Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name J.Kennedy W.Clegg A.Franken T.Jininek C.A.Kilner D.L.Ormsby R.G.Taylor _publ_contact_author_name 'John D. Kennedy' _publ_contact_author_address ; School of Chemistry University of Leeds LEEDS LS2 9JT UNITED KINGDOM ; _publ_section_title ; Polyhedral monocarbaborane chemistry. Some C-phenylated seven, eight, nine, ten, eleven and twelve-vertex species ; data_tom10305 _database_code_depnum_ccdc_archive 'CCDC 164850' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H38 B11 Cl2 N' _chemical_formula_weight 434.28 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c 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 15.7334(5) _cell_length_b 10.8812(4) _cell_length_c 15.7928(6) _cell_angle_alpha 90.00 _cell_angle_beta 110.9350(14) _cell_angle_gamma 90.00 _cell_volume 2525.22(16) _cell_formula_units_Z 4 _cell_measurement_temperature 150(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 0.55 _exptl_crystal_size_mid 0.51 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.142 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 920 _exptl_absorpt_coefficient_mu 0.262 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8692 _exptl_absorpt_correction_T_max 0.9445 _exptl_absorpt_process_details ; Using multiple and symmetry-related data measurements via the program SORTAV See R.H. Blessing, Acta Cryst (1995), A51, 33-38 ; _exptl_special_details ; PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 15 degree phi range. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD area detector diffractometer' _diffrn_measurement_method ; Detector set at 30mm from sample with different 2theta offsets 1 degree phi exposures for chi==0 degree settings 1 degree omega exposures for chi==90 degree settings ; _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13299 _diffrn_reflns_av_R_equivalents 0.0419 _diffrn_reflns_av_sigmaI/netI 0.0454 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 5.13 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4857 _reflns_number_gt 3750 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1999)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1996)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1996)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 for Windows (Farrugia, 1997)' _computing_publication_material 'WC (Thornton-Pett, 2000)' _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^)+(0.0618P)^2^+1.9900P] 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 4857 _refine_ls_number_parameters 310 _refine_ls_number_restraints 64 _refine_ls_R_factor_all 0.0863 _refine_ls_R_factor_gt 0.0654 _refine_ls_wR_factor_ref 0.1731 _refine_ls_wR_factor_gt 0.1568 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.129 _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 C1 C 0.18561(16) 0.3959(2) 0.45889(15) 0.0357(5) Uani 1 1 d . . . C11 C 0.11439(17) 0.3356(2) 0.37832(15) 0.0370(5) Uani 1 1 d . . . C12 C 0.02280(18) 0.3650(3) 0.35345(17) 0.0434(6) Uani 1 1 d . . . H12 H 0.0042 0.4256 0.3865 0.052 Uiso 1 1 calc R . . C13 C -0.0422(2) 0.3059(3) 0.28019(18) 0.0511(7) Uani 1 1 d . . . H13 H -0.1047 0.3271 0.2636 0.061 Uiso 1 1 calc R . . C14 C -0.0166(2) 0.2172(3) 0.23174(17) 0.0497(7) Uani 1 1 d . . . H14 H -0.0610 0.1774 0.1819 0.060 Uiso 1 1 calc R . . C15 C 0.0737(2) 0.1867(3) 0.25605(17) 0.0493(7) Uani 1 1 d . . . H15 H 0.0917 0.1254 0.2230 0.059 Uiso 1 1 calc R . . C16 C 0.1389(2) 0.2448(3) 0.32851(17) 0.0464(6) Uani 1 1 d . . . H16 H 0.2011 0.2227 0.3446 0.056 Uiso 1 1 calc R . . B2 B 0.1627(2) 0.5351(3) 0.49908(19) 0.0414(6) Uani 1 1 d . . . H2 H 0.0974 0.5870 0.4680 0.050 Uiso 1 1 calc R . . B3 B 0.1675(2) 0.3971(3) 0.55973(18) 0.0397(6) Uani 1 1 d . . . H3 H 0.1053 0.3581 0.5685 0.048 Uiso 1 1 calc R . . B4 B 0.25218(19) 0.3008(3) 0.54418(19) 0.0398(6) Uani 1 1 d . . . H4 H 0.2463 0.1982 0.5428 0.048 Uiso 1 1 calc R . . B5 B 0.2988(2) 0.3809(3) 0.47286(19) 0.0405(6) Uani 1 1 d . . . H5 H 0.3237 0.3311 0.4241 0.049 Uiso 1 1 calc R . . B6 B 0.2431(2) 0.5250(3) 0.4444(2) 0.0417(6) Uani 1 1 d . . . H6 H 0.2309 0.5699 0.3773 0.050 Uiso 1 1 calc R . . B7 B 0.2689(2) 0.6114(3) 0.5461(2) 0.0458(7) Uani 1 1 d . . . H7 H 0.2745 0.7140 0.5467 0.055 Uiso 1 1 calc R . . B8 B 0.2221(2) 0.5314(3) 0.6174(2) 0.0456(7) Uani 1 1 d . . . H8 H 0.1967 0.5817 0.6655 0.055 Uiso 1 1 calc R . . B9 B 0.2770(2) 0.3864(3) 0.64584(19) 0.0434(7) Uani 1 1 d . . . H9 H 0.2877 0.3408 0.7125 0.052 Uiso 1 1 calc R . . B10 B 0.3580(2) 0.3755(3) 0.5914(2) 0.0437(7) Uani 1 1 d . . . H10 H 0.4227 0.3222 0.6219 0.052 Uiso 1 1 calc R . . B11 B 0.3533(2) 0.5148(3) 0.5300(2) 0.0445(7) Uani 1 1 d . . . H11 H 0.4149 0.5539 0.5200 0.053 Uiso 1 1 calc R . . B12 B 0.3405(2) 0.5185(3) 0.6373(2) 0.0455(7) Uani 1 1 d . . . H12A H 0.3936 0.5598 0.6983 0.055 Uiso 1 1 calc R . . N2 N 0.5000 0.0000 0.5000 0.0437(7) Uani 1 2 d SD . . C22 C 0.3379(3) -0.0494(5) 0.3959(3) 0.0994(15) Uani 1 1 d DU . . H22A H 0.3308 0.0149 0.4363 0.149 Uiso 0.50 1 calc PR A 1 H22B H 0.3071 -0.1244 0.4038 0.149 Uiso 0.50 1 calc PR A 1 H22C H 0.3111 -0.0217 0.3328 0.149 Uiso 0.50 1 calc PR A 1 H22D H 0.3586 -0.0326 0.3454 0.149 Uiso 0.50 1 calc PR A 2 H22E H 0.2733 -0.0282 0.3780 0.149 Uiso 0.50 1 calc PR A 2 H22F H 0.3463 -0.1369 0.4115 0.149 Uiso 0.50 1 calc PR A 2 C24 C 0.4972(3) 0.1783(5) 0.3936(4) 0.1148(18) Uani 1 1 d DU . . H24A H 0.5591 0.1605 0.3960 0.172 Uiso 0.50 1 calc PR B 1 H24B H 0.4863 0.2670 0.3871 0.172 Uiso 0.50 1 calc PR B 1 H24C H 0.4533 0.1357 0.3417 0.172 Uiso 0.50 1 calc PR B 1 H24D H 0.4357 0.1891 0.3491 0.172 Uiso 0.50 1 calc PR B 2 H24E H 0.5416 0.2117 0.3692 0.172 Uiso 0.50 1 calc PR B 2 H24F H 0.5025 0.2217 0.4496 0.172 Uiso 0.50 1 calc PR B 2 C21A C 0.4514(4) -0.0794(7) 0.4216(4) 0.0589(15) Uani 0.50 1 d PDU C 1 H21A H 0.4648 -0.1671 0.4374 0.071 Uiso 0.50 1 calc PR C 1 H21B H 0.4699 -0.0595 0.3694 0.071 Uiso 0.50 1 calc PR C 1 C23A C 0.4855(5) 0.1307(5) 0.4876(5) 0.0723(19) Uani 0.50 1 d PDU C 1 H23A H 0.5297 0.1743 0.5399 0.087 Uiso 0.50 1 calc PR C 1 H23B H 0.4236 0.1510 0.4858 0.087 Uiso 0.50 1 calc PR C 1 C21B C 0.3951(3) 0.0300(5) 0.4806(4) 0.0477(12) Uani 0.50 1 d PDU C 2 H21C H 0.3790 0.0083 0.5339 0.057 Uiso 0.50 1 calc PR C 2 H21D H 0.3829 0.1186 0.4676 0.057 Uiso 0.50 1 calc PR C 2 C23B C 0.5160(5) 0.0402(7) 0.4141(4) 0.0671(18) Uani 0.50 1 d PDU C 2 H23C H 0.4759 -0.0082 0.3620 0.081 Uiso 0.50 1 calc PR C 2 H23D H 0.5798 0.0221 0.4210 0.081 Uiso 0.50 1 calc PR C 2 N3 N 0.0000 0.0000 0.5000 0.0384(6) Uani 1 2 d SD . . C32 C 0.1343(2) -0.0627(4) 0.4557(3) 0.0827(12) Uani 1 1 d DU . . H32A H 0.1121 0.0059 0.4133 0.124 Uiso 0.50 1 calc PR D 1 H32B H 0.1549 -0.1293 0.4258 0.124 Uiso 0.50 1 calc PR D 1 H32C H 0.1852 -0.0349 0.5090 0.124 Uiso 0.50 1 calc PR D 1 H32D H 0.1858 -0.0710 0.5130 0.124 Uiso 0.50 1 calc PR D 2 H32E H 0.1571 -0.0496 0.4061 0.124 Uiso 0.50 1 calc PR D 2 H32F H 0.0975 -0.1378 0.4441 0.124 Uiso 0.50 1 calc PR D 2 C34 C -0.1156(2) -0.0193(4) 0.3388(2) 0.0702(10) Uani 1 1 d DU . . H34A H -0.0811 -0.0689 0.3103 0.105 Uiso 0.50 1 calc PR E 1 H34B H -0.1600 0.0315 0.2927 0.105 Uiso 0.50 1 calc PR E 1 H34C H -0.1476 -0.0737 0.3669 0.105 Uiso 0.50 1 calc PR E 1 H34D H -0.1368 0.0609 0.3514 0.105 Uiso 0.50 1 calc PR E 2 H34E H -0.1680 -0.0697 0.3038 0.105 Uiso 0.50 1 calc PR E 2 H34F H -0.0757 -0.0078 0.3039 0.105 Uiso 0.50 1 calc PR E 2 C31A C 0.0502(3) -0.1138(4) 0.4879(4) 0.0418(11) Uani 0.50 1 d PDU F 1 H31A H 0.0089 -0.1685 0.4410 0.050 Uiso 0.50 1 calc PR F 1 H31B H 0.0752 -0.1600 0.5455 0.050 Uiso 0.50 1 calc PR F 1 C33A C -0.0467(4) 0.0680(5) 0.4152(3) 0.0454(12) Uani 0.50 1 d PDU F 1 H33A H -0.0009 0.1023 0.3921 0.054 Uiso 0.50 1 calc PR F 1 H33B H -0.0812 0.1374 0.4278 0.054 Uiso 0.50 1 calc PR F 1 C31B C 0.0721(3) 0.0538(5) 0.4618(4) 0.0431(11) Uani 0.50 1 d PDU F 2 H31C H 0.1098 0.1176 0.5030 0.052 Uiso 0.50 1 calc PR F 2 H31D H 0.0415 0.0907 0.4012 0.052 Uiso 0.50 1 calc PR F 2 C33B C -0.0610(4) -0.0863(5) 0.4316(3) 0.0471(12) Uani 0.50 1 d PDU F 2 H33C H -0.1046 -0.1236 0.4563 0.057 Uiso 0.50 1 calc PR F 2 H33D H -0.0240 -0.1534 0.4200 0.057 Uiso 0.50 1 calc PR F 2 C1S C 0.3947(2) -0.0360(3) 0.8011(2) 0.0552(7) Uani 1 1 d . . . H1SA H 0.3705 -0.0155 0.8493 0.066 Uiso 1 1 calc R . . H1SB H 0.4616 -0.0445 0.8299 0.066 Uiso 1 1 calc R . . Cl1 Cl 0.37006(7) 0.08389(9) 0.72287(6) 0.0779(3) Uani 1 1 d . . . Cl2 Cl 0.34890(8) -0.17618(9) 0.75227(9) 0.1004(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0381(12) 0.0380(12) 0.0301(11) 0.0001(9) 0.0112(10) 0.0035(10) C11 0.0444(13) 0.0389(12) 0.0264(11) 0.0014(9) 0.0110(10) -0.0004(11) C12 0.0448(14) 0.0492(15) 0.0366(13) -0.0037(11) 0.0151(11) -0.0016(12) C13 0.0447(14) 0.0639(18) 0.0417(14) -0.0033(13) 0.0118(12) -0.0063(13) C14 0.0588(17) 0.0560(16) 0.0305(13) -0.0036(11) 0.0114(12) -0.0131(14) C15 0.0676(18) 0.0448(15) 0.0352(13) -0.0054(11) 0.0180(13) -0.0019(13) C16 0.0543(16) 0.0461(14) 0.0373(13) -0.0020(11) 0.0145(12) 0.0063(13) B2 0.0417(15) 0.0403(15) 0.0389(15) -0.0035(12) 0.0106(12) 0.0067(12) B3 0.0412(15) 0.0461(16) 0.0317(13) -0.0009(11) 0.0129(11) 0.0034(13) B4 0.0427(15) 0.0392(14) 0.0353(14) 0.0018(11) 0.0113(12) 0.0042(12) B5 0.0409(15) 0.0424(15) 0.0392(15) -0.0013(12) 0.0157(12) 0.0035(12) B6 0.0433(15) 0.0415(15) 0.0388(15) 0.0024(12) 0.0128(12) 0.0009(13) B7 0.0486(17) 0.0392(15) 0.0440(16) -0.0028(12) 0.0097(13) 0.0012(13) B8 0.0460(16) 0.0507(17) 0.0349(15) -0.0073(12) 0.0080(12) 0.0076(14) B9 0.0441(15) 0.0493(17) 0.0323(14) -0.0001(12) 0.0080(12) 0.0048(13) B10 0.0399(15) 0.0445(16) 0.0413(15) 0.0001(12) 0.0081(12) 0.0056(13) B11 0.0400(15) 0.0468(17) 0.0440(16) -0.0016(13) 0.0118(12) -0.0005(13) B12 0.0443(16) 0.0473(17) 0.0386(15) -0.0056(12) 0.0070(12) 0.0034(13) N2 0.0494(17) 0.0449(17) 0.0424(16) -0.0072(13) 0.0232(14) 0.0007(14) C22 0.073(2) 0.150(4) 0.058(2) 0.000(2) 0.0019(18) -0.048(3) C24 0.086(3) 0.110(4) 0.140(4) 0.070(3) 0.030(3) -0.001(3) C21A 0.054(3) 0.078(4) 0.042(3) -0.016(3) 0.014(3) -0.010(3) C23A 0.057(4) 0.041(3) 0.112(5) 0.001(3) 0.021(4) 0.016(3) C21B 0.040(3) 0.055(3) 0.049(3) 0.006(2) 0.017(2) 0.009(2) C23B 0.052(3) 0.110(5) 0.046(3) 0.006(3) 0.027(3) -0.002(4) N3 0.0387(15) 0.0402(15) 0.0357(15) -0.0006(12) 0.0125(12) -0.0027(13) C32 0.0575(19) 0.131(4) 0.066(2) -0.008(2) 0.0299(17) 0.030(2) C34 0.0604(19) 0.100(3) 0.0384(15) -0.0078(16) 0.0037(14) 0.0057(18) C31A 0.043(3) 0.037(3) 0.043(3) -0.003(2) 0.014(2) 0.000(2) C33A 0.048(3) 0.049(3) 0.039(3) 0.011(2) 0.015(2) 0.004(2) C31B 0.041(3) 0.050(3) 0.041(3) 0.004(2) 0.019(2) -0.006(2) C33B 0.046(3) 0.049(3) 0.047(3) -0.010(2) 0.017(2) -0.011(2) C1S 0.0603(17) 0.0479(16) 0.0521(16) -0.0017(13) 0.0137(14) 0.0059(14) Cl1 0.0846(6) 0.0676(5) 0.0738(6) 0.0209(4) 0.0190(5) 0.0118(5) Cl2 0.1070(8) 0.0541(5) 0.1272(10) -0.0262(5) 0.0261(7) -0.0066(5) _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 C1 C11 1.512(3) . ? C1 B3 1.715(3) . ? C1 B5 1.722(4) . ? C1 B4 1.725(4) . ? C1 B2 1.729(4) . ? C1 B6 1.730(4) . ? C11 C12 1.389(4) . ? C11 C16 1.400(4) . ? C12 C13 1.397(4) . ? C12 H12 0.9500 . ? C13 C14 1.379(4) . ? C13 H13 0.9500 . ? C14 C15 1.373(4) . ? C14 H14 0.9500 . ? C15 C16 1.386(4) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? B2 B8 1.765(4) . ? B2 B3 1.767(4) . ? B2 B6 1.772(4) . ? B2 B7 1.774(4) . ? B2 H2 1.1200 . ? B3 B8 1.772(4) . ? B3 B9 1.777(4) . ? B3 B4 1.780(4) . ? B3 H3 1.1200 . ? B4 B10 1.761(4) . ? B4 B9 1.774(4) . ? B4 B5 1.776(4) . ? B4 H4 1.1200 . ? B5 B11 1.766(4) . ? B5 B10 1.769(4) . ? B5 B6 1.774(4) . ? B5 H5 1.1200 . ? B6 B7 1.777(4) . ? B6 B11 1.780(4) . ? B6 H6 1.1200 . ? B7 B8 1.778(5) . ? B7 B11 1.781(4) . ? B7 B12 1.791(4) . ? B7 H7 1.1200 . ? B8 B9 1.778(4) . ? B8 B12 1.781(4) . ? B8 H8 1.1200 . ? B9 B10 1.779(4) . ? B9 B12 1.783(5) . ? B9 H9 1.1200 . ? B10 B12 1.779(4) . ? B10 B11 1.787(4) . ? B10 H10 1.1200 . ? B11 B12 1.777(4) . ? B11 H11 1.1200 . ? B12 H12A 1.1200 . ? N2 C23A 1.442(6) . ? N2 C21A 1.479(5) . ? N2 C23B 1.530(5) . ? N2 C21B 1.601(5) . ? C22 C21B 1.577(6) . ? C22 C21A 1.715(7) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C22 H22D 0.9800 . ? C22 H22E 0.9800 . ? C22 H22F 0.9800 . ? C24 C23B 1.543(8) . ? C24 C23A 1.643(8) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C24 H24D 0.9800 . ? C24 H24E 0.9800 . ? C24 H24F 0.9800 . ? C21A H21A 0.9900 . ? C21A H21B 0.9900 . ? C23A H23A 0.9900 . ? C23A H23B 0.9900 . ? C21B H21C 0.9900 . ? C21B H21D 0.9900 . ? C23B H23C 0.9900 . ? C23B H23D 0.9900 . ? N3 C33A 1.476(5) . ? N3 C33B 1.493(5) . ? N3 C31A 1.518(5) . ? N3 C31B 1.576(5) . ? C32 C31B 1.626(6) . ? C32 C31A 1.673(6) . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C32 H32D 0.9800 . ? C32 H32E 0.9800 . ? C32 H32F 0.9800 . ? C34 C33B 1.586(6) . ? C34 C33A 1.612(6) . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C34 H34D 0.9800 . ? C34 H34E 0.9800 . ? C34 H34F 0.9800 . ? C31A H31A 0.9900 . ? C31A H31B 0.9900 . ? C33A H33A 0.9900 . ? C33A H33B 0.9900 . ? C31B H31C 0.9900 . ? C31B H31D 0.9900 . ? C33B H33C 0.9900 . ? C33B H33D 0.9900 . ? C1S Cl1 1.743(3) . ? C1S Cl2 1.745(3) . ? C1S H1SA 0.9900 . ? C1S H1SB 0.9900 . ? 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 C11 C1 B3 117.7(2) . . ? C11 C1 B5 119.19(19) . . ? B3 C1 B5 112.90(18) . . ? C11 C1 B4 117.2(2) . . ? B3 C1 B4 62.33(15) . . ? B5 C1 B4 62.04(16) . . ? C11 C1 B2 120.0(2) . . ? B3 C1 B2 61.75(16) . . ? B5 C1 B2 112.24(19) . . ? B4 C1 B2 112.78(18) . . ? C11 C1 B6 120.45(19) . . ? B3 C1 B6 112.65(19) . . ? B5 C1 B6 61.87(16) . . ? B4 C1 B6 112.98(19) . . ? B2 C1 B6 61.66(17) . . ? C12 C11 C16 118.0(2) . . ? C12 C11 C1 121.3(2) . . ? C16 C11 C1 120.6(2) . . ? C11 C12 C13 120.5(2) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C14 C13 C12 120.5(3) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C15 C14 C13 119.5(3) . . ? C15 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? C14 C15 C16 120.5(3) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C15 C16 C11 121.0(3) . . ? C15 C16 H16 119.5 . . ? C11 C16 H16 119.5 . . ? C1 B2 B8 105.5(2) . . ? C1 B2 B3 58.75(15) . . ? B8 B2 B3 60.21(17) . . ? C1 B2 B6 59.19(16) . . ? B8 B2 B6 108.3(2) . . ? B3 B2 B6 108.2(2) . . ? C1 B2 B7 105.9(2) . . ? B8 B2 B7 60.31(18) . . ? B3 B2 B7 108.6(2) . . ? B6 B2 B7 60.16(17) . . ? C1 B2 H2 124.1 . . ? B8 B2 H2 122.1 . . ? B3 B2 H2 121.4 . . ? B6 B2 H2 121.4 . . ? B7 B2 H2 121.8 . . ? C1 B3 B2 59.50(15) . . ? C1 B3 B8 105.8(2) . . ? B2 B3 B8 59.84(17) . . ? C1 B3 B9 105.8(2) . . ? B2 B3 B9 108.2(2) . . ? B8 B3 B9 60.12(17) . . ? C1 B3 B4 59.09(15) . . ? B2 B3 B4 108.3(2) . . ? B8 B3 B4 107.9(2) . . ? B9 B3 B4 59.85(16) . . ? C1 B3 H3 123.7 . . ? B2 B3 H3 121.3 . . ? B8 B3 H3 122.3 . . ? B9 B3 H3 122.1 . . ? B4 B3 H3 121.6 . . ? C1 B4 B10 105.8(2) . . ? C1 B4 B9 105.5(2) . . ? B10 B4 B9 60.40(17) . . ? C1 B4 B5 58.91(15) . . ? B10 B4 B5 59.99(17) . . ? B9 B4 B5 108.0(2) . . ? C1 B4 B3 58.58(15) . . ? B10 B4 B3 108.1(2) . . ? B9 B4 B3 59.98(16) . . ? B5 B4 B3 107.3(2) . . ? C1 B4 H4 124.1 . . ? B10 B4 H4 121.9 . . ? B9 B4 H4 122.0 . . ? B5 B4 H4 121.8 . . ? B3 B4 H4 121.9 . . ? C1 B5 B11 106.1(2) . . ? C1 B5 B10 105.57(19) . . ? B11 B5 B10 60.71(17) . . ? C1 B5 B6 59.27(16) . . ? B11 B5 B6 60.36(17) . . ? B10 B5 B6 108.8(2) . . ? C1 B5 B4 59.05(15) . . ? B11 B5 B4 108.4(2) . . ? B10 B5 B4 59.58(17) . . ? B6 B5 B4 108.4(2) . . ? C1 B5 H5 123.9 . . ? B11 B5 H5 121.6 . . ? B10 B5 H5 122.0 . . ? B6 B5 H5 121.0 . . ? B4 B5 H5 121.6 . . ? C1 B6 B2 59.15(16) . . ? C1 B6 B5 58.86(15) . . ? B2 B6 B5 107.8(2) . . ? C1 B6 B7 105.7(2) . . ? B2 B6 B7 59.96(17) . . ? B5 B6 B7 107.8(2) . . ? C1 B6 B11 105.2(2) . . ? B2 B6 B11 107.8(2) . . ? B5 B6 B11 59.60(17) . . ? B7 B6 B11 60.08(17) . . ? C1 B6 H6 124.0 . . ? B2 B6 H6 121.6 . . ? B5 B6 H6 121.8 . . ? B7 B6 H6 122.1 . . ? B11 B6 H6 122.5 . . ? B2 B7 B6 59.88(16) . . ? B2 B7 B8 59.61(17) . . ? B6 B7 B8 107.5(2) . . ? B2 B7 B11 107.7(2) . . ? B6 B7 B11 60.03(17) . . ? B8 B7 B11 107.5(2) . . ? B2 B7 B12 107.5(2) . . ? B6 B7 B12 107.7(2) . . ? B8 B7 B12 59.86(18) . . ? B11 B7 B12 59.68(17) . . ? B2 B7 H7 122.0 . . ? B6 B7 H7 121.8 . . ? B8 B7 H7 122.1 . . ? B11 B7 H7 121.9 . . ? B12 B7 H7 122.0 . . ? B2 B8 B3 59.96(16) . . ? B2 B8 B9 108.3(2) . . ? B3 B8 B9 60.07(17) . . ? B2 B8 B7 60.08(17) . . ? B3 B8 B7 108.2(2) . . ? B9 B8 B7 108.7(2) . . ? B2 B8 B12 108.3(2) . . ? B3 B8 B12 108.1(2) . . ? B9 B8 B12 60.13(17) . . ? B7 B8 B12 60.44(18) . . ? B2 B8 H8 121.6 . . ? B3 B8 H8 121.8 . . ? B9 B8 H8 121.4 . . ? B7 B8 H8 121.3 . . ? B12 B8 H8 121.5 . . ? B4 B9 B3 60.17(16) . . ? B4 B9 B8 107.9(2) . . ? B3 B9 B8 59.80(16) . . ? B4 B9 B10 59.43(16) . . ? B3 B9 B10 107.5(2) . . ? B8 B9 B10 107.7(2) . . ? B4 B9 B12 107.6(2) . . ? B3 B9 B12 107.8(2) . . ? B8 B9 B12 60.02(18) . . ? B10 B9 B12 59.94(17) . . ? B4 B9 H9 121.9 . . ? B3 B9 H9 121.9 . . ? B8 B9 H9 121.8 . . ? B10 B9 H9 122.1 . . ? B12 B9 H9 121.8 . . ? B4 B10 B5 60.43(16) . . ? B4 B10 B9 60.17(17) . . ? B5 B10 B9 108.2(2) . . ? B4 B10 B12 108.4(2) . . ? B5 B10 B12 107.6(2) . . ? B9 B10 B12 60.15(18) . . ? B4 B10 B11 108.2(2) . . ? B5 B10 B11 59.58(17) . . ? B9 B10 B11 107.9(2) . . ? B12 B10 B11 59.80(18) . . ? B4 B10 H10 121.3 . . ? B5 B10 H10 121.8 . . ? B9 B10 H10 121.6 . . ? B12 B10 H10 121.8 . . ? B11 B10 H10 121.9 . . ? B5 B11 B12 107.8(2) . . ? B5 B11 B6 60.04(17) . . ? B12 B11 B6 108.2(2) . . ? B5 B11 B7 108.0(2) . . ? B12 B11 B7 60.45(17) . . ? B6 B11 B7 59.89(17) . . ? B5 B11 B10 59.70(17) . . ? B12 B11 B10 59.90(17) . . ? B6 B11 B10 107.8(2) . . ? B7 B11 B10 108.2(2) . . ? B5 B11 H11 121.9 . . ? B12 B11 H11 121.6 . . ? B6 B11 H11 121.8 . . ? B7 B11 H11 121.5 . . ? B10 B11 H11 121.9 . . ? B11 B12 B10 60.31(17) . . ? B11 B12 B8 107.5(2) . . ? B10 B12 B8 107.5(2) . . ? B11 B12 B9 108.1(2) . . ? B10 B12 B9 59.91(18) . . ? B8 B12 B9 59.84(18) . . ? B11 B12 B7 59.87(17) . . ? B10 B12 B7 108.0(2) . . ? B8 B12 B7 59.70(18) . . ? B9 B12 B7 107.9(2) . . ? B11 B12 H12A 121.7 . . ? B10 B12 H12A 121.7 . . ? B8 B12 H12A 122.2 . . ? B9 B12 H12A 121.7 . . ? B7 B12 H12A 121.8 . . ? C23A N2 C21A 116.9(4) . . ? C23A N2 C23B 109.5(4) . 3_656 ? C21A N2 C23B 112.1(4) . 3_656 ? C23B N2 C21B 104.9(3) . . ? C23A N2 C21B 109.2(3) . 3_656 ? C21A N2 C21B 103.3(3) . 3_656 ? C23B N2 C21B 75.1(3) . 3_656 ? C21B C22 H22A 38.7 . . ? C21A C22 H22A 109.5 . . ? C21B C22 H22B 120.4 . . ? C21A C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21B C22 H22C 127.0 . . ? C21A C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21B C22 H22D 109.5 . . ? C21A C22 H22D 66.9 . . ? H22A C22 H22D 123.0 . . ? H22B C22 H22D 125.7 . . ? H22C C22 H22D 42.6 . . ? C21B C22 H22E 109.5 . . ? C21A C22 H22E 176.0 . . ? H22A C22 H22E 70.8 . . ? H22B C22 H22E 73.9 . . ? H22C C22 H22E 67.0 . . ? H22D C22 H22E 109.5 . . ? C21B C22 H22F 109.5 . . ? C21A C22 H22F 73.8 . . ? H22A C22 H22F 124.4 . . ? H22B C22 H22F 35.7 . . ? H22C C22 H22F 121.7 . . ? H22D C22 H22F 109.5 . . ? H22E C22 H22F 109.5 . . ? C23B C24 H24A 71.7 . . ? C23A C24 H24A 109.5 . . ? C23B C24 H24B 174.3 . . ? C23A C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23B C24 H24C 74.9 . . ? C23A C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C23B C24 H24D 109.5 . . ? C23A C24 H24D 106.6 . . ? H24A C24 H24D 139.9 . . ? H24B C24 H24D 73.4 . . ? H24C C24 H24D 40.1 . . ? C23B C24 H24E 109.5 . . ? C23A C24 H24E 142.9 . . ? H24A C24 H24E 41.5 . . ? H24B C24 H24E 73.5 . . ? H24C C24 H24E 103.6 . . ? H24D C24 H24E 109.5 . . ? C23B C24 H24F 109.5 . . ? C23A C24 H24F 48.5 . . ? H24A C24 H24F 107.3 . . ? H24B C24 H24F 64.8 . . ? H24C C24 H24F 142.2 . . ? H24D C24 H24F 109.5 . . ? H24E C24 H24F 109.5 . . ? N2 C21A C22 105.7(4) . . ? N2 C21A H21A 110.6 . . ? C22 C21A H21A 110.6 . . ? N2 C21A H21B 110.6 . . ? C22 C21A H21B 110.6 . . ? H21A C21A H21B 108.7 . . ? N2 C23A C24 111.7(5) . . ? N2 C23A H23A 109.3 . . ? C24 C23A H23A 109.3 . . ? N2 C23A H23B 109.3 . . ? C24 C23A H23B 109.3 . . ? H23A C23A H23B 107.9 . . ? C22 C21B N2 106.7(4) . . ? C22 C21B H21C 110.4 . . ? N2 C21B H21C 110.4 . . ? C22 C21B H21D 110.4 . . ? N2 C21B H21D 110.4 . . ? H21C C21B H21D 108.6 . . ? N2 C23B C24 112.6(5) . . ? N2 C23B H23C 109.1 . . ? C24 C23B H23C 109.1 . . ? N2 C23B H23D 109.1 . . ? C24 C23B H23D 109.1 . . ? H23C C23B H23D 107.8 . . ? C33A N3 C33B 108.9(3) . 3_556 ? C33A N3 C31A 114.0(3) . . ? C33B N3 C31A 112.1(3) . 3_556 ? C33A N3 C31B 109.9(3) . 3_556 ? C31A N3 C31B 102.9(3) . 