) 0.0218(9) 0.0250(10) -0.0020(8) -0.0022(8) -0.0068(7) C18 0.0110(7) 0.0141(8) 0.0158(8) -0.0058(6) 0.0011(6) -0.0037(6) C19 0.0163(8) 0.0165(8) 0.0158(8) -0.0056(7) 0.0012(7) -0.0040(6) C20 0.0200(9) 0.0225(9) 0.0164(9) -0.0090(7) -0.0007(7) -0.0062(7) C21 0.0192(9) 0.0187(9) 0.0261(10) -0.0112(7) 0.0030(7) -0.0093(7) C22 0.0196(9) 0.0142(8) 0.0202(9) -0.0026(7) 0.0046(7) -0.0061(7) C23 0.0121(8) 0.0166(8) 0.0146(8) -0.0035(6) 0.0017(6) -0.0022(6) C24 0.0195(9) 0.0223(9) 0.0150(9) -0.0005(7) -0.0009(7) -0.0071(7) C25 0.0368(12) 0.0373(12) 0.0145(9) -0.0066(8) -0.0016(8) 0.0057(9) C26 0.0314(11) 0.0300(11) 0.0212(10) 0.0023(8) -0.0002(8) -0.0002(9) C27 0.0344(11) 0.0171(9) 0.0143(9) -0.0020(7) -0.0013(8) -0.0090(8) C28 0.0459(13) 0.0230(10) 0.0188(10) -0.0023(8) -0.0086(9) -0.0009(9) C29 0.0382(12) 0.0402(12) 0.0246(11) 0.0043(9) 0.0056(9) -0.0197(10) _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 B1 1.923(2) . ? P1 H1 1.22(2) . ? P1 H2 1.21(2) . ? B1 N2 1.427(2) . ? B1 N5 1.432(2) . ? N2 C3 1.404(2) . ? N2 C18 1.434(2) . ? C3 C4 1.336(2) . ? C3 H3 0.9500 . ? C4 N5 1.401(2) . ? C4 H4 0.9500 . ? N5 C6 1.437(2) . ? C6 C11 1.406(2) . ? C6 C7 1.406(2) . ? C7 C8 1.394(2) . ? C7 C15 1.521(2) . ? C8 C9 1.383(3) . ? C8 H8 0.9500 . ? C9 C10 1.387(3) . ? C9 H9 0.9500 . ? C10 C11 1.394(2) . ? C10 H10 0.9500 . ? C11 C12 1.524(2) . ? C12 C14 1.522(3) . ? C12 C13 1.533(3) . ? C12 H12 1.0000 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C17 1.529(2) . ? C15 C16 1.531(2) . ? C15 H15 1.0000 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C19 1.403(2) . ? C18 C23 1.406(2) . ? C19 C20 1.396(2) . ? C19 C27 1.519(2) . ? C20 C21 1.383(3) . ? C20 H20 0.9500 . ? C21 C22 1.382(3) . ? C21 H21 0.9500 . ? C22 C23 1.394(2) . ? C22 H22 0.9500 . ? C23 C24 1.521(2) . ? C24 C25 1.525(3) . ? C24 C26 1.528(3) . ? C24 H24 1.0000 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 C28 1.525(3) . ? C27 C29 1.529(3) . ? C27 H27 1.0000 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? 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 B1 P1 H1 95.6(11) . . ? B1 P1 H2 96.0(12) . . ? H1 P1 H2 92.4(16) . . ? N2 B1 N5 104.99(15) . . ? N2 B1 P1 126.85(13) . . ? N5 B1 P1 127.71(13) . . ? C3 N2 B1 108.27(14) . . ? C3 N2 C18 120.94(14) . . ? B1 N2 C18 130.79(14) . . ? C4 C3 N2 109.16(15) . . ? C4 C3 H3 125.4 . . ? N2 C3 H3 125.4 . . ? C3 C4 N5 109.62(15) . . ? C3 C4 H4 125.2 . . ? N5 C4 H4 125.2 . . ? C4 N5 B1 107.96(14) . . ? C4 N5 C6 121.83(14) . . ? B1 N5 C6 130.05(15) . . ? C11 C6 C7 122.01(15) . . ? C11 C6 N5 118.60(15) . . ? C7 C6 N5 119.38(15) . . ? C8 C7 C6 117.88(16) . . ? C8 C7 C15 121.01(15) . . ? C6 C7 C15 121.08(15) . . ? C9 C8 C7 121.05(16) . . ? C9 C8 H8 119.5 . . ? C7 C8 H8 119.5 . . ? C8 C9 C10 120.19(16) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C9 C10 C11 121.14(17) . . ? C9 C10 H10 119.4 . . ? C11 C10 H10 119.4 . . ? C10 C11 C6 117.70(16) . . ? C10 C11 C12 120.86(16) . . ? C6 C11 C12 121.33(16) . . ? C14 C12 C11 113.69(16) . . ? C14 C12 C13 109.73(16) . . ? C11 C12 C13 110.14(16) . . ? C14 C12 H12 107.7 . . ? C11 C12 H12 107.7 . . ? C13 C12 H12 107.7 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C7 C15 C17 113.45(15) . . ? C7 C15 C16 109.85(15) . . ? C17 C15 C16 110.29(15) . . ? C7 C15 H15 107.7 . . ? C17 C15 H15 107.7 . . ? C16 C15 H15 107.7 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C19 C18 C23 121.94(15) . . ? C19 C18 N2 118.84(14) . . ? C23 C18 N2 