# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_130725_ny_wyf_62b _audit_creation_date 2013-07-26 _audit_creation_method ; Olex2 1.2 (compiled Apr 23 2013 17:54:37, GUI svn.r4466) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C9 H17 B10 N O' _chemical_formula_sum 'C9 H17 B10 N O' _chemical_formula_weight 263.34 _chemical_melting_point ? _chemical_oxdiff_formula 'C H B N O' 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 7.1110(7) _cell_length_b 9.6524(8) _cell_length_c 12.4183(8) _cell_angle_alpha 104.922(6) _cell_angle_beta 104.856(7) _cell_angle_gamma 103.257(8) _cell_volume 755.24(11) _cell_formula_units_Z 2 _cell_measurement_reflns_used 1781 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 27.4710 _cell_measurement_theta_min 3.3620 _exptl_absorpt_coefficient_mu 0.062 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.95965 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.158 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 272 _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.18 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0401 _diffrn_reflns_av_unetI/netI 0.0479 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 7825 _diffrn_reflns_theta_full 26.37 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_min 3.12 _diffrn_ambient_temperature 293.15 _diffrn_detector_area_resol_mean 16.0355 _diffrn_measured_fraction_theta_full 0.9987 _diffrn_measured_fraction_theta_max 0.8733 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -21.00 34.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 17.7426 -57.0000 -120.0000 55 #__ type_ start__ end____ width___ exp.time_ 2 omega -22.00 56.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 17.7426 -99.0000 0.0000 78 #__ type_ start__ end____ width___ exp.time_ 3 omega -7.00 86.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 17.7426 37.0000 -150.0000 93 #__ type_ start__ end____ width___ exp.time_ 4 omega -49.00 41.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 17.7426 -37.0000 30.0000 90 #__ type_ start__ end____ width___ exp.time_ 5 omega -19.00 23.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - -18.8363 -99.0000 150.0000 42 #__ type_ start__ end____ width___ exp.time_ 6 omega -26.00 91.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 17.7426 19.0000 60.0000 117 #__ type_ start__ end____ width___ exp.time_ 7 omega 32.00 57.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 17.7426 -178.0000 -90.0000 25 #__ type_ start__ end____ width___ exp.time_ 8 omega -25.00 23.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - -18.8363 -99.0000 30.0000 48 ; _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0136489000 _diffrn_orient_matrix_UB_12 0.0778010000 _diffrn_orient_matrix_UB_13 0.0092039000 _diffrn_orient_matrix_UB_21 -0.0999090000 _diffrn_orient_matrix_UB_22 -0.0102973000 _diffrn_orient_matrix_UB_23 0.0036482000 _diffrn_orient_matrix_UB_31 0.0408008000 _diffrn_orient_matrix_UB_32 0.0163415000 _diffrn_orient_matrix_UB_33 0.0619586000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2017 _reflns_number_total 3071 _reflns_odcompleteness_completeness 99.87 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.224 _refine_diff_density_min -0.193 _refine_diff_density_rms 0.038 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 190 _refine_ls_number_reflns 3071 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0935 _refine_ls_R_factor_gt 0.0590 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0907P)^2^+0.0480P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1537 _refine_ls_wR_factor_ref 0.1761 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All B(H) groups, All C(H) groups, All N(H) groups 2.a Aromatic/amide H refined with riding coordinates: N1(H1), C9(H9), C5(H5), C6(H6), C7(H7A), C8(H8A) 2.b Boron cage BH refined with riding coordinates: C1(H1A), B12(H12), B7(H7), B11(H11), B9(H9A), B4(H4), B3(H3), B10(H10), B6(H6A), B8(H8), B5(H5A) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.1348(2) 0.32808(17) 0.24893(13) 0.0409(4) Uani 1 1 d . . . H1 H 0.1196 0.3480 0.3172 0.049 Uiso 1 1 calc R . . C2 C -0.0223(3) 0.5228(2) 0.23926(14) 0.0344(4) Uani 1 1 d . . . C3 C 0.0572(3) 0.4006(2) 0.17979(16) 0.0420(5) Uani 1 1 d . . . C4 C 0.2402(3) 0.2213(2) 0.22290(17) 0.0392(5) Uani 1 1 d . . . C9 C 0.3678(3) 0.2009(2) 0.31713(18) 0.0528(6) Uani 1 1 d . . . H9 H 0.3811 0.2548 0.3939 0.063 Uiso 1 1 calc R . . C1 C -0.1296(3) 0.6031(2) 0.15206(16) 0.0474(6) Uani 1 1 d . . . H1A H -0.1428 0.5674 0.0581 0.057 Uiso 1 1 calc R . . C5 C 0.2185(3) 0.1414(2) 0.10887(18) 0.0498(6) Uani 1 1 d . . . H5 H 0.1329 0.1551 0.0447 0.060 Uiso 1 1 calc R . . B12 B -0.0871(4) 0.7040(3) 0.4262(2) 0.0520(7) Uani 1 1 d . . . H12 H -0.0725 0.7396 0.5203 0.062 Uiso 1 1 calc R . . B7 B 0.1051(4) 0.6490(3) 0.37806(18) 0.0451(6) Uani 1 1 d . . . H7 H 0.2453 0.6458 0.4393 0.054 Uiso 1 1 calc R . . B11 B -0.1337(4) 0.5136(3) 0.3437(2) 0.0471(6) Uani 1 1 d . . . H11 H -0.1475 0.4232 0.3829 0.057 Uiso 1 1 calc R . . B9 B -0.2065(4) 0.7887(3) 0.3298(2) 0.0558(7) Uani 1 1 d . . . H9A H -0.2710 0.8787 0.3602 0.067 Uiso 1 1 calc R . . B4 B -0.0829(5) 0.7890(3) 0.2240(2) 0.0564(7) Uani 1 1 d . . . H4 H -0.0658 0.8785 0.1841 0.068 Uiso 1 1 calc R . . B3 B 0.1100(4) 0.7029(3) 0.2526(2) 0.0486(6) Uani 1 1 d . . . H3 H 0.2509 0.7338 0.2307 0.058 Uiso 1 1 calc R . . B10 B -0.3271(4) 0.5994(3) 0.3142(2) 0.0585(7) Uani 1 1 d . . . H10 H -0.4686 0.5659 0.3349 0.070 Uiso 1 1 calc R . . C6 C 0.3272(4) 0.0400(2) 0.0917(2) 0.0613(7) Uani 1 1 d . . . H6 H 0.3117 -0.0160 0.0150 0.074 Uiso 1 1 calc R . . B6 B -0.2849(4) 0.4805(3) 0.1960(2) 0.0518(6) Uani 1 1 d . . . H6A H -0.3965 0.3698 0.1382 0.062 Uiso 1 1 calc R . . B8 B 0.0639(4) 0.8207(3) 0.3709(2) 0.0549(7) Uani 1 1 d . . . H8 H 0.1764 0.9312 0.4282 0.066 Uiso 1 1 calc R . . B5 B -0.3240(4) 0.6531(3) 0.1882(2) 0.0594(8) Uani 1 1 d . . . H5A H -0.4629 0.6543 0.1246 0.071 Uiso 1 1 calc R . . C7 C 0.4565(4) 0.0207(3) 0.1848(2) 0.0656(7) Uani 1 1 d . . . H7A H 0.5305 -0.0461 0.1716 0.079 Uiso 1 1 calc R . . C8 C 0.4764(4) 0.1007(3) 0.2983(2) 0.0641(7) Uani 1 1 d . . . H8A H 0.5628 0.0873 0.3623 0.077 Uiso 1 1 calc R . . O1 O 0.0476(3) 0.3771(2) 0.07815(13) 0.0860(7) 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 N1 0.0525(10) 0.0470(10) 0.0379(8) 0.0200(7) 0.0219(7) 0.0288(8) C2 0.0405(10) 0.0391(10) 0.0317(9) 0.0161(8) 0.0157(8) 0.0189(8) C3 0.0556(13) 0.0438(11) 0.0386(10) 0.0189(8) 0.0222(9) 0.0248(10) C4 0.0414(11) 0.0348(10) 0.0496(11) 0.0174(8) 0.0202(9) 0.0180(8) C9 0.0622(14) 0.0525(13) 0.0529(12) 0.0209(10) 0.0198(11) 0.0310(11) C1 0.0690(14) 0.0521(12) 0.0372(10) 0.0222(9) 0.0207(10) 0.0369(11) C5 0.0573(14) 0.0470(12) 0.0481(12) 0.0132(9) 0.0184(10) 0.0241(11) B12 0.0690(17) 0.0672(17) 0.0410(12) 0.0227(12) 0.0293(12) 0.0427(14) B7 0.0499(14) 0.0514(14) 0.0333(11) 0.0088(10) 0.0115(10) 0.0239(12) B11 0.0602(15) 0.0554(15) 0.0513(13) 0.0317(11) 0.0348(12) 0.0315(12) B9 0.0764(19) 0.0604(16) 0.0497(14) 0.0208(12) 0.0269(13) 0.0475(15) B4 0.089(2) 0.0467(14) 0.0558(14) 0.0278(12) 0.0356(14) 0.0384(14) B3 0.0560(15) 0.0419(13) 0.0589(14) 0.0224(11) 0.0302(12) 0.0170(11) B10 0.0483(15) 0.0726(18) 0.0731(17) 0.0308(14) 0.0325(13) 0.0324(14) C6 0.0746(16) 0.0522(14) 0.0660(14) 0.0131(11) 0.0332(13) 0.0332(12) B6 0.0377(13) 0.0521(15) 0.0583(14) 0.0136(12) 0.0083(11) 0.0152(11) B8 0.0671(17) 0.0428(14) 0.0538(14) 0.0095(11) 0.0235(13) 0.0195(13) B5 0.0622(17) 0.0741(18) 0.0500(14) 0.0204(13) 0.0110(13) 0.0454(15) C7 0.0663(16) 0.0525(14) 0.0963(19) 0.0285(13) 0.0365(14) 0.0380(12) C8 0.0678(16) 0.0635(15) 0.0737(16) 0.0311(13) 0.0193(13) 0.0398(13) O1 0.1708(19) 0.0948(14) 0.0509(9) 0.0436(9) 0.0629(11) 0.0986(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 H1 0.8600 . ? N1 C3 1.332(2) . ? N1 C4 1.426(2) . ? C2 C3 1.525(3) . ? C2 C1 1.624(2) . ? C2 B7 1.699(3) . ? C2 B11 1.695(3) . ? C2 B3 1.719(3) . ? C2 B6 1.722(3) . ? C3 O1 1.204(2) . ? C4 C9 1.374(3) . ? C4 C5 1.377(3) . ? C9 H9 0.9300 . ? C9 C8 1.380(3) . ? C1 H1A 1.1000 . ? C1 B4 1.697(3) . ? C1 B3 1.711(3) . ? C1 B6 1.720(3) . ? C1 B5 1.691(3) . ? C5 H5 0.9300 . ? C5 C6 1.388(3) . ? B12 H12 1.1000 . ? B12 B7 1.760(3) . ? B12 B11 1.765(3) . ? B12 B9 1.767(3) . ? B12 B10 1.771(4) . ? B12 B8 1.765(4) . ? B7 H7 1.1000 . ? B7 B11 1.760(4) . ? B7 B3 1.771(3) . ? B7 B8 1.769(3) . ? B11 H11 1.1000 . ? B11 B10 1.770(3) . ? B11 B6 1.776(3) . ? B9 H9A 1.1000 . ? B9 B4 1.758(4) . ? B9 B10 1.768(4) . ? B9 B8 1.787(4) . ? B9 B5 1.750(3) . ? B4 H4 1.1000 . ? B4 B3 1.768(4) . ? B4 B8 1.760(4) . ? B4 B5 1.771(4) . ? B3 H3 1.1000 . ? B3 B8 1.765(3) . ? B10 H10 1.1000 . ? B10 B6 1.755(4) . ? B10 B5 1.774(4) . ? C6 H6 0.9300 . ? C6 C7 1.364(3) . ? B6 H6A 1.1000 . ? B6 B5 1.773(4) . ? B8 H8 1.1000 . ? B5 H5A 1.1000 . ? C7 H7A 0.9300 . ? C7 C8 1.376(3) . ? C8 H8A 0.9300 . ? 