3_556 ? C33B N3 C31B 108.7(3) . . ? C31B C32 H32A 51.0 . . ? C31A C32 H32A 109.5 . . ? C31B C32 H32B 156.1 . . ? C31A C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31B C32 H32C 91.8 . . ? C31A C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C31B C32 H32D 109.5 . . ? C31A C32 H32D 99.9 . . ? H32A C32 H32D 132.5 . . ? H32B C32 H32D 94.0 . . ? H32C C32 H32D 23.4 . . ? C31B C32 H32E 109.5 . . ? C31A C32 H32E 147.7 . . ? H32A C32 H32E 59.1 . . ? H32B C32 H32E 56.4 . . ? H32C C32 H32E 102.8 . . ? H32D C32 H32E 109.5 . . ? C31B C32 H32F 109.5 . . ? C31A C32 H32F 45.6 . . ? H32A C32 H32F 117.8 . . ? H32B C32 H32F 64.5 . . ? H32C C32 H32F 131.6 . . ? H32D C32 H32F 109.5 . . ? H32E C32 H32F 109.5 . . ? C33B C34 H34A 88.0 . . ? C33A C34 H34A 109.5 . . ? C33B C34 H34B 162.3 . . ? C33A C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33B C34 H34C 60.0 . . ? C33A C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C33B C34 H34D 109.5 . . ? C33A C34 H34D 60.6 . . ? H34A C34 H34D 150.1 . . ? H34B C34 H34D 56.3 . . ? H34C C34 H34D 100.3 . . ? C33B C34 H34E 109.5 . . ? C33A C34 H34E 163.1 . . ? H34A C34 H34E 85.8 . . ? H34B C34 H34E 70.3 . . ? H34C C34 H34E 56.9 . . ? H34D C34 H34E 109.5 . . ? C33B C34 H34F 109.5 . . ? C33A C34 H34F 87.2 . . ? H34A C34 H34F 40.7 . . ? H34B C34 H34F 86.5 . . ? H34C C34 H34F 150.2 . . ? H34D C34 H34F 109.5 . . ? H34E C34 H34F 109.5 . . ? N3 C31A C32 105.7(3) . . ? N3 C31A H31A 110.6 . . ? C32 C31A H31A 110.6 . . ? N3 C31A H31B 110.6 . . ? C32 C31A H31B 110.6 . . ? H31A C31A H31B 108.7 . . ? N3 C33A C34 111.6(4) . . ? N3 C33A H33A 109.3 . . ? C34 C33A H33A 109.3 . . ? N3 C33A H33B 109.3 . . ? C34 C33A H33B 109.3 . . ? H33A C33A H33B 108.0 . . ? N3 C31B C32 105.3(3) . . ? N3 C31B H31C 110.7 . . ? C32 C31B H31C 110.7 . . ? N3 C31B H31D 110.7 . . ? C32 C31B H31D 110.7 . . ? H31C C31B H31D 108.8 . . ? N3 C33B C34 112.0(4) . . ? N3 C33B H33C 109.2 . . ? C34 C33B H33C 109.2 . . ? N3 C33B H33D 109.2 . . ? C34 C33B H33D 109.2 . . ? H33C C33B H33D 107.9 . . ? Cl1 C1S Cl2 112.87(17) . . ? Cl1 C1S H1SA 109.0 . . ? Cl2 C1S H1SA 109.0 . . ? Cl1 C1S H1SB 109.0 . . ? Cl2 C1S H1SB 109.0 . . ? H1SA C1S H1SB 107.8 . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.394 _refine_diff_density_min -0.499 _refine_diff_density_rms 0.042 data_tom10306 _database_code_depnum_ccdc_archive 'CCDC 164851' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H34 B9 N' _chemical_formula_weight 325.72 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 24.4404(16) _cell_length_b 10.5641(6) _cell_length_c 16.7478(14) _cell_angle_alpha 90.00 _cell_angle_beta 99.099(3) _cell_angle_gamma 90.00 _cell_volume 4269.7(5) _cell_formula_units_Z 8 _cell_measurement_temperature 150(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 0.19 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.013 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1408 _exptl_absorpt_coefficient_mu 0.051 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9904 _exptl_absorpt_correction_T_max 0.9964 _exptl_absorpt_process_details ; Using multiple and symmetry-related data measurements via the program SORTAV See R.H. Blessing, Acta Cryst (1995), A51, 33-38 ; _exptl_special_details ; PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 15 degree phi range. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD area detector diffractometer' _diffrn_measurement_method ; Detector set at 30mm from sample with different 2theta offsets 1 degree phi exposures for chi==0 degree settings 1 degree omega exposures for chi==90 degree settings ; _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13065 _diffrn_reflns_av_R_equivalents 0.1604 _diffrn_reflns_av_sigmaI/netI 0.1407 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.51 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4147 _reflns_number_gt 2212 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1999)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1996)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1996)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 for Windows (Farrugia, 1997)' _computing_publication_material 'WC (Thornton-Pett, 2000)' _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^)+(0.0720P)^2^+2.7654P] 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 SHELXL _refine_ls_extinction_coef 0.0040(12) _refine_ls_extinction_expression Fc^*^==kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4147 _refine_ls_number_parameters 309 _refine_ls_number_restraints 38 _refine_ls_R_factor_all 0.1567 _refine_ls_R_factor_gt 0.0826 _refine_ls_wR_factor_ref 0.2285 _refine_ls_wR_factor_gt 0.1790 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.104 _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 C1 C 0.12797(12) 0.1959(3) 0.03531(16) 0.0427(7) Uani 1 1 d . . . C11 C 0.11282(13) 0.1097(3) -0.03613(17) 0.0465(7) Uani 1 1 d . . . C12 C 0.14384(14) 0.1112(3) -0.09905(18) 0.0537(8) Uani 1 1 d . . . H12 H 0.1750 0.1656 -0.0965 0.064 Uiso 1 1 calc R . . C13 C 0.12902(17) 0.0328(4) -0.1656(2) 0.0680(10) Uani 1 1 d . . . H13 H 0.1503 0.0338 -0.2084 0.082 Uiso 1 1 calc R . . C14 C 0.08406(19) -0.0458(4) -0.1702(2) 0.0774(12) Uani 1 1 d . . . H14 H 0.0742 -0.0985 -0.2162 0.093 Uiso 1 1 calc R . . C15 C 0.05301(17) -0.0483(3) -0.1079(2) 0.0703(10) Uani 1 1 d . . . H15 H 0.0218 -0.1026 -0.1108 0.084 Uiso 1 1 calc R . . C16 C 0.06800(14) 0.0297(3) -0.04067(19) 0.0565(9) Uani 1 1 d . . . H16 H 0.0470 0.0275 0.0024 0.068 Uiso 1 1 calc R . . B2 B 0.12191(14) 0.1638(3) 0.12764(19) 0.0454(8) Uani 1 1 d . . . H2 H 0.1066 0.0697 0.1455 0.054 Uiso 1 1 calc R . . B3 B 0.18698(15) 0.2083(3) 0.0925(2) 0.0492(9) Uani 1 1 d . . . H3 H 0.2235 0.1498 0.0825 0.059 Uiso 1 1 calc R . . B4 B 0.15100(15) 0.3372(3) 0.0325(2) 0.0476(8) Uani 1 1 d . . . H4 H 0.1587 0.3814 -0.0255 0.057 Uiso 1 1 calc R . . B5 B 0.08582(14) 0.2930(3) 0.0675(2) 0.0448(8) Uani 1 1 d . . . H5 H 0.0416 0.3018 0.0377 0.054 Uiso 1 1 calc R . . B6 B 0.10401(16) 0.3080(3) 0.1761(2) 0.0512(9) Uani 1 1 d . . . H6 H 0.0709 0.3074 0.2153 0.061 Uiso 1 1 calc R . . B7 B 0.17514(17) 0.2474(4) 0.1937(2) 0.0575(10) Uani 1 1 d . . . H7 H 0.1991 0.1978 0.2472 0.069 Uiso 1 1 calc R . . B8 B 0.19609(17) 0.3699(4) 0.1267(2) 0.0561(10) Uani 1 1 d . . . H8 H 0.2367 0.4188 0.1265 0.067 Uiso 1 1 calc R . . B9 B 0.12475(15) 0.4305(3) 0.1085(2) 0.0495(9) Uani 1 1 d . . . H9 H 0.1082 0.5280 0.0935 0.059 Uiso 1 1 calc R . . B10 B 0.15975(17) 0.4029(4) 0.2029(2) 0.0598(10) Uani 1 1 d . . . H10 H 0.1698 0.4685 0.2558 0.072 Uiso 1 1 calc R . . N3 N 0.2500 0.7500 0.0000 0.0495(9) Uani 1 2 d S . . C31A C 0.2279(3) 0.8654(6) 0.0293(4) 0.0573(17) Uani 0.50 1 d PU A 1 H31A H 0.1959 0.8942 -0.0104 0.069 Uiso 0.50 1 calc PR A 1 H31B H 0.2566 0.9323 0.0337 0.069 Uiso 0.50 1 calc PR A 1 C32A C 0.2095(14) 0.848(2) 0.1108(13) 0.069(4) Uani 0.50 1 d PU A 1 H32A H 0.2421 0.8359 0.1524 0.104 Uiso 0.50 1 calc PR A 1 H32B H 0.1856 0.7730 0.1090 0.104 Uiso 0.50 1 calc PR A 1 H32C H 0.1889 0.9226 0.1236 0.104 Uiso 0.50 1 calc PR A 1 C33A C 0.3037(3) 0.7055(7) 0.0543(4) 0.0560(16) Uani 0.50 1 d PU A 1 H33A H 0.2942 0.6785 0.1070 0.067 Uiso 0.50 1 calc PR A 1 H33B H 0.3179 0.6303 0.0290 0.067 Uiso 0.50 1 calc PR A 1 C34A C 0.3505(10) 0.804(3) 0.0701(14) 0.069(5) Uani 0.50 1 d PU A 1 H34A H 0.3688 0.8109 0.0223 0.104 Uiso 0.50 1 calc PR A 1 H34B H 0.3775 0.7777 0.1167 0.104 Uiso 0.50 1 calc PR A 1 H34C H 0.3349 0.8865 0.0813 0.104 Uiso 0.50 1 calc PR A 1 C31B C 0.2321(3) 0.7120(7) 0.0857(4) 0.0556(16) Uani 0.50 1 d PU A 2 H31C H 0.2044 0.6432 0.0761 0.067 Uiso 0.50 1 calc PR A 2 H31D H 0.2651 0.6775 0.1210 0.067 Uiso 0.50 1 calc PR A 2 C32B C 0.2083(13) 0.817(3) 0.1311(13) 0.080(5) Uani 0.50 1 d PU A 2 H32D H 0.2367 0.8822 0.1465 0.121 Uiso 0.50 1 calc PR A 2 H32E H 0.1963 0.7829 0.1797 0.121 Uiso 0.50 1 calc PR A 2 H32F H 0.1765 0.8554 0.0962 0.121 Uiso 0.50 1 calc PR A 2 C33B C 0.2868(3) 0.8617(6) 0.0129(4) 0.0606(17) Uani 0.50 1 d PU A 2 H33C H 0.2674 0.9307 0.0371 0.073 Uiso 0.50 1 calc PR A 2 H33D H 0.2949 0.8917 -0.0400 0.073 Uiso 0.50 1 calc PR A 2 C34B C 0.3411(10) 0.832(3) 0.0682(18) 0.082(6) Uani 0.50 1 d PU A 2 H34D H 0.3336 0.8123 0.1225 0.123 Uiso 0.50 1 calc PR A 2 H34E H 0.3656 0.9064 0.0708 0.123 Uiso 0.50 1 calc PR A 2 H34F H 0.3591 0.7600 0.0466 0.123 Uiso 0.50 1 calc PR A 2 N2 N 0.0000 0.3469(4) -0.2500 0.0639(11) Uani 1 2 d SD . . C21A C 0.0454(3) 0.3791(8) -0.1654(5) 0.0586(19) Uani 0.50 1 d PDU B 1 H21A H 0.0490 0.3027 -0.1307 0.070 Uiso 0.50 1 calc PR B 1 H21B H 0.0821 0.3957 -0.1811 0.070 Uiso 0.50 1 calc PR B 1 C22A C 0.0304(5) 0.4917(9) -0.1148(8) 0.060(3) Uani 0.50 1 d PDU B 1 H22A H 0.0274 0.5687 -0.1479 0.090 Uiso 0.50 1 calc PR B 1 H22B H 0.0594 0.5031 -0.0677 0.090 Uiso 0.50 1 calc PR B 1 H22C H -0.0051 0.4752 -0.0966 0.090 Uiso 0.50 1 calc PR B 1 C23A C -0.0524(3) 0.3252(7) -0.2138(4) 0.0584(17) Uani 0.50 1 d PDU B 1 H23A H -0.0817 0.2997 -0.2586 0.070 Uiso 0.50 1 calc PR B 1 H23B H -0.0636 0.4081 -0.1941 0.070 Uiso 0.50 1 calc PR B 1 C24A C -0.0534(4) 0.2302(11) -0.1455(6) 0.066(3) Uani 0.50 1 d PDU B 1 H24A H -0.0407 0.1476 -0.1618 0.099 Uiso 0.50 1 calc PR B 1 H24B H -0.0913 0.2226 -0.1337 0.099 Uiso 0.50 1 calc PR B 1 H24C H -0.0289 0.2595 -0.0970 0.099 Uiso 0.50 1 calc PR B 1 C21B C -0.0008(3) 0.4586(6) -0.2033(3) 0.0540(16) Uani 0.50 1 d PDU B 2 H21C H -0.0388 0.4759 -0.1926 0.065 Uiso 0.50 1 calc PR B 2 H21D H 0.0118 0.5320 -0.2323 0.065 Uiso 0.50 1 calc PR B 2 C22B C 0.0374(6) 0.4360(13) -0.1260(7) 0.090(5) Uani 0.50 1 d PDU B 2 H22D H 0.0178 0.3899 -0.0884 0.134 Uiso 0.50 1 calc PR B 2 H22E H 0.0504 0.5174 -0.1020 0.134 Uiso 0.50 1 calc PR B 2 H22F H 0.0693 0.3860 -0.1367 0.134 Uiso 0.50 1 calc PR B 2 C23B C -0.0210(3) 0.2251(6) -0.2233(5) 0.070(2) Uani 0.50 1 d PDU B 2 H23C H 0.0079 0.1863 -0.1826 0.084 Uiso 0.50 1 calc PR B 2 H23D H -0.0280 0.1671 -0.2702 0.084 Uiso 0.50 1 calc PR B 2 C24B C -0.0741(5) 0.2382(11) -0.1869(7) 0.082(3) Uani 0.50 1 d PDU B 2 H24D H -0.0683 0.2995 -0.1425 0.123 Uiso 0.50 1 calc PR B 2 H24E H -0.0840 0.1559 -0.1663 0.123 Uiso 0.50 1 calc PR B 2 H24F H -0.1041 0.2676 -0.2286 0.123 Uiso 0.50 1 calc PR B 2 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 C1 0.0465(16) 0.0433(17) 0.0383(15) 0.0023(12) 0.0066(12) 0.0042(13) C11 0.0548(18) 0.0428(18) 0.0418(16) 0.0027(12) 0.0074(13) 0.0040(14) C12 0.061(2) 0.052(2) 0.0507(18) 0.0033(14) 0.0164(15) 0.0054(15) C13 0.094(3) 0.066(2) 0.0491(19) -0.0049(17) 0.0270(19) 0.000(2) C14 0.112(3) 0.067(3) 0.056(2) -0.0186(18) 0.022(2) -0.004(2) C15 0.086(3) 0.062(2) 0.063(2) -0.0151(18) 0.013(2) -0.018(2) C16 0.066(2) 0.055(2) 0.0506(18) -0.0062(15) 0.0165(16) -0.0078(16) B2 0.048(2) 0.047(2) 0.0398(18) 0.0023(14) 0.0042(15) 0.0026(15) B3 0.045(2) 0.046(2) 0.054(2) 0.0047(16) 0.0024(16) 0.0034(16) B4 0.048(2) 0.043(2) 0.053(2) 0.0038(15) 0.0105(16) 0.0049(15) B5 0.0457(19) 0.0447(19) 0.0438(18) 0.0032(14) 0.0066(14) 0.0006(15) B6 0.062(2) 0.050(2) 0.0426(19) 0.0014(15) 0.0114(16) 0.0052(17) B7 0.060(2) 0.062(2) 0.046(2) 0.0001(17) -0.0061(17) 0.0013(19) B8 0.052(2) 0.048(2) 0.065(2) -0.0006(17) -0.0014(17) -0.0011(17) B9 0.055(2) 0.040(2) 0.054(2) -0.0017(15) 0.0105(16) 0.0017(16) B10 0.066(3) 0.059(2) 0.052(2) -0.0093(17) 0.0004(18) 0.0011(19) N3 0.053(2) 0.040(2) 0.051(2) 0.0108(16) -0.0058(16) 0.0022(17) C31A 0.058(4) 0.052(4) 0.059(4) 0.006(3) -0.002(3) 0.011(3) C32A 0.079(8) 0.070(8) 0.060(10) 0.001(6) 0.013(8) 0.014(7) C33A 0.056(4) 0.054(4) 0.054(4) 0.016(3) -0.001(3) 0.011(3) C34A 0.055(7) 0.088(13) 0.058(7) 0.017(6) -0.010(5) -0.005(6) C31B 0.054(4) 0.063(4) 0.047(4) 0.017(3) 0.000(3) -0.005(3) C32B 0.065(7) 0.117(17) 0.059(10) -0.002(8) 0.007(8) 0.020(11) C33B 0.061(4) 0.048(4) 0.070(4) 0.015(3) 0.002(3) -0.007(3) C34B 0.060(8) 0.073(11) 0.105(12) 0.011(7) -0.014(7) -0.018(8) N2 0.058(2) 0.039(2) 0.102(3) 0.000 0.032(2) 0.000 C21A 0.048(4) 0.066(5) 0.060(5) 0.003(4) 0.002(4) 0.005(4) C22A 0.051(5) 0.056(7) 0.066(6) -0.004(4) -0.012(4) -0.004(5) C23A 0.047(4) 0.061(5) 0.066(4) -0.008(3) 0.008(3) -0.008(3) C24A 0.059(6) 0.062(5) 0.082(7) -0.004(5) 0.026(5) -0.012(4) C21B 0.067(4) 0.042(4) 0.050(3) 0.007(3) 0.001(3) -0.002(3) C22B 0.122(10) 0.083(12) 0.051(7) 0.000(7) -0.025(6) 0.007(9) C23B 0.091(5) 0.038(4) 0.090(5) 0.004(3) 0.045(4) 0.000(4) C24B 0.112(10) 0.053(6) 0.093(8) -0.008(6) 0.052(7) -0.016(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C11 1.503(4) . ? C1 B4 1.598(5) . ? C1 B3 1.606(4) . ? C1 B5 1.606(4) . ? C1 B2 1.613(4) . ? C11 C16 1.376(4) . ? C11 C12 1.392(4) . ? C12 C13 1.389(5) . ? C13 C14 1.370(5) . ? C14 C15 1.385(5) . ? C15 C16 1.396(4) . ? B2 B7 1.800(5) . ? B2 B6 1.812(5) . ? B2 B5 1.836(5) . ? B2 B3 1.842(5) . ? B3 B8 1.803(5) . ? B3 B7 1.812(5) . ? B3 B4 1.832(5) . ? B4 B9 1.807(5) . ? B4 B8 1.809(5) . ? B4 B5 1.843(5) . ? B5 B6 1.810(5) . ? B5 B9 1.811(5) . ? B6 B10 1.694(6) . ? B6 B7 1.832(6) . ? B6 B9 1.843(5) . ? B7 B10 1.698(6) . ? B7 B8 1.839(6) . ? B8 B10 1.703(6) . ? B8 B9 1.837(5) . ? B9 B10 1.700(5) . ? N3 C31A 1.451(7) . ? N3 C33B 1.478(7) . ? N3 C33A 1.547(6) . ? N3 C31B 1.615(6) . ? C31A C32A 1.515(19) . ? C33A C34A 1.54(3) . ? C31B C32B 1.52(3) . ? C33B C34B 1.53(2) . ? N2 C21B 1.418(6) . ? N2 C23B 1.480(7) . ? N2 C23A 1.518(6) . ? N2 C21A 1.690(7) . ? C21A C22A 1.538(10) . ? C23A C24A 1.524(10) . ? C21B C22B 1.492(11) . ? C23B C24B 1.524(11) . ? 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 C11 C1 B4 125.9(3) . . ? C11 C1 B3 127.5(3) . . ? B4 C1 B3 69.8(2) . . ? C11 C1 B5 124.4(3) . . ? B4 C1 B5 70.2(2) . . ? B3 C1 B5 108.1(2) . . ? C11 C1 B2 126.0(3) . . ? B4 C1 B2 108.1(2) . . ? B3 C1 B2 69.8(2) . . ? B5 C1 B2 69.6(2) . . ? C16 C11 C12 119.3(3) . . ? C16 C11 C1 120.7(3) . . ? C12 C11 C1 120.0(3) . . ? C13 C12 C11 119.7(3) . . ? C14 C13 C12 120.8(3) . . ? C13 C14 C15 119.9(3) . . ? C14 C15 C16 119.4(4) . . ? C11 C16 C15 120.8(3) . . ? C1 B2 B7 108.6(3) . . ? C1 B2 B6 108.6(2) . . ? B7 B2 B6 61.0(2) . . ? C1 B2 B5 55.05(18) . . ? B7 B2 B5 102.1(2) . . ? B6 B2 B5 59.46(19) . . ? C1 B2 B3 54.90(18) . . ? B7 B2 B3 59.6(2) . . ? B6 B2 B3 102.1(2) . . ? B5 B2 B3 90.0(2) . . ? C1 B3 B8 108.7(3) . . ? C1 B3 B7 108.4(3) . . ? B8 B3 B7 61.2(2) . . ? C1 B3 B4 54.93(19) . . ? B8 B3 B4 59.7(2) . . ? B7 B3 B4 102.2(2) . . ? C1 B3 B2 55.26(18) . . ? B8 B3 B2 102.1(3) . . ? B7 B3 B2 59.0(2) . . ? B4 B3 B2 90.1(2) . . ? C1 B4 B9 108.8(3) . . ? C1 B4 B8 108.8(3) . . ? B9 B4 B8 61.1(2) . . ? C1 B4 B3 55.31(19) . . ? B9 B4 B3 102.2(2) . . ? B8 B4 B3 59.4(2) . . ? C1 B4 B5 55.09(19) . . ? B9 B4 B5 59.5(2) . . ? B8 B4 B5 102.0(2) . . ? B3 B4 B5 90.1(2) . . ? C1 B5 B6 109.0(2) . . ? C1 B5 B9 108.2(2) . . ? B6 B5 B9 61.2(2) . . ? C1 B5 B2 55.38(18) . . ? B6 B5 B2 59.60(19) . . ? B9 B5 B2 102.1(2) . . ? C1 B5 B4 54.68(19) . . ? B6 B5 B4 102.2(2) . . ? B9 B5 B4 59.26(19) . . ? B2 B5 B4 89.9(2) . . ? B10 B6 B5 112.2(3) . . ? B10 B6 B2 112.0(3) . . ? B5 B6 B2 60.94(19) . . ? B10 B6 B7 57.4(2) . . ? B5 B6 B7 101.9(2) . . ? B2 B6 B7 59.2(2) . . ? B10 B6 B9 57.3(2) . . ? B5 B6 B9 59.45(19) . . ? B2 B6 B9 101.9(2) . . ? B7 B6 B9 89.9(2) . . ? B10 B7 B2 112.4(3) . . ? B10 B7 B3 112.1(3) . . ? B2 B7 B3 61.3(2) . . ? B10 B7 B6 57.2(2) . . ? B2 B7 B6 59.8(2) . . ? B3 B7 B6 102.5(2) . . ? B10 B7 B8 57.4(2) . . ? B2 B7 B8 102.3(2) . . ? B3 B7 B8 59.2(2) . . ? B6 B7 B8 90.3(2) . . ? B10 B8 B3 112.3(3) . . ? B10 B8 B4 112.0(3) . . ? B3 B8 B4 60.96(19) . . ? B10 B8 B9 57.2(2) . . ? B3 B8 B9 102.2(3) . . ? B4 B8 B9 59.4(2) . . ? B10 B8 B7 57.1(2) . . ? B3 B8 B7 59.7(2) . . ? B4 B8 B7 102.0(2) . . ? B9 B8 B7 89.9(3) . . ? B10 B9 B4 112.3(3) . . ? B10 B9 B5 111.8(3) . . ? B4 B9 B5 61.25(19) . . ? B10 B9 B8 57.4(2) . . ? B4 B9 B8 59.5(2) . . ? B5 B9 B8 102.2(2) . . ? B10 B9 B6 57.0(2) . . ? B4 B9 B6 102.3(2) . . ? B5 B9 B6 59.36(19) . . ? B8 B9 B6 90.0(2) . . ? B6 B10 B7 65.4(2) . . ? B6 B10 B9 65.8(2) . . ? B7 B10 B9 99.6(3) . . ? B6 B10 B8 100.0(3) . . ? B7 B10 B8 65.5(2) . . ? B9 B10 B8 65.3(2) . . ? C31A N3 C33B 118.0(4) . 7_565 ? C31A N3 C33A 112.6(4) . . ? C33B N3 C33A 106.5(4) . 7_565 ? C31A N3 C31B 105.0(4) . 7_565 ? C33A N3 C31B 105.9(3) . 7_565 ? C33B N3 C31B 108.2(4) . . ? N3 C31A C32A 112.3(10) . . ? C34A C33A N3 115.7(9) . . ? C32B C31B N3 116.2(8) . . ? N3 C33B C34B 112.2(12) . . ? C21B N2 C23B 121.4(4) . . ? C21B N2 C23A 115.6(4) . 2_554 ? C23B N2 C23A 110.2(5) . 2_554 ? C21B N2 C21A 103.3(4) . 2_554 ? C23B N2 C21A 102.4(5) . 2_554 ? C23B N2 C21A 97.8(5) . . ? C23A N2 C21A 100.3(4) . . ? C22A C21A N2 115.8(7) . . ? N2 C23A C24A 120.9(6) . . ? N2 C21B C22B 106.5(6) . . ? N2 C23B C24B 113.6(6) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.188 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.051 data_tom42c _database_code_depnum_ccdc_archive 'CCDC 164852' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H20 N, C7 H13 B8' _chemical_formula_sum 'C15 H33 B8 N' _chemical_formula_weight 313.90 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.6480(3) _cell_length_b 10.5204(3) _cell_length_c 17.5709(6) _cell_angle_alpha 90.00 _cell_angle_beta 107.9740(10) _cell_angle_gamma 90.00 _cell_volume 2048.08(11) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8229 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.018 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 0.052 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9740 _exptl_absorpt_correction_T_max 0.9938 _exptl_absorpt_process_details ; Using multiple and symmetry-related data measurements via the program SORTAV See R.H. Blessing, Acta Cryst (1995), A51, 33-38 ; _exptl_special_details ; PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 15 degree phi range. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD area detector diffractometer' _diffrn_measurement_method ; Detector set at 30mm from sample with different 2theta offsets 1 degree phi exposures for chi=0 degree settings 1 degree omega exposures for chi=90 degree settings ; _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17606 _diffrn_reflns_av_R_equivalents 0.0675 _diffrn_reflns_av_sigmaI/netI 0.0480 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4011 _reflns_number_gt 2417 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1999)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1996)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1996)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 for Windows (Farrugia, 1997)' _computing_publication_material 'WC (Thornton-Pett, 2000)' _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^)+(0.0696P)^2^+0.5711P] 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 SHELXL _refine_ls_extinction_coef 0.017(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4011 _refine_ls_number_parameters 330 _refine_ls_number_restraints 14 _refine_ls_R_factor_all 0.0911 _refine_ls_R_factor_gt 0.0548 _refine_ls_wR_factor_ref 0.1703 _refine_ls_wR_factor_gt 0.1432 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.008 _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 0.76304(16) 0.56855(17) -0.07144(11) 0.0318(4) Uani 1 1 d . . . H1 H 0.7877(15) 0.5246(16) -0.1210(10) 0.038(4) Uiso 1 1 d . . . B2 B 0.86893(16) 0.56300(17) 0.04057(11) 0.0314(4) Uani 1 1 d . . . H2 H 0.9586(14) 0.5117(15) 0.0601(9) 0.035(4) Uiso 1 1 d . . . B3 B 0.81740(17) 0.72696(18) -0.01356(13) 0.0378(5) Uani 1 1 d . . . H3 H 0.8746(15) 0.8010(16) -0.0290(10) 0.043(5) Uiso 1 1 d . . . C4 C 0.74983(13) 0.47751(13) -0.00006(9) 0.0264(3) Uani 1 1 d . . . C41 C 0.74833(13) 0.33589(14) -0.00216(9) 0.0269(3) Uani 1 1 d . . . C42 C 0.83859(14) 0.26826(15) -0.02141(10) 0.0345(4) Uani 1 1 d . . . H42 H 0.9016 0.3127 -0.0338 0.041 Uiso 1 1 calc R . . C43 C 0.83694(15) 0.13620(16) -0.02265(11) 0.0417(5) Uani 1 1 d . . . H43 H 0.8986 0.0912 -0.0362 0.050 Uiso 1 1 calc R . . C44 C 0.74645(16) 0.06944(16) -0.00437(11) 0.0425(4) Uani 1 1 d . . . H44 H 0.7459 -0.0209 -0.0051 0.051 Uiso 1 1 calc R . . C45 C 0.65691(15) 0.13598(16) 0.01499(11) 0.0428(5) Uani 1 1 d . . . H45 H 0.5946 0.0910 0.0278 0.051 Uiso 1 1 calc R . . C46 C 0.65724(14) 0.26811(15) 0.01584(10) 0.0347(4) Uani 1 1 d . . . H46 H 0.5948 0.3126 0.0288 0.042 Uiso 1 1 calc R . . B5 B 0.82885(17) 0.69326(18) 0.08374(12) 0.0389(5) Uani 1 1 d . . . H5 H 0.8833(18) 0.7409(18) 0.1415(12) 0.057(6) Uiso 1 1 d . . . B6 B 0.67500(17) 0.70000(18) -0.07686(13) 0.0390(5) Uani 1 1 d . . . H6 H 0.6206(18) 0.7521(18) -0.1324(12) 0.060(6) Uiso 1 1 d . . . B7 B 0.63304(16) 0.56726(17) -0.03777(11) 0.0313(4) Uani 1 1 d . . . H7 H 0.5461(15) 0.5216(16) -0.0600(10) 0.041(5) Uiso 1 1 d . . . B8 B 0.73847(16) 0.56316(17) 0.07412(11) 0.0314(4) Uani 1 1 d . . . H8 H 0.7145(14) 0.5155(15) 0.1212(10) 0.034(4) Uiso 1 1 d . . . B9 B 0.68802(17) 0.72619(19) 0.02118(13) 0.0385(5) Uani 1 1 d . . . H9 H 0.6307(16) 0.8021(17) 0.0376(11) 0.052(5) Uiso 1 1 d . . . N1 N 0.99831(13) 0.24231(13) 0.24720(8) 0.0423(4) Uani 1 1 d . . . C11A C 0.9986(4) 0.3720(4) 0.2048(2) 0.0572(11) Uani 0.50 1 d PU A 1 H11A H 1.0611 0.3700 0.1772 0.069 Uiso 0.50 1 calc PR A 1 H11B H 0.9194 0.3845 0.1636 0.069 Uiso 0.50 1 calc PR A 1 C12A C 1.023(2) 0.4840(13) 0.2630(9) 0.086(4) Uani 0.50 1 d PU A 1 H12A H 0.9653 0.4829 0.2931 0.129 Uiso 0.50 1 calc PR A 1 H12B H 1.0155 0.5638 0.2330 0.129 Uiso 0.50 1 calc PR A 1 H12C H 1.1055 0.4771 0.3002 0.129 Uiso 0.50 1 calc PR A 1 C13A C 0.9242(4) 0.2326(5) 0.2949(3) 0.0629(12) Uani 0.50 1 d PU A 1 H13A H 0.9474 0.2974 0.3378 0.075 Uiso 0.50 1 calc PR A 1 H13B H 0.9340 0.1477 0.3204 0.075 Uiso 0.50 1 calc PR A 1 C14A C 0.7927(10) 0.252(2) 0.2450(10) 0.082(4) Uani 0.50 1 d PU A 1 H14A H 0.7838 0.3346 0.2181 0.123 Uiso 0.50 1 calc PR A 1 H14B H 0.7415 0.2493 0.2800 