119.21(14) . . ? C20 C19 C18 117.88(16) . . ? C20 C19 C27 121.01(15) . . ? C18 C19 C27 121.03(15) . . ? C21 C20 C19 121.06(16) . . ? C21 C20 H20 119.5 . . ? C19 C20 H20 119.5 . . ? C22 C21 C20 120.06(16) . . ? C22 C21 H21 120.0 . . ? C20 C21 H21 120.0 . . ? C21 C22 C23 121.37(16) . . ? C21 C22 H22 119.3 . . ? C23 C22 H22 119.3 . . ? C22 C23 C18 117.67(15) . . ? C22 C23 C24 120.85(15) . . ? C18 C23 C24 121.46(15) . . ? C23 C24 C25 111.03(15) . . ? C23 C24 C26 112.84(15) . . ? C25 C24 C26 110.28(15) . . ? C23 C24 H24 107.5 . . ? C25 C24 H24 107.5 . . ? C26 C24 H24 107.5 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C24 C26 H26A 109.5 . . ? C24 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C24 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C19 C27 C28 113.43(16) . . ? C19 C27 C29 109.46(16) . . ? C28 C27 C29 110.25(16) . . ? C19 C27 H27 107.8 . . ? C28 C27 H27 107.8 . . ? C29 C27 H27 107.8 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C27 C29 H29A 109.5 . . ? C27 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C27 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N5 B1 N2 C3 -0.10(18) . . . . ? P1 B1 N2 C3 -172.86(13) . . . . ? N5 B1 N2 C18 179.70(15) . . . . ? P1 B1 N2 C18 6.9(3) . . . . ? B1 N2 C3 C4 -0.1(2) . . . . ? C18 N2 C3 C4 -179.88(15) . . . . ? N2 C3 C4 N5 0.2(2) . . . . ? C3 C4 N5 B1 -0.3(2) . . . . ? C3 C4 N5 C6 175.65(15) . . . . ? N2 B1 N5 C4 0.21(18) . . . . ? P1 B1 N5 C4 172.89(14) . . . . ? N2 B1 N5 C6 -175.24(16) . . . . ? P1 B1 N5 C6 -2.6(3) . . . . ? C4 N5 C6 C11 -99.43(19) . . . . ? B1 N5 C6 C11 75.5(2) . . . . ? C4 N5 C6 C7 79.6(2) . . . . ? B1 N5 C6 C7 -105.5(2) . . . . ? C11 C6 C7 C8 -0.3(2) . . . . ? N5 C6 C7 C8 -179.29(15) . . . . ? C11 C6 C7 C15 -178.28(15) . . . . ? N5 C6 C7 C15 2.7(2) . . . . ? C6 C7 C8 C9 -1.0(3) . . . . ? C15 C7 C8 C9 177.00(16) . . . . ? C7 C8 C9 C10 0.9(3) . . . . ? C8 C9 C10 C11 0.5(3) . . . . ? C9 C10 C11 C6 -1.7(3) . . . . ? C9 C10 C11 C12 174.45(17) . . . . ? C7 C6 C11 C10 1.6(3) . . . . ? N5 C6 C11 C10 -179.35(15) . . . . ? C7 C6 C11 C12 -174.55(16) . . . . ? N5 C6 C11 C12 4.5(2) . . . . ? C10 C11 C12 C14 28.8(2) . . . . ? C6 C11 C12 C14 -155.19(16) . . . . ? C10 C11 C12 C13 -94.8(2) . . . . ? C6 C11 C12 C13 81.2(2) . . . . ? C8 C7 C15 C17 29.4(2) . . . . ? C6 C7 C15 C17 -152.66(16) . . . . ? C8 C7 C15 C16 -94.57(19) . . . . ? C6 C7 C15 C16 83.4(2) . . . . ? C3 N2 C18 C19 -75.8(2) . . . . ? B1 N2 C18 C19 104.4(2) . . . . ? C3 N2 C18 C23 102.88(18) . . . . ? B1 N2 C18 C23 -76.9(2) . . . . ? C23 C18 C19 C20 -1.6(2) . . . . ? N2 C18 C19 C20 177.00(15) . . . . ? C23 C18 C19 C27 175.27(16) . . . . ? N2 C18 C19 C27 -6.1(2) . . . . ? C18 C19 C20 C21 0.7(3) . . . . ? C27 C19 C20 C21 -176.17(17) . . . . ? C19 C20 C21 C22 0.2(3) . . . . ? C20 C21 C22 C23 -0.3(3) . . . . ? C21 C22 C23 C18 -0.6(2) . . . . ? C21 C22 C23 C24 -178.66(16) . . . . ? C19 C18 C23 C22 1.5(2) . . . . ? N2 C18 C23 C22 -177.08(14) . . . . ? C19 C18 C23 C24 179.64(15) . . . . ? N2 C18 C23 C24 1.0(2) . . . . ? C22 C23 C24 C25 94.5(2) . . . . ? C18 C23 C24 C25 -83.6(2) . . . . ? C22 C23 C24 C26 -29.9(2) . . . . ? C18 C23 C24 C26 152.05(16) . . . . ? C20 C19 C27 C28 -35.2(2) . . . . ? C18 C19 C27 C28 147.99(17) . . . . ? C20 C19 C27 C29 88.4(2) . . . . ? C18 C19 C27 C29 -88.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.025 _refine_diff_density_min -0.901 _refine_diff_density_rms 0.054 _database_code_depnum_ccdc_archive 'CCDC 957951'