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 C3 N1 H1 116.2 . . ? C3 N1 C4 127.55(16) . . ? C4 N1 H1 116.2 . . ? C3 C2 C1 114.36(14) . . ? C3 C2 B7 123.58(15) . . ? C3 C2 B11 124.52(16) . . ? C3 C2 B3 114.23(16) . . ? C3 C2 B6 115.86(16) . . ? C1 C2 B7 110.74(14) . . ? C1 C2 B11 111.16(15) . . ? C1 C2 B3 61.48(13) . . ? C1 C2 B6 61.80(13) . . ? B7 C2 B3 62.40(13) . . ? B7 C2 B6 114.41(15) . . ? B11 C2 B7 62.48(13) . . ? B11 C2 B3 114.45(15) . . ? B11 C2 B6 62.62(14) . . ? B3 C2 B6 115.10(16) . . ? N1 C3 C2 114.75(16) . . ? O1 C3 N1 125.37(18) . . ? O1 C3 C2 119.89(16) . . ? C9 C4 N1 117.28(17) . . ? C9 C4 C5 120.30(18) . . ? C5 C4 N1 122.42(17) . . ? C4 C9 H9 119.8 . . ? C4 C9 C8 120.3(2) . . ? C8 C9 H9 119.8 . . ? C2 C1 H1A 120.5 . . ? C2 C1 B4 111.61(15) . . ? C2 C1 B3 62.02(12) . . ? C2 C1 B6 61.92(12) . . ? C2 C1 B5 111.86(16) . . ? B4 C1 H1A 118.4 . . ? B4 C1 B3 62.51(14) . . ? B4 C1 B6 114.96(17) . . ? B3 C1 H1A 117.0 . . ? B3 C1 B6 115.65(15) . . ? B6 C1 H1A 117.1 . . ? B5 C1 H1A 118.1 . . ? B5 C1 B4 63.03(16) . . ? B5 C1 B3 115.24(16) . . ? B5 C1 B6 62.63(15) . . ? C4 C5 H5 120.7 . . ? C4 C5 C6 118.57(19) . . ? C6 C5 H5 120.7 . . ? B7 B12 H12 121.6 . . ? B7 B12 B11 59.91(13) . . ? B7 B12 B9 108.51(17) . . ? B7 B12 B10 108.24(17) . . ? B7 B12 B8 60.23(14) . . ? B11 B12 H12 121.8 . . ? B11 B12 B9 108.05(16) . . ? B11 B12 B10 60.06(15) . . ? B11 B12 B8 108.51(16) . . ? B9 B12 H12 121.5 . . ? B9 B12 B10 59.98(15) . . ? B10 B12 H12 121.4 . . ? B8 B12 H12 120.9 . . ? B8 B12 B9 60.80(15) . . ? B8 B12 B10 109.01(18) . . ? C2 B7 B12 104.58(16) . . ? C2 B7 H7 124.6 . . ? C2 B7 B11 58.65(12) . . ? C2 B7 B3 59.36(12) . . ? C2 B7 B8 105.04(15) . . ? B12 B7 H7 122.5 . . ? B12 B7 B11 60.19(14) . . ? B12 B7 B3 107.98(16) . . ? B12 B7 B8 60.03(14) . . ? B11 B7 H7 121.0 . . ? B11 B7 B3 108.79(16) . . ? B11 B7 B8 108.57(17) . . ? B3 B7 H7 121.1 . . ? B8 B7 H7 122.2 . . ? B8 B7 B3 59.83(14) . . ? C2 B11 B12 104.53(17) . . ? C2 B11 B7 58.87(12) . . ? C2 B11 H11 124.6 . . ? C2 B11 B10 104.70(16) . . ? C2 B11 B6 59.44(12) . . ? B12 B11 H11 122.6 . . ? B12 B11 B10 60.13(15) . . ? B12 B11 B6 107.72(16) . . ? B7 B11 B12 59.90(14) . . ? B7 B11 H11 121.0 . . ? B7 B11 B10 108.29(18) . . ? B7 B11 B6 108.84(17) . . ? B10 B11 H11 122.5 . . ? B10 B11 B6 59.33(14) . . ? B6 B11 H11 121.3 . . ? B12 B9 H9A 122.1 . . ? B12 B9 B10 60.12(15) . . ? B12 B9 B8 59.55(15) . . ? B4 B9 B12 107.35(17) . . ? B4 B9 H9A 121.7 . . ? B4 B9 B10 108.76(17) . . ? B4 B9 B8 59.52(15) . . ? B10 B9 H9A 121.2 . . ? B10 B9 B8 108.13(17) . . ? B8 B9 H9A 122.0 . . ? B5 B9 B12 108.35(17) . . ? B5 B9 H9A 121.1 . . ? B5 B9 B4 60.63(15) . . ? B5 B9 B10 60.56(16) . . ? B5 B9 B8 108.32(17) . . ? C1 B4 B9 104.01(18) . . ? C1 B4 H4 125.2 . . ? C1 B4 B3 59.14(13) . . ? C1 B4 B8 104.84(16) . . ? C1 B4 B5 58.32(14) . . ? B9 B4 H4 122.3 . . ? B9 B4 B3 108.85(17) . . ? B9 B4 B8 61.08(14) . . ? B9 B4 B5 59.48(16) . . ? B3 B4 H4 120.9 . . ? B3 B4 B5 108.54(18) . . ? B8 B4 H4 121.8 . . ? B8 B4 B3 60.05(14) . . ? B8 B4 B5 108.64(19) . . ? B5 B4 H4 121.5 . . ? C2 B3 B7 58.24(12) . . ? C2 B3 B4 103.91(17) . . ? C2 B3 H3 125.0 . . ? C2 B3 B8 104.33(17) . . ? C1 B3 C2 56.50(11) . . ? C1 B3 B7 103.50(17) . . ? C1 B3 B4 58.36(13) . . ? C1 B3 H3 125.3 . . ? C1 B3 B8 104.01(18) . . ? B7 B3 H3 122.6 . . ? B4 B3 B7 107.30(18) . . ? B4 B3 H3 122.5 . . ? B8 B3 B7 60.03(13) . . ? B8 B3 B4 59.75(14) . . ? B8 B3 H3 123.1 . . ? B12 B10 H10 122.0 . . ? B12 B10 B5 107.1(2) . . ? B11 B10 B12 59.81(14) . . ? B11 B10 H10 121.6 . . ? B11 B10 B5 107.90(18) . . ? B9 B10 B12 59.90(15) . . ? B9 B10 B11 107.80(19) . . ? B9 B10 H10 122.0 . . ? B9 B10 B5 59.21(15) . . ? B6 B10 B12 108.41(17) . . ? B6 B10 B11 60.52(14) . . ? B6 B10 B9 108.17(19) . . ? B6 B10 H10 121.1 . . ? B6 B10 B5 60.31(14) . . ? B5 B10 H10 122.3 . . ? C5 C6 H6 119.3 . . ? C7 C6 C5 121.4(2) . . ? C7 C6 H6 119.3 . . ? C2 B6 B11 57.94(12) . . ? C2 B6 B10 104.19(17) . . ? C2 B6 H6A 125.3 . . ? C2 B6 B5 103.53(18) . . ? C1 B6 C2 56.28(12) . . ? C1 B6 B11 103.08(16) . . ? C1 B6 B10 103.94(18) . . ? C1 B6 H6A 125.7 . . ? C1 B6 B5 57.86(14) . . ? B11 B6 H6A 122.6 . . ? B10 B6 B11 60.15(14) . . ? B10 B6 H6A 122.8 . . ? B10 B6 B5 60.39(15) . . ? B5 B6 B11 107.67(17) . . ? B5 B6 H6A 122.4 . . ? B12 B8 B7 59.74(14) . . ? B12 B8 B9 59.65(15) . . ? B12 B8 B3 107.99(17) . . ? B12 B8 H8 122.0 . . ? B7 B8 B9 107.21(19) . . ? B7 B8 H8 122.0 . . ? B9 B8 H8 122.3 . . ? B4 B8 B12 107.33(19) . . ? B4 B8 B7 107.74(16) . . ? B4 B8 B9 59.40(15) . . ? B4 B8 B3 60.20(13) . . ? B4 B8 H8 122.0 . . ? B3 B8 B7 60.14(13) . . ? B3 B8 B9 107.64(18) . . ? B3 B8 H8 121.5 . . ? C1 B5 B9 104.60(18) . . ? C1 B5 B4 58.66(14) . . ? C1 B5 B10 104.36(16) . . ? C1 B5 B6 59.51(13) . . ? C1 B5 H5A 124.7 . . ? B9 B5 B4 59.90(15) . . ? B9 B5 B10 60.23(15) . . ? B9 B5 B6 108.17(17) . . ? B9 B5 H5A 122.3 . . ? B4 B5 B10 107.91(18) . . ? B4 B5 B6 108.79(17) . . ? B4 B5 H5A 121.3 . . ? B10 B5 H5A 122.8 . . ? B6 B5 B10 59.30(15) . . ? B6 B5 H5A 121.1 . . ? C6 C7 H7A 120.3 . . ? C6 C7 C8 119.5(2) . . ? C8 C7 H7A 120.3 . . ? C9 C8 H8A 120.1 . . ? C7 C8 C9 119.9(2) . . ? C7 C8 H8A 120.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C4 C9 C8 -179.2(2) . . . . ? N1 C4 C5 C6 179.9(2) . . . . ? C2 C1 B4 B9 -64.6(2) . . . . ? C2 C1 B4 B3 39.19(17) . . . . ? C2 C1 B4 B8 -1.3(2) . . . . ? C2 C1 B4 B5 -104.35(18) . . . . ? C2 C1 B3 B7 -36.10(13) . . . . ? C2 C1 B3 B4 -138.29(17) . . . . ? C2 C1 B3 B8 -98.09(17) . . . . ? C2 C1 B6 B11 35.89(13) . . . . ? C2 C1 B6 B10 97.93(16) . . . . ? C2 C1 B6 B5 138.71(16) . . . . ? C2 C1 B5 B9 63.9(2) . . . . ? C2 C1 B5 B4 103.95(18) . . . . ? C2 C1 B5 B10 1.5(2) . . . . ? C2 C1 B5 B6 -38.85(16) . . . . ? C2 B7 B11 B12 -133.54(16) . . . . ? C2 B7 B11 B10 -96.46(17) . . . . ? C2 B7 B11 B6 -33.52(14) . . . . ? C2 B7 B3 C1 35.30(13) . . . . ? C2 B7 B3 B4 95.94(18) . . . . ? C2 B7 B3 B8 133.87(18) . . . . ? C2 B7 B8 B12 98.39(17) . . . . ? C2 B7 B8 B9 60.9(2) . . . . ? C2 B7 B8 B4 -1.7(2) . . . . ? C2 B7 B8 B3 -39.96(15) . . . . ? C2 B11 B10 B12 -98.54(18) . . . . ? C2 B11 B10 B9 -61.3(2) . . . . ? C2 B11 B10 B6 39.94(16) . . . . ? C2 B11 B10 B5 1.2(2) . . . . ? C2 B11 B6 C1 -35.12(13) . . . . ? C2 B11 B6 B10 -133.85(19) . . . . ? C2 B11 B6 B5 -95.17(19) . . . . ? C2 B3 B8 B12 2.1(2) . . . . ? C2 B3 B8 B7 39.25(15) . . . . ? C2 B3 B8 B9 -60.9(2) . . . . ? C2 B3 B8 B4 -97.95(18) . . . . ? C2 B6 B5 C1 34.37(14) . . . . ? C2 B6 B5 B9 -62.2(2) . . . . ? C2 B6 B5 B4 1.3(2) . . . . ? C2 B6 B5 B10 -98.82(18) . . . . ? C3 N1 C4 C9 157.5(2) . . . . ? C3 N1 C4 C5 -22.1(3) . . . . ? C3 C2 C1 B4 -144.87(18) . . . . ? C3 C2 C1 B3 -105.47(18) . . . . ? C3 C2 C1 B6 107.49(18) . . . . ? C3 C2 C1 B5 146.64(18) . . . . ? C3 C2 B7 B12 -155.44(18) . . . . ? C3 C2 B7 B11 -114.9(2) . . . . ? C3 C2 B7 B3 102.1(2) . . . . ? C3 C2 B7 B8 142.25(19) . . . . ? C3 C2 B11 B12 153.87(17) . . . . ? C3 C2 B11 B7 113.49(19) . . . . ? C3 C2 B11 B10 -143.77(18) . . . . ? C3 C2 B11 B6 -103.9(2) . . . . ? C3 C2 B3 C1 105.68(16) . . . . ? C3 C2 B3 B7 -116.68(17) . . . . ? C3 C2 B3 B4 141.38(16) . . . . ? C3 C2 B3 B8 -156.82(16) . . . . ? C3 C2 B6 C1 -105.08(17) . . . . ? C3 C2 B6 B11 117.27(18) . . . . ? C3 C2 B6 B10 157.45(16) . . . . ? C3 C2 B6 B5 -140.16(17) . . . . ? C4 N1 C3 C2 -172.48(17) . . . . ? C4 N1 C3 O1 7.1(4) . . . . ? C4 C9 C8 C7 -0.1(4) . . . . ? C4 C5 C6 C7 -1.2(4) . . . . ? C9 C4 C5 C6 0.3(3) . . . . ? C1 C2 C3 N1 -176.31(17) . . . . ? C1 C2 C3 O1 4.1(3) . . . . ? C1 C2 B7 B12 63.2(2) . . . . ? C1 C2 B7 B11 103.77(17) . . . . ? C1 C2 B7 B3 -39.28(16) . . . . ? C1 C2 B7 B8 0.9(2) . . . . ? C1 C2 B11 B12 -62.71(19) . . . . ? C1 C2 B11 B7 -103.09(16) . . . . ? C1 C2 B11 B10 -0.3(2) . . . . ? C1 C2 B11 B6 39.54(16) . . . . ? C1 C2 B3 B7 137.64(16) . . . . ? C1 C2 B3 B4 35.70(14) . . . . ? C1 C2 B3 B8 97.51(17) . . . . ? C1 C2 B6 B11 -137.65(16) . . . . ? C1 C2 B6 B10 -97.47(18) . . . . ? C1 C2 B6 B5 -35.08(14) . . . . ? C1 B4 B3 C2 -34.86(14) . . . . ? C1 B4 B3 B7 -95.47(18) . . . . ? C1 B4 B3 B8 -133.53(18) . . . . ? C1 B4 B8 B12 -61.1(2) . . . . ? C1 B4 B8 B7 1.9(2) . . . . ? C1 B4 B8 B9 -98.0(2) . . . . ? C1 B4 B8 B3 40.08(16) . . . . ? C1 B4 B5 B9 133.97(16) . . . . ? C1 B4 B5 B10 96.21(18) . . . . ? C1 B4 B5 B6 33.39(15) . . . . ? C1 B3 B8 B12 60.6(2) . . . . ? C1 B3 B8 B7 97.69(17) . . . . ? C1 B3 B8 B9 -2.4(2) . . . . ? C1 B3 B8 B4 -39.51(16) . . . . ? C1 B6 B5 B9 -96.6(2) . . . . ? C1 B6 B5 B4 -33.06(15) . . . . ? C1 B6 B5 B10 -133.18(18) . . . . ? C5 C4 C9 C8 0.4(3) . . . . ? C5 C6 C7 C8 1.5(4) . . . . ? B12 B7 B11 C2 133.54(16) . . . . ? B12 B7 B11 B10 37.07(16) . . . . ? B12 B7 B11 B6 100.02(17) . . . . ? B12 B7 B3 C2 -96.62(18) . . . . ? B12 B7 B3 C1 -61.3(2) . . . . ? B12 B7 B3 B4 -0.7(2) . . . . ? B12 B7 B3 B8 37.24(18) . . . . ? B12 B7 B8 B9 -37.52(16) . . . . ? B12 B7 B8 B4 -100.1(2) . . . . ? B12 B7 B8 B3 -138.36(19) . . . . ? B12 B11 B10 B9 37.24(16) . . . . ? B12 B11 B10 B6 138.47(19) . . . . ? B12 B11 B10 B5 99.8(2) . . . . ? B12 B11 B6 C2 96.73(18) . . . . ? B12 B11 B6 C1 61.6(2) . . . . ? B12 B11 B6 B10 -37.13(18) . . . . ? B12 B11 B6 B5 1.6(2) . . . . ? B12 B9 B4 C1 62.5(2) . . . . ? B12 B9 B4 B3 0.8(3) . . . . ? B12 B9 B4 B8 -36.88(17) . . . . ? B12 B9 B4 B5 101.7(2) . . . . ? B12 B9 B10 B11 -37.20(16) . . . . ? B12 B9 B10 B6 -101.18(18) . . . . ? B12 B9 B10 B5 -137.83(18) . . . . ? B12 B9 B8 B7 37.56(16) . . . . ? B12 B9 B8 B4 138.36(18) . . . . ? B12 B9 B8 B3 100.92(19) . . . . ? B12 B9 B5 C1 -60.6(2) . . . . ? B12 B9 B5 B4 -100.0(2) . . . . ? B12 B9 B5 B10 37.83(18) . . . . ? B12 B9 B5 B6 1.6(3) . . . . ? B12 B10 B6 C2 -1.9(2) . . . . ? B12 B10 B6 C1 -60.1(2) . . . . ? B12 B10 B6 B11 37.15(17) . . . . ? B12 B10 B6 B5 -99.6(2) . . . . ? B12 B10 B5 C1 61.4(2) . . . . ? B12 B10 B5 B9 -37.43(17) . . . . ? B12 B10 B5 B4 0.2(2) . . . . ? B12 B10 B5 B6 101.82(19) . . . . ? B7 C2 C3 N1 43.6(3) . . . . ? B7 C2 C3 O1 -136.0(2) . . . . ? B7 C2 C1 B4 0.3(2) . . . . ? B7 C2 C1 B3 39.68(16) . . . . ? B7 C2 C1 B6 -107.37(17) . . . . ? B7 C2 C1 B5 -68.2(2) . . . . ? B7 C2 B11 B12 40.38(15) . . . . ? B7 C2 B11 B10 102.75(18) . . . . ? B7 C2 B11 B6 142.63(16) . . . . ? B7 C2 B3 C1 -137.64(16) . . . . ? B7 C2 B3 B4 -101.94(18) . . . . ? B7 C2 B3 B8 -40.13(15) . . . . ? B7 C2 B6 C1 101.41(17) . . . . ? B7 C2 B6 B11 -36.24(16) . . . . ? B7 C2 B6 B10 3.9(2) . . . . ? B7 C2 B6 B5 66.3(2) . . . . ? B7 B12 B11 C2 -39.87(14) . . . . ? B7 B12 B11 B10 -138.70(18) . . . . ? B7 B12 B11 B6 -101.93(18) . . . . ? B7 B12 B9 B4 -1.2(2) . . . . ? B7 B12 B9 B10 100.83(19) . . . . ? B7 B12 B9 B8 -38.10(17) . . . . ? B7 B12 B9 B5 62.8(3) . . . . ? B7 B12 B10 B11 36.97(17) . . . . ? B7 B12 B10 B9 -101.28(19) . . . . ? B7 B12 B10 B6 -0.5(2) . . . . ? B7 B12 B10 B5 -64.2(2) . . . . ? B7 B12 B8 B9 137.61(17) . . . . ? B7 B12 B8 B4 100.80(17) . . . . ? B7 B12 B8 B3 37.30(16) . . . . ? B7 B11 B10 B12 -36.97(16) . . . . ? B7 B11 B10 B9 0.3(2) . . . . ? B7 B11 B10 B6 101.50(18) . . . . ? B7 B11 B10 B5 62.8(2) . . . . ? B7 B11 B6 C2 33.30(14) . . . . ? B7 B11 B6 C1 -1.8(2) . . . . ? B7 B11 B6 B10 -100.56(19) . . . . ? B7 B11 B6 B5 -61.9(2) . . . . ? B7 B3 B8 B12 -37.12(17) . . . . ? B7 B3 B8 B9 -100.1(2) . . . . ? B7 B3 B8 B4 -137.2(2) . . . . ? B11 C2 C3 N1 -33.9(3) . . . . ? B11 C2 C3 O1 146.5(2) . . . . ? B11 C2 C1 B4 67.7(2) . . . . ? B11 C2 C1 B3 107.14(17) . . . . ? B11 C2 C1 B6 -39.90(16) . . . . ? B11 C2 C1 B5 -0.7(2) . . . . ? B11 C2 B7 B12 -40.54(15) . . . . ? B11 C2 B7 B3 -143.05(17) . . . . ? B11 C2 B7 B8 -102.85(18) . . . . ? B11 C2 B3 C1 -101.79(17) . . . . ? B11 C2 B3 B7 35.85(16) . . . . ? B11 C2 B3 B4 -66.1(2) . . . . ? B11 C2 B3 B8 -4.3(2) . . . . ? B11 C2 B6 C1 137.65(16) . . . . ? B11 C2 B6 B10 40.18(16) . . . . ? B11 C2 B6 B5 102.57(18) . . . . ? B11 B12 B7 C2 39.77(14) . . . . ? B11 B12 B7 B3 101.79(18) . . . . ? B11 B12 B7 B8 138.94(17) . . . . ? B11 B12 B9 B4 -64.7(2) . . . . ? B11 B12 B9 B10 37.37(18) . . . . ? B11 B12 B9 B8 -101.56(18) . . . . ? B11 B12 B9 B5 -0.7(3) . . . . ? B11 B12 B10 B9 -138.24(18) . . . . ? B11 B12 B10 B6 -37.46(17) . . . . ? B11 B12 B10 B5 -101.12(19) . . . . ? B11 B12 B8 B7 -36.82(16) . . . . ? B11 B12 B8 B9 100.79(18) . . . . ? B11 B12 B8 B4 64.0(2) . . . . ? B11 B12 B8 B3 0.5(2) . . . . ? B11 B7 B3 C2 -32.84(14) . . . . ? B11 B7 B3 C1 2.5(2) . . . . ? B11 B7 B3 B4 63.1(2) . . . . ? B11 B7 B3 B8 101.03(18) . . . . ? B11 B7 B8 B12 36.95(15) . . . . ? B11 B7 B8 B9 -0.6(2) . . . . ? B11 B7 B8 B4 -63.2(2) . . . . ? B11 B7 B8 B3 -101.40(18) . . . . ? B11 B10 B6 C2 -39.08(16) . . . . ? B11 B10 B6 C1 -97.26(17) . . . . ? B11 B10 B6 B5 -136.8(2) . . . . ? B11 B10 B5 C1 -1.6(3) . . . . ? B11 B10 B5 B9 -100.5(2) . . . . ? B11 B10 B5 B4 -62.8(2) . . . . ? B11 B10 B5 B6 38.79(18) . . . . ? B11 B6 B5 C1 94.61(17) . . . . ? B11 B6 B5 B9 -2.0(3) . . . . ? B11 B6 B5 B4 61.6(2) . . . . ? B11 B6 B5 B10 -38.57(18) . . . . ? B9 B12 B7 C2 -60.8(2) . . . . ? B9 B12 B7 B11 -100.59(19) . . . . ? B9 B12 B7 B3 1.2(2) . . . . ? B9 B12 B7 B8 38.35(18) . . . . ? B9 B12 B11 C2 61.5(2) . . . . ? B9 B12 B11 B7 101.36(19) . . . . ? B9 B12 B11 B10 -37.34(18) . . . . ? B9 B12 B11 B6 -0.6(2) . . . . ? B9 B12 B10 B11 138.24(18) . . . . ? B9 B12 B10 B6 100.8(2) . . . . ? B9 B12 B10 B5 37.12(16) . . . . ? B9 B12 B8 B7 -137.61(17) . . . . ? B9 B12 B8 B4 -36.81(16) . . . . ? B9 B12 B8 B3 -100.32(19) . . . . ? B9 B4 B3 C2 60.5(2) . . . . ? B9 B4 B3 C1 95.4(2) . . . . ? B9 B4 B3 B7 -0.1(2) . . . . ? B9 B4 B3 B8 -38.13(18) . . . . ? B9 B4 B8 B12 36.92(16) . . . . ? B9 B4 B8 B7 99.9(2) . . . . ? B9 B4 B8 B3 138.11(19) . . . . ? B9 B4 B5 C1 -133.97(16) . . . . ? B9 B4 B5 B10 -37.75(16) . . . . ? B9 B4 B5 B6 -100.57(18) . . . . ? B9 B10 B6 C2 61.5(2) . . . . ? B9 B10 B6 C1 3.3(2) . . . . ? B9 B10 B6 B11 100.6(2) . . . . ? B9 B10 B6 B5 -36.17(17) . . . . ? B9 B10 B5 C1 98.8(2) . . . . ? B9 B10 B5 B4 37.61(17) . . . . ? B9 B10 B5 B6 139.25(19) . . . . ? B4 C1 B3 C2 138.29(17) . . . . ? B4 C1 B3 B7 102.19(18) . . . . ? B4 C1 B3 B8 40.21(16) . . . . ? B4 C1 B6 C2 -102.24(18) . . . . ? B4 C1 B6 B11 -66.4(2) . . . . ? B4 C1 B6 B10 -4.3(2) . . . . ? B4 C1 B6 B5 36.47(17) . . . . ? B4 C1 B5 B9 -40.05(16) . . . . ? B4 C1 B5 B10 -102.5(2) . . . . ? B4 C1 B5 B6 -142.80(16) . . . . ? B4 B9 B10 B12 99.68(19) . . . . ? B4 B9 B10 B11 62.5(2) . . . . ? B4 B9 B10 B6 -1.5(2) . . . . ? B4 B9 B10 B5 -38.15(17) . . . . ? B4 B9 B8 B12 -138.36(18) . . . . ? B4 B9 B8 B7 -100.80(17) . . . . ? B4 B9 B8 B3 -37.44(17) . . . . ? B4 B9 B5 C1 39.44(16) . . . . ? B4 B9 B5 B10 137.84(18) . . . . ? B4 B9 B5 B6 101.6(2) . . . . ? B4 B3 B8 B12 100.1(2) . . . . ? B4 B3 B8 B7 137.2(2) . . . . ? B4 B3 B8 B9 37.09(17) . . . . ? B3 C2 C3 N1 115.46(19) . . . . ? B3 C2 C3 O1 -64.1(3) . . . . ? B3 C2 C1 B4 -39.40(17) . . . . ? B3 C2 C1 B6 -147.04(16) . . . . ? B3 C2 C1 B5 -107.89(19) . . . . ? B3 C2 B7 B12 102.51(18) . . . . ? B3 C2 B7 B11 143.05(17) . . . . ? B3 C2 B7 B8 40.19(16) . . . . ? B3 C2 B11 B12 4.6(2) . . . . ? B3 C2 B11 B7 -35.82(16) . . . . ? B3 C2 B11 B10 66.9(2) . . . . ? B3 C2 B11 B6 106.81(18) . . . . ? B3 C2 B6 C1 31.86(15) . . . . ? B3 C2 B6 B11 -105.79(17) . . . . ? B3 C2 B6 B10 -65.6(2) . . . . ? B3 C2 B6 B5 -3.2(2) . . . . ? B3 C1 B4 B9 -103.82(18) . . . . ? B3 C1 B4 B8 -40.54(17) . . . . ? B3 C1 B4 B5 -143.54(17) . . . . ? B3 C1 B6 C2 -32.20(15) . . . . ? B3 C1 B6 B11 3.7(2) . . . . ? B3 C1 B6 B10 65.7(2) . . . . ? B3 C1 B6 B5 106.51(18) . . . . ? B3 C1 B5 B9 -4.4(2) . . . . ? B3 C1 B5 B4 35.65(17) . . . . ? B3 C1 B5 B10 -66.8(2) . . . . ? B3 C1 B5 B6 -107.15(18) . . . . ? B3 B7 B11 C2 33.12(14) . . . . ? B3 B7 B11 B12 -100.42(17) . . . . ? B3 B7 B11 B10 -63.3(2) . . . . ? B3 B7 B11 B6 -0.4(2) . . . . ? B3 B7 B8 B12 138.36(19) . . . . ? B3 B7 B8 B9 100.84(19) . . . . ? B3 B7 B8 B4 38.25(18) . . . . ? B3 B4 B8 B12 -101.19(18) . . . . ? B3 B4 B8 B7 -38.22(18) . . . . ? B3 B4 B8 B9 -138.11(19) . . . . ? B3 B4 B5 C1 -32.55(15) . . . . ? B3 B4 B5 B9 101.42(18) . . . . ? B3 B4 B5 B10 63.7(2) . . . . ? B3 B4 B5 B6 0.8(2) . . . . ? B10 B12 B7 C2 2.7(2) . . . . ? B10 B12 B7 B11 -37.03(17) . . . . ? B10 B12 B7 B3 64.8(2) . . . . ? B10 B12 B7 B8 101.92(19) . . . . ? B10 B12 B11 C2 98.83(18) . . . . ? B10 B12 B11 B7 138.70(18) . . . . ? B10 B12 B11 B6 36.77(17) . . . . ? B10 B12 B9 B4 -102.1(2) . . . . ? B10 B12 B9 B8 -138.93(18) . . . . ? B10 B12 B9 B5 -38.03(19) . . . . ? B10 B12 B8 B7 -100.63(18) . . . . ? B10 B12 B8 B9 36.99(16) . . . . ? B10 B12 B8 B4 0.2(2) . . . . ? B10 B12 B8 B3 -63.3(2) . . . . ? B10 B11 B6 C2 133.85(19) . . . . ? B10 B11 B6 C1 98.73(19) . . . . ? B10 B11 B6 B5 38.68(19) . . . . ? B10 B9 B4 C1 -1.0(2) . . . . ? B10 B9 B4 B3 -62.8(2) . . . . ? B10 B9 B4 B8 -100.45(19) . . . . ? B10 B9 B4 B5 38.12(17) . . . . ? B10 B9 B8 B12 -36.83(17) . . . . ? B10 B9 B8 B7 0.7(2) . . . . ? B10 B9 B8 B4 101.53(19) . . . . ? B10 B9 B8 B3 64.1(2) . . . . ? B10 B9 B5 C1 -98.41(18) . . . . ? B10 B9 B5 B4 -137.84(18) . . . . ? B10 B9 B5 B6 -36.21(18) . . . . ? B10 B6 B5 C1 133.18(18) . . . . ? B10 B6 B5 B9 36.61(18) . . . . ? B10 B6 B5 B4 100.1(2) . . . . ? C6 C7 C8 C9 -0.8(4) . . . . ? B6 C2 C3 N1 -107.2(2) . . . . ? B6 C2 C3 O1 73.2(3) . . . . ? B6 C2 C1 B4 107.64(19) . . . . ? B6 C2 C1 B3 147.04(16) . . . . ? B6 C2 C1 B5 39.15(17) . . . . ? B6 C2 B7 B12 -4.2(2) . . . . ? B6 C2 B7 B11 36.29(16) . . . . ? B6 C2 B7 B3 -106.76(18) . . . . ? B6 C2 B7 B8 -66.6(2) . . . . ? B6 C2 B11 B12 -102.25(17) . . . . ? B6 C2 B11 B7 -142.63(16) . . . . ? B6 C2 B11 B10 -39.89(17) . . . . ? B6 C2 B3 C1 -31.97(16) . . . . ? B6 C2 B3 B7 105.67(17) . . . . ? B6 C2 B3 B4 3.7(2) . . . . ? B6 C2 B3 B8 65.5(2) . . . . ? B6 C1 B4 B9 3.4(2) . . . . ? B6 C1 B4 B3 107.22(18) . . . . ? B6 C1 B4 B8 66.7(2) . . . . ? B6 C1 B4 B5 -36.32(17) . . . . ? B6 C1 B3 C2 32.17(15) . . . . ? B6 C1 B3 B7 -3.9(2) . . . . ? B6 C1 B3 B4 -106.12(18) . . . . ? B6 C1 B3 B8 -65.9(2) . . . . ? B6 C1 B5 B9 102.75(19) . . . . ? B6 C1 B5 B4 142.80(16) . . . . ? B6 C1 B5 B10 40.33(18) . . . . ? B6 B11 B10 B12 -138.47(19) . . . . ? B6 B11 B10 B9 -101.2(2) . . . . ? B6 B11 B10 B5 -38.70(18) . . . . ? B6 B10 B5 C1 -40.43(16) . . . . ? B6 B10 B5 B9 -139.25(19) . . . . ? B6 B10 B5 B4 -101.64(19) . . . . ? B8 B12 B7 C2 -99.17(17) . . . . ? B8 B12 B7 B11 -138.94(17) . . . . ? B8 B12 B7 B3 -37.16(17) . . . . ? B8 B12 B11 C2 -2.9(2) . . . . ? B8 B12 B11 B7 36.96(16) . . . . ? B8 B12 B11 B10 -101.74(19) . . . . ? B8 B12 B11 B6 -65.0(2) . . . . ? B8 B12 B9 B4 36.87(17) . . . . ? B8 B12 B9 B10 138.93(18) . . . . ? B8 B12 B9 B5 100.9(2) . . . . ? B8 B12 B10 B11 100.90(18) . . . . ? B8 B12 B10 B9 -37.34(17) . . . . ? B8 B12 B10 B6 63.4(2) . . . . ? B8 B12 B10 B5 -0.2(2) . . . . ? B8 B7 B11 C2 96.65(16) . . . . ? B8 B7 B11 B12 -36.89(15) . . . . ? B8 B7 B11 B10 0.2(2) . . . . ? B8 B7 B11 B6 63.13(19) . . . . ? B8 B7 B3 C2 -133.87(17) . . . . ? B8 B7 B3 C1 -98.57(18) . . . . ? B8 B7 B3 B4 -37.93(17) . . . . ? B8 B9 B4 C1 99.43(18) . . . . ? B8 B9 B4 B3 37.69(18) . . . . ? B8 B9 B4 B5 138.57(18) . . . . ? B8 B9 B10 B12 36.58(16) . . . . ? B8 B9 B10 B11 -0.6(2) . . . . ? B8 B9 B10 B6 -64.6(2) . . . . ? B8 B9 B10 B5 -101.25(19) . . . . ? B8 B9 B5 C1 2.5(2) . . . . ? B8 B9 B5 B4 -36.92(17) . . . . ? B8 B9 B5 B10 100.92(19) . . . . ? B8 B9 B5 B6 64.7(2) . . . . ? B8 B4 B3 C2 98.67(18) . . . . ? B8 B4 B3 C1 133.53(18) . . . . ? B8 B4 B3 B7 38.06(17) . . . . ? B8 B4 B5 C1 -96.29(17) . . . . ? B8 B4 B5 B9 37.68(16) . . . . ? B8 B4 B5 B10 -0.1(2) . . . . ? B8 B4 B5 B6 -62.9(2) . . . . ? B5 C1 B4 B9 39.72(16) . . . . ? B5 C1 B4 B3 143.54(17) . . . . ? B5 C1 B4 B8 103.00(19) . . . . ? B5 C1 B3 C2 102.45(18) . . . . ? B5 C1 B3 B7 66.4(2) . . . . ? B5 C1 B3 B4 -35.84(18) . . . . ? B5 C1 B3 B8 4.4(2) . . . . ? B5 C1 B6 C2 -138.71(16) . . . . ? B5 C1 B6 B11 -102.83(17) . . . . ? B5 C1 B6 B10 -40.78(16) . . . . ? B5 B9 B4 C1 -39.14(15) . . . . ? B5 B9 B4 B3 -100.88(19) . . . . ? B5 B9 B4 B8 -138.57(18) . . . . ? B5 B9 B10 B12 137.83(18) . . . . ? B5 B9 B10 B11 100.63(19) . . . . ? B5 B9 B10 B6 36.64(17) . . . . ? B5 B9 B8 B12 -101.0(2) . . . . ? B5 B9 B8 B7 -63.4(2) . . . . ? B5 B9 B8 B4 37.40(17) . . . . ? B5 B9 B8 B3 0.0(2) . . . . ? B5 B4 B3 C2 -2.6(2) . . . . ? B5 B4 B3 C1 32.23(16) . . . . ? B5 B4 B3 B7 -63.2(2) . . . . ? B5 B4 B3 B8 -101.3(2) . . . . ? B5 B4 B8 B12 -0.1(2) . . . . ? B5 B4 B8 B7 62.9(2) . . . . ? B5 B4 B8 B9 -36.98(16) . . . . ? B5 B4 B8 B3 101.13(19) . . . . ? B5 B10 B6 C2 97.69(19) . . . . ? B5 B10 B6 C1 39.51(16) . . . . ? B5 B10 B6 B11 136.8(2) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 952824' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_130624_ny_wyf_57_1a _audit_creation_date 2013-06-27 _audit_creation_method ; Olex2 1.2 (compiled Apr 23 2013 17:54:37, GUI svn.r4466) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C8 H23 B10 N O' _chemical_formula_sum 'C8 H23 B10 N O' _chemical_formula_weight 257.37 _chemical_melting_point ? _chemical_oxdiff_formula 'C H B N' 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system orthorhombic _space_group_IT_number 61 _space_group_name_H-M_alt 'P b