Supplementary Material (ESI) for Chemical Communications This journal is (C) The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Toma Jelinek' 'Colin A. Kilner' 'Mark Thornton-Pett' 'John D. Kennedy' _publ_contact_author_name 'Prof John D. Kennedy' _publ_contact_author_address ; Prof John D. Kennedy School of Chemistry University of Leeds Leeds LS2 9JT UNITED KINGDOM ; _publ_contact_author_email 'JOHNK@CHEM.LEEDS.AC.UK' _publ_section_title ; Monocarbaborane anion chemistry. The elusive C-arylated [PhCB11H11]-,[PhCb9H9]- and [PhCB8H8]-anions ; data_tom10305 _database_code_CSD 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_CSD 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_CSD 164852 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _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 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 ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _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 mixed _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