0.123 Uiso 0.50 1 calc PR A 1 H14C H 0.7683 0.1843 0.2049 0.123 Uiso 0.50 1 calc PR A 1 C15A C 0.9774(4) 0.1476(4) 0.1771(2) 0.0634(12) Uani 0.50 1 d PU A 1 H15A H 1.0377 0.1634 0.1489 0.076 Uiso 0.50 1 calc PR A 1 H15B H 0.8962 0.1621 0.1385 0.076 Uiso 0.50 1 calc PR A 1 C16A C 0.9873(12) 0.0079(9) 0.2056(6) 0.089(3) Uani 0.50 1 d PU A 1 H16A H 1.0726 -0.0153 0.2283 0.134 Uiso 0.50 1 calc PR A 1 H16B H 0.9489 -0.0477 0.1601 0.134 Uiso 0.50 1 calc PR A 1 H16C H 0.9468 -0.0019 0.2466 0.134 Uiso 0.50 1 calc PR A 1 C17A C 1.1336(3) 0.2213(4) 0.3013(2) 0.0510(10) Uani 0.50 1 d PU A 1 H17A H 1.1512 0.2828 0.3461 0.061 Uiso 0.50 1 calc PR A 1 H17B H 1.1399 0.1351 0.3248 0.061 Uiso 0.50 1 calc PR A 1 C18A C 1.2310(14) 0.2346(18) 0.2609(10) 0.071(3) Uani 0.50 1 d PU A 1 H18A H 1.2118 0.1795 0.2136 0.106 Uiso 0.50 1 calc PR A 1 H18B H 1.3091 0.2096 0.2984 0.106 Uiso 0.50 1 calc PR A 1 H18C H 1.2350 0.3232 0.2446 0.106 Uiso 0.50 1 calc PR A 1 C11B C 1.0220(3) 0.3412(3) 0.3153(2) 0.0443(9) Uani 0.50 1 d PU A 2 H11C H 0.9618 0.3288 0.3439 0.053 Uiso 0.50 1 calc PR A 2 H11D H 1.1027 0.3249 0.3539 0.053 Uiso 0.50 1 calc PR A 2 C12B C 1.017(2) 0.4759(15) 0.2886(10) 0.099(5) Uani 0.50 1 d PU A 2 H12D H 1.0727 0.4884 0.2575 0.148 Uiso 0.50 1 calc PR A 2 H12E H 1.0395 0.5319 0.3354 0.148 Uiso 0.50 1 calc PR A 2 H12F H 0.9345 0.4962 0.2552 0.148 Uiso 0.50 1 calc PR A 2 C13B C 0.8643(3) 0.2625(3) 0.19305(18) 0.0348(7) Uani 0.50 1 d PU A 2 H13C H 0.8597 0.3465 0.1669 0.042 Uiso 0.50 1 calc PR A 2 H13D H 0.8466 0.1976 0.1501 0.042 Uiso 0.50 1 calc PR A 2 C14B C 0.7616(10) 0.2565(19) 0.2325(8) 0.061(2) Uani 0.50 1 d PU A 2 H14D H 0.7588 0.1712 0.2542 0.092 Uiso 0.50 1 calc PR A 2 H14E H 0.6841 0.2754 0.1922 0.092 Uiso 0.50 1 calc PR A 2 H14F H 0.7773 0.3191 0.2757 0.092 Uiso 0.50 1 calc PR A 2 C15B C 1.0013(3) 0.1140(3) 0.29109(19) 0.0376(8) Uani 0.50 1 d PU A 2 H15C H 1.0832 0.1021 0.3293 0.045 Uiso 0.50 1 calc PR A 2 H15D H 0.9442 0.1189 0.3226 0.045 Uiso 0.50 1 calc PR A 2 C16B C 0.9706(11) 0.0002(9) 0.2384(5) 0.077(2) Uani 0.50 1 d PU A 2 H16D H 0.8835 -0.0012 0.2108 0.116 Uiso 0.50 1 calc PR A 2 H16E H 0.9939 -0.0769 0.2708 0.116 Uiso 0.50 1 calc PR A 2 H16F H 1.0141 0.0037 0.1988 0.116 Uiso 0.50 1 calc PR A 2 C17B C 1.0748(3) 0.2501(4) 0.1990(2) 0.0448(9) Uani 0.50 1 d PU A 2 H17C H 1.0679 0.3359 0.1749 0.054 Uiso 0.50 1 calc PR A 2 H17D H 1.0485 0.1875 0.1551 0.054 Uiso 0.50 1 calc PR A 2 C18B C 1.2071(14) 0.2247(19) 0.2468(9) 0.086(5) Uani 0.50 1 d PU A 2 H18D H 1.2343 0.2880 0.2895 0.129 Uiso 0.50 1 calc PR A 2 H18E H 1.2570 0.2305 0.2111 0.129 Uiso 0.50 1 calc PR A 2 H18F H 1.2146 0.1395 0.2703 0.129 Uiso 0.50 1 calc PR A 2 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 0.0308(9) 0.0300(10) 0.0371(10) 0.0043(8) 0.0141(7) -0.0002(7) B2 0.0273(9) 0.0297(10) 0.0389(10) -0.0023(8) 0.0125(7) -0.0031(7) B3 0.0338(10) 0.0260(10) 0.0601(13) -0.0007(8) 0.0238(9) -0.0002(8) C4 0.0247(7) 0.0254(7) 0.0304(7) -0.0001(7) 0.0104(5) 0.0004(6) C41 0.0274(7) 0.0253(7) 0.0262(7) -0.0006(6) 0.0057(5) -0.0002(6) C42 0.0321(8) 0.0291(9) 0.0451(10) -0.0013(7) 0.0158(7) 0.0009(6) C43 0.0386(9) 0.0301(10) 0.0579(12) -0.0058(8) 0.0172(8) 0.0056(7) C44 0.0425(9) 0.0240(8) 0.0570(11) -0.0008(8) 0.0092(8) 0.0008(8) C45 0.0377(10) 0.0310(10) 0.0597(12) 0.0029(8) 0.0152(8) -0.0043(7) C46 0.0316(8) 0.0304(9) 0.0443(9) 0.0016(7) 0.0150(7) 0.0001(6) B5 0.0374(10) 0.0319(10) 0.0493(12) -0.0113(9) 0.0160(8) -0.0034(8) B6 0.0374(10) 0.0293(10) 0.0533(12) 0.0092(9) 0.0187(9) 0.0061(8) B7 0.0270(9) 0.0294(10) 0.0384(10) 0.0025(8) 0.0115(7) 0.0017(7) B8 0.0315(9) 0.0306(10) 0.0345(10) -0.0032(7) 0.0136(7) 0.0006(7) B9 0.0363(10) 0.0277(10) 0.0577(13) -0.0022(9) 0.0236(9) 0.0006(8) N1 0.0487(9) 0.0423(9) 0.0312(7) 0.0076(6) 0.0055(6) 0.0015(6) C11A 0.056(2) 0.054(2) 0.055(2) 0.022(2) 0.0080(19) -0.001(2) C12A 0.114(6) 0.034(3) 0.078(8) 0.004(4) -0.017(7) -0.011(4) C13A 0.054(2) 0.092(3) 0.049(2) 0.024(2) 0.0243(19) 0.010(2) C14A 0.034(6) 0.136(7) 0.077(6) 0.038(5) 0.020(4) 0.010(6) C15A 0.071(3) 0.060(3) 0.051(2) -0.002(2) 0.008(2) 0.001(2) C16A 0.123(7) 0.043(3) 0.094(7) -0.006(4) 0.023(6) -0.007(3) C17A 0.044(2) 0.065(3) 0.042(2) 0.0124(18) 0.0100(16) 0.0073(19) C18A 0.044(5) 0.107(7) 0.067(5) 0.005(4) 0.025(4) 0.001(4) C11B 0.048(2) 0.042(2) 0.0351(18) -0.0050(15) 0.0015(15) -0.0049(16) C12B 0.119(7) 0.057(5) 0.089(10) -0.004(5) -0.013(8) 0.014(5) C13B 0.0315(16) 0.046(2) 0.0259(16) 0.0100(14) 0.0074(12) 0.0032(14) C14B 0.026(5) 0.112(6) 0.050(4) 0.020(4) 0.018(3) 0.006(4) C15B 0.0404(18) 0.0369(18) 0.0316(17) 0.0134(14) 0.0056(13) -0.0011(15) C16B 0.107(6) 0.052(4) 0.065(5) 0.003(3) 0.015(4) -0.005(3) C17B 0.0375(18) 0.066(3) 0.0353(18) 0.0192(16) 0.0178(14) 0.0047(16) C18B 0.053(6) 0.146(10) 0.069(6) 0.048(7) 0.033(5) 0.001(5) _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 C4 1.623(2) . ? B1 B6 1.707(3) . ? B1 B7 1.788(2) . ? B1 B3 1.953(3) . ? B1 B2 1.975(3) . ? B1 H1 1.100(17) . ? B2 C4 1.622(2) . ? B2 B5 1.700(3) . ? B2 B8 1.792(2) . ? B2 B3 1.972(3) . ? B2 H2 1.131(16) . ? B3 B5 1.710(3) . ? B3 B6 1.712(3) . ? B3 B9 1.792(3) . ? B3 H3 1.112(17) . ? C4 C41 1.490(2) . ? C4 B7 1.620(2) . ? C4 B8 1.623(2) . ? C41 C46 1.393(2) . ? C41 C42 1.395(2) . ? C42 C43 1.390(2) . ? C42 H42 0.9500 . ? C43 C44 1.384(2) . ? C43 H43 0.9500 . ? C44 C45 1.383(2) . ? C44 H44 0.9500 . ? C45 C46 1.390(2) . ? C45 H45 0.9500 . ? C46 H46 0.9500 . ? B5 B8 1.703(3) . ? B5 B9 1.705(3) . ? B5 H5 1.13(2) . ? B6 B7 1.694(3) . ? B6 B9 1.705(3) . ? B6 H6 1.13(2) . ? B7 B9 1.967(3) . ? B7 B8 1.971(3) . ? B7 H7 1.079(17) . ? B8 B9 1.953(3) . ? B8 H8 1.075(16) . ? B9 H9 1.134(19) . ? N1 C13A 1.380(4) . ? N1 C17B 1.408(4) . ? N1 C15A 1.544(4) . ? N1 C11B 1.544(4) . ? N1 C15B 1.550(3) . ? N1 C11A 1.555(4) . ? N1 C13B 1.572(3) . ? N1 C17A 1.585(4) . ? C11A C12A 1.529(16) . ? C11A H11A 0.9900 . ? C11A H11B 0.9900 . ? C12A H12A 0.9800 . ? C12A H12B 0.9800 . ? C12A H12C 0.9800 . ? C13A C14A 1.526(11) . ? C13A H13A 0.9900 . ? C13A H13B 0.9900 . ? C14A H14A 0.9800 . ? C14A H14B 0.9800 . ? C14A H14C 0.9800 . ? C15A C16A 1.546(10) . ? C15A H15A 0.9900 . ? C15A H15B 0.9900 . ? C16A H16A 0.9800 . ? C16A H16B 0.9800 . ? C16A H16C 0.9800 . ? C17A C18A 1.519(15) . ? C17A H17A 0.9900 . ? C17A H17B 0.9900 . ? C18A H18A 0.9800 . ? C18A H18B 0.9800 . ? C18A H18C 0.9800 . ? C11B C12B 1.488(15) . ? C11B H11C 0.9900 . ? C11B H11D 0.9900 . ? C12B H12D 0.9800 . ? C12B H12E 0.9800 . ? C12B H12F 0.9800 . ? C13B C14B 1.557(14) . ? C13B H13C 0.9900 . ? C13B H13D 0.9900 . ? C14B H14D 0.9800 . ? C14B H14E 0.9800 . ? C14B H14F 0.9800 . ? C15B C16B 1.488(11) . ? C15B H15C 0.9900 . ? C15B H15D 0.9900 . ? C16B H16D 0.9800 . ? C16B H16E 0.9800 . ? C16B H16F 0.9800 . ? C17B C18B 1.534(16) . ? C17B H17C 0.9900 . ? C17B H17D 0.9900 . ? C18B H18D 0.9800 . ? C18B H18E 0.9800 . ? C18B H18F 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 C4 B1 B6 108.83(13) . . ? C4 B1 B7 56.48(9) . . ? B6 B1 B7 57.92(10) . . ? C4 B1 B3 101.18(12) . . ? B6 B1 B3 55.28(10) . . ? B7 B1 B3 90.33(11) . . ? C4 B1 B2 52.50(9) . . ? B6 B1 B2 105.03(13) . . ? B7 B1 B2 90.13(11) . . ? B3 B1 B2 60.26(10) . . ? C4 B1 H1 118.3(9) . . ? B6 B1 H1 126.6(9) . . ? B7 B1 H1 135.6(9) . . ? B3 B1 H1 130.5(9) . . ? B2 B1 H1 122.8(9) . . ? C4 B2 B5 109.15(13) . . ? C4 B2 B8 56.52(9) . . ? B5 B2 B8 58.32(10) . . ? C4 B2 B3 100.43(12) . . ? B5 B2 B3 54.93(11) . . ? B8 B2 B3 89.72(11) . . ? C4 B2 B1 52.52(9) . . ? B5 B2 B1 104.35(13) . . ? B8 B2 B1 89.75(11) . . ? B3 B2 B1 59.33(10) . . ? C4 B2 H2 116.9(8) . . ? B5 B2 H2 127.2(8) . . ? B8 B2 H2 134.3(8) . . ? B3 B2 H2 132.8(8) . . ? B1 B2 H2 123.4(8) . . ? B5 B3 B6 112.10(14) . . ? B5 B3 B9 58.20(11) . . ? B6 B3 B9 58.16(11) . . ? B5 B3 B1 104.86(13) . . ? B6 B3 B1 55.03(10) . . ? B9 B3 B1 90.11(12) . . ? B5 B3 B2 54.43(10) . . ? B6 B3 B2 104.96(13) . . ? B9 B3 B2 89.69(12) . . ? B1 B3 B2 60.42(9) . . ? B5 B3 H3 121.4(9) . . ? B6 B3 H3 119.4(9) . . ? B9 B3 H3 135.8(9) . . ? B1 B3 H3 126.4(9) . . ? B2 B3 H3 127.9(9) . . ? C41 C4 B7 124.79(13) . . ? C41 C4 B2 124.55(13) . . ? B7 C4 B2 110.67(12) . . ? C41 C4 B1 125.04(13) . . ? B7 C4 B1 66.91(10) . . ? B2 C4 B1 74.98(11) . . ? C41 C4 B8 124.85(13) . . ? B7 C4 B8 74.85(11) . . ? B2 C4 B8 67.01(10) . . ? B1 C4 B8 110.10(12) . . ? C46 C41 C42 118.54(14) . . ? C46 C41 C4 120.67(14) . . ? C42 C41 C4 120.79(14) . . ? C43 C42 C41 120.40(15) . . ? C43 C42 H42 119.8 . . ? C41 C42 H42 119.8 . . ? C44 C43 C42 120.76(15) . . ? C44 C43 H43 119.6 . . ? C42 C43 H43 119.6 . . ? C45 C44 C43 119.10(15) . . ? C45 C44 H44 120.5 . . ? C43 C44 H44 120.5 . . ? C44 C45 C46 120.60(15) . . ? C44 C45 H45 119.7 . . ? C46 C45 H45 119.7 . . ? C45 C46 C41 120.60(15) . . ? C45 C46 H46 119.7 . . ? C41 C46 H46 119.7 . . ? B2 B5 B8 63.53(11) . . ? B2 B5 B9 102.60(14) . . ? B8 B5 B9 69.94(12) . . ? B2 B5 B3 70.64(12) . . ? B8 B5 B3 102.25(14) . . ? B9 B5 B3 63.30(12) . . ? B2 B5 H5 126.9(10) . . ? B8 B5 H5 127.0(10) . . ? B9 B5 H5 130.4(10) . . ? B3 B5 H5 130.7(10) . . ? B7 B6 B9 70.74(12) . . ? B7 B6 B1 63.44(11) . . ? B9 B6 B1 102.13(14) . . ? B7 B6 B3 102.48(14) . . ? B9 B6 B3 63.28(11) . . ? B1 B6 B3 69.69(11) . . ? B7 B6 H6 126.6(10) . . ? B9 B6 H6 130.3(10) . . ? B1 B6 H6 127.5(10) . . ? B3 B6 H6 130.9(10) . . ? C4 B7 B6 109.60(13) . . ? C4 B7 B1 56.61(9) . . ? B6 B7 B1 58.64(10) . . ? C4 B7 B9 100.61(12) . . ? B6 B7 B9 54.89(11) . . ? B1 B7 B9 89.80(11) . . ? C4 B7 B8 52.64(9) . . ? B6 B7 B8 104.69(13) . . ? B1 B7 B8 89.98(11) . . ? B9 B7 B8 59.47(10) . . ? C4 B7 H7 117.7(9) . . ? B6 B7 H7 125.2(9) . . ? B1 B7 H7 132.8(9) . . ? B9 B7 H7 133.3(9) . . ? B8 B7 H7 125.3(9) . . ? C4 B8 B5 108.95(13) . . ? C4 B8 B2 56.47(9) . . ? B5 B8 B2 58.15(10) . . ? C4 B8 B9 101.08(12) . . ? B5 B8 B9 55.07(10) . . ? B2 B8 B9 90.30(11) . . ? C4 B8 B7 52.50(9) . . ? B5 B8 B7 104.90(13) . . ? B2 B8 B7 90.14(11) . . ? B9 B8 B7 60.16(10) . . ? C4 B8 H8 117.6(9) . . ? B5 B8 H8 126.7(9) . . ? B2 B8 H8 134.5(9) . . ? B9 B8 H8 131.7(9) . . ? B7 B8 H8 123.2(9) . . ? B6 B9 B5 112.74(14) . . ? B6 B9 B3 58.56(11) . . ? B5 B9 B3 58.50(11) . . ? B6 B9 B8 105.02(13) . . ? B5 B9 B8 54.99(10) . . ? B3 B9 B8 90.29(12) . . ? B6 B9 B7 54.37(10) . . ? B5 B9 B7 105.01(13) . . ? B3 B9 B7 89.76(12) . . ? B8 B9 B7 60.37(9) . . ? B6 B9 H9 119.7(9) . . ? B5 B9 H9 120.3(9) . . ? B3 B9 H9 135.0(9) . . ? B8 B9 H9 127.7(9) . . ? B7 B9 H9 127.7(9) . . ? C13A N1 C17B 179.0(3) . . ? C13A N1 C15A 117.5(3) . . ? C17B N1 C15A 62.1(2) . . ? C13A N1 C11B 64.9(3) . . ? C17B N1 C11B 115.5(2) . . ? C15A N1 C11B 177.4(2) . . ? C13A N1 C15B 63.6(2) . . ? C17B N1 C15B 115.4(2) . . ? C15A N1 C15B 79.0(2) . . ? C11B N1 C15B 103.3(2) . . ? C13A N1 C11A 116.8(3) . . ? C17B N1 C11A 64.2(2) . . ? C15A N1 C11A 101.9(2) . . ? C11B N1 C11A 75.8(2) . . ? C15B N1 C11A 178.5(2) . . ? C13A N1 C13B 71.8(2) . . ? C17B N1 C13B 108.9(2) . . ? C15A N1 C13B 73.8(2) . . ? C11B N1 C13B 106.5(2) . . ? C15B N1 C13B 106.53(19) . . ? C11A N1 C13B 74.9(2) . . ? C13A N1 C17A 108.5(2) . . ? C17B N1 C17A 70.8(2) . . ? C15A N1 C17A 105.8(3) . . ? C11B N1 C17A 73.9(2) . . ? C15B N1 C17A 73.4(2) . . ? C11A N1 C17A 105.1(2) . . ? C13B N1 C17A 179.6(2) . . ? C12A C11A N1 112.5(6) . . ? C12A C11A H11A 109.1 . . ? N1 C11A H11A 109.1 . . ? C12A C11A H11B 109.1 . . ? N1 C11A H11B 109.1 . . ? H11A C11A H11B 107.8 . . ? N1 C13A C14A 110.3(7) . . ? N1 C13A H13A 109.6 . . ? C14A C13A H13A 109.6 . . ? N1 C13A H13B 109.6 . . ? C14A C13A H13B 109.6 . . ? H13A C13A H13B 108.1 . . ? N1 C15A C16A 112.1(4) . . ? N1 C15A H15A 109.2 . . ? C16A C15A H15A 109.2 . . ? N1 C15A H15B 109.2 . . ? C16A C15A H15B 109.2 . . ? H15A C15A H15B 107.9 . . ? C18A C17A N1 117.0(7) . . ? C18A C17A H17A 108.0 . . ? N1 C17A H17A 108.0 . . ? C18A C17A H17B 108.0 . . ? N1 C17A H17B 108.0 . . ? H17A C17A H17B 107.3 . . ? C12B C11B N1 114.7(7) . . ? C12B C11B H11C 108.6 . . ? N1 C11B H11C 108.6 . . ? C12B C11B H11D 108.6 . . ? N1 C11B H11D 108.6 . . ? H11C C11B H11D 107.6 . . ? C11B C12B H12D 109.5 . . ? C11B C12B H12E 109.5 . . ? H12D C12B H12E 109.5 . . ? C11B C12B H12F 109.5 . . ? H12D C12B H12F 109.5 . . ? H12E C12B H12F 109.5 . . ? C14B C13B N1 118.8(5) . . ? C14B C13B H13C 107.6 . . ? N1 C13B H13C 107.6 . . ? C14B C13B H13D 107.6 . . ? N1 C13B H13D 107.6 . . ? H13C C13B H13D 107.1 . . ? C13B C14B H14D 109.5 . . ? C13B C14B H14E 109.5 . . ? H14D C14B H14E 109.5 . . ? C13B C14B H14F 109.5 . . ? H14D C14B H14F 109.5 . . ? H14E C14B H14F 109.5 . . ? C16B C15B N1 115.3(4) . . ? C16B C15B H15C 108.5 . . ? N1 C15B H15C 108.5 . . ? C16B C15B H15D 108.5 . . ? N1 C15B H15D 108.5 . . ? H15C C15B H15D 107.5 . . ? C15B C16B H16D 109.5 . . ? C15B C16B H16E 109.5 . . ? H16D C16B H16E 109.5 . . ? C15B C16B H16F 109.5 . . ? H16D C16B H16F 109.5 . . ? H16E C16B H16F 109.5 . . ? N1 C17B C18B 112.1(6) . . ? N1 C17B H17C 109.2 . . ? C18B C17B H17C 109.2 . . ? N1 C17B H17D 109.2 . . ? C18B C17B H17D 109.2 . . ? H17C C17B H17D 107.9 . . ? C17B C18B H18D 109.5 . . ? C17B C18B H18E 109.5 . . ? H18D C18B H18E 109.5 . . ? C17B C18B H18F 109.5 . . ? H18D C18B H18F 109.5 . . ? H18E C18B H18F 109.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.175 _refine_diff_density_min -0.161 _refine_diff_density_rms 0.033 data_af33 _database_code_depnum_ccdc_archive 'CCDC 172016' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H32 B7 N' _chemical_formula_weight 302.09 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.5758(2) _cell_length_b 16.5323(4) _cell_length_c 12.2821(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.0110(10) _cell_angle_gamma 90.00 _cell_volume 1925.40(8) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 31989 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.042 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.054 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9783 _exptl_absorpt_correction_T_max 0.9878 _exptl_absorpt_process_details ; Using multiple and symmetry-related data measurements via the program SORTAV See R.H. Blessing, Acta Cryst (1995), A51, 33-38 ; _exptl_special_details ; PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 15 degree phi range. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD area detector diffractometer' _diffrn_measurement_method ; Detector set at 30mm from sample with different 2theta offsets 1 degree phi exposures for chi=0 degree settings 1 degree omega exposures for chi=90 degree settings ; _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24624 _diffrn_reflns_av_R_equivalents 0.0868 _diffrn_reflns_av_sigmaI/netI 0.0446 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.53 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3772 _reflns_number_gt 3410 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1999)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1996)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1996)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; ORTEP3 for Windows (Farrugia, 1997) XSeed (Barbour, 2001) ; _computing_publication_material 'WC (Thornton-Pett, 2000)' _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^)+(0.0596P)^2^+1.1033P] 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 3772 _refine_ls_number_parameters 212 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0639 _refine_ls_R_factor_gt 0.0588 _refine_ls_wR_factor_ref 0.1520 _refine_ls_wR_factor_gt 0.1483 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.091 _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 C1 C 0.17966(16) 0.09539(10) 0.15692(12) 0.0227(3) Uani 1 1 d . . . C11 C 0.13239(16) 0.16523(10) 0.08526(12) 0.0225(3) Uani 1 1 d . . . C12 C 0.01720(17) 0.15617(10) 0.00202(12) 0.0243(3) Uani 1 1 d . . . H12 H -0.0294 0.1054 -0.0080 0.029 Uiso 1 1 calc R . . C13 C -0.02930(18) 0.22094(11) -0.06600(13) 0.0280(4) Uani 1 1 d . . . H13 H -0.1078 0.2142 -0.1217 0.034 Uiso 1 1 calc R . . C14 C 0.03844(18) 0.29519(10) -0.05275(13) 0.0288(4) Uani 1 1 d . . . H14 H 0.0070 0.3392 -0.0996 0.035 Uiso 1 1 calc R . . C15 C 0.15331(19) 0.30492(10) 0.02991(13) 0.0295(4) Uani 1 1 d . . . H15 H 0.2002 0.3556 0.0392 0.035 Uiso 1 1 calc R . . C16 C 0.19883(18) 0.24050(10) 0.09845(13) 0.0265(4) Uani 1 1 d . . . H16 H 0.2762 0.2478 0.1550 0.032 Uiso 1 1 calc R . . B2 B 0.21861(19) 0.01189(11) 0.11703(15) 0.0255(4) Uani 1 1 d . . . H2 H 0.2235 -0.0116 0.0321 0.031 Uiso 1 1 calc R . . B3 B 0.3417(2) 0.06306(12) 0.22095(15) 0.0272(4) Uani 1 1 d . . . H3 H 0.4497 0.0856 0.2119 0.033 Uiso 1 1 calc R . . B4 B 0.0835(2) 0.01985(12) 0.20705(14) 0.0256(4) Uani 1 1 d . . . H4 H -0.0312 0.0051 0.1859 0.031 Uiso 1 1 calc R . . B5 B 0.19011(19) 0.10196(12) 0.28958(14) 0.0248(4) Uani 1 1 d . . . H5 H 0.1648 0.1612 0.3264 0.030 Uiso 1 1 calc R . . B6 B 0.2533(2) -0.04077(12) 0.23726(15) 0.0261(4) Uani 1 1 d . . . H6 H 0.2830 -0.1058 0.2292 0.031 Uiso 1 1 calc R . . B7 B 0.3197(2) 0.02844(12) 0.34774(15) 0.0267(4) Uani 1 1 d . . . H7 H 0.4033 0.0255 0.4211 0.032 Uiso 1 1 calc R . . B8 B 0.1552(2) 0.00258(12) 0.33957(15) 0.0271(4) Uani 1 1 d . . . H8 H 0.0988 -0.0219 0.4064 0.033 Uiso 1 1 calc R . . N2 N 0.28499(14) 0.15131(8) 0.72508(11) 0.0266(3) Uani 1 1 d . . . C21 C 0.34655(18) 0.08318(10) 0.66327(14) 0.0294(4) Uani 1 1 d . . . H21A H 0.3378 0.0980 0.5845 0.035 Uiso 1 1 calc R . . H21B H 0.4483 0.0784 0.6910 0.035 Uiso 1 1 calc R . . C22 C 0.27840(19) 0.00144(11) 0.67266(15) 0.0329(4) Uani 1 1 d . . . H22A H 0.2897 -0.0152 0.7500 0.049 Uiso 1 1 calc R . . H22B H 0.3235 -0.0385 0.6299 0.049 Uiso 1 1 calc R . . H22C H 0.1778 0.0049 0.6442 0.049 Uiso 1 1 calc R . . C23 C 0.36936(19) 0.22662(11) 0.70595(15) 0.0324(4) Uani 1 1 d . . . H23A H 0.4688 0.2175 0.7381 0.039 Uiso 1 1 calc R . . H23B H 0.3673 0.2338 0.6257 0.039 Uiso 1 1 calc R . . C24 C 0.3192(2) 0.30423(12) 0.75311(18) 0.0425(5) Uani 1 1 d . . . H24A H 0.2250 0.3178 0.7154 0.064 Uiso 1 1 calc R . . H24B H 0.3848 0.3481 0.7426 0.064 Uiso 1 1 calc R . . H24C H 0.3152 0.2971 0.8318 0.064 Uiso 1 1 calc R . . C25 C 0.29537(18) 0.13316(11) 0.84767(13) 0.0296(4) Uani 1 1 d . . . H25A H 0.2340 0.0863 0.8573 0.036 Uiso 1 1 calc R . . H25B H 0.2575 0.1801 0.8841 0.036 Uiso 1 1 calc R . . C26 C 0.4430(2) 0.11489(13) 0.90650(15) 0.0401(5) Uani 1 1 d . . . H26A H 0.4792 0.0659 0.8752 0.060 Uiso 1 1 calc R . . H26B H 0.4390 0.1065 0.9850 0.060 Uiso 1 1 calc R . . H26C H 0.5056 0.1605 0.8971 0.060 Uiso 1 1 calc R . . C27 C 0.12821(18) 0.16238(11) 0.68435(13) 0.0290(4) Uani 1 1 d . . . H27A H 0.0777 0.1127 0.7013 0.035 Uiso 1 1 calc R . . H27B H 0.0923 0.2074 0.7257 0.035 Uiso 1 1 calc R . . C28 C 0.0931(2) 0.17985(13) 0.56262(15) 0.0417(5) Uani 1 1 d . . . H28A H 0.1418 0.2292 0.5447 0.063 Uiso 1 1 calc R . . H28B H -0.0090 0.1872 0.5438 0.063 Uiso 1 1 calc R . . H28C H 0.1237 0.1344 0.5205 0.063 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 C1 0.0218(8) 0.0273(8) 0.0186(7) -0.0002(6) 0.0015(6) -0.0018(6) C11 0.0239(8) 0.0274(8) 0.0167(7) -0.0014(6) 0.0046(6) 0.0016(6) C12 0.0255(8) 0.0282(8) 0.0192(7) -0.0014(6) 0.0029(6) -0.0009(6) C13 0.0280(8) 0.0365(9) 0.0192(7) 0.0002(6) 0.0026(6) 0.0049(7) C14 0.0362(9) 0.0295(9) 0.0219(8) 0.0043(6) 0.0080(7) 0.0078(7) C15 0.0386(10) 0.0265(9) 0.0245(8) -0.0024(6) 0.0088(7) -0.0019(7) C16 0.0299(8) 0.0289(9) 0.0205(7) -0.0028(6) 0.0028(6) -0.0017(7) B2 0.0264(9) 0.0282(9) 0.0213(8) -0.0016(7) 0.0015(7) 0.0008(7) B3 0.0242(9) 0.0331(10) 0.0234(9) -0.0030(7) -0.0003(7) 0.0005(8) B4 0.0255(9) 0.0298(9) 0.0211(8) 0.0003(7) 0.0025(7) -0.0009(7) B5 0.0272(9) 0.0287(9) 0.0183(8) -0.0009(7) 0.0023(7) 0.0006(7) B6 0.0277(9) 0.0263(9) 0.0234(9) 0.0003(7) 0.0006(7) 0.0005(7) B7 0.0289(9) 0.0279(9) 0.0219(8) 0.0002(7) -0.0022(7) 0.0014(7) B8 0.0301(10) 0.0302(10) 0.0209(8) 0.0013(7) 0.0029(7) 0.0009(8) N2 0.0284(7) 0.0283(7) 0.0248(7) -0.0025(5) 0.0090(6) -0.0030(6) C21 0.0308(9) 0.0308(9) 0.0285(8) -0.0060(7) 0.0104(7) 0.0000(7) C22 0.0348(9) 0.0296(9) 0.0349(9) -0.0055(7) 0.0073(7) -0.0003(7) C23 0.0349(9) 0.0301(9) 0.0349(9) -0.0012(7) 0.0142(7) -0.0053(7) C24 0.0466(12) 0.0318(10) 0.0528(12) -0.0057(8) 0.0202(9) -0.0068(8) C25 0.0312(9) 0.0360(9) 0.0225(8) -0.0022(7) 0.0067(7) -0.0007(7) C26 0.0346(10) 0.0562(13) 0.0289(9) -0.0016(8) 0.0024(7) 0.0025(9) C27 0.0301(9) 0.0322(9) 0.0256(8) -0.0007(7) 0.0064(7) 0.0015(7) C28 0.0454(11) 0.0508(12) 0.0288(9) 0.0054(8) 0.0044(8) 0.0079(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 C1 C11 1.484(2) . ? C1 B2 1.528(2) . ? C1 B5 1.622(2) . ? C1 B4 1.716(2) . ? C1 B3 1.723(2) . ? C11 C16 1.397(2) . ? C11 C12 1.404(2) . ? C12 C13 1.393(2) . ? C13 C14 1.387(2) . ? C14 C15 1.398(2) . ? C15 C16 1.389(2) . ? B2 B6 1.707(3) . ? B2 B4 1.820(3) . ? B2 B3 1.820(3) . ? B3 B7 1.700(3) . ? B3 B5 1.890(3) . ? B3 B6 1.937(3) . ? B4 B8 1.700(2) . ? B4 B6 1.902(3) . ? B4 B5 1.904(3) . ? B5 B8 1.801(3) . ? B5 B7 1.811(3) . ? B6 B8 1.818(3) . ? B6 B7 1.821(3) . ? B7 B8 1.622(3) . ? N2 C23 1.520(2) . ? N2 C21 1.522(2) . ? N2 C25 1.525(2) . ? N2 C27 1.526(2) . ? C21 C22 1.512(2) . ? C23 C24 1.513(2) . ? C25 C26 1.525(2) . ? C27 C28 1.514(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 