c a' _space_group_name_Hall '-P 2ac 2ab' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, -y, z+1/2' 3 'x+1/2, -y+1/2, -z' 4 '-x, y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x-1/2, y, -z-1/2' 7 '-x-1/2, y-1/2, z' 8 'x, -y-1/2, z-1/2' _cell_length_a 11.6375(6) _cell_length_b 10.1626(6) _cell_length_c 27.496(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3251.8(3) _cell_formula_units_Z 8 _cell_measurement_reflns_used 1789 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 25.8950 _cell_measurement_theta_min 3.9790 _exptl_absorpt_coefficient_mu 0.055 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.66515 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_density_diffrn 1.051 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.23 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0500 _diffrn_reflns_av_unetI/netI 0.0444 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_number 10775 _diffrn_reflns_theta_full 26.37 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_min 3.05 _diffrn_ambient_temperature 293.15 _diffrn_detector_area_resol_mean 16.0355 _diffrn_measured_fraction_theta_full 0.9955 _diffrn_measured_fraction_theta_max 0.8880 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -39.00 83.10 0.3000 40.0000 omega____ theta____ kappa____ phi______ frames - 17.7426 0.0000 -60.0000 407 #__ type_ start__ end____ width___ exp.time_ 2 omega -11.00 21.10 0.3000 40.0000 omega____ theta____ kappa____ phi______ frames - -18.8363 -99.0000 60.0000 107 #__ type_ start__ end____ width___ exp.time_ 3 omega 32.00 66.20 0.3000 40.0000 omega____ theta____ kappa____ phi______ frames - 17.7426 -178.0000 -60.0000 114 ; _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0129799000 _diffrn_orient_matrix_UB_12 -0.0678686000 _diffrn_orient_matrix_UB_13 0.0024138000 _diffrn_orient_matrix_UB_21 -0.0285818000 _diffrn_orient_matrix_UB_22 0.0130458000 _diffrn_orient_matrix_UB_23 0.0222747000 _diffrn_orient_matrix_UB_31 -0.0522002000 _diffrn_orient_matrix_UB_32 0.0097585000 _diffrn_orient_matrix_UB_33 -0.0128169000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2057 _reflns_number_total 3326 _reflns_odcompleteness_completeness 99.55 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.388 _refine_diff_density_min -0.218 _refine_diff_density_rms 0.059 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 182 _refine_ls_number_reflns 3326 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1169 _refine_ls_R_factor_gt 0.0744 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1303P)^2^+0.2731P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2061 _refine_ls_wR_factor_ref 0.2380 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All B(H) groups, All C(H) groups, All C(H,H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Secondary CH2 refined with riding coordinates: C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B) 2.b Aromatic/amide H refined with riding coordinates: N1(H1) 2.c Idealised Me refined as rotating group: C8(H8A,H8B,H8C) 2.d Boron cage BH refined with riding coordinates: B4(H4), C1(H1A), B9(H9), B6(H6), B5(H5), B3(H3), B12(H12), B8(H8), B7(H7), B10(H10), B11(H11) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 O1 O 0.70564(15) -0.00700(15) 0.34917(8) 0.0672(6) Uani 1 1 d . . . N1 N 0.77268(15) 0.20193(18) 0.35138(8) 0.0517(6) Uani 1 1 d . . . H1 H 0.7547 0.2832 0.3471 0.062 Uiso 1 1 calc R . . C3 C 0.69152(19) 0.1119(2) 0.34653(9) 0.0456(6) Uani 1 1 d . . . C2 C 0.57169(18) 0.1666(2) 0.33811(8) 0.0403(6) Uani 1 1 d . . . B4 B 0.5207(2) 0.3006(2) 0.36832(10) 0.0406(6) Uani 1 1 d . . . H4 H 0.5721 0.3629 0.3928 0.049 Uiso 1 1 calc R . . C1 C 0.4711(2) 0.0568(2) 0.33182(10) 0.0529(7) Uani 1 1 d . . . H1A H 0.4926 -0.0485 0.3329 0.063 Uiso 1 1 calc R . . B9 B 0.4128(2) 0.3656(3) 0.32955(11) 0.0462(7) Uani 1 1 d . . . H9 H 0.3926 0.4714 0.3288 0.055 Uiso 1 1 calc R . . C4 C 0.8909(2) 0.1700(2) 0.36356(10) 0.0553(7) Uani 1 1 d . . . H4A H 0.9419 0.2208 0.3429 0.066 Uiso 1 1 calc R . . H4B H 0.9044 0.0775 0.3570 0.066 Uiso 1 1 calc R . . B6 B 0.5135(3) 0.1431(3) 0.28108(11) 0.0538(8) Uani 1 1 d . . . H6 H 0.5598 0.1023 0.2496 0.065 Uiso 1 1 calc R . . B5 B 0.5422(2) 0.3033(2) 0.30450(10) 0.0444(7) Uani 1 1 d . . . H5 H 0.6074 0.3674 0.2878 0.053 Uiso 1 1 calc R . . B3 B 0.4783(2) 0.1394(3) 0.38551(11) 0.0485(7) Uani 1 1 d . . . H3 H 0.5023 0.0959 0.4207 0.058 Uiso 1 1 calc R . . B12 B 0.3042(3) 0.2445(3) 0.32252(11) 0.0551(8) Uani 1 1 d . . . H12 H 0.2135 0.2714 0.3173 0.066 Uiso 1 1 calc R . . B8 B 0.3739(2) 0.2642(3) 0.37958(11) 0.0509(7) Uani 1 1 d . . . H8 H 0.3286 0.3038 0.4115 0.061 Uiso 1 1 calc R . . B7 B 0.3451(2) 0.1047(3) 0.35669(12) 0.0562(8) Uani 1 1 d . . . H7 H 0.2816 0.0385 0.3735 0.067 Uiso 1 1 calc R . . B10 B 0.4084(2) 0.2680(3) 0.27583(11) 0.0547(8) Uani 1 1 d . . . H10 H 0.3854 0.3098 0.2402 0.066 Uiso 1 1 calc R . . C5 C 0.9188(3) 0.1978(4) 0.41572(12) 0.0857(10) Uani 1 1 d . . . H5A H 0.9037 0.2900 0.4222 0.103 Uiso 1 1 calc R . . H5B H 0.8674 0.1466 0.4361 0.103 Uiso 1 1 calc R . . B11 B 0.3664(3) 0.1062(3) 0.29301(13) 0.0614(9) Uani 1 1 d . . . H11 H 0.3170 0.0410 0.2688 0.074 Uiso 1 1 calc R . . C6 C 1.0396(3) 0.1679(4) 0.43008(12) 0.0956(12) Uani 1 1 d . . . H6A H 1.0549 0.0759 0.4232 0.115 Uiso 1 1 calc R . . H6B H 1.0909 0.2200 0.4100 0.115 Uiso 1 1 calc R . . C7 C 1.0670(4) 0.1935(8) 0.48168(16) 0.181(3) Uani 1 1 d . . . H7A H 1.0629 0.2875 0.4874 0.217 Uiso 1 1 calc R . . H7B H 1.0088 0.1520 0.5017 0.217 Uiso 1 1 calc R . . C8 C 1.1802(4) 0.1463(9) 0.49734(19) 0.220(4) Uani 1 1 d . . . H8A H 1.2294 0.1371 0.4695 0.330 Uiso 1 1 calc R . . H8B H 1.1720 0.0626 0.5131 0.330 Uiso 1 1 calc R . . H8C H 1.2133 0.2084 0.5196 0.330 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 O1 0.0518(11) 0.0289(8) 0.1210(17) 0.0041(9) -0.0020(10) 0.0060(8) N1 0.0368(11) 0.0307(9) 0.0877(16) 0.0053(10) 0.0018(10) 0.0029(8) C3 0.0403(12) 0.0317(11) 0.0648(16) 0.0014(11) 0.0049(11) 0.0027(9) C2 0.0381(12) 0.0278(10) 0.0550(14) -0.0006(10) 0.0024(10) -0.0015(9) B4 0.0396(13) 0.0315(12) 0.0506(15) -0.0051(11) 0.0042(12) -0.0007(10) C1 0.0478(14) 0.0299(11) 0.0810(19) -0.0047(11) 0.0011(13) -0.0056(10) B9 0.0381(14) 0.0377(13) 0.0628(18) -0.0030(12) 0.0011(12) 0.0050(11) C4 0.0363(13) 0.0461(13) 0.083(2) 0.0011(13) 0.0005(13) 0.0029(10) B6 0.0633(18) 0.0470(15) 0.0510(17) -0.0133(13) 0.0023(14) 0.0035(14) B5 0.0450(15) 0.0340(12) 0.0542(16) 0.0047(12) 0.0052(12) 0.0016(11) B3 0.0461(15) 0.0419(14) 0.0575(17) 0.0053(13) 0.0072(13) -0.0060(12) B12 0.0393(15) 0.0484(15) 0.077(2) -0.0100(15) -0.0050(14) 0.0020(12) B8 0.0411(15) 0.0501(15) 0.0614(18) -0.0060(14) 0.0090(13) -0.0006(12) B7 0.0403(15) 0.0459(15) 0.082(2) -0.0005(15) 0.0060(15) -0.0085(13) B10 0.0564(17) 0.0542(16) 0.0536(17) -0.0043(14) -0.0066(14) 0.0055(14) C5 0.0581(19) 0.116(3) 0.083(2) -0.003(2) 0.0036(16) 0.0099(18) B11 0.0534(17) 0.0510(16) 0.080(2) -0.0179(16) -0.0130(16) -0.0036(14) C6 0.067(2) 0.139(3) 0.080(2) -0.010(2) -0.0030(17) -0.003(2) C7 0.112(3) 0.357(10) 0.074(3) -0.019(4) -0.017(3) -0.010(5) C8 0.120(4) 0.445(12) 0.095(4) 0.022(5) -0.018(3) -0.084(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 O1 C3 1.222(3) . ? N1 H1 0.8600 . ? N1 C3 1.321(3) . ? N1 C4 1.452(3) . ? C3 C2 1.519(3) . ? C2 B4 1.702(3) . ? C2 C1 1.626(3) . ? C2 B6 1.724(4) . ? C2 B5 1.703(3) . ? C2 B3 1.719(4) . ? B4 H4 1.1000 . ? B4 B9 1.775(4) . ? B4 B5 1.773(4) . ? B4 B3 1.774(4) . ? B4 B8 1.774(4) . ? C1 H1A 1.1000 . ? C1 B6 1.720(4) . ? C1 B3 1.700(4) . ? C1 B7 1.690(4) . ? C1 B11 1.696(4) . ? B9 H9 1.1000 . ? B9 B5 1.773(4) . ? B9 B12 1.774(4) . ? B9 B8 1.777(4) . ? B9 B10 1.780(4) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C4 C5 1.497(4) . ? B6 H6 1.1000 . ? B6 B5 1.782(4) . ? B6 B10 1.769(4) . ? B6 B11 1.784(4) . ? B5 H5 1.1000 . ? B5 B10 1.782(4) . ? B3 H3 1.1000 . ? B3 B8 1.764(4) . ? B3 B7 1.777(4) . ? B12 H12 1.1000 . ? B12 B8 1.778(4) . ? B12 B7 1.769(4) . ? B12 B10 1.781(5) . ? B12 B11 1.777(4) . ? B8 H8 1.1000 . ? B8 B7 1.772(4) . ? B7 H7 1.1000 . ? B7 B11 1.769(5) . ? B10 H10 1.1000 . ? B10 B11 1.779(4) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C5 C6 1.492(4) . ? B11 H11 1.1000 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C6 C7 1.477(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C7 C8 1.466(6) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? 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 C3 N1 H1 118.5 . . ? C3 N1 C4 123.1(2) . . ? C4 N1 H1 118.5 . . ? O1 C3 N1 125.6(2) . . ? O1 C3 C2 119.6(2) . . ? N1 C3 C2 114.73(19) . . ? C3 C2 B4 122.58(18) . . ? C3 C2 C1 115.22(17) . . ? C3 C2 B6 116.63(19) . . ? C3 C2 B5 124.47(18) . . ? C3 C2 B3 113.95(19) . . ? B4 C2 B6 114.69(18) . . ? B4 C2 B5 62.75(15) . . ? B4 C2 B3 62.48(14) . . ? C1 C2 B4 110.47(17) . . ? C1 C2 B6 61.70(16) . . ? C1 C2 B5 110.91(18) . . ? C1 C2 B3 61.01(15) . . ? B5 C2 B6 62.65(15) . . ? B5 C2 B3 114.52(18) . . ? B3 C2 B6 114.8(2) . . ? C2 B4 H4 124.7 . . ? C2 B4 B9 104.58(18) . . ? C2 B4 B5 58.67(13) . . ? C2 B4 B3 59.25(14) . . ? C2 B4 B8 104.75(17) . . ? B9 B4 H4 122.5 . . ? B5 B4 H4 121.3 . . ? B5 B4 B9 59.98(15) . . ? B5 B4 B3 108.51(18) . . ? B5 B4 B8 108.18(19) . . ? B3 B4 H4 121.3 . . ? B3 B4 B9 107.90(19) . . ? B8 B4 H4 122.4 . . ? B8 B4 B9 60.10(16) . . ? B8 B4 B3 59.61(15) . . ? C2 C1 H1A 120.1 . . ? C2 C1 B6 61.96(15) . . ? C2 C1 B3 62.20(14) . . ? C2 C1 B7 112.61(18) . . ? C2 C1 B11 112.41(19) . . ? B6 C1 H1A 116.9 . . ? B3 C1 H1A 116.5 . . ? B3 C1 B6 116.00(18) . . ? B7 C1 H1A 117.8 . . ? B7 C1 B6 115.5(2) . . ? B7 C1 B3 63.22(17) . . ? B7 C1 B11 62.98(18) . . ? B11 C1 H1A 117.9 . . ? B11 C1 B6 62.95(18) . . ? B11 C1 B3 115.83(19) . . ? B4 B9 H9 121.8 . . ? B4 B9 B8 59.94(15) . . ? B4 B9 B10 108.12(18) . . ? B5 B9 B4 59.95(15) . . ? B5 B9 H9 121.6 . . ? B5 B9 B12 108.32(19) . . ? B5 B9 B8 108.03(18) . . ? B5 B9 B10 60.20(15) . . ? B12 B9 B4 108.10(19) . . ? B12 B9 H9 121.5 . . ? B12 B9 B8 