C1 B2 125.50(13) . . ? C11 C1 B5 120.98(13) . . ? B2 C1 B5 113.50(13) . . ? C11 C1 B4 130.14(13) . . ? B2 C1 B4 67.96(11) . . ? B5 C1 B4 69.47(11) . . ? C11 C1 B3 133.85(13) . . ? B2 C1 B3 67.78(11) . . ? B5 C1 B3 68.70(11) . . ? B4 C1 B3 95.99(12) . . ? C16 C11 C12 118.60(14) . . ? C16 C11 C1 121.88(14) . . ? C12 C11 C1 119.52(14) . . ? C13 C12 C11 120.53(15) . . ? C14 C13 C12 120.32(15) . . ? C13 C14 C15 119.64(15) . . ? C16 C15 C14 120.03(16) . . ? C15 C16 C11 120.88(15) . . ? C1 B2 B6 102.14(13) . . ? C1 B2 B4 60.93(10) . . ? B6 B2 B4 65.18(11) . . ? C1 B2 B3 61.22(10) . . ? B6 B2 B3 66.52(11) . . ? B4 B2 B3 89.19(11) . . ? B7 B3 C1 107.71(13) . . ? B7 B3 B2 109.59(14) . . ? C1 B3 B2 51.00(9) . . ? B7 B3 B5 60.34(10) . . ? C1 B3 B5 53.11(9) . . ? B2 B3 B5 90.49(11) . . ? B7 B3 B6 59.67(10) . . ? C1 B3 B6 86.77(11) . . ? B2 B3 B6 53.92(9) . . ? B5 B3 B6 83.21(11) . . ? B8 B4 C1 107.49(13) . . ? B8 B4 B2 110.07(13) . . ? C1 B4 B2 51.12(9) . . ? B8 B4 B6 60.30(10) . . ? C1 B4 B6 88.10(11) . . ? B2 B4 B6 54.54(9) . . ? B8 B4 B5 59.66(10) . . ? C1 B4 B5 52.94(9) . . ? B2 B4 B5 90.07(11) . . ? B6 B4 B5 83.78(11) . . ? C1 B5 B8 107.04(13) . . ? C1 B5 B7 107.11(13) . . ? B8 B5 B7 53.34(10) . . ? C1 B5 B3 58.19(9) . . ? B8 B5 B3 91.84(12) . . ? B7 B5 B3 54.62(10) . . ? C1 B5 B4 57.58(9) . . ? B8 B5 B4 54.55(10) . . ? B7 B5 B4 91.06(12) . . ? B3 B5 B4 84.72(11) . . ? B2 B6 B8 109.88(13) . . ? B2 B6 B7 109.26(13) . . ? B8 B6 B7 52.94(10) . . ? B2 B6 B4 60.28(10) . . ? B8 B6 B4 54.35(9) . . ? B7 B6 B4 90.83(12) . . ? B2 B6 B3 59.56(10) . . ? B8 B6 B3 89.84(12) . . ? B7 B6 B3 53.68(9) . . ? B4 B6 B3 83.49(11) . . ? B8 B7 B3 105.97(13) . . ? B8 B7 B5 63.02(11) . . ? B3 B7 B5 65.04(11) . . ? B8 B7 B6 63.44(11) . . ? B3 B7 B6 66.65(11) . . ? B5 B7 B6 88.79(11) . . ? B7 B8 B4 105.91(14) . . ? B7 B8 B5 63.64(11) . . ? B4 B8 B5 65.78(11) . . ? B7 B8 B6 63.63(11) . . ? B4 B8 B6 65.35(11) . . ? B5 B8 B6 89.18(11) . . ? C23 N2 C21 106.13(12) . . ? C23 N2 C25 110.55(13) . . ? C21 N2 C25 111.73(13) . . ? C23 N2 C27 111.77(13) . . ? C21 N2 C27 110.91(12) . . ? C25 N2 C27 105.85(12) . . ? C22 C21 N2 114.97(13) . . ? C24 C23 N2 115.54(14) . . ? N2 C25 C26 115.81(13) . . ? C28 C27 N2 114.81(14) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.332 _refine_diff_density_min -0.267 _refine_diff_density_rms 0.058 data_af37b _database_code_depnum_ccdc_archive 'CCDC 172017' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H35 B10 N' _chemical_formula_weight 337.54 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 17.4206(4) _cell_length_b 13.9339(4) _cell_length_c 19.5909(5) _cell_angle_alpha 90.00 _cell_angle_beta 113.5340(15) _cell_angle_gamma 90.00 _cell_volume 4359.9(2) _cell_formula_units_Z 8 _cell_measurement_temperature 150(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 0.48 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.36 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.028 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1456 _exptl_absorpt_coefficient_mu 0.051 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9758 _exptl_absorpt_correction_T_max 0.9817 _exptl_absorpt_process_details ; Using multiple and symmetry-related data measurements via the program SORTAV See R.H. Blessing, Acta Cryst (1995), A51, 33-38 ; _exptl_special_details ; PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 15 degree phi range. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD area detector diffractometer' _diffrn_measurement_method ; Detector set at 30mm from sample with different 2theta offsets 1 degree phi exposures for chi=0 degree settings 1 degree omega exposures for chi=90 degree settings ; _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21127 _diffrn_reflns_av_R_equivalents 0.0690 _diffrn_reflns_av_sigmaI/netI 0.0439 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.70 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4216 _reflns_number_gt 3179 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1999)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1996)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1996)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; ORTEP3 for Windows (Farrugia, 1997) XSeed (Barbour, 2001) ; _computing_publication_material 'WC (Thornton-Pett, 2000)' _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^)+(0.0963P)^2^+4.0009P] 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 4216 _refine_ls_number_parameters 321 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0958 _refine_ls_R_factor_gt 0.0726 _refine_ls_wR_factor_ref 0.2019 _refine_ls_wR_factor_gt 0.1829 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.003 _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 0.18519(17) 0.26976(18) 0.12939(16) 0.0508(6) Uani 1 1 d . . . H1 H 0.2270(18) 0.306(2) 0.1090(16) 0.081(8) Uiso 1 1 d . . . C2 C 0.20944(12) 0.15539(13) 0.14303(10) 0.0360(4) Uani 1 1 d . . . C21 C 0.28185(12) 0.11067(14) 0.13265(10) 0.0382(4) Uani 1 1 d . . . C22 C 0.29884(13) 0.13141(15) 0.07032(12) 0.0456(5) Uani 1 1 d . . . H22 H 0.2637 0.1748 0.0338 0.055 Uiso 1 1 calc R . . C23 C 0.36613(15) 0.08963(18) 0.06104(15) 0.0591(6) Uani 1 1 d . . . H23 H 0.3779 0.1057 0.0191 0.071 Uiso 1 1 calc R . . C24 C 0.41670(15) 0.02380(19) 0.11356(17) 0.0660(7) Uani 1 1 d . . . H24 H 0.4629 -0.0051 0.1075 0.079 Uiso 1 1 calc R . . C25 C 0.39918(14) 0.00114(18) 0.17400(15) 0.0609(7) Uani 1 1 d . . . H25 H 0.4327 -0.0447 0.2091 0.073 Uiso 1 1 calc R . . C26 C 0.33296(13) 0.04463(15) 0.18421(12) 0.0488(5) Uani 1 1 d . . . H26 H 0.3223 0.0292 0.2269 0.059 Uiso 1 1 calc R . . B3 B 0.11373(18) 0.3482(2) 0.13747(16) 0.0554(7) Uani 1 1 d . . . H3 H 0.1128 0.4267 0.1249 0.067 Uiso 1 1 calc R . . B4 B 0.11644(16) 0.1491(2) 0.08226(13) 0.0488(6) Uani 1 1 d . . . H4 H 0.1011 0.1099 0.0285 0.059 Uiso 1 1 calc R . . B5 B 0.21816(17) 0.18851(19) 0.22362(13) 0.0491(6) Uani 1 1 d . . . H5 H 0.2781 0.1779 0.2736 0.059 Uiso 1 1 calc R . . B6 B 0.16094(19) 0.2996(2) 0.21991(15) 0.0565(7) Uani 1 1 d . . . H6 H 0.1896 0.3495 0.2683 0.068 Uiso 1 1 calc R . . B7 B 0.05941(16) 0.2620(2) 0.07917(14) 0.0534(7) Uani 1 1 d . . . H7 H 0.0129 0.2846 0.0230 0.064 Uiso 1 1 calc R . . B8 B 0.14545(15) 0.09683(16) 0.17384(14) 0.0430(5) Uani 1 1 d . . . H8 H 0.1485 0.0187 0.1882 0.052 Uiso 1 1 calc R . . B9 B 0.05077(18) 0.27518(19) 0.16642(15) 0.0511(6) Uani 1 1 d . . . H9 H -0.0046 0.3029 0.1758 0.061 Uiso 1 1 calc R . . B10 B 0.04810(17) 0.15785(19) 0.13010(15) 0.0509(6) Uani 1 1 d . . . H10 H -0.0113 0.1154 0.1117 0.061 Uiso 1 1 calc R . . B11 B 0.11730(18) 0.18492(19) 0.22574(13) 0.0511(6) Uani 1 1 d . . . H11 H 0.1080 0.1626 0.2768 0.061 Uiso 1 1 calc R . . N1 N 0.0000 -0.14986(15) 0.2500 0.0375(5) Uani 1 2 d S . . C2A C -0.0059(3) -0.2383(3) 0.2046(2) 0.0532(11) Uani 0.50 1 d PD A 2 H2A1 H -0.0654 -0.2563 0.1779 0.064 Uiso 0.50 1 calc PR A 2 H2A2 H 0.0230 -0.2919 0.2382 0.064 Uiso 0.50 1 calc PR A 2 C3A C 0.0338(13) -0.2230(12) 0.1475(9) 0.079(4) Uani 0.50 1 d PD A 2 H3A1 H 0.0065 -0.1688 0.1151 0.118 Uiso 0.50 1 calc PR A 2 H3A2 H 0.0265 -0.2811 0.1174 0.118 Uiso 0.50 1 calc PR A 2 H3A3 H 0.0937 -0.2095 0.1740 0.118 Uiso 0.50 1 calc PR A 2 C4A C 0.0943(3) -0.1413(3) 0.3061(2) 0.0488(10) Uani 0.50 1 d PD . 2 H4A1 H 0.1118 -0.2029 0.3330 0.059 Uiso 0.50 1 calc PR . 2 H4A2 H 0.1291 -0.1308 0.2773 0.059 Uiso 0.50 1 calc PR . 2 C5A C 0.1120(5) -0.0603(10) 0.3635(8) 0.064(4) Uani 0.50 1 d PD B 2 H5A1 H 0.1005 0.0018 0.3379 0.096 Uiso 0.50 1 calc PR B 2 H5A2 H 0.1709 -0.0628 0.3984 0.096 Uiso 0.50 1 calc PR B 2 H5A3 H 0.0761 -0.0681 0.3909 0.096 Uiso 0.50 1 calc PR B 2 C2B C 0.0533(3) -0.1632(4) 0.2057(3) 0.0592(12) Uani 0.50 1 d PD A 3 H2B1 H 0.1125 -0.1677 0.2412 0.071 Uiso 0.50 1 calc PR A 3 H2B2 H 0.0477 -0.1050 0.1751 0.071 Uiso 0.50 1 calc PR A 3 C3B C 0.0330(14) -0.2516(11) 0.1537(9) 0.077(4) Uani 0.50 1 d PD A 3 H3B1 H 0.0400 -0.3102 0.1832 0.115 Uiso 0.50 1 calc PR A 3 H3B2 H 0.0712 -0.2532 0.1280 0.115 Uiso 0.50 1 calc PR A 3 H3B3 H -0.0249 -0.2473 0.1169 0.115 Uiso 0.50 1 calc PR A 3 C4B C 0.0227(3) -0.0577(3) 0.2931(3) 0.0571(12) Uani 0.50 1 d PD A 3 H4B1 H -0.0174 -0.0455 0.3164 0.069 Uiso 0.50 1 calc PR A 3 H4B2 H 0.0184 -0.0041 0.2586 0.069 Uiso 0.50 1 calc PR A 3 C5B C 0.1127(7) -0.0615(10) 0.3543(8) 0.078(5) Uani 0.50 1 d PD A 3 H5B1 H 0.1194 -0.1195 0.3843 0.117 Uiso 0.50 1 calc PR A 3 H5B2 H 0.1226 -0.0048 0.3863 0.117 Uiso 0.50 1 calc PR A 3 H5B3 H 0.1531 -0.0625 0.3310 0.117 Uiso 0.50 1 calc PR A 3 N2 N 0.2500 -0.2500 0.0000 0.0611(8) Uani 1 2 d S . . C6A C 0.2531(3) -0.1886(4) 0.0668(2) 0.0524(11) Uani 0.50 1 d P C 4 H6A1 H 0.2615 -0.2325 0.1089 0.063 Uiso 0.50 1 calc PR C 4 H6A2 H 0.3030 -0.1467 0.0818 0.063 Uiso 0.50 1 calc PR C 4 C7A C 0.1782(9) -0.1260(10) 0.0558(5) 0.051(2) Uani 0.50 1 d P C 4 H7A1 H 0.1685 -0.0817 0.0143 0.077 Uiso 0.50 1 calc PR C 4 H7A2 H 0.1888 -0.0892 0.1013 0.077 Uiso 0.50 1 calc PR C 4 H7A3 H 0.1286 -0.1665 0.0446 0.077 Uiso 0.50 1 calc PR C 4 C8A C 0.1673(3) -0.3217(4) -0.0129(2) 0.0536(11) Uani 0.50 1 d PD C 4 H8A1 H 0.1167 -0.2808 -0.0282 0.064 Uiso 0.50 1 calc PR C 4 H8A2 H 0.1598 -0.3652 -0.0551 0.064 Uiso 0.50 1 calc PR C 4 C9A C 0.1708(5) -0.3829(7) 0.0527(5) 0.073(2) Uani 0.50 1 d PD C 4 H9A1 H 0.2151 -0.4311 0.0638 0.110 Uiso 0.50 1 calc PR C 4 H9A2 H 0.1168 -0.4152 0.0401 0.110 Uiso 0.50 1 calc PR C 4 H9A3 H 0.1826 -0.3419 0.0963 0.110 Uiso 0.50 1 calc PR C 4 C6B C 0.1767(3) -0.1886(4) -0.0237(2) 0.0578(12) Uani 0.50 1 d P C 5 H6B1 H 0.1265 -0.2296 -0.0364 0.069 Uiso 0.50 1 calc PR C 5 H6B2 H 0.1719 -0.1548 -0.0697 0.069 Uiso 0.50 1 calc PR C 5 C7B C 0.1761(10) -0.1134(11) 0.0332(6) 0.068(3) Uani 0.50 1 d P C 5 H7B1 H 0.1856 -0.1451 0.0806 0.102 Uiso 0.50 1 calc PR C 5 H7B2 H 0.1217 -0.0808 0.0147 0.102 Uiso 0.50 1 calc PR C 5 H7B3 H 0.2205 -0.0663 0.0408 0.102 Uiso 0.50 1 calc PR C 5 C8B C 0.2786(3) -0.2989(3) 0.0702(2) 0.0524(11) Uani 0.50 1 d PD C 5 H8B1 H 0.2877 -0.2523 0.1108 0.063 Uiso 0.50 1 calc PR C 5 H8B2 H 0.3323 -0.3318 0.0798 0.063 Uiso 0.50 1 calc PR C 5 C9B C 0.2123(4) -0.3722(7) 0.0676(5) 0.066(2) Uani 0.50 1 d PD C 5 H9B1 H 0.1587 -0.3395 0.0557 0.099 Uiso 0.50 1 calc PR C 5 H9B2 H 0.2296 -0.4038 0.1161 0.099 Uiso 0.50 1 calc PR C 5 H9B3 H 0.2061 -0.4203 0.0292 0.099 Uiso 0.50 1 calc PR C 5 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 0.0541(15) 0.0421(13) 0.0679(16) 0.0076(12) 0.0368(13) 0.0031(11) C2 0.0407(10) 0.0373(10) 0.0306(9) 0.0013(7) 0.0150(8) -0.0041(8) C21 0.0344(10) 0.0378(10) 0.0383(10) 0.0047(8) 0.0104(8) -0.0024(8) C22 0.0445(11) 0.0463(11) 0.0500(12) 0.0128(9) 0.0230(9) 0.0098(9) C23 0.0535(14) 0.0568(14) 0.0795(17) 0.0143(12) 0.0397(13) 0.0105(11) C24 0.0441(13) 0.0573(15) 0.100(2) 0.0123(14) 0.0323(13) 0.0122(11) C25 0.0420(12) 0.0525(14) 0.0719(16) 0.0151(12) 0.0058(11) 0.0095(10) C26 0.0468(12) 0.0437(12) 0.0463(11) 0.0090(9) 0.0087(9) -0.0016(9) B3 0.0593(16) 0.0493(14) 0.0667(17) 0.0112(12) 0.0345(14) 0.0117(12) B4 0.0450(13) 0.0623(16) 0.0372(11) -0.0110(11) 0.0142(10) 0.0080(11) B5 0.0630(16) 0.0470(13) 0.0345(11) -0.0009(10) 0.0165(11) -0.0007(12) B6 0.0776(19) 0.0448(14) 0.0465(14) -0.0081(11) 0.0240(13) 0.0062(13) B7 0.0489(14) 0.0754(18) 0.0416(13) 0.0097(12) 0.0240(11) 0.0248(13) B8 0.0511(13) 0.0349(11) 0.0507(13) 0.0012(10) 0.0286(11) -0.0018(10) B9 0.0676(17) 0.0469(14) 0.0542(14) 0.0086(11) 0.0406(13) 0.0135(12) B10 0.0464(14) 0.0526(15) 0.0567(15) -0.0054(12) 0.0236(12) 0.0033(11) B11 0.0763(18) 0.0473(13) 0.0397(12) 0.0074(10) 0.0338(12) 0.0086(12) N1 0.0441(13) 0.0320(11) 0.0355(11) 0.000 0.0151(10) 0.000 C2A 0.054(3) 0.056(3) 0.046(2) -0.023(2) 0.017(2) -0.004(2) C3A 0.073(6) 0.116(10) 0.055(5) -0.022(6) 0.034(5) 0.018(6) C4A 0.051(3) 0.039(2) 0.043(2) -0.0008(17) 0.0044(19) -0.0011(19) C5A 0.035(4) 0.074(9) 0.058(5) -0.026(5) -0.007(3) -0.004(4) C2B 0.074(3) 0.066(3) 0.050(3) -0.002(2) 0.038(2) 0.001(3) C3B 0.086(7) 0.090(7) 0.049(5) -0.020(5) 0.021(5) 0.008(6) C4B 0.044(2) 0.048(3) 0.062(3) -0.021(2) 0.004(2) 0.002(2) C5B 0.108(10) 0.044(7) 0.071(7) -0.023(5) 0.024(6) 0.003(6) N2 0.0740(19) 0.0613(17) 0.0320(13) -0.0118(12) 0.0043(12) 0.0291(15) C6A 0.062(3) 0.057(3) 0.034(2) -0.0152(19) 0.0157(19) 0.011(2) C7A 0.062(4) 0.051(3) 0.045(5) -0.003(4) 0.027(4) 0.015(3) C8A 0.058(3) 0.059(3) 0.041(2) -0.007(2) 0.017(2) 0.011(2) C9A 0.094(6) 0.068(4) 0.065(5) 0.008(4) 0.040(5) 0.020(5) C6B 0.054(3) 0.070(3) 0.042(2) -0.011(2) 0.011(2) 0.024(2) C7B 0.072(5) 0.079(7) 0.048(6) -0.015(5) 0.019(4) 0.027(4) C8B 0.058(3) 0.065(3) 0.034(2) 0.0007(19) 0.0171(19) 0.019(2) C9B 0.075(5) 0.078(4) 0.054(4) -0.002(3) 0.035(4) 0.013(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B1 C2 1.643(3) . ? B1 B3 1.711(4) . ? B1 B7 2.015(4) . ? B1 B6 2.023(4) . ? B1 B5 2.043(4) . ? B1 B4 2.057(4) . ? C2 C21 1.492(3) . ? C2 B4 1.584(3) . ? C2 B5 1.593(3) . ? C2 B8 1.676(3) . ? C21 C26 1.393(3) . ? C21 C22 1.397(3) . ? C22 C23 1.384(3) . ? C23 C24 1.397(4) . ? C24 C25 1.372(4) . ? C25 C26 1.387(3) . ? B3 B6 1.638(4) . ? B3 B7 1.667(4) . ? B3 B9 1.748(4) . ? B4 B10 1.789(4) . ? B4 B8 1.811(3) . ? B4 B7 1.849(4) . ? B5 B11 1.775(4) . ? B5 B8 1.789(4) . ? B5 B6 1.826(4) . ? B6 B11 1.792(4) . ? B6 B9 1.814(4) . ? B7 B9 1.784(3) . ? B7 B10 1.816(4) . ? B8 B10 1.781(4) . ? B8 B11 1.783(3) . ? B9 B10 1.776(4) . ? B9 B11 1.789(4) . ? B10 B11 1.817(4) . ? N1 C2A 1.499(4) . ? N1 C2A 1.499(4) 2 ? N1 C4B 1.500(5) . ? N1 C4B 1.500(5) 2 ? N1 C2B 1.514(4) 2 ? N1 C2B 1.514(4) . ? N1 C4A 1.574(4) . ? N1 C4A 1.574(4) 2 ? C2A C3A 1.547(9) . ? C4A C5A 1.535(9) . ? C4A C2A 1.997(6) 2 ? C2B C3B 1.546(9) . ? C4B C5B 1.548(9) . ? N2 C8B 1.434(4) 7_545 ? N2 C8B 1.434(4) . ? N2 C6B 1.451(4) 7_545 ? N2 C6B 1.451(4) . ? N2 C6A 1.546(4) 7_545 ? N2 C6A 1.546(4) . ? N2 C8A 1.688(5) 7_545 ? N2 C8A 1.688(5) . ? C6A C7A 1.512(15) . ? C8A C9A 1.523(8) . ? C6B C7B 1.533(14) . ? C8B C9B 1.527(7) . ? 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 C2 B1 B3 138.94(19) . . ? C2 B1 B7 100.75(17) . . ? B3 B1 B7 52.38(15) . . ? C2 B1 B6 100.75(16) . . ? B3 B1 B6 51.21(14) . . ? B7 B1 B6 82.65(15) . . ? C2 B1 B5 49.77(12) . . ? B3 B1 B5 102.88(17) . . ? B7 B1 B5 105.68(16) . . ? B6 B1 B5 53.38(13) . . ? C2 B1 B4 49.15(12) . . ? B3 B1 B4 104.42(18) . . ? B7 B1 B4 54.02(13) . . ? B6 B1 B4 105.85(16) . . ? B5 B1 B4 81.70(14) . . ? C21 C2 B4 122.75(16) . . ? C21 C2 B5 120.33(17) . . ? B4 C2 B5 115.15(17) . . ? C21 C2 B1 124.03(16) . . ? B4 C2 B1 79.18(17) . . ? B5 C2 B1 78.27(16) . . ? C21 C2 B8 124.46(16) . . ? B4 C2 B8 67.41(15) . . ? B5 C2 B8 66.30(14) . . ? B1 C2 B8 111.46(16) . . ? C26 C21 C22 118.25(19) . . ? C26 C21 C2 120.49(18) . . ? C22 C21 C2 121.24(17) . . ? C23 C22 C21 120.9(2) . . ? C22 C23 C24 119.8(2) . . ? C25 C24 C23 119.6(2) . . ? C24 C25 C26 120.6(2) . . ? C25 C26 C21 120.8(2) . . ? B6 B3 B7 107.6(2) . . ? B6 B3 B1 74.30(17) . . ? B7 B3 B1 73.22(17) . . ? B6 B3 B9 64.69(17) . . ? B7 B3 B9 62.94(16) . . ? B1 B3 B9 103.43(19) . . ? C2 B4 B10 107.30(17) . . ? C2 B4 B8 58.72(13) . . ? B10 B4 B8 59.30(14) . . ? C2 B4 B7 110.62(18) . . ? B10 B4 B7 59.86(14) . . ? B8 B4 B7 107.96(15) . . ? C2 B4 B1 51.67(13) . . ? B10 B4 B1 95.68(15) . . ? B8 B4 B1 90.10(15) . . ? B7 B4 B1 61.82(14) . . ? C2 B5 B11 108.16(18) . . ? C2 B5 B8 59.09(13) . . ? B11 B5 B8 60.04(14) . . ? C2 B5 B6 111.81(17) . . ? B11 B5 B6 59.67(15) . . ? B8 B5 B6 109.08(19) . . ? C2 B5 B1 51.95(12) . . ? B11 B5 B1 96.49(16) . . ? B8 B5 B1 91.19(15) . . ? B6 B5 B1 62.76(14) . . ? B3 B6 B11 111.9(2) . . ? B3 B6 B9 60.60(16) . . ? B11 B6 B9 59.47(15) . . ? B3 B6 B5 116.17(18) . . ? B11 B6 B5 58.74(15) . . ? B9 B6 B5 107.41(18) . . ? B3 B6 B1 54.49(14) . . ? B11 B6 B1 96.63(16) . . ? B9 B6 B1 89.91(16) . . ? B5 B6 B1 63.86(13) . . ? B3 B7 B9 60.76(15) . . ? B3 B7 B10 110.83(18) . . ? B9 B7 B10 59.11(14) . . ? B3 B7 B4 116.10(18) . . ? B9 B7 B4 107.79(17) . . ? B10 B7 B4 58.42(14) . . ? B3 B7 B1 54.39(14) . . ? B9 B7 B1 91.03(17) . . ? B10 B7 B1 96.30(16) . . ? B4 B7 B1 64.16(13) . . ? C2 B8 B10 103.69(16) . . ? C2 B8 B11 104.13(16) . . ? B10 B8 B11 61.31(14) . . ? C2 B8 B5 54.61(12) . . ? B10 B8 B5 104.61(17) . . ? B11 B8 B5 59.59(15) . . ? C2 B8 B4 53.87(12) . . ? B10 B8 B4 59.74(14) . . ? B11 B8 B4 104.88(16) . . ? B5 B8 B4 96.30(16) . . ? B3 B9 B10 108.97(17) . . ? B3 B9 B7 56.29(16) . . ? B10 B9 B7 61.34(15) . . ? B3 B9 B11 106.99(19) . . ? B10 B9 B11 61.29(15) . . ? B7 B9 B11 105.64(16) . . ? B3 B9 B6 54.71(15) . . ? B10 B9 B6 104.84(18) . . ? B7 B9 B6 95.62(17) . . ? B11 B9 B6 59.65(16) . . ? B9 B10 B8 112.27(19) . . ? B9 B10 B4 110.88(19) . . ? B8 B10 B4 60.96(14) . . ? B9 B10 B7 59.55(14) . . ? B8 B10 B7 110.77(17) . . ? B4 B10 B7 61.72(14) . . ? B9 B10 B11 59.70(15) . . ? B8 B10 B11 59.39(14) . . ? B4 B10 B11 104.36(18) . . ? B7 B10 B11 103.17(18) . . ? B5 B11 B8 60.38(14) . . ? B5 B11 B9 110.84(17) . . ? B8 B11 B9 111.59(17) . . ? B5 B11 B6 61.59(16) . . ? B8 B11 B6 110.91(17) . . ? B9 B11 B6 60.87(16) . . ? B5 B11 B10 103.71(16) . . ? B8 B11 B10 59.30(14) . . ? B9 B11 B10 59.01(15) . . ? B6 B11 B10 104.05(17) . . ? C2A N1 C2A 69.4(4) . 2 ? C2A N1 C4B 167.8(3) . . ? C2A N1 C4B 115.5(3) 2 . ? C2A N1 C4B 115.5(3) . 2 ? C2A N1 C4B 167.8(3) 2 2 ? C4B N1 C4B 62.3(4) . 2 ? C2A N1 C2B 109.1(3) . 2 ? C2A N1 C2B 58.1(3) 2 2 ? C4B N1 C2B 82.4(3) . 2 ? C4B N1 C2B 110.1(3) 2 2 ? C2A N1 C2B 58.1(3) . . ? C2A N1 C2B 109.1(3) 2 . ? C4B N1 C2B 110.1(3) . . ? C4B N1 C2B 82.4(3) 2 . ? C2B N1 C2B 165.9(4) 2 . ? C2A N1 C4A 106.4(3) . . ? C2A N1 C4A 81.0(3) 2 . ? C4B N1 C4A 64.8(2) . . ? C4B N1 C4A 107.1(3) 2 . ? C2B N1 C4A 108.5(3) 2 . ? C2B N1 C4A 72.7(3) . . ? C2A N1 C4A 81.0(3) . 2 ? C2A N1 C4A 106.4(3) 2 2 ? C4B N1 C4A 107.1(3) . 2 ? C4B N1 C4A 64.8(2) 2 2 ? C2B N1 C4A 72.7(3) 2 2 ? C2B N1 C4A 108.5(3) . 2 ? C4A N1 C4A 171.3(3) . 2 ? N1 C2A C3A 111.8(6) . . ? C5A C4A N1 114.6(4) . . ? C5A C4A C2A 119.8(7) . 2 ? N1 C4A C2A 47.85(18) . 2 ? N1 C2B C3B 116.4(7) . . ? N1 C4B C5B 111.4(5) . . ? C8B N2 C8B 180.0(4) 7_545 . ? C8B N2 C6B 120.8(3) 7_545 7_545 ? C8B N2 C6B 59.2(3) . 7_545 ? C8B N2 C6B 59.2(3) 7_545 . ? C8B N2 C6B 120.8(3) . . ? C6B N2 C6B 180.0(4) 7_545 . ? C8B N2 C6A 64.6(3) 7_545 7_545 ? C8B N2 C6A 115.4(3) . 7_545 ? C6B N2 C6A 70.9(2) 7_545 7_545 ? C6B N2 C6A 109.1(2) . 7_545 ? C8B N2 C6A 115.4(3) 7_545 . ? C8B N2 C6A 64.6(3) . . ? C6B N2 C6A 109.1(2) 7_545 . ? C6B N2 C6A 70.9(2) . . ? C6A N2 C6A 180.0(3) 7_545 . ? C8B N2 C8A 79.1(2) 7_545 7_545 ? C8B N2 C8A 100.9(2) . 7_545 ? C6B N2 C8A 73.2(3) 7_545 7_545 ? C6B N2 C8A 106.8(3) . 7_545 ? C6A N2 C8A 101.2(2) 7_545 7_545 ? C6A N2 C8A 78.8(2) . 7_545 ? C8B N2 C8A 100.9(2) 7_545 . ? C8B N2 C8A 79.1(2) . . ? C6B N2 C8A 106.8(3) 7_545 . ? C6B N2 C8A 73.2(3) . . ? C6A N2 C8A 78.8(2) 7_545 . ? C6A N2 C8A 101.2(2) . . ? C8A N2 C8A 180.0(4) 7_545 . ? C7A C6A N2 117.5(5) . . ? C9A C8A N2 117.4(4) . . ? N2 C6B C7B 115.5(6) . . ? N2 C8B C9B 108.5(4) . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.538 _refine_diff_density_min -0.169 _refine_diff_density_rms 0.038 data_tom007b _database_code_depnum_ccdc_archive 'CCDC 184220' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H36 B9 N' _chemical_formula_weight 327.74 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 18.6342(4) _cell_length_b 10.2871(2) _cell_length_c 23.4709(5) _cell_angle_alpha 90.00 _cell_angle_beta 109.0190(10) _cell_angle_gamma 90.00 _cell_volume 4253.57(15) _cell_formula_units_Z 8 _cell_measurement_temperature 150(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 0.74 _exptl_crystal_size_mid 0.52 _exptl_crystal_size_min 0.37 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.024 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1424 _exptl_absorpt_coefficient_mu 0.052 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9629 _exptl_absorpt_correction_T_max 0.9812 _exptl_absorpt_process_details ; Using multiple and symmetry-related data measurements via the program SORTAV See R.H. Blessing, Acta Cryst (1995), A51, 33-38 ; _exptl_special_details ; PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 15 degree phi range. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD area detector diffractometer' _diffrn_measurement_method ; Detector set at 30mm from sample with different 2theta offsets 1 degree phi exposures for chi=0 degree settings 1 degree omega exposures for chi=90 degree settings ; _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15050 _diffrn_reflns_av_R_equivalents 0.0832 _diffrn_reflns_av_sigmaI/netI 0.0577 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4128 _reflns_number_gt 3262 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1999)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1996)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1996)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 for Windows (Farrugia, 1997)' _computing_publication_material 'WC (Thornton-Pett, 2000)' _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^)+(0.0905P)^2^+2.2258P] 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 SHELXL _refine_ls_extinction_coef 0.004(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4128 _refine_ls_number_parameters 322 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0742 _refine_ls_R_factor_gt 0.0598 _refine_ls_wR_factor_ref 0.1763 _refine_ls_wR_factor_gt 0.1630 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 B1 B 0.38389(11) 0.37608(19) 0.37557(9) 0.0403(5) Uani 1 1 d . . . H1 H 0.3905(12) 0.4798(19) 0.3601(9) 0.056(5) Uiso 1 1 d . . . B2 B 0.32427(11) 0.2628(2) 0.32696(9) 0.0409(5) Uani 1 1 d . . . H2 H 0.2903(11) 0.2800(19) 0.2796(9) 0.057(6) Uiso 1 1 d . . . B3 B 0.42137(11) 0.2296(2) 0.35361(10) 0.0431(5) Uani 1 1 d . . . H3 H 0.4552(12) 0.220(2) 0.3214(10) 0.061(6) Uiso 1 1 d . . . B4 B 0.47063(11) 0.30535(19) 0.42509(9) 0.0421(5) Uani 1 1 d . . . H4 H 0.5258(11) 0.3515(19) 0.4323(9) 0.051(5) Uiso 1 1 d . . . B5 B 0.30350(11) 0.32028(18) 0.39245(8) 0.0382(4) Uani 1 1 d . . . H5 H 0.2568(11) 0.3851(19) 0.3936(9) 0.055(5) Uiso 1 1 d . . . C6 C 0.29224(8) 0.17567(15) 0.37554(7) 0.0342(4) Uani 1 1 d . . . C61 C 0.21621(8) 0.11250(15) 0.36017(7) 0.0342(4) Uani 1 1 d . . . C62 C 0.19019(9) 0.02467(17) 0.31246(7) 0.0410(4) Uani 1 1 d . . . H62 H 0.2207 0.0075 0.2878 0.049 Uiso 1 1 calc R . . C63 C 0.12081(9) -0.03807(18) 0.30024(8) 0.0451(4) Uani 1 1 d . . . H63 H 0.1043 -0.0971 0.2674 0.054 Uiso 1 1 calc R . . C64 C 0.07549(9) -0.01482(17) 0.33584(8) 0.0426(4) Uani 1 1 d . . . H64 H 0.0284 -0.0586 0.3279 0.051 Uiso 1 1 calc R . . C65 C 0.09971(9) 0.07262(18) 0.38281(7) 0.0411(4) Uani 1 1 d . . . H65 H 0.0688 0.0897 0.4072 0.049 Uiso 1 1 calc R . . C66 C 0.16885(9) 0.13584(17) 0.39473(7) 0.0386(4) Uani 1 1 d . . . H66 H 0.1844 0.1963 0.4271 0.046 Uiso 1 1 calc R . . B7 B 0.35763(11) 0.10893(19) 0.36032(10) 0.0415(5) Uani 1 1 d . . . H7 H 0.3490(11) 0.012(2) 0.3343(9) 0.058(6) Uiso 1 1 d . . . B8 B 0.45585(11) 0.1345(2) 0.41934(11) 0.0477(5) Uani 1 1 d . . . H8 H 0.5025(12) 0.058(2) 0.4241(9) 0.066(6) Uiso 1 1 d . . . H89 H 0.4284(12) 0.111(2) 0.4596(9) 0.061(6) Uiso 1 1 d . . . B9 B 0.45552(12) 0.2240(2) 0.48334(10) 0.0481(5) Uani 1 1 d . . . H9 H 0.4937(12) 0.214(2) 0.5291(10) 0.063(6) Uiso 1 1 d . . . H910 H 0.3915(12) 0.263(2) 0.4837(10) 0.066(6) Uiso 1 1 d . . . B10 B 0.39865(12) 0.3605(2) 0.45329(9) 0.0428(5) Uani 1 1 d . . . H10 H 0.4011(11) 0.447(2) 0.4834(8) 0.051(5) Uiso 1 1 d . . . N1 N 0.2500 0.2500 0.0000 0.0368(5) Uani 1 2 d S . . C11A C 0.18444(19) 0.1927(4) 0.01676(17) 0.0458(9) Uani 0.507(3) 1 d P A 1 H11A H 0.1799 0.0991 0.0063 0.055 Uiso 0.507(3) 1 calc PR A 1 H11B H 0.1368 0.2357 -0.0076 0.055 Uiso 0.507(3) 1 calc PR A 1 C12A C 0.1932(8) 0.2074(13) 0.0837(6) 0.066(3) Uani 0.507(3) 1 d P A 1 H12A H 0.2401 0.1646 0.1081 0.099 Uiso 0.507(3) 1 calc PR A 1 H12B H 0.1498 0.1672 0.0916 0.099 Uiso 0.507(3) 1 calc PR A 1 H12C H 0.1955 0.2999 0.0941 0.099 Uiso 0.507(3) 1 calc PR A 1 C13A C 0.32311(19) 0.1800(4) 0.03074(17) 0.0460(9) Uani 0.507(3) 1 d P A 1 H13A H 0.3371 0.1920 0.0749 0.055 Uiso 0.507(3) 1 calc PR A 1 H13B H 0.3640 0.2180 0.0176 0.055 Uiso 0.507(3) 1 calc PR A 1 C11B C 0.2735(2) 0.2737(3) 0.07016(15) 0.0420(9) Uani 0.493(3) 1 d P A 2 H11C H 0.3203 0.2237 0.0903 0.050 Uiso 0.493(3) 1 calc PR A 2 H11D H 0.2855 0.3670 0.0783 0.050 Uiso 0.493(3) 1 calc PR A 2 C12B C 0.2139(8) 0.2359(13) 0.0975(7) 0.064(3) Uani 0.493(3) 1 d P A 2 H12D H 0.1667 0.2827 0.0770 0.096 Uiso 0.493(3) 1 calc PR A 2 H12E H 0.2314 0.2584 0.1404 0.096 Uiso 0.493(3) 1 calc PR A 2 H12F H 0.2048 0.1421 0.0929 0.096 Uiso 0.493(3) 1 calc PR A 2 C13B C 0.23948(19) 0.1093(3) -0.01332(17) 0.0413(9) Uani 0.493(3) 1 d P A 2 H13C H 0.2214 0.0964 -0.0575 0.050 Uiso 0.493(3) 1 calc PR A 2 H13D H 0.2001 0.0753 0.0026 0.050 Uiso 0.493(3) 1 calc PR A 2 C14 C 0.31627(12) 0.02967(19) 0.01567(10) 0.0579(5) Uani 1 1 d . . . H14A H 0.2644 0.0098 -0.0100 0.087 Uiso 0.507(3) 1 calc PR A 1 H14B H 0.3282 -0.0203 0.0532 0.087 Uiso 0.507(3) 1 calc PR A 1 H14C H 0.3520 0.0064 -0.0055 0.087 Uiso 0.507(3) 1 calc PR A 1 H14D H 0.3588 0.0780 0.0100 0.087 Uiso 0.493(3) 1 d PR A 2 H14E H 0.3120 -0.0552 -0.0041 0.087 Uiso 0.493(3) 1 d PR A 2 H14F H 0.3252 0.0172 0.0588 0.087 Uiso 0.493(3) 1 d PR A 2 N2 N 0.0000 0.38450(17) 0.2500 0.0348(5) Uani 1 2 d S . . C21A C 0.07647(19) 0.4043(4) 0.30270(15) 0.0457(9) Uani 0.496(3) 1 d P B 1 H21A H 0.0643 0.4183 0.3403 0.055 Uiso 0.496(3) 1 calc PR B 1 H21B H 0.1059 0.3226 0.3077 0.055 Uiso 0.496(3) 1 calc PR B 1 C23A C 0.01738(19) 0.3696(3) 0.19163(14) 0.0381(8) Uani 0.496(3) 1 d P B 1 H23A H -0.0313 0.3550 0.1590 0.046 Uiso 0.496(3) 1 calc PR B 1 H23B H 0.0379 0.4535 0.1832 0.046 Uiso 0.496(3) 1 calc PR B 1 C21B C 0.04706(18) 0.5022(3) 0.25169(15) 0.0377(8) Uani 0.504(3) 1 d P B 2 H21C H 0.0523 0.5126 0.2113 0.045 Uiso 0.504(3) 1 calc PR B 2 H21D H 0.0183 0.5783 0.2584 0.045 Uiso 0.504(3) 1 calc PR B 2 C23B C 0.0349(2) 0.2610(3) 0.23749(16) 0.0414(9) Uani 0.504(3) 1 d P B 2 H23C H -0.0048 0.1928 0.2271 0.050 Uiso 0.504(3) 1 calc PR B 2 H23D H 0.0745 0.2335 0.2751 0.050 Uiso 0.504(3) 1 calc PR B 2 C22 C 0.12407(11) 0.5083(2) 0.29665(9) 0.0647(6) Uani 1 1 d . . . H22A H 0.1443 0.4886 0.2640 0.097 Uiso 0.496(3) 1 calc PR B 1 H22B H 0.1661 0.5189 0.3344 0.097 Uiso 0.496(3) 1 calc PR B 1 H22C H 0.0945 0.5889 0.2874 0.097 Uiso 0.496(3) 1 calc PR B 1 H22D H 0.1359 0.4260 0.3188 0.097 Uiso 0.504(3) 1 d PR B 2 H22E H 0.1263 0.5794 0.3249 0.097 Uiso 0.504(3) 1 d PR B 2 H22F H 0.1611 0.5240 0.2759 0.097 Uiso 0.504(3) 1 d PR B 2 C24 C 0.07031(13) 0.26649(18) 0.18746(10) 0.0547(5) Uani 1 1 d . . . H24A H 0.1206 0.2836 0.2166 0.082 Uiso 0.496(3) 1 calc PR B 1 H24B H 0.0737 0.2650 0.1467 0.082 Uiso 0.496(3) 1 calc PR B 1 H24C H 0.0518 0.1822 0.1964 0.082 Uiso 0.496(3) 1 calc PR B 1 H24D H 0.0497 0.3409 0.1611 0.082 Uiso 0.504(3) 1 d PR B 2 H24E H 0.0588 0.1861 0.1638 0.082 Uiso 0.504(3) 1 d PR B 2 H24F H 0.1254 0.2760 0.2054 0.082 Uiso 0.504(3) 1 d PR B 2 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 0.0447(11) 0.0326(10) 0.0426(10) 0.0022(8) 0.0129(8) -0.0036(8) B2 0.0422(10) 0.0418(11) 0.0387(10) 0.0001(8) 0.0134(8) -0.0092(8) B3 0.0416(11) 0.0410(11) 0.0528(11) -0.0079(9) 0.0236(9) -0.0105(8) B4 0.0381(10) 0.0357(10) 0.0518(11) 0.0002(8) 0.0135(8) -0.0045(8) B5 0.0365(9) 0.0332(10) 0.0441(10) -0.0013(8) 0.0119(8) 0.0029(8) C6 0.0334(8) 0.0320(8) 0.0376(8) 0.0025(6) 0.0123(6) -0.0006(6) C61 0.0313(8) 0.0313(8) 0.0396(8) 0.0042(6) 0.0112(6) 0.0019(6) C62 0.0367(9) 0.0420(9) 0.0463(9) -0.0027(7) 0.0160(7) -0.0008(7) C63 0.0392(9) 0.0458(10) 0.0471(9) -0.0054(8) 0.0097(7) -0.0043(8) C64 0.0324(8) 0.0443(10) 0.0478(9) 0.0070(7) 0.0084(7) -0.0043(7) C65 0.0337(8) 0.0479(10) 0.0435(9) 0.0069(7) 0.0149(7) 0.0027(7) C66 0.0355(8) 0.0394(9) 0.0409(8) 0.0010(7) 0.0126(7) 0.0017(7) B7 0.0376(10) 0.0349(10) 0.0566(11) -0.0065(8) 0.0215(9) -0.0049(8) B8 0.0351(10) 0.0355(10) 0.0735(14) 0.0024(9) 0.0192(10) 0.0005(8) B9 0.0386(10) 0.0469(12) 0.0522(12) 0.0091(9) 0.0060(9) -0.0046(9) B10 0.0454(11) 0.0392(10) 0.0433(10) -0.0030(8) 0.0140(8) -0.0034(8) N1 0.0300(9) 0.0324(10) 0.0477(11) -0.0039(8) 0.0122(8) -0.0035(8) C11A 0.0351(18) 0.0420(19) 0.065(2) -0.0060(17) 0.0222(16) -0.0078(14) C12A 0.084(7) 0.045(6) 0.089(7) 0.004(4) 0.056(6) 0.002(4) C13A 0.0328(17) 0.044(2) 0.056(2) -0.0076(16) 0.0064(15) 0.0015(14) C11B 0.046(2) 0.0347(18) 0.0425(18) -0.0063(14) 0.0107(15) -0.0019(15) C12B 0.095(9) 0.042(6) 0.076(6) 0.000(4) 0.056(6) -0.006(4) C13B 0.0411(18) 0.0270(17) 0.056(2) -0.0106(14) 0.0164(16) -0.0090(13) C14 0.0670(13) 0.0414(11) 0.0681(12) 0.0012(9) 0.0258(10) 0.0133(9) N2 0.0387(10) 0.0287(10) 0.0368(10) 0.000 0.0120(8) 0.000 C21A 0.0401(19) 0.049(2) 0.0411(18) 0.0099(15) 0.0042(15) 0.0018(16) C23A 0.0430(18) 0.0366(18) 0.0400(17) -0.0023(13) 0.0207(15) -0.0033(14) C21B 0.0386(18) 0.0274(16) 0.0465(18) -0.0001(13) 0.0129(14) -0.0041(13) C23B 0.054(2) 0.0255(16) 0.0508(19) -0.0018(13) 0.0255(16) 0.0036(14) C22 0.0448(11) 0.0862(16) 0.0544(11) -0.0031(11) 0.0042(9) -0.0143(10) C24 0.0723(13) 0.0396(10) 0.0650(12) -0.0034(9) 0.0399(11) 0.0028(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 B1 B2 1.751(3) . ? B1 B10 1.761(3) . ? B1 B5 1.765(3) . ? B1 B3 1.805(3) . ? B1 B4 1.808(3) . ? B1 H1 1.15(2) . ? B2 C6 1.704(2) . ? B2 B3 1.745(3) . ? B2 B7 1.786(3) . ? B2 B5 1.803(3) . ? B2 H2 1.10(2) . ? B3 B7 1.760(3) . ? B3 B8 1.762(3) . ? B3 B4 1.806(3) . ? B3 H3 1.14(2) . ? B4 B9 1.703(3) . ? B4 B10 1.771(3) . ? B4 B8 1.777(3) . ? B4 H4 1.095(19) . ? B5 C6 1.536(2) . ? B5 B10 1.925(3) . ? B5 H5 1.10(2) . ? C6 C61 1.492(2) . ? C6 B7 1.539(2) . ? C61 C62 1.397(2) . ? C61 C66 1.400(2) . ? C62 C63 1.389(2) . ? C62 H62 0.9500 . ? C63 C64 1.389(2) . ? C63 H63 0.9500 . ? C64 C65 1.380(2) . ? C64 H64 0.9500 . ? C65 C66 1.388(2) . ? C65 H65 0.9500 . ? C66 H66 0.9500 . ? B7 B8 1.920(3) . ? B7 H7 1.15(2) . ? B8 B9 1.763(3) . ? B8 H8 1.15(2) . ? B8 H89 1.23(2) . ? B9 B10 1.762(3) . ? B9 H89 1.31(2) . ? B9 H9 1.08(2) . ? B9 H910 1.26(2) . ? B10 H910 1.26(2) . ? B10 H10 1.13(2) . ? N1 C13B 1.480(3) 7 ? N1 C13B 1.480(3) . ? N1 C13A 1.502(3) . ? N1 C13A 1.502(3) 7 ? N1 C11A 1.519(3) 7 ? N1 C11A 1.519(3) . ? N1 C11B 1.579(3) 7 ? N1 C11B 1.579(3) . ? C11A C12A 1.532(14) . ? C11A H11A 0.9900 . ? C11A H11B 0.9900 . ? C12A H12A 0.9800 . ? C12A H12B 0.9800 . ? C12A H12C 0.9800 . ? C13A C14 1.582(4) . ? C13A H13A 0.9900 . ? C13A H13B 0.9900 . ? C13A H14D 1.4100 . ? C11B C12B 1.502(13) . ? C11B H11C 0.9900 . ? C11B H11D 0.9900 . ? C12B H12D 0.9800 . ? C12B H12E 0.9800 . ? C12B H12F 0.9800 . ? C13B C14 1.596(4) . ? C13B H13C 0.9900 . ? C13B H13D 0.9900 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C14 H14D 0.9800 . ? C14 H14E 0.9800 . ? C14 H14F 0.9800 . ? N2 C21B 1.488(3) . ? N2 C21B 1.488(3) 2 ? N2 C23B 1.499(3) 2 ? N2 C23B 1.499(3) . ? N2 C23A 1.515(3) . ? N2 C23A 1.515(3) 2 ? N2 C21A 1.566(3) . ? N2 C21A 1.566(3) 2 ? C21A C22 1.426(4) . ? C21A H21A 0.9900 . ? C21A H21B 0.9900 . ? C21A H22D 1.0699 . ? C23A C24 1.473(4) . ? C23A H23A 0.9900 . ? C23A H23B 0.9900 . ? C23A H24D 1.1157 . ? C21B C22 1.480(4) . ? C21B H21C 0.9900 . ? C21B H21D 0.9900 . ? C23B C24 1.525(4) . ? C23B H23C 0.9900 . ? C23B H23D 0.9900 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C22 H22D 0.9800 . ? C22 H22E 0.9800 . ? C22 H22F 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C24 H24D 0.9800 . ? C24 H24E 0.9800 . ? C24 H24F 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 B2 B1 B10 117.79(14) . . ? B2 B1 B5 61.67(11) . . ? B10 B1 B5 66.15(11) . . ? B2 B1 B3 58.74(11) . . ? B10 B1 B3 106.00(14) . . ? B5 B1 B3 103.19(13) . . ? B2 B1 B4 113.30(14) . . ? B10 B1 B4 59.50(11) . . ? B5 B1 B4 111.78(13) . . ? B3 B1 B4 59.97(11) . . ? B2 B1 H1 121.5(10) . . ? B10 B1 H1 114.6(10) . . ? B5 B1 H1 124.1(10) . . ? B3 B1 H1 126.5(10) . . ? B4 B1 H1 114.4(10) . . ? C6 B2 B3 101.86(13) . . ? C6 B2 B1 101.55(13) . . ? B3 B2 B1 62.17(11) . . ? C6 B2 B7 52.26(10) . . ? B3 B2 B7 59.80(11) . . ? B1 B2 B7 104.35(14) . . ? C6 B2 B5 51.87(10) . . ? B3 B2 B5 104.13(13) . . ? B1 B2 B5 59.55(11) . . ? B7 B2 B5 93.30(12) . . ? C6 B2 H2 123.3(11) . . ? B3 B2 H2 125.6(11) . . ? B1 B2 H2 125.8(11) . . ? B7 B2 H2 126.1(11) . . ? B5 B2 H2 126.6(11) . . ? B2 B3 B7 61.25(11) . . ? B2 B3 B8 117.53(14) . . ? B7 B3 B8 66.06(12) . . ? B2 B3 B1 59.09(11) . . ? B7 B3 B1 103.18(13) . . ? B8 B3 B1 106.14(14) . . ? B2 B3 B4 113.73(14) . . ? B7 B3 B4 112.00(14) . . ? B8 B3 B4 59.73(12) . . ? B1 B3 B4 60.09(11) . . ? B2 B3 H3 121.0(11) . . ? B7 B3 H3 122.4(11) . . ? B8 B3 H3 114.3(11) . . ? B1 B3 H3 127.8(11) . . ? B4 B3 H3 115.5(11) . . ? B9 B4 B10 60.92(12) . . ? B9 B4 B8 60.86(13) . . ? B10 B4 B8 103.17(14) . . ? B9 B4 B3 111.53(14) . . ? B10 B4 B3 105.54(14) . . ? B8 B4 B3 58.90(12) . . ? B9 B4 B1 111.52(15) . . ? B10 B4 B1 58.94(11) . . ? B8 B4 B1 105.38(14) . . ? B3 B4 B1 59.94(11) . . ? B9 B4 H4 118.8(10) . . ? B10 B4 H4 126.3(10) . . ? B8 B4 H4 123.7(10) . . ? B3 B4 H4 119.8(10) . . ? B1 B4 H4 121.5(10) . . ? C6 B5 B1 108.14(13) . . ? C6 B5 B2 60.76(10) . . ? B1 B5 B2 58.78(11) . . ? C6 B5 B10 114.54(14) . . ? B1 B5 B10 56.81(10) . . ? B2 B5 B10 107.54(13) . . ? C6 B5 H5 123.3(10) . . ? B1 B5 H5 122.8(10) . . ? B2 B5 H5 127.5(10) . . ? B10 B5 H5 113.2(10) . . ? C61 C6 B5 121.55(14) . . ? C61 C6 B7 120.72(14) . . ? B5 C6 B7 116.11(14) . . ? C61 C6 B2 125.41(13) . . ? B5 C6 B2 67.37(12) . . ? B7 C6 B2 66.60(12) . . ? C62 C61 C66 117.10(14) . . ? C62 C61 C6 121.98(14) . . ? C66 C61 C6 120.88(14) . . ? C63 C62 C61 121.51(16) . . ? C63 C62 H62 119.2 . . ? C61 C62 H62 119.2 . . ? C64 C63 C62 120.23(16) . . ? C64 C63 H63 119.9 . . ? C62 C63 H63 119.9 . . ? C65 C64 C63 119.23(15) . . ? C65 C64 H64 120.4 . . ? C63 C64 H64 120.4 . . ? C64 C65 C66 120.46(15) . . ? C64 C65 H65 119.8 . . ? C66 C65 H65 119.8 . . ? C65 C66 C61 121.45(16) . . ? C65 C66 H66 119.3 . . ? C61 C66 H66 119.3 . . ? C6 B7 B3 108.33(14) . . ? C6 B7 B2 61.14(11) . . ? B3 B7 B2 58.94(11) . . ? C6 B7 B8 114.34(14) . . ? B3 B7 B8 57.00(11) . . ? B2 B7 B8 107.97(13) . . ? C6 B7 H7 121.6(10) . . ? B3 B7 H7 122.9(10) . . ? B2 B7 H7 124.3(10) . . ? B8 B7 H7 116.0(10) . . ? B3 B8 B9 110.77(15) . . ? B3 B8 B4 61.36(11) . . ? B9 B8 B4 57.49(12) . . ? B3 B8 B7 56.94(11) . . ? B9 B8 B7 114.78(14) . . ? B4 B8 B7 106.16(14) . . ? B3 B8 H8 120.9(10) . . ? B9 B8 H8 119.1(10) . . ? B4 B8 H8 125.1(11) . . ? B7 B8 H8 119.3(11) . . ? B3 B8 H89 130.8(10) . . ? B9 B8 H89 48.1(10) . . ? B4 B8 H89 103.0(10) . . ? B7 B8 H89 89.5(10) . . ? H8 B8 H89 106.4(15) . . ? B4 B9 B10 61.46(12) . . ? B4 B9 B8 61.65(13) . . ? B10 B9 B8 104.10(15) . . ? B4 B9 H89 103.5(9) . . ? B10 B9 H89 115.8(9) . . ? B8 B9 H89 44.4(9) . . ? B4 B9 H9 127.9(12) . . ? B10 B9 H9 125.8(12) . . ? B8 B9 H9 127.9(12) . . ? H89 B9 H9 112.3(15) . . ? B4 B9 H910 104.6(10) . . ? B10 B9 H910 45.7(10) . . ? B8 B9 H910 116.0(10) . . ? H89 B9 H910 92.9(13) . . ? H9 B9 H910 109.8(15) . . ? B1 B10 B9 110.95(15) . . ? B1 B10 B4 61.57(11) . . ? B9 B10 B4 57.62(12) . . ? B1 B10 B5 57.03(10) . . ? B9 B10 B5 114.45(14) . . ? B4 B10 B5 106.29(13) . . ? B1 B10 H910 130.4(10) . . ? B9 B10 H910 45.7(10) . . ? B4 B10 H910 100.9(10) . . ? B5 B10 H910 90.4(10) . . ? B1 B10 H10 122.7(10) . . ? B9 B10 H10 118.7(10) . . ? B4 B10 H10 127.4(10) . . ? B5 B10 H10 118.3(10) . . ? H910 B10 H10 105.1(14) . . ? C13B N1 C13B 180.0(3) 7 . ? C13B N1 C13A 109.30(19) 7 . ? C13B N1 C13A 70.70(19) . . ? C13B N1 C13A 70.70(19) 7 7 ? C13B N1 C13A 109.30(19) . 7 ? C13A N1 C13A 180.0(4) . 7 ? C13B N1 C11A 67.22(19) 7 7 ? C13B N1 C11A 112.78(19) . 7 ? C13A N1 C11A 68.3(2) . 7 ? C13A N1 C11A 111.7(2) 7 7 ? C13B N1 C11A 112.78(19) 7 . ? C13B N1 C11A 67.22(19) . . ? C13A N1 C11A 111.7(2) . . ? C13A N1 C11A 68.3(2) 7 . ? C11A N1 C11A 180.0(2) 7 . ? C13B N1 C11B 110.11(19) 7 7 ? C13B N1 C11B 69.89(19) . 7 ? C13A N1 C11B 109.06(19) . 7 ? C13A N1 C11B 70.94(19) 7 7 ? C11A N1 C11B 76.27(19) 7 7 ? C11A N1 C11B 103.73(19) . 7 ? C13B N1 C11B 69.89(19) 7 . ? C13B N1 C11B 110.11(19) . . ? C13A N1 C11B 70.94(19) . . ? C13A N1 C11B 109.06(19) 7 . ? C11A N1 C11B 103.73(19) 7 . ? C11A N1 C11B 76.27(19) . . ? C11B N1 C11B 180.00(8) 7 . ? N1 C11A C12A 113.6(5) . . ? N1 C11A H11A 108.8 . . ? C12A C11A H11A 108.8 . . ? N1 C11A H11B 108.8 . . ? C12A C11A H11B 108.8 . . ? H11A C11A H11B 107.7 . . ? N1 C13A C14 111.5(2) . . ? N1 C13A H13A 109.3 . . ? C14 C13A H13A 109.3 . . ? N1 C13A H13B 109.3 . . ? C14 C13A H13B 109.3 . . ? H13A C13A H13B 108.0 . . ? N1 C13A H14D 130.3 . . ? C14 C13A H14D 37.7 . . ? H13A C13A H14D 117.4 . . ? H13B C13A H14D 72.0 . . ? C12B C11B N1 114.4(5) . . ? C12B C11B H11C 108.7 . . ? N1 C11B H11C 108.7 . . ? C12B C11B H11D 108.7 . . ? N1 C11B H11D 108.7 . . ? H11C C11B H11D 107.6 . . ? C11B C12B H12D 109.5 . . ? C11B C12B H12E 109.5 . . ? H12D C12B H12E 109.5 . . ? C11B C12B H12F 109.5 . . ? H12D C12B H12F 109.5 . . ? H12E C12B H12F 109.5 . . ? N1 C13B C14 111.9(2) . . ? N1 C13B H13C 109.2 . . ? C14 C13B H13C 109.2 . . ? N1 C13B H13D 109.2 . . ? C14 C13B H13D 109.2 . . ? H13C C13B H13D 107.9 . . ? C13A C14 C13B 65.75(18) . . ? C13A C14 H14A 109.5 . . ? C13B C14 H14A 43.7 . . ? C13A C14 H14B 109.5 . . ? C13B C14 H14B 124.2 . . ? H14A C14 H14B 109.5 . . ? C13A C14 H14C 109.5 . . ? C13B C14 H14C 124.9 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13A C14 H14D 61.6 . . ? C13B C14 H14D 109.5 . . ? H14A C14 H14D 134.6 . . ? H14B C14 H14D 115.5 . . ? H14C C14 H14D 49.0 . . ? C13A C14 H14E 164.8 . . ? C13B C14 H14E 109.4 . . ? H14A C14 H14E 67.0 . . ? H14B C14 H14E 85.3 . . ? H14C C14 H14E 60.4 . . ? H14D C14 H14E 109.5 . . ? C13A C14 H14F 85.6 . . ? C13B C14 H14F 109.6 . . ? H14A C14 H14F 114.2 . . ? H14B C14 H14F 24.6 . . ? H14C C14 H14F 125.2 . . ? H14D C14 H14F 109.5 . . ? H14E C14 H14F 109.5 . . ? C21B N2 C21B 71.1(3) . 2 ? C21B N2 C23B 166.86(19) . 2 ? C21B N2 C23B 113.95(18) 2 2 ? C21B N2 C23B 113.95(18) . . ? C21B N2 C23B 166.86(19) 2 . ? C23B N2 C23B 64.1(3) 2 . ? C21B N2 C23A 78.97(18) . . ? C21B N2 C23A 110.9(2) 2 . ? C23B N2 C23A 109.0(2) 2 . ? C23B N2 C23A 60.21(18) . . ? C21B N2 C23A 110.9(2) . 2 ? C21B N2 C23A 78.97(18) 2 2 ? C23B N2 C23A 60.21(18) 2 2 ? C23B N2 C23A 109.0(2) . 2 ? C23A N2 C23A 168.4(3) . 2 ? C21B N2 C21A 59.77(18) . . ? C21B N2 C21A 107.0(2) 2 . ? C23B N2 C21A 107.2(2) 2 . ? C23B N2 C21A 85.7(2) . . ? C23A N2 C21A 108.65(19) . . ? C23A N2 C21A 72.93(19) 2 . ? C21B N2 C21A 107.0(2) . 2 ? C21B N2 C21A 59.77(18) 2 2 ? C23B N2 C21A 85.7(2) 2 2 ? C23B N2 C21A 107.2(2) . 2 ? C23A N2 C21A 72.93(19) . 2 ? C23A N2 C21A 108.65(19) 2 2 ? C21A N2 C21A 165.1(3) . 2 ? C22 C21A N2 117.0(2) . . ? C22 C21A H21A 108.0 . . ? N2 C21A H21A 108.0 . . ? C22 C21A H21B 108.0 . . ? N2 C21A H21B 108.0 . . ? H21A C21A H21B 107.3 . . ? C22 C21A H22D 43.4 . . ? N2 C21A H22D 151.1 . . ? H21A C21A H22D 99.5 . . ? H21B C21A H22D 70.4 . . ? C24 C23A N2 118.6(2) . . ? C24 C23A H23A 107.7 . . ? N2 C23A H23A 107.7 . . ? C24 C23A H23B 107.7 . . ? N2 C23A H23B 107.7 . . ? H23A C23A H23B 107.1 . . ? C24 C23A H24D 41.7 . . ? N2 C23A H24D 157.9 . . ? H23A C23A H24D 90.8 . . ? H23B C23A H24D 77.1 . . ? C22 C21B N2 118.6(2) . . ? C22 C21B H21C 107.7 . . ? N2 C21B H21C 107.7 . . ? C22 C21B H21D 107.7 . . ? N2 C21B H21D 107.7 . . ? H21C C21B H21D 107.1 . . ? N2 C23B C24 116.3(2) . . ? N2 C23B H23C 108.2 . . ? C24 C23B H23C 108.2 . . ? N2 C23B H23D 108.2 . . ? C24 C23B H23D 108.2 . . ? H23C C23B H23D 107.4 . . ? C21A C22 C21B 63.21(19) . . ? C21A C22 H22A 109.5 . . ? C21B C22 H22A 87.9 . . ? C21A C22 H22B 109.5 . . ? C21B C22 H22B 162.6 . . ? H22A C22 H22B 109.5 . . ? C21A C22 H22C 109.5 . . ? C21B C22 H22C 62.1 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21A C22 H22D 48.6 . . ? C21B C22 H22D 109.8 . . ? H22A C22 H22D 99.1 . . ? H22B C22 H22D 69.0 . . ? H22C C22 H22D 149.5 . . ? C21A C22 H22E 112.5 . . ? C21B C22 H22E 109.4 . . ? H22A C22 H22E 138.0 . . ? H22B C22 H22E 57.2 . . ? H22C C22 H22E 54.2 . . ? H22D C22 H22E 109.5 . . ? C21A C22 H22F 137.3 . . ? C21B C22 H22F 109.2 . . ? H22A C22 H22F 29.7 . . ? H22B C22 H22F 86.9 . . ? H22C C22 H22F 100.8 . . ? H22D C22 H22F 109.5 . . ? H22E C22 H22F 109.5 . . ? C23A C24 C23B 60.54(18) . . ? C23A C24 H24A 109.5 . . ? C23B C24 H24A 91.5 . . ? C23A C24 H24B 109.5 . . ? C23B C24 H24B 159.0 . . ? H24A C24 H24B 109.5 . . ? C23A C24 H24C 109.5 . . ? C23B C24 H24C 62.1 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C23A C24 H24D 49.2 . . ? C23B C24 H24D 109.7 . . ? H24A C24 H24D 112.8 . . ? H24B C24 H24D 62.1 . . ? H24C C24 H24D 137.1 . . ? C23A C24 H24E 128.2 . . ? C23B C24 H24E 109.6 . . ? H24A C24 H24E 122.0 . . ? H24B C24 H24E 60.3 . . ? H24C C24 H24E 49.3 . . ? H24D C24 H24E 109.5 . . ? C23A C24 H24F 122.0 . . ? C23B C24 H24F 109.2 . . ? H24A C24 H24F 18.4 . . ? H24B C24 H24F 91.8 . . ? H24C C24 H24F 112.9 . . ? H24D C24 H24F 109.5 . . ? H24E C24 H24F 109.5 . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.269 _refine_diff_density_min -0.207 _refine_diff_density_rms 0.037 data_afx65a _database_code_depnum_ccdc_archive 'CCDC 184221' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H34 B9 N' _chemical_formula_weight 325.72 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 10.0208(2) _cell_length_b 13.6557(3) _cell_length_c 15.4382(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2112.58(7) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.024 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.052 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9781 _exptl_absorpt_correction_T_max 0.9872 _exptl_absorpt_process_details ; Using multiple and symmetry-related data measurements via the program SORTAV See R.H. Blessing, Acta Cryst (1995), A51, 33-38 ; _exptl_special_details ; PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 15 degree phi range. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD area detector diffractometer' _diffrn_measurement_method ; Detector set at 30mm from sample with different 2theta offsets 1 degree phi exposures for chi=0 degree settings 1 degree omega exposures for chi=90 degree settings ; _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19178 _diffrn_reflns_av_R_equivalents 0.0493 _diffrn_reflns_av_sigmaI/netI 0.0321 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.26 _diffrn_reflns_theta_max 25.99 _reflns_number_total 4139 _reflns_number_gt 3706 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1999)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1996)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1996)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; ORTEP3 for Windows (Farrugia, 1997) XSeed (Barbour, 2001) ; _computing_publication_material 'WC (Thornton-Pett, 2000)' _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^)+(0.0681P)^2^+0.2860P] 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 SHELXL _refine_ls_extinction_coef 0.006(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(2) _refine_ls_number_reflns 4139 _refine_ls_number_parameters 231 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0525 _refine_ls_R_factor_gt 0.0452 _refine_ls_wR_factor_ref 0.1226 _refine_ls_wR_factor_gt 0.1158 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.002 _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 0.2161(2) 0.38192(16) 0.04875(12) 0.0454(5) Uani 1 1 d . . . H1 H 0.1455 0.3270 0.0771 0.054 Uiso 1 1 calc R . . C2 C 0.37065(14) 0.40967(11) 0.07198(10) 0.0347(3) Uani 1 1 d . . . C21 C 0.43509(14) 0.35577(11) 0.14538(9) 0.0356(3) Uani 1 1 d . . . C22 C 0.51118(17) 0.27182(11) 0.13157(10) 0.0398(4) Uani 1 1 d . . . H22 H 0.5199 0.2463 0.0746 0.048 Uiso 1 1 calc R . . C23 C 0.57412(18) 0.22530(13) 0.19982(11) 0.0461(4) Uani 1 1 d . . . H23 H 0.6260 0.1683 0.1893 0.055 Uiso 1 1 calc R . . C24 C 0.56216(19) 0.26126(13) 0.28351(11) 0.0490(4) Uani 1 1 d . . . H24 H 0.6073 0.2301 0.3301 0.059 Uiso 1 1 calc R . . C25 C 0.48366(18) 0.34315(14) 0.29850(11) 0.0491(4) Uani 1 1 d . . . H25 H 0.4730 0.3673 0.3558 0.059 Uiso 1 1 calc R . . C26 C 0.42083(16) 0.38982(13) 0.23028(10) 0.0442(4) Uani 1 1 d . . . H26 H 0.3672 0.4458 0.2413 0.053 Uiso 1 1 calc R . . B3 B 0.3268(2) 0.37061(14) -0.03332(12) 0.0470(5) Uani 1 1 d . . . H3 H 0.3337 0.2986 -0.0677 0.056 Uiso 1 1 calc R . . B4 B 0.19530(19) 0.46276(14) -0.03231(13) 0.0431(4) Uani 1 1 d . . . H4 H 0.0962 0.4653 -0.0658 0.052 Uiso 1 1 calc R . . B5 B 0.24491(17) 0.49960(16) 0.07614(13) 0.0440(4) Uani 1 1 d . . . H5 H 0.1855 0.5319 0.1305 0.053 Uiso 1 1 calc R . . B6 B 0.41655(19) 0.53297(14) 0.06299(16) 0.0490(5) Uani 1 1 d . . . H6 H 0.4703 0.5728 0.1159 0.059 Uiso 1 1 calc R . . B7 B 0.4752(2) 0.44102(16) -0.01434(14) 0.0525(5) Uani 1 1 d . . . H7 H 0.5759 0.4069 -0.0235 0.063 Uiso 1 1 calc R . . B8 B 0.3499(2) 0.48227(17) -0.09221(15) 0.0553(6) Uani 1 1 d . . . H8 H 0.3495 0.4822 -0.1648 0.066 Uiso 1 1 calc R . . B9 B 0.29124(19) 0.57405(15) -0.01462(16) 0.0502(5) Uani 1 1 d . . . H9 H 0.2439 0.6474 -0.0250 0.060 Uiso 1 1 calc R . . B10 B 0.4552(2) 0.55991(19) -0.04025(19) 0.0671(7) Uani 1 1 d . . . H10 H 0.5289 0.6138 -0.0669 0.081 Uiso 1 1 calc R . . N1 N 0.83463(13) 0.59749(10) 0.18215(9) 0.0430(3) Uani 1 1 d . . . C11 C 0.71528(18) 0.59737(17) 0.24266(12) 0.0567(5) Uani 1 1 d . . . H11A H 0.6814 0.6653 0.2469 0.068 Uiso 1 1 calc R . . H11B H 0.6441 0.5575 0.2157 0.068 Uiso 1 1 calc R . . C12 C 0.7374(3) 0.5597(2) 0.33337(15) 0.0865(8) Uani 1 1 d . . . H12A H 0.7686 0.4917 0.3309 0.130 Uiso 1 1 calc R . . H12B H 0.6534 0.5627 0.3658 0.130 Uiso 1 1 calc R . . H12C H 0.8046 0.6002 0.3624 0.130 Uiso 1 1 calc R . . C13 C 0.89300(18) 0.49597(12) 0.17192(18) 0.0618(6) Uani 1 1 d . . . H13A H 0.9709 0.4998 0.1326 0.074 Uiso 1 1 calc R . . H13B H 0.9255 0.4733 0.2291 0.074 Uiso 1 1 calc R . . C14 C 0.7963(3) 0.42102(18) 0.1367(2) 0.0962(9) Uani 1 1 d . . . H14A H 0.7177 0.4177 0.1743 0.144 Uiso 1 1 calc R . . H14B H 0.8397 0.3567 0.1347 0.144 Uiso 1 1 calc R . . H14C H 0.7689 0.4400 0.0781 0.144 Uiso 1 1 calc R . . C15 C 0.7828(2) 0.63668(15) 0.09633(11) 0.0518(5) Uani 1 1 d . . . H15A H 0.7085 0.5943 0.0769 0.062 Uiso 1 1 calc R . . H15B H 0.7458 0.7030 0.1062 0.062 Uiso 1 1 calc R . . C16 C 0.8841(3) 0.64283(18) 0.02435(16) 0.0768(7) Uani 1 1 d . . . H16A H 0.9557 0.6879 0.0411 0.115 Uiso 1 1 calc R . . H16B H 0.8407 0.6669 -0.0284 0.115 Uiso 1 1 calc R . . H16C H 0.9216 0.5777 0.0135 0.115 Uiso 1 1 calc R . . C17 C 0.9455(2) 0.66007(14) 0.21804(16) 0.0646(6) Uani 1 1 d . . . H17A H 1.0231 0.6554 0.1786 0.077 Uiso 1 1 calc R . . H17B H 0.9731 0.6327 0.2747 0.077 Uiso 1 1 calc R . . C18 C 0.9117(3) 0.76677(17) 0.23036(17) 0.0887(9) Uani 1 1 d . . . H18A H 0.8904 0.7962 0.1741 0.133 Uiso 1 1 calc R . . H18B H 0.9883 0.8008 0.2559 0.133 Uiso 1 1 calc R . . H18C H 0.8345 0.7727 0.2690 0.133 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 0.0392(10) 0.0520(11) 0.0449(10) -0.0030(9) -0.0053(8) -0.0115(8) C2 0.0319(7) 0.0342(7) 0.0379(7) -0.0079(6) 0.0052(6) -0.0014(6) C21 0.0309(7) 0.0382(8) 0.0377(8) -0.0055(6) 0.0033(6) -0.0073(6) C22 0.0447(8) 0.0352(8) 0.0395(8) -0.0030(7) 0.0047(7) -0.0042(7) C23 0.0503(9) 0.0373(8) 0.0507(10) 0.0028(7) 0.0008(8) -0.0024(7) C24 0.0525(10) 0.0491(10) 0.0455(9) 0.0053(8) -0.0056(8) -0.0095(8) C25 0.0504(9) 0.0592(11) 0.0378(8) -0.0068(8) -0.0017(7) -0.0098(9) C26 0.0382(8) 0.0500(9) 0.0444(9) -0.0108(8) 0.0017(7) -0.0019(7) B3 0.0667(12) 0.0395(9) 0.0349(9) -0.0059(8) -0.0010(9) 0.0104(9) B4 0.0392(9) 0.0441(10) 0.0460(10) -0.0084(9) -0.0026(8) 0.0003(8) B5 0.0281(8) 0.0546(11) 0.0492(10) -0.0170(9) -0.0007(7) 0.0062(8) B6 0.0330(9) 0.0360(9) 0.0781(14) -0.0047(10) -0.0079(9) -0.0015(7) B7 0.0401(10) 0.0608(12) 0.0564(11) 0.0164(10) 0.0166(9) 0.0161(9) B8 0.0546(12) 0.0608(13) 0.0504(11) 0.0138(10) 0.0108(9) 0.0196(11) B9 0.0388(10) 0.0380(9) 0.0738(14) 0.0003(10) -0.0075(9) 0.0038(8) B10 0.0382(10) 0.0635(14) 0.0996(19) 0.0376(13) 0.0021(12) -0.0001(10) N1 0.0298(6) 0.0408(7) 0.0583(8) -0.0003(6) -0.0042(6) 0.0077(5) C11 0.0420(9) 0.0826(14) 0.0455(9) 0.0138(10) -0.0008(8) 0.0120(9) C12 0.0916(18) 0.112(2) 0.0559(13) 0.0279(13) -0.0150(12) 0.0059(16) C13 0.0413(9) 0.0331(8) 0.1109(17) -0.0074(10) -0.0058(10) 0.0042(7) C14 0.0866(18) 0.0560(13) 0.146(3) -0.0177(16) -0.0125(18) -0.0246(13) C15 0.0510(10) 0.0612(11) 0.0433(9) 0.0024(8) 0.0082(8) 0.0135(9) C16 0.0840(15) 0.0704(13) 0.0759(14) -0.0053(12) 0.0381(13) 0.0012(12) C17 0.0532(11) 0.0466(10) 0.0939(15) -0.0135(10) -0.0144(11) -0.0047(9) C18 0.138(3) 0.0459(11) 0.0821(16) -0.0175(11) -0.0042(16) 0.0014(14) _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 C2 1.634(2) . ? B1 B4 1.682(3) . ? B1 B5 1.687(3) . ? B1 B3 1.691(3) . ? C2 C21 1.498(2) . ? C2 B7 1.748(2) . ? C2 B6 1.751(2) . ? C2 B5 1.761(2) . ? C2 B3 1.766(2) . ? C21 C22 1.393(2) . ? C21 C26 1.398(2) . ? C22 C23 1.383(2) . ? C23 C24 1.387(3) . ? C24 C25 1.387(3) . ? C25 C26 1.383(2) . ? B3 B8 1.790(3) . ? B3 B7 1.795(3) . ? B3 B4 1.822(3) . ? B4 B5 1.818(3) . ? B4 B9 1.819(3) . ? B4 B8 1.824(3) . ? B5 B6 1.791(3) . ? B5 B9 1.792(3) . ? B6 B10 1.681(4) . ? B6 B9 1.824(3) . ? B6 B7 1.830(3) . ? B7 B10 1.684(3) . ? B7 B8 1.827(3) . ? B8 B10 1.698(4) . ? B8 B9 1.831(3) . ? B9 B10 1.701(3) . ? N1 C17 1.507(2) . ? N1 C13 1.513(2) . ? N1 C11 1.518(2) . ? N1 C15 1.520(2) . ? C11 C12 1.508(3) . ? C13 C14 1.511(3) . ? C15 C16 1.507(3) . ? C17 C18 1.508(3) . ? 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 C2 B1 B4 97.38(14) . . ? C2 B1 B5 64.00(10) . . ? B4 B1 B5 65.31(13) . . ? C2 B1 B3 64.14(11) . . ? B4 B1 B3 65.40(12) . . ? B5 B1 B3 99.35(14) . . ? C21 C2 B1 117.43(13) . . ? C21 C2 B7 116.02(12) . . ? B1 C2 B7 117.21(14) . . ? C21 C2 B6 114.79(13) . . ? B1 C2 B6 117.04(13) . . ? B7 C2 B6 63.05(12) . . ? C21 C2 B5 128.60(13) . . ? B1 C2 B5 59.44(11) . . ? B7 C2 B5 106.61(13) . . ? B6 C2 B5 61.33(10) . . ? C21 C2 B3 130.93(13) . . ? B1 C2 B3 59.50(11) . . ? B7 C2 B3 61.40(12) . . ? B6 C2 B3 106.42(13) . . ? B5 C2 B3 93.80(12) . . ? C22 C21 C26 118.24(14) . . ? C22 C21 C2 121.64(13) . . ? C26 C21 C2 120.12(14) . . ? C23 C22 C21 120.74(15) . . ? C22 C23 C24 120.51(17) . . ? C25 C24 C23 119.33(17) . . ? C26 C25 C24 120.20(16) . . ? C25 C26 C21 120.94(16) . . ? B1 B3 C2 56.37(9) . . ? B1 B3 B8 112.79(15) . . ? C2 B3 B8 100.26(14) . . ? B1 B3 B7 111.86(14) . . ? C2 B3 B7 58.80(11) . . ? B8 B3 B7 61.29(12) . . ? B1 B3 B4 57.04(11) . . ? C2 B3 B4 87.90(11) . . ? B8 B3 B4 60.63(11) . . ? B7 B3 B4 103.17(13) . . ? B1 B4 B5 57.48(11) . . ? B1 B4 B9 111.80(14) . . ? B5 B4 B9 59.06(12) . . ? B1 B4 B3 57.56(11) . . ? B5 B4 B3 90.07(12) . . ? B9 B4 B3 101.30(13) . . ? B1 B4 B8 111.60(14) . . ? B5 B4 B8 101.21(13) . . ? B9 B4 B8 60.34(12) . . ? B3 B4 B8 58.82(11) . . ? B1 B5 C2 56.56(11) . . ? B1 B5 B6 112.24(14) . . ? C2 B5 B6 59.07(9) . . ? B1 B5 B9 112.88(14) . . ? C2 B5 B9 100.47(12) . . ? B6 B5 B9 61.20(12) . . ? B1 B5 B4 57.21(11) . . ? C2 B5 B4 88.23(11) . . ? B6 B5 B4 103.22(14) . . ? B9 B5 B4 60.51(11) . . ? B10 B6 C2 110.26(16) . . ? B10 B6 B5 112.62(16) . . ? C2 B6 B5 59.60(10) . . ? B10 B6 B9 57.90(13) . . ? C2 B6 B9 99.61(13) . . ? B5 B6 B9 59.44(12) . . ? B10 B6 B7 57.14(14) . . ? C2 B6 B7 58.41(10) . . ? B5 B6 B7 101.99(14) . . ? B9 B6 B7 90.20(14) . . ? B10 B7 C2 110.24(15) . . ? B10 B7 B3 112.30(16) . . ? C2 B7 B3 59.79(10) . . ? B10 B7 B8 57.65(14) . . ? C2 B7 B8 99.51(13) . . ? B3 B7 B8 59.24(12) . . ? B10 B7 B6 56.99(14) . . ? C2 B7 B6 58.54(10) . . ? B3 B7 B6 102.02(12) . . ? B8 B7 B6 89.83(13) . . ? B10 B8 B3 111.85(16) . . ? B10 B8 B4 112.32(17) . . ? B3 B8 B4 60.55(12) . . ? B10 B8 B7 56.93(13) . . ? B3 B8 B7 59.47(12) . . ? B4 B8 B7 101.83(13) . . ? B10 B8 B9 57.51(13) . . ? B3 B8 B9 102.08(14) . . ? B4 B8 B9 59.70(11) . . ? B7 B8 B9 90.06(14) . . ? B10 B9 B5 111.57(15) . . ? B10 B9 B4 112.38(16) . . ? B5 B9 B4 60.43(11) . . ? B10 B9 B6 56.83(13) . . ? B5 B9 B6 59.36(11) . . ? B4 B9 B6 101.86(13) . . ? B10 B9 B8 57.32(15) . . ? B5 B9 B8 101.91(13) . . ? B4 B9 B8 59.96(12) . . ? B6 B9 B8 89.90(13) . . ? B6 B10 B7 65.87(13) . . ? B6 B10 B8 99.67(15) . . ? B7 B10 B8 65.41(15) . . ? B6 B10 B9 65.26(14) . . ? B7 B10 B9 99.72(16) . . ? B8 B10 B9 65.17(13) . . ? C17 N1 C13 105.83(13) . . ? C17 N1 C11 110.81(15) . . ? C13 N1 C11 111.59(15) . . ? C17 N1 C15 111.87(15) . . ? C13 N1 C15 111.32(15) . . ? C11 N1 C15 105.53(12) . . ? C12 C11 N1 117.12(17) . . ? C14 C13 N1 114.24(17) . . ? C16 C15 N1 115.62(17) . . ? N1 C17 C18 115.38(19) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.145 _refine_diff_density_min -0.163 _refine_diff_density_rms 0.028 data_afx65e _database_code_depnum_ccdc_archive 'CCDC 184222' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H36.65 B10.35 N' _chemical_formula_weight 342.99 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c 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 12.9967(5) _cell_length_b 10.1842(3) _cell_length_c 17.1010(8) _cell_angle_alpha 90.00 _cell_angle_beta 100.3030(10) _cell_angle_gamma 90.00 _cell_volume 2227.01(15) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.65 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.023 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 742 _exptl_absorpt_coefficient_mu 0.051 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9677 _exptl_absorpt_correction_T_max 0.9970 _exptl_absorpt_process_details ; Using multiple and symmetry-related data measurements via the program SORTAV See R.H. Blessing, Acta Cryst (1995), A51, 33-38 ; _exptl_special_details ; PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 15 degree phi range. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD area detector diffractometer' _diffrn_measurement_method ; Detector set at 30mm from sample with different 2theta offsets 1 degree phi exposures for chi=0 degree settings 1 degree omega exposures for chi=90 degree settings ; _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15138 _diffrn_reflns_av_R_equivalents 0.0875 _diffrn_reflns_av_sigmaI/netI 0.0729 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.65 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4350 _reflns_number_gt 3127 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1999)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1996)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1996)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; ORTEP3 for Windows (Farrugia, 1997) XSeed (Barbour, 2001) ; _computing_publication_material 'WC (Thornton-Pett, 2000)' _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^)+(0.0708P)^2^+1.0844P] 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 SHELXL _refine_ls_extinction_coef 0.020(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4350 _refine_ls_number_parameters 301 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0937 _refine_ls_R_factor_gt 0.0628 _refine_ls_wR_factor_ref 0.1772 _refine_ls_wR_factor_gt 0.1546 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _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 N1 N 0.75275(12) 0.75083(15) 0.03193(9) 0.0325(4) Uani 1 1 d . . . C11 C 0.69000(18) 0.6735(2) -0.03629(12) 0.0413(5) Uani 1 1 d . . . H11A H 0.6466 0.7360 -0.0724 0.050 Uiso 1 1 calc R . . H11B H 0.7395 0.6321 -0.0666 0.050 Uiso 1 1 calc R . . C12 C 0.6194(2) 0.5678(3) -0.01378(17) 0.0658(8) Uani 1 1 d . . . H12A H 0.6609 0.5052 0.0224 0.099 Uiso 1 1 calc R . . H12B H 0.5852 0.5217 -0.0618 0.099 Uiso 1 1 calc R . . H12C H 0.5661 0.6077 0.0126 0.099 Uiso 1 1 calc R . . C21 C 0.68129(16) 0.8109(2) 0.08337(11) 0.0354(5) Uani 1 1 d . . . H21A H 0.6482 0.7388 0.1089 0.043 Uiso 1 1 calc R . . H21B H 0.7246 0.8622 0.1262 0.043 Uiso 1 1 calc R . . C22 C 0.59601(18) 0.8991(2) 0.04056(14) 0.0480(6) Uani 1 1 d . . . H22A H 0.6275 0.9719 0.0157 0.072 Uiso 1 1 calc R . . H22B H 0.5549 0.9340 0.0787 0.072 Uiso 1 1 calc R . . H22C H 0.5503 0.8486 -0.0005 0.072 Uiso 1 1 calc R . . C31 C 0.80930(16) 0.8556(2) -0.00617(12) 0.0372(5) Uani 1 1 d . . . H31A H 0.7567 0.9108 -0.0403 0.045 Uiso 1 1 calc R . . H31B H 0.8522 0.8125 -0.0411 0.045 Uiso 1 1 calc R . . C32 C 0.8794(2) 0.9440(3) 0.05123(16) 0.0612(7) Uani 1 1 d . . . H32A H 0.8385 0.9852 0.0874 0.092 Uiso 1 1 calc R . . H32B H 0.9091 1.0122 0.0215 0.092 Uiso 1 1 calc R . . H32C H 0.9360 0.8920 0.0820 0.092 Uiso 1 1 calc R . . C41 C 0.82737(19) 0.6618(2) 0.08609(13) 0.0494(6) Uani 1 1 d . . . H41A H 0.8637 0.7145 0.1314 0.059 Uiso 1 1 calc R . . H41B H 0.7860 0.5937 0.1078 0.059 Uiso 1 1 calc R . . C42 C 0.9090(2) 0.5942(3) 0.04719(17) 0.0683(8) Uani 1 1 d . . . H42A H 0.8742 0.5398 0.0030 0.102 Uiso 1 1 calc R . . H42B H 0.9531 0.5386 0.0863 0.102 Uiso 1 1 calc R . . H42C H 0.9524 0.6604 0.0271 0.102 Uiso 1 1 calc R . . B1 B 0.7556(2) 0.1542(2) 0.23130(15) 0.0421(6) Uani 1 1 d . . . H1 H 0.7972(18) 0.073(2) 0.2097(14) 0.050(6) Uiso 1 1 d . . . B2 B 0.81617(19) 0.2745(2) 0.29813(14) 0.0363(5) Uani 1 1 d . . . H2 H 0.9017(18) 0.280(2) 0.3236(13) 0.047(6) Uiso 1 1 d . . . B3 B 0.7677(2) 0.3171(2) 0.19892(14) 0.0387(6) Uani 1 1 d . . . H3 H 0.8204(16) 0.356(2) 0.1592(12) 0.038(5) Uiso 1 1 d . . . B4 B 0.6503(3) 0.2313(3) 0.16624(19) 0.0582(8) Uani 1 1 d . . . H4 H 0.624(2) 0.199(3) 0.1021(18) 0.080(9) Uiso 1 1 d . . . B5 B 0.6277(2) 0.1318(3) 0.2476(2) 0.0554(7) Uani 1 1 d . . . H5 H 0.588(2) 0.033(3) 0.2407(16) 0.067(8) Uiso 1 1 d . . . B6 B 0.7295(2) 0.1596(2) 0.33001(16) 0.0452(6) Uani 1 1 d . . . H6 H 0.7597(19) 0.082(2) 0.3726(15) 0.056(7) Uiso 1 1 d . . . C7 C 0.74624(14) 0.41304(17) 0.27523(11) 0.0304(4) Uani 1 1 d . . . C71 C 0.79808(14) 0.54577(17) 0.28524(10) 0.0282(4) Uani 1 1 d . . . C72 C 0.90602(15) 0.56174(19) 0.29779(12) 0.0362(5) Uani 1 1 d . . . H72 H 0.9497 0.4865 0.3005 0.043 Uiso 1 1 calc R . . C73 C 0.95112(18) 0.6858(2) 0.30642(13) 0.0434(5) Uani 1 1 d . . . H73 H 1.0251 0.6944 0.3157 0.052 Uiso 1 1 calc R . . C74 C 0.88912(19) 0.7966(2) 0.30164(12) 0.0427(5) Uani 1 1 d . . . H74 H 0.9200 0.8814 0.3074 0.051 Uiso 1 1 calc R . . C75 C 0.78132(18) 0.78272(19) 0.28828(11) 0.0369(5) Uani 1 1 d . . . H75 H 0.7380 0.8584 0.2844 0.044 Uiso 1 1 calc R . . C76 C 0.73655(15) 0.65874(17) 0.28052(10) 0.0310(4) Uani 1 1 d . . . H76 H 0.6626 0.6506 0.2718 0.037 Uiso 1 1 calc R . . B8 B 0.6460(2) 0.3965(2) 0.19886(16) 0.0450(6) Uani 1 1 d . . . H8 H 0.6248(17) 0.482(2) 0.1587(14) 0.047(6) Uiso 1 1 d . . . H89 H 0.568(2) 0.388(3) 0.2321(18) 0.030(7) Uiso 0.65 1 d P . . B9 B 0.5529(3) 0.2741(3) 0.2205(3) 0.0749(11) Uani 1 1 d . . . H9 H 0.469(3) 0.274(3) 0.188(2) 0.111(11) Uiso 1 1 d . . . B10 B 0.6013(3) 0.2282(3) 0.3258(2) 0.0633(9) Uani 1 1 d . . . H10 H 0.548(2) 0.193(3) 0.3667(16) 0.067(8) Uiso 1 1 d . . . H101 H 0.603(3) 0.338(4) 0.337(2) 0.054(11) Uiso 0.65 1 d P . . B11 B 0.7188(3) 0.3306(3) 0.35239(18) 0.0565(8) Uani 1 1 d . . . H11 H 0.751(2) 0.372(2) 0.4190(16) 0.065(7) Uiso 1 1 d . . . B12 B 0.6344(7) 0.4015(8) 0.3141(6) 0.058(2) Uani 0.35 1 d P . . H12 H 0.588(4) 0.500(5) 0.340(3) 0.025(13) Uiso 0.35 1 d P . . 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 N1 0.0378(9) 0.0341(9) 0.0247(8) 0.0016(6) 0.0033(7) 0.0025(7) C11 0.0535(13) 0.0400(12) 0.0315(11) -0.0096(8) 0.0103(9) -0.0098(9) C12 0.088(2) 0.0513(15) 0.0656(17) -0.0183(12) 0.0346(15) -0.0292(14) C21 0.0394(11) 0.0384(11) 0.0284(10) -0.0021(8) 0.0060(8) 0.0030(8) C22 0.0455(13) 0.0470(13) 0.0497(13) -0.0015(10) 0.0030(10) 0.0110(10) C31 0.0394(11) 0.0401(11) 0.0318(10) -0.0010(8) 0.0058(9) -0.0087(9) C32 0.0563(16) 0.0718(17) 0.0551(15) -0.0179(13) 0.0091(12) -0.0266(13) C41 0.0539(14) 0.0547(14) 0.0396(12) 0.0137(10) 0.0081(10) 0.0212(11) C42 0.0661(18) 0.0756(19) 0.0651(17) 0.0095(14) 0.0170(14) 0.0353(14) B1 0.0558(16) 0.0269(12) 0.0451(14) -0.0011(10) 0.0130(12) -0.0017(10) B2 0.0391(13) 0.0276(11) 0.0410(13) 0.0029(9) 0.0039(10) 0.0048(9) B3 0.0511(15) 0.0294(12) 0.0350(12) 0.0000(9) 0.0059(11) -0.0044(10) B4 0.0671(19) 0.0388(15) 0.0590(18) 0.0014(12) -0.0152(15) -0.0165(13) B5 0.0529(17) 0.0336(14) 0.080(2) 0.0029(13) 0.0115(15) -0.0094(11) B6 0.0653(17) 0.0284(12) 0.0443(14) 0.0033(10) 0.0161(12) -0.0021(11) C7 0.0311(10) 0.0240(9) 0.0358(10) 0.0037(7) 0.0054(8) 0.0032(7) C71 0.0343(10) 0.0272(9) 0.0230(9) 0.0035(7) 0.0044(7) 0.0012(7) C72 0.0344(11) 0.0342(11) 0.0393(11) 0.0040(8) 0.0049(9) -0.0008(8) C73 0.0419(12) 0.0436(12) 0.0423(12) 0.0015(9) 0.0015(10) -0.0114(9) C74 0.0638(15) 0.0315(11) 0.0322(11) -0.0007(8) 0.0066(10) -0.0123(10) C75 0.0586(14) 0.0270(10) 0.0249(10) 0.0000(7) 0.0066(9) 0.0026(9) C76 0.0392(11) 0.0286(9) 0.0249(9) 0.0016(7) 0.0052(8) 0.0044(8) B8 0.0402(14) 0.0371(13) 0.0523(15) 0.0097(11) -0.0064(12) -0.0047(10) B9 0.0432(17) 0.0506(18) 0.128(3) 0.0300(19) 0.0084(18) -0.0102(13) B10 0.070(2) 0.0375(15) 0.094(2) 0.0164(15) 0.0472(19) 0.0031(13) B11 0.084(2) 0.0384(14) 0.0520(17) 0.0002(12) 0.0264(15) -0.0036(14) B12 0.056(5) 0.038(4) 0.085(6) 0.010(4) 0.024(5) 0.008(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C31 1.508(2) . ? N1 C41 1.516(2) . ? N1 C21 1.518(2) . ? N1 C11 1.519(2) . ? C11 C12 1.509(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C21 C22 1.511(3) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C31 C32 1.511(3) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C41 C42 1.514(3) . ? C41 H41A 0.9900 . ? C41 H41B 0.9900 . ? C42 H42A 0.9800 . ? C42 H42B 0.9800 . ? C42 H42C 0.9800 . ? B1 B5 1.748(4) . ? B1 B2 1.762(3) . ? B1 B3 1.765(3) . ? B1 B6 1.781(4) . ? B1 B4 1.784(4) . ? B1 H1 1.09(2) . ? B2 C7 1.686(3) . ? B2 B3 1.755(3) . ? B2 B6 1.776(3) . ? B2 B11 1.791(4) . ? B2 H2 1.12(2) . ? B3 C7 1.693(3) . ? B3 B4 1.761(4) . ? B3 B8 1.777(4) . ? B3 H3 1.12(2) . ? B4 B9 1.754(5) . ? B4 B8 1.777(4) . ? B4 B5 1.787(4) . ? B4 H4 1.14(3) . ? B5 B10 1.742(5) . ? B5 B9 1.760(4) . ? B5 B6 1.775(4) . ? B5 H5 1.13(3) . ? B6 B11 1.794(4) . ? B6 B10 1.796(4) . ? B6 H6 1.10(2) . ? C7 C71 1.506(2) . ? C7 B11 1.656(3) . ? C7 B8 1.680(3) . ? C7 B12 1.707(9) . ? C71 C72 1.390(3) . ? C71 C76 1.395(2) . ? C72 C73 1.389(3) . ? C72 H72 0.9500 . ? C73 C74 1.381(3) . ? C73 H73 0.9500 . ? C74 C75 1.386(3) . ? C74 H74 0.9500 . ? C75 C76 1.387(3) . ? C75 H75 0.9500 . ? C76 H76 0.9500 . ? B8 B9 1.822(4) . ? B8 B12 2.004(11) . ? B8 H8 1.12(2) . ? B8 H89 1.26(3) . ? B9 B10 1.858(6) . ? B9 H89 1.19(3) . ? B9 H9 1.13(4) . ? B10 B12 1.836(9) . ? B10 B11 1.837(5) . ? B10 H10 1.13(3) . ? B10 H101 1.14(4) . ? B11 B12 1.377(9) . ? B11 H101 1.48(4) . ? B11 H11 1.21(3) . ? B12 H89 1.52(3) . ? B12 H101 0.89(4) . ? B12 H12 1.29(5) . ? 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 C31 N1 C41 112.29(16) . . ? C31 N1 C21 111.17(15) . . ? C41 N1 C21 106.13(14) . . ? C31 N1 C11 105.76(14) . . ? C41 N1 C11 110.84(17) . . ? C21 N1 C11 110.74(15) . . ? C12 C11 N1 116.22(18) . . ? C12 C11 H11A 108.2 . . ? N1 C11 H11A 108.2 . . ? C12 C11 H11B 108.2 . . ? N1 C11 H11B 108.2 . . ? H11A C11 H11B 107.4 . . ? 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 . . ? C22 C21 N1 115.52(16) . . ? C22 C21 H21A 108.4 . . ? N1 C21 H21A 108.4 . . ? C22 C21 H21B 108.4 . . ? N1 C21 H21B 108.4 . . ? H21A C21 H21B 107.5 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N1 C31 C32 115.13(18) . . ? N1 C31 H31A 108.5 . . ? C32 C31 H31A 108.5 . . ? N1 C31 H31B 108.5 . . ? C32 C31 H31B 108.5 . . ? H31A C31 H31B 107.5 . . ? 