60.07(17) . . ? B12 B9 B10 60.14(17) . . ? B8 B9 H9 121.7 . . ? B8 B9 B10 108.2(2) . . ? B10 B9 H9 121.6 . . ? N1 C4 H4A 109.1 . . ? N1 C4 H4B 109.1 . . ? N1 C4 C5 112.6(2) . . ? H4A C4 H4B 107.8 . . ? C5 C4 H4A 109.1 . . ? C5 C4 H4B 109.1 . . ? C2 B6 H6 125.1 . . ? C2 B6 B5 58.09(14) . . ? C2 B6 B10 104.26(19) . . ? C2 B6 B11 103.8(2) . . ? C1 B6 C2 56.34(14) . . ? C1 B6 H6 125.8 . . ? C1 B6 B5 103.07(19) . . ? C1 B6 B10 103.5(2) . . ? C1 B6 B11 57.86(17) . . ? B5 B6 H6 122.5 . . ? B5 B6 B11 107.8(2) . . ? B10 B6 H6 123.0 . . ? B10 B6 B5 60.25(16) . . ? B10 B6 B11 60.10(17) . . ? B11 B6 H6 122.3 . . ? C2 B5 B4 58.58(14) . . ? C2 B5 B9 104.58(18) . . ? C2 B5 B6 59.26(14) . . ? C2 B5 H5 124.7 . . ? C2 B5 B10 104.58(18) . . ? B4 B5 B9 60.07(15) . . ? B4 B5 B6 108.49(18) . . ? B4 B5 H5 121.3 . . ? B4 B5 B10 108.13(19) . . ? B9 B5 B6 107.93(19) . . ? B9 B5 H5 122.4 . . ? B9 B5 B10 60.10(15) . . ? B6 B5 H5 121.3 . . ? B6 B5 B10 59.51(16) . . ? B10 B5 H5 122.5 . . ? C2 B3 B4 58.27(13) . . ? C2 B3 H3 124.8 . . ? C2 B3 B8 104.45(19) . . ? C2 B3 B7 104.2(2) . . ? B4 B3 H3 122.3 . . ? B4 B3 B7 107.9(2) . . ? C1 B3 C2 56.79(14) . . ? C1 B3 B4 103.8(2) . . ? C1 B3 H3 125.3 . . ? C1 B3 B8 103.9(2) . . ? C1 B3 B7 58.10(16) . . ? B8 B3 B4 60.19(15) . . ? B8 B3 H3 123.0 . . ? B8 B3 B7 60.05(16) . . ? B7 B3 H3 122.3 . . ? B9 B12 H12 121.7 . . ? B9 B12 B8 60.04(16) . . ? B9 B12 B10 60.09(16) . . ? B9 B12 B11 108.0(2) . . ? B8 B12 H12 121.7 . . ? B8 B12 B10 108.1(2) . . ? B7 B12 B9 108.0(2) . . ? B7 B12 H12 121.8 . . ? B7 B12 B8 59.95(17) . . ? B7 B12 B10 107.9(2) . . ? B7 B12 B11 59.84(19) . . ? B10 B12 H12 121.7 . . ? B11 B12 H12 121.8 . . ? B11 B12 B8 107.9(2) . . ? B11 B12 B10 60.00(18) . . ? B4 B8 B9 59.96(15) . . ? B4 B8 B12 108.0(2) . . ? B4 B8 H8 121.7 . . ? B9 B8 B12 59.89(17) . . ? B9 B8 H8 121.8 . . ? B3 B8 B4 60.20(15) . . ? B3 B8 B9 108.27(19) . . ? B3 B8 B12 108.3(2) . . ? B3 B8 H8 121.3 . . ? B3 B8 B7 60.34(16) . . ? B12 B8 H8 121.8 . . ? B7 B8 B4 108.12(19) . . ? B7 B8 B9 107.7(2) . . ? B7 B8 B12 59.78(17) . . ? B7 B8 H8 121.8 . . ? C1 B7 B3 58.67(16) . . ? C1 B7 B12 104.4(2) . . ? C1 B7 B8 104.02(19) . . ? C1 B7 H7 125.2 . . ? C1 B7 B11 58.68(17) . . ? B3 B7 H7 121.4 . . ? B12 B7 B3 108.1(2) . . ? B12 B7 B8 60.27(17) . . ? B12 B7 H7 122.2 . . ? B8 B7 B3 59.60(16) . . ? B8 B7 H7 122.5 . . ? B11 B7 B3 108.5(2) . . ? B11 B7 B12 60.31(18) . . ? B11 B7 B8 108.5(2) . . ? B11 B7 H7 121.0 . . ? B9 B10 B5 59.70(15) . . ? B9 B10 B12 59.76(16) . . ? B9 B10 H10 122.0 . . ? B6 B10 B9 108.2(2) . . ? B6 B10 B5 60.24(16) . . ? B6 B10 B12 108.4(2) . . ? B6 B10 H10 121.2 . . ? B6 B10 B11 60.37(17) . . ? B5 B10 H10 121.9 . . ? B12 B10 B5 107.6(2) . . ? B12 B10 H10 121.8 . . ? B11 B10 B9 107.6(2) . . ? B11 B10 B5 108.0(2) . . ? B11 B10 B12 59.88(17) . . ? B11 B10 H10 121.8 . . ? C4 C5 H5A 108.6 . . ? C4 C5 H5B 108.6 . . ? H5A C5 H5B 107.5 . . ? C6 C5 C4 114.8(3) . . ? C6 C5 H5A 108.6 . . ? C6 C5 H5B 108.6 . . ? C1 B11 B6 59.19(16) . . ? C1 B11 B12 103.8(2) . . ? C1 B11 B7 58.35(17) . . ? C1 B11 B10 104.1(2) . . ? C1 B11 H11 125.3 . . ? B6 B11 H11 121.1 . . ? B12 B11 B6 108.0(2) . . ? B12 B11 B10 60.13(17) . . ? B12 B11 H11 122.7 . . ? B7 B11 B6 108.6(2) . . ? B7 B11 B12 59.85(18) . . ? B7 B11 B10 108.0(2) . . ? B7 B11 H11 121.3 . . ? B10 B11 B6 59.53(17) . . ? B10 B11 H11 122.6 . . ? C5 C6 H6A 108.5 . . ? C5 C6 H6B 108.5 . . ? H6A C6 H6B 107.5 . . ? C7 C6 C5 115.0(3) . . ? C7 C6 H6A 108.5 . . ? C7 C6 H6B 108.5 . . ? C6 C7 H7A 108.6 . . ? C6 C7 H7B 108.6 . . ? H7A C7 H7B 107.6 . . ? C8 C7 C6 114.8(4) . . ? C8 C7 H7A 108.6 . . ? C8 C7 H7B 108.6 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8B 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C3 C2 B4 137.8(2) . . . . ? O1 C3 C2 C1 -1.6(3) . . . . ? O1 C3 C2 B6 -71.1(3) . . . . ? O1 C3 C2 B5 -144.9(2) . . . . ? O1 C3 C2 B3 66.3(3) . . . . ? N1 C3 C2 B4 -40.9(3) . . . . ? N1 C3 C2 C1 179.7(2) . . . . ? N1 C3 C2 B6 110.2(2) . . . . ? N1 C3 C2 B5 36.4(3) . . . . ? N1 C3 C2 B3 -112.4(2) . . . . ? N1 C4 C5 C6 -179.5(3) . . . . ? C3 N1 C4 C5 -102.9(3) . . . . ? C3 C2 B4 B9 155.5(2) . . . . ? C3 C2 B4 B5 115.2(2) . . . . ? C3 C2 B4 B3 -102.1(2) . . . . ? C3 C2 B4 B8 -142.2(2) . . . . ? C3 C2 C1 B6 -108.0(2) . . . . ? C3 C2 C1 B3 104.6(2) . . . . ? C3 C2 C1 B7 144.1(2) . . . . ? C3 C2 C1 B11 -147.0(2) . . . . ? C3 C2 B6 C1 105.7(2) . . . . ? C3 C2 B6 B5 -117.0(2) . . . . ? C3 C2 B6 B10 -157.38(19) . . . . ? C3 C2 B6 B11 140.5(2) . . . . ? C3 C2 B5 B4 -112.4(2) . . . . ? C3 C2 B5 B9 -152.7(2) . . . . ? C3 C2 B5 B6 104.9(2) . . . . ? C3 C2 B5 B10 145.0(2) . . . . ? C3 C2 B3 B4 115.7(2) . . . . ? C3 C2 B3 C1 -106.7(2) . . . . ? C3 C2 B3 B8 155.94(19) . . . . ? C3 C2 B3 B7 -141.86(19) . . . . ? C2 B4 B9 B5 -39.57(16) . . . . ? C2 B4 B9 B12 61.6(2) . . . . ? C2 B4 B9 B8 98.85(19) . . . . ? C2 B4 B9 B10 -2.1(2) . . . . ? C2 B4 B5 B9 133.80(19) . . . . ? C2 B4 B5 B6 33.31(18) . . . . ? C2 B4 B5 B10 96.34(19) . . . . ? C2 B4 B3 C1 -35.46(16) . . . . ? C2 B4 B3 B8 -133.8(2) . . . . ? C2 B4 B3 B7 -96.0(2) . . . . ? C2 B4 B8 B9 -98.57(19) . . . . ? C2 B4 B8 B3 39.88(17) . . . . ? C2 B4 B8 B12 -61.4(2) . . . . ? C2 B4 B8 B7 1.8(3) . . . . ? C2 C1 B6 B5 -36.23(16) . . . . ? C2 C1 B6 B10 -98.32(19) . . . . ? C2 C1 B6 B11 -139.20(19) . . . . ? C2 C1 B3 B4 36.14(16) . . . . ? C2 C1 B3 B8 98.33(19) . . . . ? C2 C1 B3 B7 138.8(2) . . . . ? C2 C1 B7 B3 -39.1(2) . . . . ? C2 C1 B7 B12 63.6(3) . . . . ? C2 C1 B7 B8 1.2(3) . . . . ? C2 C1 B7 B11 104.5(2) . . . . ? C2 C1 B11 B6 38.59(19) . . . . ? C2 C1 B11 B12 -64.3(3) . . . . ? C2 C1 B11 B7 -104.9(2) . . . . ? C2 C1 B11 B10 -2.1(3) . . . . ? C2 B6 B5 B4 -33.05(18) . . . . ? C2 B6 B5 B9 -96.6(2) . . . . ? C2 B6 B5 B10 -133.6(2) . . . . ? C2 B6 B10 B9 2.4(3) . . . . ? C2 B6 B10 B5 39.33(18) . . . . ? C2 B6 B10 B12 -60.9(2) . . . . ? C2 B6 B10 B11 -97.9(2) . . . . ? C2 B6 B11 C1 -34.06(17) . . . . ? C2 B6 B11 B12 61.7(3) . . . . ? C2 B6 B11 B7 -1.7(3) . . . . ? C2 B6 B11 B10 98.7(2) . . . . ? C2 B5 B10 B9 98.7(2) . . . . ? C2 B5 B10 B6 -40.00(18) . . . . ? C2 B5 B10 B12 61.6(2) . . . . ? C2 B5 B10 B11 -1.7(3) . . . . ? C2 B3 B8 B4 -39.33(17) . . . . ? C2 B3 B8 B9 -2.1(3) . . . . ? C2 B3 B8 B12 61.3(2) . . . . ? C2 B3 B8 B7 98.3(2) . . . . ? C2 B3 B7 C1 34.61(17) . . . . ? C2 B3 B7 B12 -61.6(2) . . . . ? C2 B3 B7 B8 -98.7(2) . . . . ? C2 B3 B7 B11 2.3(3) . . . . ? B4 C2 C1 B6 107.8(2) . . . . ? B4 C2 C1 B3 -39.61(19) . . . . ? B4 C2 C1 B7 -0.1(3) . . . . ? B4 C2 C1 B11 68.8(3) . . . . ? B4 C2 B6 C1 -100.93(19) . . . . ? B4 C2 B6 B5 36.37(19) . . . . ? B4 C2 B6 B10 -4.0(3) . . . . ? B4 C2 B6 B11 -66.2(2) . . . . ? B4 C2 B5 B9 -40.26(17) . . . . ? B4 C2 B5 B6 -142.7(2) . . . . ? B4 C2 B5 B10 -102.6(2) . . . . ? B4 C2 B3 C1 137.67(19) . . . . ? B4 C2 B3 B8 40.28(17) . . . . ? B4 C2 B3 B7 102.5(2) . . . . ? B4 B9 B5 C2 39.53(17) . . . . ? B4 B9 B5 B6 101.4(2) . . . . ? B4 B9 B5 B10 138.18(19) . . . . ? B4 B9 B12 B8 37.23(18) . . . . ? B4 B9 B12 B7 -0.2(3) . . . . ? B4 B9 B12 B10 -100.9(2) . . . . ? B4 B9 B12 B11 -63.4(3) . . . . ? B4 B9 B8 B3 -37.31(18) . . . . ? B4 B9 B8 B12 -138.4(2) . . . . ? B4 B9 B8 B7 -101.1(2) . . . . ? B4 B9 B10 B6 -0.3(3) . . . . ? B4 B9 B10 B5 -37.39(18) . . . . ? B4 B9 B10 B12 100.9(2) . . . . ? B4 B9 B10 B11 63.5(2) . . . . ? B4 B5 B10 B9 37.44(17) . . . . ? B4 B5 B10 B6 -101.21(19) . . . . ? B4 B5 B10 B12 0.3(2) . . . . ? B4 B5 B10 B11 -62.9(2) . . . . ? B4 B3 B8 B9 37.21(19) . . . . ? B4 B3 B8 B12 100.6(2) . . . . ? B4 B3 B8 B7 137.6(2) . . . . ? B4 B3 B7 C1 95.4(2) . . . . ? B4 B3 B7 B12 -0.8(3) . . . . ? B4 B3 B7 B8 -37.93(19) . . . . ? B4 B3 B7 B11 63.1(2) . . . . ? B4 B8 B7 C1 -1.8(3) . . . . ? B4 B8 B7 B3 38.0(2) . . . . ? B4 B8 B7 B12 -100.7(2) . . . . ? B4 B8 B7 B11 -63.1(3) . . . . ? C1 C2 B4 B9 -63.4(2) . . . . ? C1 C2 B4 B5 -103.7(2) . . . . ? C1 C2 B4 B3 38.96(19) . . . . ? C1 C2 B4 B8 -1.1(2) . . . . ? C1 C2 B6 B5 137.29(18) . . . . ? C1 C2 B6 B10 96.9(2) . . . . ? C1 C2 B6 B11 34.73(17) . . . . ? C1 C2 B5 B4 102.96(19) . . . . ? C1 C2 B5 B9 62.7(2) . . . . ? C1 C2 B5 B6 -39.74(19) . . . . ? C1 C2 B5 B10 0.4(2) . . . . ? C1 C2 B3 B4 -137.67(19) . . . . ? C1 C2 B3 B8 -97.4(2) . . . . ? C1 C2 B3 B7 -35.19(17) . . . . ? C1 B6 B5 C2 35.42(16) . . . . ? C1 B6 B5 B4 2.4(2) . . . . ? C1 B6 B5 B9 -61.2(2) . . . . ? C1 B6 B5 B10 -98.2(2) . . . . ? C1 B6 B10 B9 60.6(2) . . . . ? C1 B6 B10 B5 97.5(2) . . . . ? C1 B6 B10 B12 -2.7(3) . . . . ? C1 B6 B10 B11 -39.74(19) . . . . ? C1 B6 B11 B12 95.7(2) . . . . ? C1 B6 B11 B7 32.33(18) . . . . ? C1 B6 B11 B10 132.8(2) . . . . ? C1 B3 B8 B4 -98.1(2) . . . . ? C1 B3 B8 B9 -60.9(2) . . . . ? C1 B3 B8 B12 2.6(2) . . . . ? C1 B3 B8 B7 39.54(19) . . . . ? C1 B3 B7 B12 -96.2(2) . . . . ? C1 B3 B7 B8 -133.3(2) . . . . ? C1 B3 B7 B11 -32.28(19) . . . . ? C1 B7 B11 B6 -32.66(18) . . . . ? C1 B7 B11 B12 -133.1(2) . . . . ? C1 B7 B11 B10 -95.7(2) . . . . ? B9 B4 B5 C2 -133.80(19) . . . . ? B9 B4 B5 B6 -100.5(2) . . . . ? B9 B4 B5 B10 -37.46(17) . . . . ? B9 B4 B3 C2 96.6(2) . . . . ? B9 B4 B3 C1 61.2(2) . . . . ? B9 B4 B3 B8 -37.17(18) . . . . ? B9 B4 B3 B7 0.7(3) . . . . ? B9 B4 B8 B3 138.4(2) . . . . ? B9 B4 B8 B12 37.18(19) . . . . ? B9 B4 B8 B7 100.4(2) . . . . ? B9 B5 B10 B6 -138.7(2) . . . . ? B9 B5 B10 B12 -37.10(18) . . . . ? B9 B5 B10 B11 -100.3(2) . . . . ? B9 B12 B8 B4 -37.21(18) . . . . ? B9 B12 B8 B3 -100.9(2) . . . . ? B9 B12 B8 B7 -138.1(2) . . . . ? B9 B12 B7 C1 -60.7(3) . . . . ? B9 B12 B7 B3 0.6(3) . . . . ? B9 B12 B7 B8 37.44(19) . . . . ? B9 B12 B7 B11 -100.8(2) . . . . ? B9 B12 B10 B6 100.8(2) . . . . ? B9 B12 B10 B5 37.07(18) . . . . ? B9 B12 B10 B11 138.0(2) . . . . ? B9 B12 B11 C1 60.9(3) . . . . ? B9 B12 B11 B6 -0.8(3) . . . . ? B9 B12 B11 B7 100.7(2) . . . . ? B9 B12 B11 B10 -37.5(2) . . . . ? B9 B8 B7 C1 61.5(3) . . . . ? B9 B8 B7 B3 101.4(2) . . . . ? B9 B8 B7 B12 -37.31(19) . . . . ? B9 B8 B7 B11 0.3(3) . . . . ? B9 B10 B11 C1 -60.8(3) . . . . ? B9 B10 B11 B6 -101.3(2) . . . . ? B9 B10 B11 B12 37.31(19) . . . . ? B9 B10 B11 B7 0.1(3) . . . . ? C4 N1 C3 O1 -3.8(4) . . . . ? C4 N1 C3 C2 174.8(2) . . . . ? C4 C5 C6 C7 -179.2(4) . . . . ? B6 C2 B4 B9 3.9(2) . . . . ? B6 C2 B4 B5 -36.33(19) . . . . ? B6 C2 B4 B3 106.3(2) . . . . ? B6 C2 B4 B8 66.2(2) . . . . ? B6 C2 C1 B3 -147.4(2) . . . . ? B6 C2 C1 B7 -107.9(2) . . . . ? B6 C2 C1 B11 -39.0(2) . . . . ? B6 C2 B5 B4 142.7(2) . . . . ? B6 C2 B5 B9 102.4(2) . . . . ? B6 C2 B5 B10 40.12(19) . . . . ? B6 C2 B3 B4 -106.2(2) . . . . ? B6 C2 B3 C1 31.51(18) . . . . ? B6 C2 B3 B8 -65.9(2) . . . . ? B6 C2 B3 B7 -3.7(3) . . . . ? B6 C1 B3 C2 -32.0(2) . . . . ? B6 C1 B3 B4 4.2(3) . . . . ? B6 C1 B3 B8 66.4(2) . . . . ? B6 C1 B3 B7 106.9(2) . . . . ? B6 C1 B7 B3 -107.7(2) . . . . ? B6 C1 B7 B12 -5.0(3) . . . . ? B6 C1 B7 B8 -67.3(3) . . . . ? B6 C1 B7 B11 36.0(2) . . . . ? B6 C1 B11 B12 -102.9(2) . . . . ? B6 C1 B11 B7 -143.5(2) . . . . ? B6 C1 B11 B10 -40.72(19) . . . . ? B6 B5 B10 B9 138.7(2) . . . . ? B6 B5 B10 B12 101.6(2) . . . . ? B6 B5 B10 B11 38.3(2) . . . . ? B6 B10 B11 C1 40.55(19) . . . . ? B6 B10 B11 B12 138.6(2) . . . . ? B6 B10 B11 B7 101.4(2) . . . . ? B5 C2 B4 B9 40.22(17) . . . . ? B5 C2 B4 B3 142.6(2) . . . . ? B5 C2 B4 B8 102.6(2) . . . . ? B5 C2 C1 B6 40.16(18) . . . . ? B5 C2 C1 B3 -107.2(2) . . . . ? B5 C2 C1 B7 -67.7(3) . . . . ? B5 C2 C1 B11 1.1(3) . . . . ? B5 C2 B6 C1 -137.29(18) . . . . ? B5 C2 B6 B10 -40.41(18) . . . . ? B5 C2 B6 B11 -102.6(2) . . . . ? B5 C2 B3 B4 -36.38(19) . . . . ? B5 C2 B3 C1 101.3(2) . . . . ? B5 C2 B3 B8 3.9(3) . . . . ? B5 C2 B3 B7 66.1(2) . . . . ? B5 B4 B9 B12 101.1(2) . . . . ? B5 B4 B9 B8 138.42(18) . . . . ? B5 B4 B9 B10 37.50(17) . . . . ? B5 B4 B3 C2 33.15(17) . . . . ? B5 B4 B3 C1 -2.3(2) . . . . ? B5 B4 B3 B8 -100.7(2) . . . . ? B5 B4 B3 B7 -62.8(2) . . . . ? B5 B4 B8 B9 -37.22(17) . . . . ? B5 B4 B8 B3 101.22(19) . . . . ? B5 B4 B8 B12 0.0(2) . . . . ? B5 B4 B8 B7 63.2(2) . . . . ? B5 B9 B12 B8 100.7(2) . . . . ? B5 B9 B12 B7 63.3(3) . . . . ? B5 B9 B12 B10 -37.5(2) . . . . ? B5 B9 B12 B11 0.0(3) . . . . ? B5 B9 B8 B4 37.17(17) . . . . ? B5 B9 B8 B3 -0.1(3) . . . . ? B5 B9 B8 B12 -101.2(2) . . . . ? B5 B9 B8 B7 -63.9(2) . . . . ? B5 B9 B10 B6 37.13(19) . . . . ? B5 B9 B10 B12 138.3(2) . . . . ? B5 B9 B10 B11 100.9(2) . . . . ? B5 B6 B10 B9 -36.90(19) . . . . ? B5 B6 B10 B12 -100.2(2) . . . . ? B5 B6 B10 B11 -137.3(2) . . . . ? B5 B6 B11 C1 -94.5(2) . . . . ? B5 B6 B11 B12 1.2(3) . . . . ? B5 B6 B11 B7 -62.2(3) . . . . ? B5 B6 B11 B10 38.2(2) . . . . ? B5 B10 B11 C1 2.3(3) . . . . ? B5 B10 B11 B6 -38.3(2) . . . . ? B5 B10 B11 B12 100.3(2) . . . . ? B5 B10 B11 B7 63.1(3) . . . . ? B3 C2 B4 B9 -102.4(2) . . . . ? B3 C2 B4 B5 -142.6(2) . . . . ? B3 C2 B4 B8 -40.06(18) . . . . ? B3 C2 C1 B6 147.4(2) . . . . ? B3 C2 C1 B7 39.5(2) . . . . ? B3 C2 C1 B11 108.4(2) . . . . ? B3 C2 B6 C1 -31.28(18) . . . . ? B3 C2 B6 B5 106.0(2) . . . . ? B3 C2 B6 B10 65.6(2) . . . . ? B3 C2 B6 B11 3.4(3) . . . . ? B3 C2 B5 B4 36.28(19) . . . . ? B3 C2 B5 B9 -4.0(2) . . . . ? B3 C2 B5 B6 -106.4(2) . . . . ? B3 C2 B5 B10 -66.3(2) . . . . ? B3 B4 B9 B5 -101.46(19) . . . . ? B3 B4 B9 B12 -0.3(3) . . . . ? B3 B4 B9 B8 36.96(18) . . . . ? B3 B4 B9 B10 -64.0(2) . . . . ? B3 B4 B5 C2 -33.38(17) . . . . ? B3 B4 B5 B9 100.4(2) . . . . ? B3 B4 B5 B6 -0.1(2) . . . . ? B3 B4 B5 B10 63.0(2) . . . . ? B3 B4 B8 B9 -138.4(2) . . . . ? B3 B4 B8 B12 -101.3(2) . . . . ? B3 B4 B8 B7 -38.1(2) . . . . ? B3 C1 B6 C2 32.03(19) . . . . ? B3 C1 B6 B5 -4.2(3) . . . . ? B3 C1 B6 B10 -66.3(3) . . . . ? B3 C1 B6 B11 -107.2(2) . . . . ? B3 C1 B7 B12 102.7(2) . . . . ? B3 C1 B7 B8 40.31(19) . . . . ? B3 C1 B7 B11 143.6(2) . . . . ? B3 C1 B11 B6 107.4(2) . . . . ? B3 C1 B11 B12 4.6(3) . . . . ? B3 C1 B11 B7 -36.0(2) . . . . ? B3 C1 B11 B10 66.7(3) . . . . ? B3 B8 B7 C1 -39.84(19) . . . . ? B3 B8 B7 B12 -138.7(2) . . . . ? B3 B8 B7 B11 -101.1(2) . . . . ? B3 B7 B11 C1 32.28(18) . . . . ? B3 B7 B11 B6 -0.4(3) . . . . ? B3 B7 B11 B12 -100.8(2) . . . . ? B3 B7 B11 B10 -63.4(3) . . . . ? B12 B9 B5 C2 -61.2(2) . . . . ? B12 B9 B5 B4 -100.7(2) . . . . ? B12 B9 B5 B6 0.7(3) . . . . ? B12 B9 B5 B10 37.4(2) . . . . ? B12 B9 B8 B4 138.4(2) . . . . ? B12 B9 B8 B3 101.1(2) . . . . ? B12 B9 B8 B7 37.26(19) . . . . ? B12 B9 B10 B6 -101.2(2) . . . . ? B12 B9 B10 B5 -138.3(2) . . . . ? B12 B9 B10 B11 -37.4(2) . . . . ? B12 B8 B7 C1 98.8(2) . . . . ? B12 B8 B7 B3 138.7(2) . . . . ? B12 B8 B7 B11 37.6(2) . . . . ? B12 B7 B11 C1 133.1(2) . . . . ? B12 B7 B11 B6 100.4(2) . . . . ? B12 B7 B11 B10 37.36(19) . . . . ? B12 B10 B11 C1 -98.1(2) . . . . ? B12 B10 B11 B6 -138.6(2) . . . . ? B12 B10 B11 B7 -37.2(2) . . . . ? B8 B4 B9 B5 -138.42(18) . . . . ? B8 B4 B9 B12 -37.28(19) . . . . ? B8 B4 B9 B10 -100.9(2) . . . . ? B8 B4 B5 C2 -96.53(19) . . . . ? B8 B4 B5 B9 37.27(17) . . . . ? B8 B4 B5 B6 -63.2(2) . . . . ? B8 B4 B5 B10 -0.2(2) . . . . ? B8 B4 B3 C2 133.8(2) . . . . ? B8 B4 B3 C1 98.4(2) . . . . ? B8 B4 B3 B7 37.87(19) . . . . ? B8 B9 B5 C2 2.4(2) . . . . ? B8 B9 B5 B4 -37.16(17) . . . . ? B8 B9 B5 B6 64.3(2) . . . . ? B8 B9 B5 B10 101.0(2) . . . . ? B8 B9 B12 B7 -37.4(2) . . . . ? B8 B9 B12 B10 -138.2(2) . . . . ? B8 B9 B12 B11 -100.7(2) . . . . ? B8 B9 B10 B6 -63.7(3) . . . . ? B8 B9 B10 B5 -100.8(2) . . . . ? B8 B9 B10 B12 37.5(2) . . . . ? B8 B9 B10 B11 0.1(3) . . . . ? B8 B3 B7 C1 133.3(2) . . . . ? B8 B3 B7 B12 37.1(2) . . . . ? B8 B3 B7 B11 101.0(2) . . . . ? B8 B12 B7 C1 -98.1(2) . . . . ? B8 B12 B7 B3 -36.84(19) . . . . ? B8 B12 B7 B11 -138.2(2) . . . . ? B8 B12 B10 B9 -37.45(19) . . . . ? B8 B12 B10 B6 63.3(3) . . . . ? B8 B12 B10 B5 -0.4(3) . . . . ? B8 B12 B10 B11 100.6(2) . . . . ? B8 B12 B11 C1 -2.5(3) . . . . ? B8 B12 B11 B6 -64.2(3) . . . . ? B8 B12 B11 B7 37.3(2) . . . . ? B8 B12 B11 B10 -101.0(2) . . . . ? B8 B7 B11 C1 95.5(2) . . . . ? B8 B7 B11 B6 62.8(3) . . . . ? B8 B7 B11 B12 -37.6(2) . . . . ? B8 B7 B11 B10 -0.2(3) . . . . ? B7 C1 B6 C2 103.2(2) . . . . ? B7 C1 B6 B5 67.0(3) . . . . ? B7 C1 B6 B10 4.9(3) . . . . ? B7 C1 B6 B11 -36.0(2) . . . . ? B7 C1 B3 C2 -138.8(2) . . . . ? B7 C1 B3 B4 -102.7(2) . . . . ? B7 C1 B3 B8 -40.52(19) . . . . ? B7 C1 B11 B6 143.5(2) . . . . ? B7 C1 B11 B12 40.6(2) . . . . ? B7 C1 B11 B10 102.7(2) . . . . ? B7 B3 B8 B4 -137.6(2) . . . . ? B7 B3 B8 B9 -100.4(2) . . . . ? B7 B3 B8 B12 -37.0(2) . . . . ? B7 B12 B8 B4 100.9(2) . . . . ? B7 B12 B8 B9 138.1(2) . . . . ? B7 B12 B8 B3 37.21(19) . . . . ? B7 B12 B10 B9 -100.8(2) . . . . ? B7 B12 B10 B6 -0.1(3) . . . . ? B7 B12 B10 B5 -63.8(2) . . . . ? B7 B12 B10 B11 37.2(2) . . . . ? B7 B12 B11 C1 -39.82(19) . . . . ? B7 B12 B11 B6 -101.5(2) . . . . ? B7 B12 B11 B10 -138.3(2) . . . . ? B10 B9 B5 C2 -98.66(19) . . . . ? B10 B9 B5 B4 -138.18(19) . . . . ? B10 B9 B5 B6 -36.75(19) . . . . ? B10 B9 B12 B8 138.2(2) . . . . ? B10 B9 B12 B7 100.8(2) . . . . ? B10 B9 B12 B11 37.5(2) . . . . ? B10 B9 B8 B4 100.9(2) . . . . ? B10 B9 B8 B3 63.5(2) . . . . ? B10 B9 B8 B12 -37.51(19) . . . . ? B10 B9 B8 B7 -0.2(3) . . . . ? B10 B6 B5 C2 133.6(2) . . . . ? B10 B6 B5 B4 100.6(2) . . . . ? B10 B6 B5 B9 37.01(19) . . . . ? B10 B6 B11 C1 -132.8(2) . . . . ? B10 B6 B11 B12 -37.1(2) . . . . ? B10 B6 B11 B7 -100.4(2) . . . . ? B10 B12 B8 B4 0.3(3) . . . . ? B10 B12 B8 B9 37.47(19) . . . . ? B10 B12 B8 B3 -63.5(3) . . . . ? B10 B12 B8 B7 -100.7(2) . . . . ? B10 B12 B7 C1 2.8(3) . . . . ? B10 B12 B7 B3 64.1(3) . . . . ? B10 B12 B7 B8 100.9(2) . . . . ? B10 B12 B7 B11 -37.28(19) . . . . ? B10 B12 B11 C1 98.5(2) . . . . ? B10 B12 B11 B6 36.8(2) . . . . ? B10 B12 B11 B7 138.3(2) . . . . ? C5 C6 C7 C8 171.5(5) . . . . ? B11 C1 B6 C2 139.20(19) . . . . ? B11 C1 B6 B5 103.0(2) . . . . ? B11 C1 B6 B10 40.88(19) . . . . ? B11 C1 B3 C2 -102.9(2) . . . . ? B11 C1 B3 B4 -66.8(2) . . . . ? B11 C1 B3 B8 -4.6(3) . . . . ? B11 C1 B3 B7 35.9(2) . . . . ? B11 C1 B7 B3 -143.6(2) . . . . ? B11 C1 B7 B12 -40.9(2) . . . . ? B11 C1 B7 B8 -103.3(2) . . . . ? B11 B6 B5 C2 95.5(2) . . . . ? B11 B6 B5 B4 62.4(3) . . . . ? B11 B6 B5 B9 -1.2(3) . . . . ? B11 B6 B5 B10 -38.2(2) . . . . ? B11 B6 B10 B9 100.4(2) . . . . ? B11 B6 B10 B5 137.3(2) . . . . ? B11 B6 B10 B12 37.1(2) . . . . ? B11 B12 B8 B4 63.7(3) . . . . ? B11 B12 B8 B9 100.9(2) . . . . ? B11 B12 B8 B3 0.0(3) . . . . ? B11 B12 B8 B7 -37.2(2) . . . . ? B11 B12 B7 C1 40.12(19) . . . . ? B11 B12 B7 B3 101.4(2) . . . . ? B11 B12 B7 B8 138.2(2) . . . . ? B11 B12 B10 B9 -138.0(2) . . . . ? B11 B12 B10 B6 -37.3(2) . . . . ? B11 B12 B10 B5 -101.0(2) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 950184' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_130305_ny_wyf_38a _audit_creation_date 2013-03-11 _audit_creation_method ; Olex2 1.2 (compiled Dec 5 2012 16:20:19, GUI svn.r4385) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C9 H16 B10 F N O' _chemical_formula_sum 'C9 H16 B10 F N O' _chemical_formula_weight 281.33 _chemical_melting_point ? _chemical_oxdiff_formula 'C H N O B F' 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' F F 0.0171 0.0103 '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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 6.735(2) _cell_length_b 11.253(4) _cell_length_c 11.649(4) _cell_angle_alpha 114.63(3) _cell_angle_beta 90.84(3) _cell_angle_gamma 106.42(3) _cell_volume 760.9(4) _cell_formula_units_Z 2 _cell_measurement_reflns_used 1393 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 28.9067 _cell_measurement_theta_min 3.1838 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.74588 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour ? _exptl_crystal_density_diffrn 1.228 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description ? _exptl_crystal_F_000 288 _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.28 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0485 _diffrn_reflns_av_unetI/netI 0.0620 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 7806 _diffrn_reflns_theta_full 26.37 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_min 