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 . . ? C42 C41 N1 115.16(19) . . ? C42 C41 H41A 108.5 . . ? N1 C41 H41A 108.5 . . ? C42 C41 H41B 108.5 . . ? N1 C41 H41B 108.5 . . ? H41A C41 H41B 107.5 . . ? C41 C42 H42A 109.5 . . ? C41 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? C41 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? B5 B1 B2 108.31(18) . . ? B5 B1 B3 108.26(18) . . ? B2 B1 B3 59.68(13) . . ? B5 B1 B6 60.37(17) . . ? B2 B1 B6 60.16(14) . . ? B3 B1 B6 108.13(17) . . ? B5 B1 B4 60.78(17) . . ? B2 B1 B4 107.60(17) . . ? B3 B1 B4 59.49(14) . . ? B6 B1 B4 108.8(2) . . ? B5 B1 H1 119.9(12) . . ? B2 B1 H1 123.9(12) . . ? B3 B1 H1 122.2(12) . . ? B6 B1 H1 122.2(12) . . ? B4 B1 H1 119.7(12) . . ? C7 B2 B3 58.91(13) . . ? C7 B2 B1 105.75(17) . . ? B3 B2 B1 60.24(14) . . ? C7 B2 B6 106.12(17) . . ? B3 B2 B6 108.79(18) . . ? B1 B2 B6 60.44(14) . . ? C7 B2 B11 56.77(13) . . ? B3 B2 B11 104.93(18) . . ? B1 B2 B11 106.42(19) . . ? B6 B2 B11 60.38(15) . . ? C7 B2 H2 120.4(11) . . ? B3 B2 H2 121.6(11) . . ? B1 B2 H2 125.6(11) . . ? B6 B2 H2 123.5(11) . . ? B11 B2 H2 121.8(12) . . ? C7 B3 B2 58.52(12) . . ? C7 B3 B4 106.13(19) . . ? B2 B3 B4 108.96(18) . . ? C7 B3 B1 105.34(16) . . ? B2 B3 B1 60.09(14) . . ? B4 B3 B1 60.79(15) . . ? C7 B3 B8 57.85(13) . . ? B2 B3 B8 106.17(17) . . ? B4 B3 B8 60.29(16) . . ? B1 B3 B8 107.36(18) . . ? C7 B3 H3 117.9(11) . . ? B2 B3 H3 121.4(11) . . ? B4 B3 H3 124.9(11) . . ? B1 B3 H3 128.4(11) . . ? B8 B3 H3 118.7(11) . . ? B9 B4 B3 112.1(2) . . ? B9 B4 B8 62.11(18) . . ? B3 B4 B8 60.30(14) . . ? B9 B4 B1 109.0(2) . . ? B3 B4 B1 59.72(15) . . ? B8 B4 B1 106.54(18) . . ? B9 B4 B5 59.61(18) . . ? B3 B4 B5 106.7(2) . . ? B8 B4 B5 105.9(2) . . ? B1 B4 B5 58.62(16) . . ? B9 B4 H4 117.2(14) . . ? B3 B4 H4 123.2(15) . . ? B8 B4 H4 123.6(15) . . ? B1 B4 H4 122.9(15) . . ? B5 B4 H4 121.5(14) . . ? B10 B5 B1 111.9(2) . . ? B10 B5 B9 64.1(2) . . ? B1 B5 B9 110.33(19) . . ? B10 B5 B6 61.43(18) . . ? B1 B5 B6 60.73(15) . . ? B9 B5 B6 112.1(2) . . ? B10 B5 B4 111.2(2) . . ? B1 B5 B4 60.60(16) . . ? B9 B5 B4 59.25(19) . . ? B6 B5 B4 108.98(19) . . ? B10 B5 H5 115.6(13) . . ? B1 B5 H5 122.2(13) . . ? B9 B5 H5 118.8(13) . . ? B6 B5 H5 119.4(14) . . ? B4 B5 H5 124.0(14) . . ? B5 B6 B2 106.54(18) . . ? B5 B6 B1 58.90(16) . . ? B2 B6 B1 59.40(14) . . ? B5 B6 B11 104.4(2) . . ? B2 B6 B11 60.22(14) . . ? B1 B6 B11 105.51(17) . . ? B5 B6 B10 58.39(18) . . ? B2 B6 B10 111.46(18) . . ? B1 B6 B10 107.9(2) . . ? B11 B6 B10 61.57(17) . . ? B5 B6 H6 122.8(13) . . ? B2 B6 H6 120.4(13) . . ? B1 B6 H6 120.2(13) . . ? B11 B6 H6 125.9(13) . . ? B10 B6 H6 121.7(13) . . ? C71 C7 B11 121.35(17) . . ? C71 C7 B8 116.55(15) . . ? B11 C7 B8 108.75(18) . . ? C71 C7 B2 120.87(16) . . ? B11 C7 B2 64.80(15) . . ? B8 C7 B2 114.04(16) . . ? C71 C7 B3 118.25(16) . . ? B11 C7 B3 114.20(16) . . ? B8 C7 B3 63.57(15) . . ? B2 C7 B3 62.57(13) . . ? C71 C7 B12 114.3(3) . . ? B11 C7 B12 48.3(3) . . ? B8 C7 B12 72.6(4) . . ? B2 C7 B12 108.2(3) . . ? B3 C7 B12 122.0(4) . . ? C72 C71 C76 117.68(17) . . ? C72 C71 C7 122.75(16) . . ? C76 C71 C7 119.56(17) . . ? C73 C72 C71 121.18(19) . . ? C73 C72 H72 119.4 . . ? C71 C72 H72 119.4 . . ? C74 C73 C72 120.4(2) . . ? C74 C73 H73 119.8 . . ? C72 C73 H73 119.8 . . ? C73 C74 C75 119.24(19) . . ? C73 C74 H74 120.4 . . ? C75 C74 H74 120.4 . . ? C74 C75 C76 120.22(19) . . ? C74 C75 H75 119.9 . . ? C76 C75 H75 119.9 . . ? C75 C76 C71 121.26(19) . . ? C75 C76 H76 119.4 . . ? C71 C76 H76 119.4 . . ? C7 B8 B4 105.99(18) . . ? C7 B8 B3 58.57(13) . . ? B4 B8 B3 59.41(15) . . ? C7 B8 B9 111.2(2) . . ? B4 B8 B9 58.32(19) . . ? B3 B8 B9 108.20(18) . . ? C7 B8 B12 54.3(3) . . ? B4 B8 B12 110.2(3) . . ? B3 B8 B12 103.5(3) . . ? B9 B8 B12 69.4(3) . . ? C7 B8 H8 118.1(12) . . ? B4 B8 H8 124.6(12) . . ? B3 B8 H8 118.6(12) . . ? B9 B8 H8 124.2(12) . . ? B12 B8 H8 122.1(12) . . ? C7 B8 H89 103.6(14) . . ? B4 B8 H89 98.6(14) . . ? B3 B8 H89 139.7(14) . . ? B9 B8 H89 40.3(13) . . ? B12 B8 H89 49.2(14) . . ? H8 B8 H89 101.7(18) . . ? B4 B9 B5 61.14(19) . . ? B4 B9 B8 59.57(16) . . ? B5 B9 B8 105.1(2) . . ? B4 B9 B10 107.4(2) . . ? B5 B9 B10 57.48(18) . . ? B8 B9 B10 104.3(2) . . ? B4 B9 H89 102.8(15) . . ? B5 B9 H89 134.1(15) . . ? B8 B9 H89 43.2(14) . . ? B10 B9 H89 93.9(15) . . ? B4 B9 H9 118.0(18) . . ? B5 B9 H9 124.6(17) . . ? B8 B9 H9 121.4(17) . . ? B10 B9 H9 126.9(18) . . ? H89 B9 H9 101(2) . . ? B5 B10 B6 60.18(16) . . ? B5 B10 B12 112.1(4) . . ? B6 B10 B12 98.3(3) . . ? B5 B10 B11 103.9(2) . . ? B6 B10 B11 59.14(16) . . ? B12 B10 B11 44.0(3) . . ? B5 B10 B9 58.4(2) . . ? B6 B10 B9 106.7(2) . . ? B12 B10 B9 72.4(4) . . ? B11 B10 B9 102.69(19) . . ? B5 B10 H10 121.4(13) . . ? B6 B10 H10 121.2(13) . . ? B12 B10 H10 124.0(14) . . ? B11 B10 H10 127.2(14) . . ? B9 B10 H10 122.8(14) . . ? B5 B10 H101 133(2) . . ? B6 B10 H101 113(2) . . ? B12 B10 H101 22(2) . . ? B11 B10 H101 54(2) . . ? B9 B10 H101 85(2) . . ? H10 B10 H101 102(2) . . ? B12 B11 C7 67.8(4) . . ? B12 B11 B2 119.8(5) . . ? C7 B11 B2 58.43(13) . . ? B12 B11 B6 119.6(5) . . ? C7 B11 B6 106.66(19) . . ? B2 B11 B6 59.40(14) . . ? B12 B11 B10 67.9(4) . . ? C7 B11 B10 112.2(2) . . ? B2 B11 B10 108.90(19) . . ? B6 B11 B10 59.29(16) . . ? B12 B11 H101 36.0(16) . . ? C7 B11 H101 100.9(16) . . ? B2 B11 H101 135.6(15) . . ? B6 B11 H101 97.5(16) . . ? B10 B11 H101 38.2(16) . . ? B12 B11 H11 111.9(13) . . ? C7 B11 H11 119.0(12) . . ? B2 B11 H11 116.2(12) . . ? B6 B11 H11 120.6(12) . . ? B10 B11 H11 123.9(12) . . ? H101 B11 H11 108.2(19) . . ? B11 B12 C7 63.9(4) . . ? B11 B12 B10 68.0(4) . . ? C7 B12 B10 110.0(4) . . ? B11 B12 B8 105.1(5) . . ? C7 B12 B8 53.1(3) . . ? B10 B12 B8 98.2(5) . . ? B11 B12 H89 131.8(13) . . ? C7 B12 H89 91.9(12) . . ? B10 B12 H89 84.6(12) . . ? B8 B12 H89 38.8(11) . . ? B11 B12 H101 78(3) . . ? C7 B12 H101 135(3) . . ? B10 B12 H101 29(3) . . ? B8 B12 H101 123(3) . . ? H89 B12 H101 96(3) . . ? B11 B12 H12 129(2) . . ? C7 B12 H12 124(2) . . ? B10 B12 H12 125(2) . . ? B8 B12 H12 118(2) . . ? H89 B12 H12 99(3) . . ? H101 B12 H12 98(4) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.418 _refine_diff_density_min -0.361 _refine_diff_density_rms 0.063 #================================================================= data_afx08a _database_code_depnum_ccdc_archive 'CCDC 186128' _audit_creation_method SHELXL-97 _chemical_name_systematic ; [NEt4]+[2-Ph-closo-2-CB6H6]- ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H31 B6 N' _chemical_formula_weight 290.27 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, z' 'x, -y+1/2, z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, -z' '-x, y-1/2, -z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 14.438(3) _cell_length_b 15.762(3) _cell_length_c 16.877(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3840.6(14) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.004 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1264 _exptl_absorpt_coefficient_mu 0.052 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9845 _exptl_absorpt_correction_T_max 0.9984 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.6883 _diffrn_radiation_type Synchrotron _diffrn_radiation_source 'Daresbury SRS Station 9.8' _diffrn_radiation_monochromator 'Silicon 111' _diffrn_measurement_device_type 'Bruker AXS SMART 1K CCD diffractometer' _diffrn_measurement_method 'omega rotation with narrow frames' _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10306 _diffrn_reflns_av_R_equivalents 0.0434 _diffrn_reflns_av_sigmaI/netI 0.0529 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4073 _reflns_number_gt 3385 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART version 5.054 (Bruker, 1998)' _computing_cell_refinement 'Bruker SAINT version 6.02a (Bruker, 2000)' _computing_data_reduction 'Bruker SAINT version 6.02a (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 for Windows (Farrugia, 1997)' _computing_publication_material 'WC (Thornton-Pett, 2000)' _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^)+(0.1099P)^2^+1.1144P] 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 4073 _refine_ls_number_parameters 323 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0807 _refine_ls_R_factor_gt 0.0701 _refine_ls_wR_factor_ref 0.1877 _refine_ls_wR_factor_gt 0.1792 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.091 _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 C2 C 0.15835(11) 0.02098(10) 0.60613(8) 0.0209(3) Uani 1 1 d . . . C12 C 0.51708(13) 0.26695(11) 0.33658(11) 0.0301(4) Uani 1 1 d . . . H12A H 0.5022(15) 0.3039(14) 0.2938(13) 0.039(6) Uiso 1 1 d . . . H12B H 0.5250(14) 0.2988(13) 0.3837(12) 0.031(5) Uiso 1 1 d . . . C13 C 0.59863(16) 0.21095(16) 0.31663(18) 0.0513(6) Uani 1 1 d . . . H13A H 0.608(2) 0.175(2) 0.3596(19) 0.078(10) Uiso 1 1 d . . . H13B H 0.6536(19) 0.249(2) 0.3084(17) 0.066(8) Uiso 1 1 d . . . H13C H 0.583(2) 0.172(2) 0.2651(18) 0.074(9) Uiso 1 1 d . . . C14 C 0.43822(14) 0.15865(11) 0.42116(10) 0.0302(4) Uani 1 1 d . . . H14A H 0.3781(16) 0.1351(14) 0.4254(12) 0.036(5) Uiso 1 1 d . . . H14B H 0.4813(14) 0.1181(14) 0.4003(12) 0.030(5) Uiso 1 1 d . . . C15 C 0.46862(18) 0.19851(15) 0.49834(11) 0.0416(5) Uani 1 1 d . . . H15A H 0.5248(18) 0.2229(15) 0.4971(14) 0.043(7) Uiso 1 1 d . . . H15B H 0.4685(19) 0.1519(19) 0.5388(17) 0.066(8) Uiso 1 1 d . . . H15C H 0.4231(19) 0.241(2) 0.5156(16) 0.058(7) Uiso 1 1 d . . . C16 C 0.39797(15) 0.16747(11) 0.28129(10) 0.0330(4) Uani 1 1 d . . . H16A H 0.3371(16) 0.1422(15) 0.2965(13) 0.040(6) Uiso 1 1 d . . . H16B H 0.4446(15) 0.1276(14) 0.2755(12) 0.035(5) Uiso 1 1 d . . . C17 C 0.3876(2) 0.21671(15) 0.20444(12) 0.0499(6) Uani 1 1 d . . . H17A H 0.3472(19) 0.266(2) 0.2116(16) 0.063(8) Uiso 1 1 d . . . H17B H 0.367(2) 0.176(2) 0.1670(19) 0.085(10) Uiso 1 1 d . . . H17C H 0.4498(17) 0.2331(16) 0.1900(15) 0.045(7) Uiso 1 1 d . . . C18 C 0.35538(14) 0.28811(11) 0.37037(11) 0.0320(4) Uani 1 1 d . . . H18A H 0.3884(17) 0.3216(16) 0.4152(14) 0.048(6) Uiso 1 1 d . . . H18B H 0.3530(15) 0.3230(15) 0.3249(13) 0.036(5) Uiso 1 1 d . . . C19 C 0.26084(16) 0.25765(18) 0.39288(16) 0.0498(6) Uani 1 1 d . . . H19A H 0.2341(15) 0.2274(14) 0.3484(14) 0.036(6) Uiso 1 1 d . . . H19B H 0.225(2) 0.3096(19) 0.4006(16) 0.067(8) Uiso 1 1 d . . . H19C H 0.263(2) 0.226(2) 0.446(2) 0.096(11) Uiso 1 1 d . . . C21 C 0.09473(11) 0.02979(9) 0.67529(8) 0.0196(3) Uani 1 1 d . . . C22 C 0.12842(11) 0.05575(10) 0.74923(9) 0.0232(4) Uani 1 1 d . . . H22 H 0.1965(14) 0.0648(12) 0.7556(10) 0.023(4) Uiso 1 1 d . . . C23 C 0.06958(13) 0.06305(11) 0.81394(9) 0.0272(4) Uani 1 1 d . . . H23 H 0.0946(15) 0.0806(15) 0.8637(13) 0.037(6) Uiso 1 1 d . . . C24 C -0.02428(13) 0.04341(11) 0.80563(10) 0.0288(4) Uani 1 1 d . . . H24 H -0.0664(14) 0.0466(13) 0.8504(12) 0.027(5) Uiso 1 1 d . . . C25 C -0.05809(12) 0.01713(11) 0.73229(10) 0.0271(4) Uani 1 1 d . . . H25 H -0.1217(14) 0.0044(12) 0.7270(10) 0.021(4) Uiso 1 1 d . . . C26 C 0.00113(12) 0.01062(10) 0.66746(9) 0.0233(4) Uani 1 1 d . . . H26 H -0.0216(13) -0.0029(13) 0.6133(12) 0.026(5) Uiso 1 1 d . . . B1 B 0.25082(14) 0.07425(13) 0.56197(11) 0.0298(4) Uani 1 1 d . . . H1 H 0.2806(15) 0.1363(14) 0.5844(13) 0.040(6) Uiso 1 1 d . . . B3 B 0.13520(14) 0.05558(13) 0.52191(10) 0.0275(4) Uani 1 1 d . . . H3 H 0.0697(14) 0.0914(13) 0.5101(12) 0.032(5) Uiso 1 1 d . . . B4 B 0.22398(15) 0.02719(14) 0.46693(11) 0.0328(5) Uani 1 1 d . . . H4 H 0.2320(15) 0.0427(14) 0.4045(13) 0.040(6) Uiso 1 1 d . . . B5 B 0.29847(16) -0.02328(15) 0.52491(12) 0.0357(5) Uani 1 1 d . . . H5 H 0.367(2) -0.0460(18) 0.5062(16) 0.067(8) Uiso 1 1 d . . . B6 B 0.25238(14) -0.02637(13) 0.61428(11) 0.0289(4) Uani 1 1 d . . . H6 H 0.2738(16) -0.0535(15) 0.6749(14) 0.046(6) Uiso 1 1 d . . . B7 B 0.17743(15) -0.05260(13) 0.53133(11) 0.0297(4) Uani 1 1 d . . . H7 H 0.1354(18) -0.1098(17) 0.5251(15) 0.058(7) Uiso 1 1 d . . . N1 N 0.42683(10) 0.22026(8) 0.35243(7) 0.0227(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C2 0.0229(8) 0.0251(8) 0.0148(7) -0.0020(5) -0.0013(6) -0.0032(6) C12 0.0340(10) 0.0252(8) 0.0311(9) 0.0045(7) -0.0005(7) -0.0044(7) C13 0.0381(12) 0.0452(13) 0.0706(16) 0.0118(12) 0.0145(11) 0.0010(10) C14 0.0401(10) 0.0265(9) 0.0239(8) 0.0084(6) 0.0024(7) 0.0019(7) C15 0.0552(14) 0.0478(12) 0.0219(9) 0.0075(8) -0.0032(8) 0.0047(10) C16 0.0497(12) 0.0259(9) 0.0234(8) -0.0054(6) -0.0029(8) -0.0041(8) C17 0.0825(19) 0.0440(13) 0.0232(9) -0.0027(8) -0.0113(10) -0.0099(12) C18 0.0406(11) 0.0278(9) 0.0277(8) 0.0024(7) 0.0033(7) 0.0093(7) C19 0.0396(12) 0.0557(14) 0.0541(14) 0.0094(11) 0.0090(10) 0.0129(10) C21 0.0253(8) 0.0184(7) 0.0152(7) 0.0006(5) -0.0006(6) 0.0016(6) C22 0.0250(9) 0.0259(8) 0.0187(7) -0.0007(6) -0.0022(6) 0.0002(6) C23 0.0389(10) 0.0273(8) 0.0155(7) -0.0033(6) -0.0005(6) 0.0005(7) C24 0.0332(10) 0.0289(9) 0.0242(8) 0.0012(6) 0.0077(7) 0.0028(7) C25 0.0249(9) 0.0271(8) 0.0292(9) 0.0014(6) 0.0031(7) 0.0003(6) C26 0.0267(8) 0.0244(8) 0.0188(7) 0.0009(6) -0.0019(6) 0.0003(6) B1 0.0297(10) 0.0381(11) 0.0218(8) -0.0002(7) 0.0009(7) -0.0104(8) B3 0.0318(10) 0.0347(10) 0.0161(8) 0.0021(7) -0.0034(7) -0.0007(8) B4 0.0355(11) 0.0449(12) 0.0181(8) -0.0007(7) 0.0023(7) -0.0074(9) B5 0.0319(11) 0.0502(13) 0.0250(9) -0.0048(8) 0.0043(8) 0.0053(9) B6 0.0252(10) 0.0403(11) 0.0213(8) 0.0002(7) -0.0004(7) 0.0039(8) B7 0.0367(11) 0.0325(10) 0.0199(8) -0.0073(7) 0.0022(7) -0.0029(8) N1 0.0326(8) 0.0194(7) 0.0160(6) 0.0008(5) 0.0000(5) -0.0002(5) _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 C2 C21 1.492(2) . ? C2 B6 1.555(2) . ? C2 B3 1.559(2) . ? C2 B7 1.736(2) . ? C2 B1 1.744(2) . ? C12 C13 1.510(3) . ? C12 N1 1.520(2) . ? C14 C15 1.511(3) . ? C14 N1 1.522(2) . ? C16 C17 1.519(3) . ? C16 N1 1.519(2) . ? C18 C19 1.496(3) . ? C18 N1 1.516(2) . ? C21 C26 1.391(2) . ? C21 C22 1.400(2) . ? C22 C23 1.388(2) . ? C23 C24 1.397(3) . ? C24 C25 1.393(2) . ? C25 C26 1.392(2) . ? B1 B5 1.796(3) . ? B1 B4 1.809(3) . ? B1 B6 1.815(3) . ? B1 B3 1.825(3) . ? B3 B4 1.645(3) . ? B3 B7 1.818(3) . ? B4 B5 1.657(3) . ? B4 B7 1.793(3) . ? B5 B6 1.649(3) . ? B5 B7 1.811(3) . ? B6 B7 1.817(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C21 C2 B6 120.86(13) . . ? C21 C2 B3 123.29(14) . . ? B6 C2 B3 115.83(14) . . ? C21 C2 B7 136.78(13) . . ? B6 C2 B7 66.75(12) . . ? B3 C2 B7 66.71(11) . . ? C21 C2 B1 139.53(13) . . ? B6 C2 B1 66.46(12) . . ? B3 C2 B1 66.81(12) . . ? B7 C2 B1 83.65(11) . . ? C13 C12 N1 115.13(16) . . ? C15 C14 N1 115.03(15) . . ? C17 C16 N1 114.98(15) . . ? C19 C18 N1 116.43(16) . . ? C26 C21 C22 119.05(14) . . ? C26 C21 C2 120.24(13) . . ? C22 C21 C2 120.70(14) . . ? C23 C22 C21 120.83(15) . . ? C22 C23 C24 119.74(15) . . ? C25 C24 C23 119.66(15) . . ? C26 C25 C24 120.32(16) . . ? C21 C26 C25 120.39(15) . . ? C2 B1 B5 91.72(13) . . ? C2 B1 B4 91.01(12) . . ? B5 B1 B4 54.73(12) . . ? C2 B1 B6 51.77(10) . . ? B5 B1 B6 54.34(11) . . ? B4 B1 B6 94.34(13) . . ? C2 B1 B3 51.73(9) . . ? B5 B1 B3 94.78(13) . . ? B4 B1 B3 53.81(11) . . ? B6 B1 B3 92.90(13) . . ? C2 B3 B4 104.60(15) . . ? C2 B3 B7 61.32(10) . . ? B4 B3 B7 62.14(12) . . ? C2 B3 B1 61.47(11) . . ? B4 B3 B1 62.61(12) . . ? B7 B3 B1 79.16(12) . . ? B3 B4 B5 107.65(14) . . ? B3 B4 B7 63.68(12) . . ? B5 B4 B7 63.17(13) . . ? B3 B4 B1 63.59(12) . . ? B5 B4 B1 62.24(12) . . ? B7 B4 B1 80.24(12) . . ? B6 B5 B4 107.00(15) . . ? B6 B5 B1 63.41(12) . . ? B4 B5 B1 63.03(12) . . ? B6 B5 B7 63.16(12) . . ? B4 B5 B7 62.07(13) . . ? B1 B5 B7 80.10(13) . . ? C2 B6 B5 104.91(14) . . ? C2 B6 B1 61.77(11) . . ? B5 B6 B1 62.26(12) . . ? C2 B6 B7 61.40(11) . . ? B5 B6 B7 62.77(12) . . ? B1 B6 B7 79.44(12) . . ? C2 B7 B4 91.82(13) . . ? C2 B7 B5 91.49(12) . . ? B4 B7 B5 54.76(12) . . ? C2 B7 B6 51.85(9) . . ? B4 B7 B6 94.83(13) . . ? B5 B7 B6 54.08(11) . . ? C2 B7 B3 51.97(9) . . ? B4 B7 B3 54.18(11) . . ? B5 B7 B3 94.54(14) . . ? B6 B7 B3 93.08(12) . . ? C18 N1 C16 110.94(14) . . ? C18 N1 C12 106.07(13) . . ? C16 N1 C12 111.17(13) . . ? C18 N1 C14 111.80(13) . . ? C16 N1 C14 106.42(13) . . ? C12 N1 C14 110.52(13) . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.494 _refine_diff_density_min -0.214 _refine_diff_density_rms 0.085 data_af80b1 _database_code_depnum_ccdc_archive 'CCDC 194221' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H16 B11, C8 H20 N' _chemical_formula_sum 'C15 H36 B11 N' _chemical_formula_weight 349.36 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 13.0151(3) _cell_length_b 10.2266(3) _cell_length_c 16.9186(5) _cell_angle_alpha 90.00 _cell_angle_beta 100.5580(13) _cell_angle_gamma 90.00 _cell_volume 2213.74(11) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 12182 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description colourless _exptl_crystal_colour plate _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.048 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.052 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5320 _exptl_absorpt_correction_T_max 0.9974 _exptl_absorpt_process_details ; Using multiple and symmetry-related data measurements via the program SORTAV. See R.H. Blessing, Acta Cryst (1995), A51, 33-38. ; _exptl_special_details ; PLEASE NOTE cell_measurement_ fields are not relevant to area detector data since the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree range. The crystal temperature was held constant using an Oxford Cryosystems Cryostream 600 system. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_probe x-ray _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Nonius KappaCCD area-detector diffractometer ; _diffrn_radiation_detector 'CCD plate' _diffrn_measurement_method ; phi and omega scans to fill the asymmetric unit ; _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 20696 _diffrn_reflns_av_R_equivalents 0.0766 _diffrn_reflns_av_sigmaI/netI 0.0563 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4335 _reflns_number_gt 3216 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1996)' _computing_data_reduction ; DENZO-SMN and COLLECT (Otwinowski & Minor, 1996) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Farrugia, 2001)' _computing_publication_material ; local program ; _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^)+(0.0735P)^2^+1.6208P] 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 SHELXL _refine_ls_extinction_coef 0.008(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4335 _refine_ls_number_parameters 249 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0950 _refine_ls_R_factor_gt 0.0686 _refine_ls_wR_factor_ref 0.1839 _refine_ls_wR_factor_gt 0.1641 _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 N1 N 0.74742(13) 0.75039(17) 0.03114(9) 0.0302(4) Uani 1 1 d . . . C21 C 0.68259(18) 0.8233(2) -0.03877(12) 0.0352(5) Uani 1 1 d . . . H21A H 0.7309 0.8661 -0.0697 0.042 Uiso 1 1 calc R . . H21B H 0.6411 0.7585 -0.0747 0.042 Uiso 1 1 calc R . . C23 C 0.67847(17) 0.6891(2) 0.08467(12) 0.0343(5) Uani 1 1 d . . . H23A H 0.7238 0.6418 0.1289 0.041 Uiso 1 1 calc R . . H23B H 0.6431 0.7601 0.1091 0.041 Uiso 1 1 calc R . . C24 C 0.59633(19) 0.5955(2) 0.04284(15) 0.0435(6) Uani 1 1 d . . . H24A H 0.5556 0.5617 0.0817 0.052 Uiso 1 1 calc R . . H24B H 0.6303 0.5227 0.0201 0.052 Uiso 1 1 calc R . . H24C H 0.5498 0.6415 -0.0004 0.052 Uiso 1 1 calc R . . C25 C 0.80697(17) 0.6473(2) -0.00569(13) 0.0363(5) Uani 1 1 d . . . H25A H 0.8471 0.6906 -0.0427 0.044 Uiso 1 1 calc R . . H25B H 0.7561 0.5876 -0.0382 0.044 Uiso 1 1 calc R . . C27 C 0.8201(2) 0.8440(3) 0.08443(14) 0.0451(6) Uani 1 1 d . . . H27A H 0.7771 0.9119 0.1045 0.054 Uiso 1 1 calc R . . H27B H 0.8571 0.7949 0.1316 0.054 Uiso 1 1 calc R . . C22 C 0.6089(2) 0.9258(3) -0.01734(17) 0.0540(7) Uani 1 1 d . . . H22A H 0.5730 0.9689 -0.0665 0.065 Uiso 1 1 calc R . . H22B H 0.6486 0.9909 0.0184 0.065 Uiso 1 1 calc R . . H22C H 0.5572 0.8843 0.0100 0.065 Uiso 1 1 calc R . . C28 C 0.9010(2) 0.9115(3) 0.04418(17) 0.0613(8) Uani 1 1 d . . . H28A H 0.9436 0.9702 0.0827 0.074 Uiso 1 1 calc R . . H28B H 0.8655 0.9621 -0.0020 0.074 Uiso 1 1 calc R . . H28C H 0.9461 0.8456 0.0259 0.074 Uiso 1 1 calc R . . C26 C 0.8816(2) 0.5668(3) 0.05419(17) 0.0597(8) Uani 1 1 d . . . H26A H 0.9153 0.5009 0.0255 0.072 Uiso 1 1 calc R . . H26B H 0.8428 0.5232 0.0912 0.072 Uiso 1 1 calc R . . H26C H 0.9349 0.6241 0.0847 0.072 Uiso 1 1 calc R . . C11 C 0.19893(15) 0.44913(18) 0.21201(11) 0.0262(4) Uani 1 1 d . . . C16 C 0.25978(16) 0.33604(18) 0.21861(11) 0.0265(4) Uani 1 1 d . . . H16 H 0.3338 0.3432 0.2280 0.032 Uiso 1 1 calc R . . C1 C 0.24976(15) 0.58191(19) 0.21977(12) 0.0294(5) Uani 1 1 d . . . C12 C 0.09091(16) 0.4350(2) 0.19894(13) 0.0342(5) Uani 1 1 d . . . H12 H 0.0480 0.5108 0.1951 0.041 Uiso 1 1 calc R . . C13 C 0.04457(18) 0.3123(2) 0.19139(14) 0.0396(5) Uani 1 1 d . . . H13 H -0.0294 0.3048 0.1819 0.048 Uiso 1 1 calc R . . C14 C 0.10569(19) 0.2006(2) 0.19757(13) 0.0380(5) Uani 1 1 d . . . H14 H 0.0740 0.1166 0.1922 0.046 Uiso 1 1 calc R . . C15 C 0.21357(18) 0.21285(19) 0.21170(12) 0.0320(5) Uani 1 1 d . . . H15 H 0.2562 0.1368 0.2167 