3.19 _diffrn_ambient_temperature 293.15 _diffrn_detector_area_resol_mean 16.0355 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -47.00 48.00 1.0000 21.8900 omega____ theta____ kappa____ phi______ frames - 17.6043 -77.0000 -180.0000 95 #__ type_ start__ end____ width___ exp.time_ 2 omega -46.00 36.00 1.0000 21.8900 omega____ theta____ kappa____ phi______ frames - 17.6043 -57.0000 -90.0000 82 #__ type_ start__ end____ width___ exp.time_ 3 omega -40.00 38.00 1.0000 21.8900 omega____ theta____ kappa____ phi______ frames - 17.6043 -57.0000 30.0000 78 #__ type_ start__ end____ width___ exp.time_ 4 omega 11.00 45.00 1.0000 21.8900 omega____ theta____ kappa____ phi______ frames - 17.6043 54.0000 24.0000 34 #__ type_ start__ end____ width___ exp.time_ 5 omega -16.00 23.00 1.0000 21.8900 omega____ theta____ kappa____ phi______ frames - -18.8543 -99.0000 60.0000 39 #__ type_ start__ end____ width___ exp.time_ 6 omega -24.00 4.00 1.0000 21.8900 omega____ theta____ kappa____ phi______ frames - -18.8543 -99.0000 -120.0000 28 #__ type_ start__ end____ width___ exp.time_ 7 omega -4.00 86.00 1.0000 21.8900 omega____ theta____ kappa____ phi______ frames - 17.6043 57.0000 90.0000 90 #__ type_ start__ end____ width___ exp.time_ 8 omega -4.00 21.00 1.0000 21.8900 omega____ theta____ kappa____ phi______ frames - 17.6043 57.0000 -30.0000 25 #__ type_ start__ end____ width___ exp.time_ 9 omega -4.00 86.00 1.0000 21.8900 omega____ theta____ kappa____ phi______ frames - 17.6043 57.0000 -150.0000 90 ; _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0804559000 _diffrn_orient_matrix_UB_12 0.0294278000 _diffrn_orient_matrix_UB_13 -0.0279684000 _diffrn_orient_matrix_UB_21 0.0751071000 _diffrn_orient_matrix_UB_22 -0.0103540000 _diffrn_orient_matrix_UB_23 0.0350506000 _diffrn_orient_matrix_UB_31 -0.0149751000 _diffrn_orient_matrix_UB_32 -0.0661409000 _diffrn_orient_matrix_UB_33 -0.0508116000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 1870 _reflns_number_total 3110 _reflns_odcompleteness_completeness 99.68 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.203 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.041 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 199 _refine_ls_number_reflns 3110 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0986 _refine_ls_R_factor_gt 0.0623 _refine_ls_restrained_S_all 1.077 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0899P)^2^+0.0084P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1672 _refine_ls_wR_factor_ref 0.2001 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: H1 of N1, H9 of C9, H1A of C1, H5 of B5, H1B of B1, H7 of B7, H6 of C6, H9A of B9, H10 of B10, H8 of B8, H6A of B6, H8A of C8, H2 of B2, H4 of B4, H7A of C7, H3 of B3 2.a Aromatic/amide H refined with riding coordinates: N1(H1), C9(H9), C6(H6), C8(H8A), C7(H7A) 2.b Boron cage BH refined with riding coordinates: C1(H1A), B5(H5), B1(H1B), B7(H7), B9(H9A), B10(H10), B8(H8), B6(H6A), B2(H2), B4(H4), B3(H3) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.4524(3) 0.73358(18) 0.94455(17) 0.0508(5) Uani 1 1 d . . . H1 H 0.5404 0.7195 0.8915 0.061 Uiso 1 1 calc R . . F1 F 0.8528(2) 0.87652(15) 1.01005(16) 0.0836(6) Uani 1 1 d . . . C2 C 0.2703(3) 0.4987(2) 0.79838(19) 0.0431(5) Uani 1 1 d . . . C4 C 0.5131(4) 0.8644(2) 1.0522(2) 0.0469(6) Uani 1 1 d . . . C9 C 0.3760(4) 0.9234(2) 1.1262(2) 0.0571(7) Uani 1 1 d . . . H9 H 0.2326 0.8774 1.1057 0.068 Uiso 1 1 calc R . . C3 C 0.2759(4) 0.6304(2) 0.9162(2) 0.0520(6) Uani 1 1 d . . . C5 C 0.7215(4) 0.9362(2) 1.0849(2) 0.0554(6) Uani 1 1 d . . . C1 C 0.0604(3) 0.3690(2) 0.7672(2) 0.0501(6) Uani 1 1 d . . . H1A H -0.0630 0.3797 0.8280 0.060 Uiso 1 1 calc R . . B5 B 0.3586(4) 0.4970(3) 0.6619(2) 0.0499(7) Uani 1 1 d . . . H5 H 0.4398 0.5896 0.6497 0.060 Uiso 1 1 calc R . . O1 O 0.1297(3) 0.63451(17) 0.97556(19) 0.0929(8) Uani 1 1 d . . . B1 B 0.2886(4) 0.3658(3) 0.8295(3) 0.0500(7) Uani 1 1 d . . . H1B H 0.3211 0.3733 0.9255 0.060 Uiso 1 1 calc R . . B7 B 0.3836(5) 0.2634(3) 0.6964(2) 0.0541(7) Uani 1 1 d . . . H7 H 0.4806 0.2026 0.7047 0.065 Uiso 1 1 calc R . . C6 C 0.8010(4) 1.0629(3) 1.1877(3) 0.0693(8) Uani 1 1 d . . . H6 H 0.9444 1.1089 1.2075 0.083 Uiso 1 1 calc R . . B9 B 0.1819(5) 0.3486(3) 0.5381(3) 0.0569(7) Uani 1 1 d . . . H9A H 0.1471 0.3428 0.4431 0.068 Uiso 1 1 calc R . . B10 B 0.4258(4) 0.3443(3) 0.5913(2) 0.0518(7) Uani 1 1 d . . . H10 H 0.5496 0.3356 0.5306 0.062 Uiso 1 1 calc R . . B8 B 0.1970(5) 0.2030(3) 0.5591(3) 0.0587(8) Uani 1 1 d . . . H8 H 0.1720 0.1020 0.4775 0.070 Uiso 1 1 calc R . . B6 B 0.4821(4) 0.4445(3) 0.7585(2) 0.0491(7) Uani 1 1 d . . . H6A H 0.6433 0.5031 0.8086 0.059 Uiso 1 1 calc R . . C8 C 0.4537(5) 1.0510(3) 1.2306(2) 0.0681(8) Uani 1 1 d . . . H8A H 0.3623 1.0902 1.2809 0.082 Uiso 1 1 calc R . . B2 B 0.1125(5) 0.2176(3) 0.7061(2) 0.0562(7) Uani 1 1 d . . . H2 H 0.0307 0.1271 0.7215 0.067 Uiso 1 1 calc R . . B4 B 0.0858(4) 0.4508(3) 0.6707(3) 0.0558(7) Uani 1 1 d . . . H4 H -0.0115 0.5123 0.6645 0.067 Uiso 1 1 calc R . . C7 C 0.6656(5) 1.1202(3) 1.2605(2) 0.0698(8) Uani 1 1 d . . . H7A H 0.7167 1.2062 1.3304 0.084 Uiso 1 1 calc R . . B3 B -0.0129(5) 0.2690(3) 0.6087(3) 0.0600(8) Uani 1 1 d . . . H3 H -0.1756 0.2116 0.5610 0.072 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 0.0539(12) 0.0497(11) 0.0446(11) 0.0167(8) 0.0213(9) 0.0159(9) F1 0.0567(9) 0.0691(10) 0.0999(13) 0.0143(9) 0.0252(8) 0.0185(8) C2 0.0444(12) 0.0506(12) 0.0377(12) 0.0224(10) 0.0154(9) 0.0149(10) C4 0.0558(14) 0.0455(12) 0.0428(13) 0.0223(10) 0.0150(11) 0.0163(11) C9 0.0682(16) 0.0552(14) 0.0496(15) 0.0209(11) 0.0214(12) 0.0247(13) C3 0.0578(14) 0.0528(13) 0.0483(13) 0.0235(11) 0.0237(11) 0.0189(12) C5 0.0570(14) 0.0516(13) 0.0592(15) 0.0238(12) 0.0168(12) 0.0199(12) C1 0.0426(12) 0.0562(13) 0.0491(14) 0.0239(11) 0.0141(10) 0.0107(11) B5 0.0574(16) 0.0549(15) 0.0467(16) 0.0303(12) 0.0202(12) 0.0184(13) O1 0.0862(14) 0.0617(12) 0.0960(15) 0.0108(11) 0.0619(12) 0.0076(10) B1 0.0598(16) 0.0550(15) 0.0426(15) 0.0283(12) 0.0108(12) 0.0183(13) B7 0.0689(18) 0.0605(16) 0.0467(16) 0.0281(13) 0.0189(13) 0.0327(14) C6 0.0665(17) 0.0596(16) 0.0675(18) 0.0187(14) -0.0033(14) 0.0144(14) B9 0.0654(18) 0.0707(18) 0.0392(15) 0.0278(13) 0.0088(13) 0.0224(15) B10 0.0585(16) 0.0590(15) 0.0397(15) 0.0217(12) 0.0191(12) 0.0205(13) B8 0.0682(19) 0.0534(16) 0.0433(16) 0.0153(12) 0.0167(14) 0.0119(14) B6 0.0463(14) 0.0576(15) 0.0470(16) 0.0233(12) 0.0145(12) 0.0209(12) C8 0.091(2) 0.0645(16) 0.0528(16) 0.0215(13) 0.0251(14) 0.0366(16) B2 0.0706(18) 0.0484(15) 0.0466(16) 0.0212(12) 0.0191(14) 0.0136(14) B4 0.0531(16) 0.0679(18) 0.0554(18) 0.0327(14) 0.0075(13) 0.0236(14) C7 0.095(2) 0.0560(15) 0.0491(16) 0.0120(12) 0.0022(15) 0.0279(16) B3 0.0524(16) 0.0677(18) 0.0467(17) 0.0184(14) 0.0021(13) 0.0106(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 H1 0.8600 . ? N1 C4 1.419(3) . ? N1 C3 1.327(3) . ? F1 C5 1.365(3) . ? C2 C3 1.533(3) . ? C2 C1 1.624(3) . ? C2 B5 1.700(3) . ? C2 B1 1.714(3) . ? C2 B6 1.703(3) . ? C2 B4 1.716(4) . ? C4 C9 1.389(3) . ? C4 C5 1.362(3) . ? C9 H9 0.9300 . ? C9 C8 1.385(3) . ? C3 O1 1.212(3) . ? C5 C6 1.371(3) . ? C1 H1A 1.1000 . ? C1 B1 1.706(4) . ? C1 B2 1.694(4) . ? C1 B4 1.708(4) . ? C1 B3 1.687(4) . ? B5 H5 1.1000 . ? B5 B9 1.762(4) . ? B5 B10 1.762(4) . ? B5 B6 1.764(4) . ? B5 B4 1.780(4) . ? B1 H1B 1.1000 . ? B1 B7 1.760(4) . ? B1 B6 1.776(4) . ? B1 B2 1.757(4) . ? B7 H7 1.1000 . ? B7 B10 1.790(4) . ? B7 B8 1.775(4) . ? B7 B6 1.763(4) . ? B7 B2 1.771(4) . ? C6 H6 0.9300 . ? C6 C7 1.366(4) . ? B9 H9A 1.1000 . ? B9 B10 1.767(4) . ? B9 B8 1.783(4) . ? B9 B4 1.760(4) . ? B9 B3 1.783(4) . ? B10 H10 1.1000 . ? B10 B8 1.774(4) . ? B10 B6 1.765(4) . ? B8 H8 1.1000 . ? B8 B2 1.769(4) . ? B8 B3 1.773(4) . ? B6 H6A 1.1000 . ? C8 H8A 0.9300 . ? C8 C7 1.377(4) . ? B2 H2 1.1000 . ? B2 B3 1.770(4) . ? B4 H4 1.1000 . ? B4 B3 1.770(4) . ? C7 H7A 0.9300 . ? B3 H3 1.1000 . ? 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 N1 H1 116.2 . . ? C3 N1 H1 116.2 . . ? C3 N1 C4 127.57(19) . . ? C3 C2 C1 114.17(17) . . ? C3 C2 B5 123.94(18) . . ? C3 C2 B1 115.25(17) . . ? C3 C2 B6 124.29(18) . . ? C3 C2 B4 114.90(19) . . ? C1 C2 B5 111.15(17) . . ? C1 C2 B1 61.41(15) . . ? C1 C2 B6 110.97(17) . . ? C1 C2 B4 61.43(15) . . ? B5 C2 B1 114.50(17) . . ? B5 C2 B6 62.44(14) . . ? B5 C2 B4 62.80(15) . . ? B1 C2 B4 114.67(18) . . ? B6 C2 B1 62.64(15) . . ? B6 C2 B4 114.46(17) . . ? C9 C4 N1 124.8(2) . . ? C5 C4 N1 117.1(2) . . ? C5 C4 C9 118.1(2) . . ? C4 C9 H9 120.2 . . ? C8 C9 C4 119.7(2) . . ? C8 C9 H9 120.2 . . ? N1 C3 C2 113.66(19) . . ? O1 C3 N1 125.3(2) . . ? O1 C3 C2 121.0(2) . . ? F1 C5 C6 120.1(2) . . ? C4 C5 F1 117.0(2) . . ? C4 C5 C6 122.9(2) . . ? C2 C1 H1A 120.5 . . ? C2 C1 B1 61.91(14) . . ? C2 C1 B2 111.54(18) . . ? C2 C1 B4 61.95(15) . . ? C2 C1 B3 111.95(18) . . ? B1 C1 H1A 117.3 . . ? B1 C1 B4 115.53(18) . . ? B2 C1 H1A 118.4 . . ? B2 C1 B1 62.22(16) . . ? B2 C1 B4 115.30(18) . . ? B4 C1 H1A 116.9 . . ? B3 C1 H1A 118.1 . . ? B3 C1 B1 114.96(19) . . ? B3 C1 B2 63.15(16) . . ? B3 C1 B4 62.85(16) . . ? C2 B5 H5 124.6 . . ? C2 B5 B9 104.65(18) . . ? C2 B5 B10 105.02(18) . . ? C2 B5 B6 58.86(14) . . ? C2 B5 B4 59.04(14) . . ? B9 B5 H5 122.5 . . ? B9 B5 B6 108.14(19) . . ? B9 B5 B4 59.58(16) . . ? B10 B5 H5 122.2 . . ? B10 B5 B9 60.21(16) . . ? B10 B5 B6 60.10(15) . . ? B10 B5 B4 108.2(2) . . ? B6 B5 H5 121.2 . . ? B6 B5 B4 108.44(18) . . ? B4 B5 H5 121.4 . . ? C2 B1 H1B 124.8 . . ? C2 B1 B7 104.57(17) . . ? C2 B1 B6 58.37(14) . . ? C2 B1 B2 104.43(18) . . ? C1 B1 C2 56.69(13) . . ? C1 B1 H1B 125.0 . . ? C1 B1 B7 104.69(19) . . ? C1 B1 B6 103.84(18) . . ? C1 B1 B2 58.55(15) . . ? B7 B1 H1B 122.8 . . ? B7 B1 B6 59.81(15) . . ? B6 B1 H1B 122.6 . . ? B2 B1 H1B 122.0 . . ? B2 B1 B7 60.47(16) . . ? B2 B1 B6 107.82(19) . . ? B1 B7 H7 121.5 . . ? B1 B7 B10 108.08(18) . . ? B1 B7 B8 107.7(2) . . ? B1 B7 B6 60.56(15) . . ? B1 B7 B2 59.68(15) . . ? B10 B7 H7 