0.038 Uiso 1 1 calc R . . B4 B 0.2396(2) 0.6784(2) 0.30059(16) 0.0373(6) Uani 1 1 d . . . H4 H 0.1942 0.6513 0.3484 0.045 Uiso 1 1 calc R . . B8 B 0.2456(2) 0.8417(2) 0.26608(17) 0.0395(6) Uani 1 1 d . . . H8 H 0.2033 0.9229 0.2910 0.047 Uiso 1 1 calc R . . B5 B 0.3592(2) 0.6009(2) 0.29069(17) 0.0412(6) Uani 1 1 d . . . H5 H 0.3947 0.5207 0.3319 0.049 Uiso 1 1 calc R . . B3 B 0.1788(2) 0.7213(2) 0.20182(16) 0.0393(6) Uani 1 1 d . . . H3 H 0.0916 0.7213 0.1840 0.047 Uiso 1 1 calc R . . B7 B 0.2577(3) 0.8385(3) 0.16400(18) 0.0492(7) Uani 1 1 d . . . H7 H 0.2247 0.9181 0.1213 0.059 Uiso 1 1 calc R . . B9 B 0.3593(3) 0.7656(3) 0.3230(2) 0.0526(8) Uani 1 1 d . . . H9 H 0.3936 0.7949 0.3861 0.063 Uiso 1 1 calc R . . B2 B 0.2524(3) 0.6735(3) 0.1319(2) 0.0572(8) Uani 1 1 d . . . H2 H 0.2152 0.6421 0.0698 0.069 Uiso 1 1 calc R . . B10 B 0.4386(2) 0.7171(3) 0.2525(3) 0.0628(10) Uani 1 1 d . . . H10 H 0.5259 0.7133 0.2691 0.075 Uiso 1 1 calc R . . B6 B 0.3634(3) 0.6013(3) 0.1839(2) 0.0550(8) Uani 1 1 d . . . H6 H 0.3999 0.5210 0.1536 0.066 Uiso 1 1 calc R . . B11 B 0.3752(3) 0.7643(3) 0.1549(3) 0.0727(12) Uani 1 1 d . . . H11 H 0.4214 0.7933 0.1079 0.087 Uiso 1 1 calc R . . B12 B 0.3691(2) 0.8682(3) 0.2391(2) 0.0561(8) Uani 1 1 d . . . H12' H 0.4093 0.9654 0.2475 0.067 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 N1 0.0337(10) 0.0337(9) 0.0225(8) -0.0014(7) 0.0033(7) -0.0045(7) C21 0.0424(13) 0.0344(11) 0.0290(11) 0.0048(9) 0.0074(9) 0.0050(9) C23 0.0379(12) 0.0385(12) 0.0273(10) 0.0008(9) 0.0082(9) -0.0056(9) C24 0.0436(14) 0.0433(13) 0.0436(13) -0.0014(10) 0.0082(10) -0.0119(11) C25 0.0353(12) 0.0424(12) 0.0316(11) 0.0026(9) 0.0068(9) 0.0061(10) C27 0.0503(15) 0.0509(14) 0.0331(12) -0.0077(10) 0.0054(10) -0.0203(12) C22 0.0661(18) 0.0443(14) 0.0558(16) 0.0094(12) 0.0222(14) 0.0198(13) C28 0.0597(18) 0.0723(19) 0.0513(16) -0.0048(14) 0.0087(13) -0.0330(15) C26 0.0533(17) 0.0684(18) 0.0567(17) 0.0156(14) 0.0083(13) 0.0228(14) C11 0.0293(11) 0.0240(10) 0.0253(10) 0.0011(7) 0.0053(8) -0.0014(8) C16 0.0335(11) 0.0244(9) 0.0219(9) 0.0002(7) 0.0057(8) 0.0009(8) C1 0.0255(11) 0.0240(10) 0.0381(11) 0.0011(8) 0.0044(8) 0.0009(8) C12 0.0281(11) 0.0312(11) 0.0430(12) 0.0012(9) 0.0056(9) -0.0001(9) C13 0.0346(12) 0.0415(13) 0.0419(13) 0.0018(10) 0.0047(10) -0.0105(10) C14 0.0511(14) 0.0303(11) 0.0321(11) 0.0002(9) 0.0065(10) -0.0126(10) C15 0.0488(13) 0.0244(10) 0.0233(10) 0.0028(8) 0.0082(9) 0.0033(9) B4 0.0468(15) 0.0276(12) 0.0366(13) -0.0026(10) 0.0050(11) -0.0031(11) B8 0.0467(16) 0.0240(11) 0.0491(15) -0.0034(11) 0.0124(12) 0.0001(11) B5 0.0339(14) 0.0267(12) 0.0559(16) 0.0013(11) -0.0101(12) -0.0028(10) B3 0.0427(15) 0.0292(12) 0.0438(15) 0.0044(11) 0.0023(11) 0.0003(11) B7 0.075(2) 0.0254(12) 0.0498(16) 0.0049(11) 0.0175(15) -0.0018(13) B9 0.0552(19) 0.0303(14) 0.0632(19) -0.0052(13) -0.0134(15) -0.0072(13) B2 0.080(2) 0.0412(16) 0.0530(18) 0.0055(14) 0.0183(16) 0.0006(15) B10 0.0308(15) 0.0317(14) 0.125(3) 0.0052(17) 0.0113(17) -0.0065(12) B6 0.0520(19) 0.0498(17) 0.069(2) 0.0000(15) 0.0264(16) -0.0180(14) B11 0.091(3) 0.0354(16) 0.112(3) 0.0208(18) 0.070(3) 0.0127(16) B12 0.0453(17) 0.0282(13) 0.097(3) 0.0071(14) 0.0177(17) -0.0039(12) _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 N1 C25 1.509(3) . ? N1 C21 1.517(3) . ? N1 C27 1.520(3) . ? N1 C23 1.522(3) . ? C21 C22 1.509(3) . ? C23 C24 1.511(3) . ? C25 C26 1.512(3) . ? C27 C28 1.520(3) . ? C11 C12 1.390(3) . ? C11 C16 1.395(3) . ? C11 C1 1.506(3) . ? C16 C15 1.392(3) . ? C1 B3 1.695(3) . ? C1 B5 1.697(3) . ? C1 B6 1.710(4) . ? C1 B4 1.711(3) . ? C1 B2 1.763(4) . ? C12 C13 1.389(3) . ? C13 C14 1.385(3) . ? C14 C15 1.386(3) . ? B4 B3 1.768(4) . ? B4 B9 1.774(4) . ? B4 B8 1.776(4) . ? B4 B5 1.782(4) . ? B8 B3 1.763(4) . ? B8 B7 1.763(4) . ? B8 B12 1.770(4) . ? B8 B9 1.789(4) . ? B5 B9 1.771(4) . ? B5 B10 1.774(4) . ? B5 B6 1.817(4) . ? B3 B2 1.724(4) . ? B3 B7 1.772(4) . ? B7 B11 1.739(5) . ? B7 B2 1.770(4) . ? B7 B12 1.771(5) . ? B9 B10 1.785(5) . ? B9 B12 1.788(5) . ? B2 B6 1.715(5) . ? B2 B11 1.829(6) . ? B10 B11 1.772(6) . ? B10 B12 1.784(4) . ? B10 B6 1.814(5) . ? B6 B11 1.752(4) . ? B11 B12 1.791(5) . ? 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 C25 N1 C21 106.02(15) . . ? C25 N1 C27 111.97(18) . . ? C21 N1 C27 110.46(17) . . ? C25 N1 C23 111.18(16) . . ? C21 N1 C23 111.23(16) . . ? C27 N1 C23 106.08(15) . . ? C22 C21 N1 116.19(18) . . ? C24 C23 N1 115.21(17) . . ? N1 C25 C26 114.77(19) . . ? C28 C27 N1 115.26(19) . . ? C12 C11 C16 118.02(18) . . ? C12 C11 C1 121.52(18) . . ? C16 C11 C1 120.46(17) . . ? C15 C16 C11 120.91(19) . . ? C11 C1 B3 121.78(17) . . ? C11 C1 B5 117.59(17) . . ? B3 C1 B5 112.93(17) . . ? C11 C1 B6 117.94(18) . . ? B3 C1 B6 108.46(18) . . ? B5 C1 B6 64.47(18) . . ? C11 C1 B4 119.52(17) . . ? B3 C1 B4 62.54(14) . . ? B5 C1 B4 63.06(15) . . ? B6 C1 B4 114.54(19) . . ? C11 C1 B2 118.79(18) . . ? B3 C1 B2 59.75(16) . . ? B5 C1 B2 113.09(19) . . ? B6 C1 B2 59.15(18) . . ? B4 C1 B2 112.59(17) . . ? C13 C12 C11 121.2(2) . . ? C14 C13 C12 120.3(2) . . ? C13 C14 C15 119.24(19) . . ? C14 C15 C16 120.31(19) . . ? C1 B4 B3 58.30(13) . . ? C1 B4 B9 105.5(2) . . ? B3 B4 B9 107.5(2) . . ? C1 B4 B8 105.38(18) . . ? B3 B4 B8 59.65(15) . . ? B9 B4 B8 60.52(15) . . ? C1 B4 B5 58.10(14) . . ? B3 B4 B5 105.59(19) . . ? B9 B4 B5 59.71(16) . . ? B8 B4 B5 107.20(19) . . ? B3 B8 B7 60.33(16) . . ? B3 B8 B12 108.4(2) . . ? B7 B8 B12 60.14(19) . . ? B3 B8 B4 59.95(14) . . ? B7 B8 B4 108.74(18) . . ? B12 B8 B4 108.98(19) . . ? B3 B8 B9 107.05(18) . . ? B7 B8 B9 107.8(2) . . ? B12 B8 B9 60.31(18) . . ? B4 B8 B9 59.69(15) . . ? C1 B5 B9 106.23(18) . . ? C1 B5 B10 106.8(2) . . ? B9 B5 B10 60.50(19) . . ? C1 B5 B4 58.84(13) . . ? B9 B5 B4 59.92(16) . . ? B10 B5 B4 108.28(18) . . ? C1 B5 B6 58.10(15) . . ? B9 B5 B6 107.8(2) . . ? B10 B5 B6 60.68(19) . . ? B4 B5 B6 106.13(19) . . ? C1 B3 B2 62.08(16) . . ? C1 B3 B8 106.64(18) . . ? B2 B3 B8 110.4(2) . . ? C1 B3 B4 59.15(14) . . ? B2 B3 B4 111.7(2) . . ? B8 B3 B4 60.40(15) . . ? C1 B3 B7 107.5(2) . . ? B2 B3 B7 60.83(17) . . ? B8 B3 B7 59.84(16) . . ? B4 B3 B7 108.7(2) . . ? B11 B7 B8 109.4(2) . . ? B11 B7 B2 62.8(2) . . ? B8 B7 B2 108.26(19) . . ? B11 B7 B12 61.4(2) . . ? B8 B7 B12 60.13(18) . . ? B2 B7 B12 111.4(2) . . ? B11 B7 B3 108.3(2) . . ? B8 B7 B3 59.83(15) . . ? B2 B7 B3 58.24(16) . . ? B12 B7 B3 108.0(2) . . ? B5 B9 B4 60.37(15) . . ? B5 B9 B10 59.83(17) . . ? B4 B9 B10 108.1(2) . . ? B5 B9 B12 108.0(2) . . ? B4 B9 B12 108.3(2) . . ? B10 B9 B12 59.90(19) . . ? B5 B9 B8 107.14(19) . . ? B4 B9 B8 59.79(15) . . ? B10 B9 B8 106.5(2) . . ? B12 B9 B8 59.32(17) . . ? B6 B2 B3 106.9(2) . . ? B6 B2 C1 58.87(16) . . ? B3 B2 C1 58.17(15) . . ? B6 B2 B7 105.7(3) . . ? B3 B2 B7 60.93(17) . . ? C1 B2 B7 104.7(2) . . ? B6 B2 B11 59.17(19) . . ? B3 B2 B11 106.5(2) . . ? C1 B2 B11 104.0(2) . . ? B7 B2 B11 57.77(18) . . ? B11 B10 B5 108.6(2) . . ? B11 B10 B12 60.5(2) . . ? B5 B10 B12 108.1(2) . . ? B11 B10 B9 108.6(2) . . ? B5 B10 B9 59.67(17) . . ? B12 B10 B9 60.13(18) . . ? B11 B10 B6 58.5(2) . . ? B5 B10 B6 60.86(16) . . ? B12 B10 B6 106.4(2) . . ? B9 B10 B6 107.3(2) . . ? C1 B6 B2 61.98(17) . . ? C1 B6 B11 109.6(2) . . ? B2 B6 B11 63.6(2) . . ? C1 B6 B10 104.5(2) . . ? B2 B6 B10 110.7(2) . . ? B11 B6 B10 59.5(2) . . ? C1 B6 B5 57.43(14) . . ? B2 B6 B5 109.6(2) . . ? B11 B6 B5 107.5(2) . . ? B10 B6 B5 58.47(18) . . ? B7 B11 B6 105.4(2) . . ? B7 B11 B10 107.7(2) . . ? B6 B11 B10 61.97(19) . . ? B7 B11 B12 60.18(18) . . ? B6 B11 B12 108.8(2) . . ? B10 B11 B12 60.1(2) . . ? B7 B11 B2 59.43(19) . . ? B6 B11 B2 57.18(19) . . ? B10 B11 B2 107.5(2) . . ? B12 B11 B2 107.8(2) . . ? B8 B12 B7 59.73(17) . . ? B8 B12 B10 107.4(2) . . ? B7 B12 B10 105.8(2) . . ? B8 B12 B9 60.36(17) . . ? B7 B12 B9 107.5(2) . . ? B10 B12 B9 60.0(2) . . ? B8 B12 B11 106.8(2) . . ? B7 B12 B11 58.5(2) . . ? B10 B12 B11 59.4(2) . . ? B9 B12 B11 107.6(2) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.384 _refine_diff_density_min -0.328 _refine_diff_density_rms 0.048 data_af08 _database_code_depnum_ccdc_archive 'CCDC 194222' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H16 B11, C8 H20 N' _chemical_formula_sum 'C15 H36 B11 N' _chemical_formula_weight 349.36 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, z' 'x, -y+1/2, z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, -z' '-x, y-1/2, -z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 10.2352(2) _cell_length_b 16.9027(5) _cell_length_c 25.6191(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4432.2(2) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 15879 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.047 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1504 _exptl_absorpt_coefficient_mu 0.052 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.768 _exptl_absorpt_correction_T_max 0.998 _exptl_absorpt_process_details ; Using multiple and symmetry-related data measurements via the program SORTAV. See R.H. Blessing, Acta Cryst (1995), A51, 33-38. ; _exptl_special_details ; PLEASE NOTE cell_measurement_ fields are not relevant to area detector data since the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree range. The crystal temperature was held constant using an Oxford Cryosystems Cryostream 600 system. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_probe x-ray _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Nonius KappaCCD area-detector diffractometer ; _diffrn_radiation_detector 'CCD plate' _diffrn_measurement_method ; phi and omega scans to fill the asymmetric unit ; _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 20245 _diffrn_reflns_av_R_equivalents 0.0999 _diffrn_reflns_av_sigmaI/netI 0.0775 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 2.82 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4353 _reflns_number_gt 2533 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1996)' _computing_data_reduction ; DENZO-SMN and COLLECT (Otwinowski & Minor, 1996) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Farrugia, 2001)' _computing_publication_material ; local program ; _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^)+(0.0469P)^2^+2.8338P] 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 SHELXL _refine_ls_extinction_coef 0.0022(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4353 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1233 _refine_ls_R_factor_gt 0.0615 _refine_ls_wR_factor_ref 0.1646 _refine_ls_wR_factor_gt 0.1317 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 N1 N 0.74698(18) 0.06614(11) 0.37333(7) 0.0282(4) Uani 1 1 d . . . C27 C 0.6755(2) 0.00508(14) 0.34078(10) 0.0332(6) Uani 1 1 d . . . H27A H 0.7408 -0.0246 0.3201 0.040 Uiso 1 1 calc R . . H27B H 0.6329 -0.0330 0.3647 0.040 Uiso 1 1 calc R . . C21 C 0.8089(2) 0.12972(14) 0.33896(10) 0.0340(6) Uani 1 1 d . . . H21A H 0.7383 0.1593 0.3212 0.041 Uiso 1 1 calc R . . H21B H 0.8561 0.1675 0.3617 0.041 Uiso 1 1 calc R . . C26 C 0.5863(3) 0.05818(18) 0.44993(12) 0.0561(8) Uani 1 1 d . . . H26A H 0.5283 0.0910 0.4713 0.067 Uiso 1 1 calc R . . H26B H 0.6521 0.0332 0.4723 0.067 Uiso 1 1 calc R . . H26C H 0.5349 0.0172 0.4323 0.067 Uiso 1 1 calc R . . C23 C 0.8504(2) 0.02125(14) 0.40349(9) 0.0338(6) Uani 1 1 d . . . H23A H 0.9105 -0.0041 0.3782 0.041 Uiso 1 1 calc R . . H23B H 0.8071 -0.0214 0.4235 0.041 Uiso 1 1 calc R . . C25 C 0.6535(3) 0.10939(15) 0.40946(10) 0.0420(7) Uani 1 1 d . . . H25A H 0.7025 0.1515 0.4278 0.050 Uiso 1 1 calc R . . H25B H 0.5856 0.1354 0.3879 0.050 Uiso 1 1 calc R . . C22 C 0.9029(2) 0.09907(16) 0.29808(10) 0.0419(7) Uani 1 1 d . . . H22A H 0.9378 0.1436 0.2779 0.050 Uiso 1 1 calc R . . H22B H 0.8568 0.0628 0.2746 0.050 Uiso 1 1 calc R . . H22C H 0.9749 0.0710 0.3152 0.050 Uiso 1 1 calc R . . C28 C 0.5731(3) 0.03691(18) 0.30392(12) 0.0505(8) Uani 1 1 d . . . H28A H 0.5329 -0.0070 0.2848 0.061 Uiso 1 1 calc R . . H28B H 0.6141 0.0734 0.2791 0.061 Uiso 1 1 calc R . . H28C H 0.5059 0.0650 0.3239 0.061 Uiso 1 1 calc R . . C24 C 0.9303(3) 0.07103(18) 0.44091(12) 0.0528(8) Uani 1 1 d . . . H24A H 0.9944 0.0374 0.4587 0.063 Uiso 1 1 calc R . . H24B H 0.8724 0.0953 0.4668 0.063 Uiso 1 1 calc R . . H24C H 0.9760 0.1126 0.4214 0.063 Uiso 1 1 calc R . . C11 C 0.05082(19) 0.18331(14) 0.59919(8) 0.0251(5) Uani 1 1 d . . . C16 C 0.16420(19) 0.18179(13) 0.62945(8) 0.0263(5) Uani 1 1 d . . . H16 H 0.1574 0.1806 0.6664 0.032 Uiso 1 1 calc R . . C12 C 0.0643(2) 0.18536(15) 0.54522(9) 0.0324(5) Uani 1 1 d . . . H12 H -0.0114 0.1872 0.5238 0.039 Uiso 1 1 calc R . . C1 C -0.08168(19) 0.18367(15) 0.62512(8) 0.0273(5) Uani 1 1 d . . . C14 C 0.2985(2) 0.18319(15) 0.55246(10) 0.0361(6) Uani 1 1 d . . . H14 H 0.3823 0.1829 0.5366 0.043 Uiso 1 1 calc R . . C15 C 0.2871(2) 0.18198(14) 0.60618(9) 0.0306(5) Uani 1 1 d . . . H15 H 0.3633 0.1813 0.6273 0.037 Uiso 1 1 calc R . . C13 C 0.1875(2) 0.18482(16) 0.52219(9) 0.0384(6) Uani 1 1 d . . . H13 H 0.1950 0.1856 0.4852 0.046 Uiso 1 1 calc R . . B3 B -0.2221(2) 0.17636(19) 0.58903(11) 0.0367(7) Uani 1 1 d . . . H3 H -0.2229 0.1710 0.5455 0.044 Uiso 1 1 calc R . . B8 B -0.3381(3) 0.12687(19) 0.62859(14) 0.0442(8) Uani 1 1 d . . . H8 H -0.4172 0.0887 0.6119 0.053 Uiso 1 1 calc R . . B2 B -0.1781(3) 0.26637(17) 0.61978(11) 0.0349(7) Uani 1 1 d . . . H2 H -0.1506 0.3205 0.5971 0.042 Uiso 1 1 calc R . . B7 B -0.3417(3) 0.23117(18) 0.62286(12) 0.0371(7) Uani 1 1 d . . . H7 H -0.4230 0.2623 0.6020 0.045 Uiso 1 1 calc R . . B6 B -0.1004(3) 0.24030(19) 0.67938(12) 0.0379(7) Uani 1 1 d . . . H6 H -0.0204 0.2773 0.6966 0.046 Uiso 1 1 calc R . . B5 B -0.0983(3) 0.1345(2) 0.68305(13) 0.0474(8) Uani 1 1 d . . . H5 H -0.0169 0.1011 0.7022 0.057 Uiso 1 1 calc R . . B10 B -0.2157(3) 0.1907(3) 0.71932(12) 0.0573(10) Uani 1 1 d . . . H10 H -0.2123 0.1953 0.7629 0.069 Uiso 1 1 calc R . . B11 B -0.2658(3) 0.2720(2) 0.67951(13) 0.0466(8) Uani 1 1 d . . . H11 H -0.2960 0.3302 0.6966 0.056 Uiso 1 1 calc R . . B12 B -0.3667(3) 0.1862(2) 0.68436(12) 0.0499(8) Uani 1 1 d . . . H12' H -0.4638 0.1882 0.7045 0.060 Uiso 1 1 calc R . . B9 B -0.2617(3) 0.1016(2) 0.68775(15) 0.0616(11) Uani 1 1 d . . . H9 H -0.2895 0.0476 0.7106 0.074 Uiso 1 1 calc R . . B4 B -0.1724(3) 0.0967(2) 0.62713(14) 0.0483(8) Uani 1 1 d . . . H4 H -0.1404 0.0396 0.6091 0.058 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 N1 0.0306(10) 0.0229(9) 0.0312(10) -0.0006(9) 0.0021(9) 0.0010(7) C27 0.0311(12) 0.0293(13) 0.0392(14) -0.0003(11) -0.0056(11) -0.0039(10) C21 0.0371(13) 0.0259(13) 0.0390(14) 0.0025(11) 0.0047(11) -0.0010(10) C26 0.0617(19) 0.0507(19) 0.0557(19) -0.0007(15) 0.0290(16) -0.0034(15) C23 0.0363(13) 0.0310(14) 0.0342(14) 0.0008(11) -0.0055(11) 0.0009(10) C25 0.0444(14) 0.0339(15) 0.0478(16) -0.0041(12) 0.0164(13) 0.0056(11) C22 0.0431(14) 0.0419(16) 0.0408(15) 0.0024(12) 0.0109(12) -0.0018(12) C28 0.0415(15) 0.0496(18) 0.0604(19) 0.0104(15) -0.0173(14) -0.0047(13) C24 0.0580(18) 0.0512(19) 0.0494(18) -0.0042(15) -0.0164(14) -0.0082(14) C11 0.0239(10) 0.0236(11) 0.0279(11) -0.0008(11) 0.0006(9) -0.0007(9) C16 0.0248(10) 0.0225(11) 0.0316(12) -0.0011(11) -0.0016(9) -0.0007(10) C12 0.0302(11) 0.0401(14) 0.0269(12) 0.0006(12) -0.0005(9) -0.0034(11) C1 0.0218(10) 0.0349(13) 0.0252(11) 0.0001(11) -0.0015(9) -0.0006(10) C14 0.0274(12) 0.0320(13) 0.0489(15) -0.0015(13) 0.0131(10) -0.0031(10) C15 0.0225(10) 0.0238(11) 0.0456(14) -0.0008(12) -0.0025(10) 0.0007(9) C13 0.0396(13) 0.0422(14) 0.0333(13) -0.0004(12) 0.0102(10) -0.0038(12) B3 0.0258(12) 0.0452(18) 0.0391(15) -0.0046(15) -0.0031(11) -0.0028(12) B8 0.0240(14) 0.0445(18) 0.064(2) 0.0046(16) 0.0003(14) -0.0054(13) B2 0.0251(13) 0.0371(16) 0.0424(17) 0.0002(13) -0.0006(12) 0.0020(12) B7 0.0234(13) 0.0451(18) 0.0428(17) 0.0039(14) -0.0005(12) 0.0004(12) B6 0.0272(13) 0.0528(19) 0.0338(16) -0.0128(14) 0.0025(12) -0.0014(13) B5 0.0364(16) 0.062(2) 0.0442(19) 0.0197(17) 0.0081(14) -0.0040(15) B10 0.0318(15) 0.108(3) 0.0318(16) 0.0047(19) 0.0062(13) -0.0050(18) B11 0.0271(14) 0.063(2) 0.0495(19) -0.0195(17) 0.0072(13) 0.0051(14) B12 0.0256(14) 0.080(3) 0.0445(18) 0.0077(19) 0.0052(12) -0.0036(16) B9 0.0302(16) 0.081(3) 0.074(3) 0.039(2) -0.0040(16) -0.0121(17) B4 0.0337(15) 0.0425(18) 0.069(2) 0.0046(16) 0.0005(16) -0.0043(14) _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 N1 C23 1.514(3) . ? N1 C27 1.515(3) . ? N1 C25 1.519(3) . ? N1 C21 1.527(3) . ? C27 C28 1.510(3) . ? C21 C22 1.513(3) . ? C26 C25 1.516(4) . ? C23 C24 1.516(3) . ? C11 C12 1.390(3) . ? C11 C16 1.396(3) . ? C11 C1 1.510(3) . ? C16 C15 1.392(3) . ? C12 C13 1.392(3) . ? C1 B6 1.699(4) . ? C1 B5 1.709(4) . ? C1 B3 1.713(3) . ? C1 B2 1.717(4) . ? C1 B4 1.739(4) . ? C14 C13 1.376(3) . ? C14 C15 1.381(3) . ? B3 B4 1.739(4) . ? B3 B7 1.763(4) . ? B3 B8 1.771(4) . ? B3 B2 1.771(4) . ? B8 B9 1.758(5) . ? B8 B7 1.769(4) . ? B8 B12 1.770(5) . ? B8 B4 1.771(4) . ? B2 B11 1.776(4) . ? B2 B6 1.777(4) . ? B2 B7 1.778(4) . ? B7 B12 1.768(4) . ? B7 B11 1.785(4) . ? B6 B10 1.772(4) . ? B6 B11 1.776(4) . ? B6 B5 1.790(5) . ? B5 B4 1.743(5) . ? B5 B9 1.767(4) . ? B5 B10 1.791(5) . ? B10 B9 1.774(6) . ? B10 B11 1.786(5) . ? B10 B12 1.788(4) . ? B11 B12 1.785(5) . ? B12 B9 1.791(5) . ? B9 B4 1.804(5) . ? 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 C23 N1 C27 106.08(18) . . ? C23 N1 C25 111.74(18) . . ? C27 N1 C25 111.03(19) . . ? C23 N1 C21 110.90(18) . . ? C27 N1 C21 111.26(17) . . ? C25 N1 C21 105.92(18) . . ? C28 C27 N1 115.9(2) . . ? C22 C21 N1 115.0(2) . . ? N1 C23 C24 115.0(2) . . ? C26 C25 N1 115.3(2) . . ? C12 C11 C16 118.06(19) . . ? C12 C11 C1 121.78(19) . . ? C16 C11 C1 120.16(19) . . ? C15 C16 C11 120.9(2) . . ? C11 C12 C13 120.8(2) . . ? C11 C1 B6 117.60(18) . . ? C11 C1 B5 117.99(19) . . ? B6 C1 B5 63.38(18) . . ? C11 C1 B3 121.04(18) . . ? B6 C1 B3 112.83(18) . . ? B5 C1 B3 110.50(19) . . ? C11 C1 B2 119.0(2) . . ? B6 C1 B2 62.72(16) . . ? B5 C1 B2 114.05(19) . . ? B3 C1 B2 62.19(16) . . ? C11 C1 B4 119.3(2) . . ? B6 C1 B4 113.1(2) . . ? B5 C1 B4 60.70(19) . . ? B3 C1 B4 60.48(17) . . ? B2 C1 B4 112.54(17) . . ? C13 C14 C15 119.5(2) . . ? C14 C15 C16 120.2(2) . . ? C14 C13 C12 120.6(2) . . ? C1 B3 B4 60.51(16) . . ? C1 B3 B7 106.22(19) . . ? B4 B3 B7 109.5(2) . . ? C1 B3 B8 106.7(2) . . ? B4 B3 B8 60.59(17) . . ? B7 B3 B8 60.09(16) . . ? C1 B3 B2 59.01(15) . . ? B4 B3 B2 110.0(2) . . ? B7 B3 B2 60.42(16) . . ? B8 B3 B2 108.7(2) . . ? B9 B8 B7 108.8(2) . . ? B9 B8 B12 61.0(2) . . ? B7 B8 B12 59.94(19) . . ? B9 B8 B4 61.47(19) . . ? B7 B8 B4 107.8(2) . . ? B12 B8 B4 109.8(2) . . ? B9 B8 B3 108.1(2) . . ? B7 B8 B3 59.74(17) . . ? B12 B8 B3 107.8(2) . . ? B4 B8 B3 58.80(17) . . ? C1 B2 B3 58.80(15) . . ? C1 B2 B11 105.4(2) . . ? B3 B2 B11 107.5(2) . . ? C1 B2 B6 58.14(15) . . ? B3 B2 B6 106.4(2) . . ? B11 B2 B6 59.96(16) . . ? C1 B2 B7 105.4(2) . . ? B3 B2 B7 59.56(16) . . ? B11 B2 B7 60.29(17) . . ? B6 B2 B7 107.5(2) . . ? B3 B7 B12 108.2(2) . . ? B3 B7 B8 60.18(17) . . ? B12 B7 B8 60.0(2) . . ? B3 B7 B2 60.02(16) . . ? B12 B7 B2 108.6(2) . . ? B8 B7 B2 108.5(2) . . ? B3 B7 B11 107.48(19) . . ? B12 B7 B11 60.31(19) . . ? B8 B7 B11 108.0(2) . . ? B2 B7 B11 59.80(16) . . ? C1 B6 B10 106.3(2) . . ? C1 B6 B11 106.2(2) . . ? B10 B6 B11 60.44(19) . . ? C1 B6 B2 59.14(15) . . ? B10 B6 B2 108.4(2) . . ? B11 B6 B2 59.99(16) . . ? C1 B6 B5 58.60(17) . . ? B10 B6 B5 60.4(2) . . ? B11 B6 B5 108.2(2) . . ? B2 B6 B5 107.3(2) . . ? C1 B5 B4 60.51(17) . . ? C1 B5 B9 107.8(2) . . ? B4 B5 B9 61.8(2) . . ? C1 B5 B6 58.02(17) . . ? B4 B5 B6 108.5(2) . . ? B9 B5 B6 107.9(2) . . ? C1 B5 B10 105.0(2) . . ? B4 B5 B10 109.2(2) . . ? B9 B5 B10 59.8(2) . . ? B6 B5 B10 59.3(2) . . ? B6 B10 B9 108.4(2) . . ? B6 B10 B11 59.88(18) . . ? B9 B10 B11 108.5(2) . . ? B6 B10 B12 107.9(2) . . ? B9 B10 B12 60.4(2) . . ? B11 B10 B12 59.92(19) . . ? B6 B10 B5 60.31(17) . . ? B9 B10 B5 59.4(2) . . ? B11 B10 B5 107.7(2) . . ? B12 B10 B5 107.3(2) . . ? B6 B11 B2 60.05(16) . . ? B6 B11 B12 107.9(2) . . ? B2 B11 B12 108.0(2) . . ? B6 B11 B7 107.3(2) . . ? B2 B11 B7 59.91(16) . . ? B12 B11 B7 59.38(17) . . ? B6 B11 B10 59.68(18) . . ? B2 B11 B10 107.8(2) . . ? B12 B11 B10 60.10(19) . . ? B7 B11 B10 107.0(2) . . ? B7 B12 B8 60.01(17) . . ? B7 B12 B11 60.32(18) . . ? B8 B12 B11 108.0(2) . . ? B7 B12 B10 107.6(2) . . ? B8 B12 B10 106.6(2) . . ? B11 B12 B10 60.0(2) . . ? B7 B12 B9 107.4(2) . . ? B8 B12 B9 59.2(2) . . ? B11 B12 B9 107.7(2) . . ? B10 B12 B9 59.4(2) . . ? B8 B9 B5 106.6(2) . . ? B8 B9 B10 107.7(3) . . ? B5 B9 B10 60.78(19) . . ? B8 B9 B12 59.83(19) . . ? B5 B9 B12 108.2(3) . . ? B10 B9 B12 60.2(2) . . ? B8 B9 B4 59.61(18) . . ? B5 B9 B4 58.41(18) . . ? B10 B9 B4 107.3(2) . . ? B12 B9 B4 107.4(2) . . ? B3 B4 C1 59.01(16) . . ? B3 B4 B5 107.7(2) . . ? C1 B4 B5 58.79(16) . . ? B3 B4 B8 60.60(17) . . ? C1 B4 B8 105.6(2) . . ? B5 B4 B8 107.1(3) . . ? B3 B4 B9 107.4(2) . . ? C1 B4 B9 104.9(2) . . ? B5 B4 B9 59.74(19) . . ? B8 B4 B9 58.91(18) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.226 _refine_diff_density_min -0.211 _refine_diff_density_rms 0.058