122.0 . . ? B8 B7 H7 122.1 . . ? B8 B7 B10 59.67(15) . . ? B6 B7 H7 121.8 . . ? B6 B7 B10 59.59(15) . . ? B6 B7 B8 107.4(2) . . ? B6 B7 B2 107.80(19) . . ? B2 B7 H7 122.0 . . ? B2 B7 B10 107.54(19) . . ? B2 B7 B8 59.85(15) . . ? C5 C6 H6 120.6 . . ? C7 C6 C5 118.7(3) . . ? C7 C6 H6 120.6 . . ? B5 B9 H9A 121.7 . . ? B5 B9 B10 59.89(15) . . ? B5 B9 B8 107.6(2) . . ? B5 B9 B3 108.03(19) . . ? B10 B9 H9A 121.5 . . ? B10 B9 B8 59.94(16) . . ? B10 B9 B3 107.9(2) . . ? B8 B9 H9A 122.1 . . ? B4 B9 B5 60.72(16) . . ? B4 B9 H9A 121.2 . . ? B4 B9 B10 108.81(19) . . ? B4 B9 B8 107.98(19) . . ? B4 B9 B3 59.96(16) . . ? B3 B9 H9A 122.0 . . ? B3 B9 B8 59.63(17) . . ? B5 B10 B7 107.70(18) . . ? B5 B10 B9 59.89(16) . . ? B5 B10 H10 121.7 . . ? B5 B10 B8 108.1(2) . . ? B5 B10 B6 60.01(15) . . ? B7 B10 H10 122.0 . . ? B9 B10 B7 108.2(2) . . ? B9 B10 H10 121.5 . . ? B9 B10 B8 60.48(17) . . ? B8 B10 B7 59.76(16) . . ? B8 B10 H10 121.8 . . ? B6 B10 B7 59.45(15) . . ? B6 B10 B9 107.82(19) . . ? B6 B10 H10 122.2 . . ? B6 B10 B8 107.31(19) . . ? B7 B8 B9 108.08(19) . . ? B7 B8 H8 121.5 . . ? B9 B8 H8 121.8 . . ? B10 B8 B7 60.57(16) . . ? B10 B8 B9 59.58(16) . . ? B10 B8 H8 121.6 . . ? B2 B8 B7 59.94(16) . . ? B2 B8 B9 108.0(2) . . ? B2 B8 B10 108.32(19) . . ? B2 B8 H8 121.7 . . ? B2 B8 B3 59.97(16) . . ? B3 B8 B7 108.09(18) . . ? B3 B8 B9 60.16(17) . . ? B3 B8 B10 108.01(19) . . ? B3 B8 H8 121.7 . . ? C2 B6 B5 58.70(14) . . ? C2 B6 B1 58.99(13) . . ? C2 B6 B7 104.92(18) . . ? C2 B6 B10 104.74(19) . . ? C2 B6 H6A 124.8 . . ? B5 B6 B1 108.40(18) . . ? B5 B6 B10 59.89(16) . . ? B5 B6 H6A 121.2 . . ? B1 B6 H6A 121.4 . . ? B7 B6 B5 108.8(2) . . ? B7 B6 B1 59.63(15) . . ? B7 B6 B10 60.96(15) . . ? B7 B6 H6A 121.9 . . ? B10 B6 B1 108.42(19) . . ? B10 B6 H6A 122.1 . . ? C9 C8 H8A 119.8 . . ? C7 C8 C9 120.3(3) . . ? C7 C8 H8A 119.8 . . ? C1 B2 B1 59.23(14) . . ? C1 B2 B7 104.74(19) . . ? C1 B2 B8 104.2(2) . . ? C1 B2 H2 125.0 . . ? C1 B2 B3 58.24(16) . . ? B1 B2 B7 59.85(16) . . ? B1 B2 B8 108.12(19) . . ? B1 B2 H2 121.2 . . ? B1 B2 B3 108.43(19) . . ? B7 B2 H2 122.2 . . ? B8 B2 B7 60.21(16) . . ? B8 B2 H2 122.4 . . ? B8 B2 B3 60.13(17) . . ? B3 B2 B7 108.43(19) . . ? B3 B2 H2 121.3 . . ? C2 B4 B5 58.16(14) . . ? C2 B4 B9 104.06(19) . . ? C2 B4 H4 125.2 . . ? C2 B4 B3 103.8(2) . . ? C1 B4 C2 56.62(13) . . ? C1 B4 B5 103.65(18) . . ? C1 B4 B9 104.3(2) . . ? C1 B4 H4 125.2 . . ? C1 B4 B3 58.00(15) . . ? B5 B4 H4 122.6 . . ? B9 B4 B5 59.70(16) . . ? B9 B4 H4 122.9 . . ? B9 B4 B3 60.66(17) . . ? B3 B4 B5 107.8(2) . . ? B3 B4 H4 122.2 . . ? C6 C7 C8 120.2(2) . . ? C6 C7 H7A 119.9 . . ? C8 C7 H7A 119.9 . . ? C1 B3 B9 104.19(19) . . ? C1 B3 B8 104.4(2) . . ? C1 B3 B2 58.61(15) . . ? C1 B3 B4 59.15(15) . . ? C1 B3 H3 125.0 . . ? B9 B3 H3 122.7 . . ? B8 B3 B9 60.21(16) . . ? B8 B3 H3 122.4 . . ? B2 B3 B9 108.0(2) . . ? B2 B3 B8 59.90(17) . . ? B2 B3 H3 121.3 . . ? B4 B3 B9 59.38(17) . . ? B4 B3 B8 108.0(2) . . ? B4 B3 B2 108.5(2) . . ? B4 B3 H3 121.3 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C4 C9 C8 178.9(2) . . . . ? N1 C4 C5 F1 0.9(3) . . . . ? N1 C4 C5 C6 -179.1(2) . . . . ? F1 C5 C6 C7 179.7(2) . . . . ? C2 C1 B1 B7 -97.99(18) . . . . ? C2 C1 B1 B6 -36.08(15) . . . . ? C2 C1 B1 B2 -138.72(18) . . . . ? C2 C1 B2 B1 38.73(17) . . . . ? C2 C1 B2 B7 -1.7(2) . . . . ? C2 C1 B2 B8 -64.1(2) . . . . ? C2 C1 B2 B3 -104.5(2) . . . . ? C2 C1 B4 B5 35.89(16) . . . . ? C2 C1 B4 B9 97.60(19) . . . . ? C2 C1 B4 B3 138.5(2) . . . . ? C2 C1 B3 B9 1.2(3) . . . . ? C2 C1 B3 B8 63.5(2) . . . . ? C2 C1 B3 B2 103.9(2) . . . . ? C2 C1 B3 B4 -39.06(19) . . . . ? C2 B5 B9 B10 -99.15(19) . . . . ? C2 B5 B9 B8 -61.5(2) . . . . ? C2 B5 B9 B4 39.65(17) . . . . ? C2 B5 B9 B3 1.5(2) . . . . ? C2 B5 B10 B7 -2.6(2) . . . . ? C2 B5 B10 B9 98.5(2) . . . . ? C2 B5 B10 B8 60.5(2) . . . . ? C2 B5 B10 B6 -39.47(17) . . . . ? C2 B5 B6 B1 33.10(16) . . . . ? C2 B5 B6 B7 96.38(19) . . . . ? C2 B5 B6 B10 134.17(19) . . . . ? C2 B5 B4 C1 -35.19(15) . . . . ? C2 B5 B4 B9 -134.0(2) . . . . ? C2 B5 B4 B3 -95.5(2) . . . . ? C2 B1 B7 B10 1.6(2) . . . . ? C2 B1 B7 B8 -61.4(2) . . . . ? C2 B1 B7 B6 38.90(17) . . . . ? C2 B1 B7 B2 -98.55(19) . . . . ? C2 B1 B6 B5 -32.98(16) . . . . ? C2 B1 B6 B7 -134.45(19) . . . . ? C2 B1 B6 B10 -96.5(2) . . . . ? C2 B1 B2 C1 -34.70(16) . . . . ? C2 B1 B2 B7 98.79(18) . . . . ? C2 B1 B2 B8 61.4(2) . . . . ? C2 B1 B2 B3 -2.3(2) . . . . ? C2 B4 B3 C1 34.72(16) . . . . ? C2 B4 B3 B9 -98.5(2) . . . . ? C2 B4 B3 B8 -61.6(2) . . . . ? C2 B4 B3 B2 1.8(2) . . . . ? C4 N1 C3 C2 -174.8(2) . . . . ? C4 N1 C3 O1 4.5(4) . . . . ? C4 C9 C8 C7 0.7(4) . . . . ? C4 C5 C6 C7 -0.2(4) . . . . ? C9 C4 C5 F1 -179.5(2) . . . . ? C9 C4 C5 C6 0.5(4) . . . . ? C9 C8 C7 C6 -0.5(4) . . . . ? C3 N1 C4 C9 -20.6(4) . . . . ? C3 N1 C4 C5 159.0(2) . . . . ? C3 C2 C1 B1 -106.7(2) . . . . ? C3 C2 C1 B2 -145.6(2) . . . . ? C3 C2 C1 B4 106.3(2) . . . . ? C3 C2 C1 B3 145.8(2) . . . . ? C3 C2 B5 B9 -142.9(2) . . . . ? C3 C2 B5 B10 154.6(2) . . . . ? C3 C2 B5 B6 114.5(2) . . . . ? C3 C2 B5 B4 -103.0(2) . . . . ? C3 C2 B1 C1 105.0(2) . . . . ? C3 C2 B1 B7 -156.82(19) . . . . ? C3 C2 B1 B6 -117.2(2) . . . . ? C3 C2 B1 B2 140.50(19) . . . . ? C3 C2 B6 B5 -114.0(2) . . . . ? C3 C2 B6 B1 103.2(2) . . . . ? C3 C2 B6 B7 142.8(2) . . . . ? C3 C2 B6 B10 -153.9(2) . . . . ? C3 C2 B4 C1 -105.1(2) . . . . ? C3 C2 B4 B5 117.0(2) . . . . ? C3 C2 B4 B9 156.81(18) . . . . ? C3 C2 B4 B3 -140.48(19) . . . . ? C5 C4 C9 C8 -0.7(3) . . . . ? C5 C6 C7 C8 0.2(4) . . . . ? C1 C2 C3 N1 176.80(18) . . . . ? C1 C2 C3 O1 -2.5(3) . . . . ? C1 C2 B5 B9 -0.8(2) . . . . ? C1 C2 B5 B10 -63.3(2) . . . . ? C1 C2 B5 B6 -103.35(19) . . . . ? C1 C2 B5 B4 39.15(18) . . . . ? C1 C2 B1 B7 98.2(2) . . . . ? C1 C2 B1 B6 137.81(18) . . . . ? C1 C2 B1 B2 35.53(16) . . . . ? C1 C2 B6 B5 103.64(19) . . . . ? C1 C2 B6 B1 -39.16(17) . . . . ? C1 C2 B6 B7 0.4(2) . . . . ? C1 C2 B6 B10 63.7(2) . . . . ? C1 C2 B4 B5 -137.89(19) . . . . ? C1 C2 B4 B9 -98.0(2) . . . . ? C1 C2 B4 B3 -35.34(17) . . . . ? C1 B1 B7 B10 60.4(2) . . . . ? C1 B1 B7 B8 -2.7(2) . . . . ? C1 B1 B7 B6 97.67(19) . . . . ? C1 B1 B7 B2 -39.78(17) . . . . ? C1 B1 B6 C2 35.31(15) . . . . ? C1 B1 B6 B5 2.3(2) . . . . ? C1 B1 B6 B7 -99.1(2) . . . . ? C1 B1 B6 B10 -61.2(2) . . . . ? C1 B1 B2 B7 133.49(19) . . . . ? C1 B1 B2 B8 96.1(2) . . . . ? C1 B1 B2 B3 32.43(18) . . . . ? C1 B2 B3 B9 96.0(2) . . . . ? C1 B2 B3 B8 133.6(2) . . . . ? C1 B2 B3 B4 33.08(18) . . . . ? C1 B4 B3 B9 -133.3(2) . . . . ? C1 B4 B3 B8 -96.3(2) . . . . ? C1 B4 B3 B2 -32.87(18) . . . . ? B5 C2 C3 N1 -42.1(3) . . . . ? B5 C2 C3 O1 138.7(3) . . . . ? B5 C2 C1 B1 107.19(19) . . . . ? B5 C2 C1 B2 68.3(2) . . . . ? B5 C2 C1 B4 -39.75(18) . . . . ? B5 C2 C1 B3 -0.3(3) . . . . ? B5 C2 B1 C1 -101.72(19) . . . . ? B5 C2 B1 B7 -3.5(2) . . . . ? B5 C2 B1 B6 36.08(18) . . . . ? B5 C2 B1 B2 -66.2(2) . . . . ? B5 C2 B6 B1 -142.80(19) . . . . ? B5 C2 B6 B7 -103.2(2) . . . . ? B5 C2 B6 B10 -39.91(18) . . . . ? B5 C2 B4 C1 137.89(18) . . . . ? B5 C2 B4 B9 39.84(18) . . . . ? B5 C2 B4 B3 102.6(2) . . . . ? B5 B9 B10 B7 100.35(19) . . . . ? B5 B9 B10 B8 137.72(19) . . . . ? B5 B9 B10 B6 37.51(18) . . . . ? B5 B9 B8 B7 0.1(3) . . . . ? B5 B9 B8 B10 -37.64(18) . . . . ? B5 B9 B8 B2 63.5(2) . . . . ? B5 B9 B8 B3 101.0(2) . . . . ? B5 B9 B4 C2 -39.08(17) . . . . ? B5 B9 B4 C1 -97.65(19) . . . . ? B5 B9 B4 B3 -137.2(2) . . . . ? B5 B9 B3 C1 -1.6(3) . . . . ? B5 B9 B3 B8 -100.3(2) . . . . ? B5 B9 B3 B2 -62.8(2) . . . . ? B5 B9 B3 B4 38.51(19) . . . . ? B5 B10 B8 B7 -100.4(2) . . . . ? B5 B10 B8 B9 37.75(18) . . . . ? B5 B10 B8 B2 -62.8(3) . . . . ? B5 B10 B8 B3 0.7(3) . . . . ? B5 B10 B6 C2 39.33(17) . . . . ? B5 B10 B6 B1 101.04(19) . . . . ? B5 B10 B6 B7 138.4(2) . . . . ? B5 B4 B3 C1 95.27(19) . . . . ? B5 B4 B3 B9 -37.99(18) . . . . ? B5 B4 B3 B8 -1.0(2) . . . . ? B5 B4 B3 B2 62.4(2) . . . . ? B1 C2 C3 N1 108.4(2) . . . . ? B1 C2 C3 O1 -70.9(3) . . . . ? B1 C2 C1 B2 -38.86(18) . . . . ? B1 C2 C1 B4 -146.94(19) . . . . ? B1 C2 C1 B3 -107.5(2) . . . . ? B1 C2 B5 B9 66.4(2) . . . . ? B1 C2 B5 B10 3.9(2) . . . . ? B1 C2 B5 B6 -36.16(18) . . . . ? B1 C2 B5 B4 106.3(2) . . . . ? B1 C2 B6 B5 142.80(19) . . . . ? B1 C2 B6 B7 39.59(17) . . . . ? B1 C2 B6 B10 102.9(2) . . . . ? B1 C2 B4 C1 31.81(18) . . . . ? B1 C2 B4 B5 -106.1(2) . . . . ? B1 C2 B4 B9 -66.2(2) . . . . ? B1 C2 B4 B3 -3.5(2) . . . . ? B1 C1 B2 B7 -40.45(17) . . . . ? B1 C1 B2 B8 -102.8(2) . . . . ? B1 C1 B2 B3 -143.2(2) . . . . ? B1 C1 B4 C2 -32.23(18) . . . . ? B1 C1 B4 B5 3.7(2) . . . . ? B1 C1 B4 B9 65.4(2) . . . . ? B1 C1 B4 B3 106.3(2) . . . . ? B1 C1 B3 B9 -66.9(2) . . . . ? B1 C1 B3 B8 -4.6(3) . . . . ? B1 C1 B3 B2 35.73(19) . . . . ? B1 C1 B3 B4 -107.2(2) . . . . ? B1 B7 B10 B5 0.6(3) . . . . ? B1 B7 B10 B9 -62.7(2) . . . . ? B1 B7 B10 B8 -100.4(2) . . . . ? B1 B7 B10 B6 37.72(18) . . . . ? B1 B7 B8 B9 63.7(2) . . . . ? B1 B7 B8 B10 101.0(2) . . . . ? B1 B7 B8 B2 -37.04(18) . . . . ? B1 B7 B8 B3 0.1(3) . . . . ? B1 B7 B6 C2 -39.28(16) . . . . ? B1 B7 B6 B5 -100.78(19) . . . . ? B1 B7 B6 B10 -138.1(2) . . . . ? B1 B7 B2 C1 40.14(17) . . . . ? B1 B7 B2 B8 138.3(2) . . . . ? B1 B7 B2 B3 101.1(2) . . . . ? B1 B2 B3 C1 -32.82(18) . . . . ? B1 B2 B3 B9 63.1(2) . . . . ? B1 B2 B3 B8 100.8(2) . . . . ? B1 B2 B3 B4 0.3(3) . . . . ? B7 B1 B6 C2 134.45(19) . . . . ? B7 B1 B6 B5 101.5(2) . . . . ? B7 B1 B6 B10 37.98(18) . . . . ? B7 B1 B2 C1 -133.49(19) . . . . ? B7 B1 B2 B8 -37.38(19) . . . . ? B7 B1 B2 B3 -101.1(2) . . . . ? B7 B10 B8 B9 138.12(19) . . . . ? B7 B10 B8 B2 37.57(19) . . . . ? B7 B10 B8 B3 101.0(2) . . . . ? B7 B10 B6 C2 -99.11(19) . . . . ? B7 B10 B6 B5 -138.4(2) . . . . ? B7 B10 B6 B1 -37.40(18) . . . . ? B7 B8 B2 C1 99.0(2) . . . . ? B7 B8 B2 B1 37.22(19) . . . . ? B7 B8 B2 B3 138.5(2) . . . . ? B7 B8 B3 C1 2.6(3) . . . . ? B7 B8 B3 B9 100.9(2) . . . . ? B7 B8 B3 B2 -37.11(18) . . . . ? B7 B8 B3 B4 64.3(2) . . . . ? B7 B2 B3 C1 -96.3(2) . . . . ? B7 B2 B3 B9 -0.3(2) . . . . ? B7 B2 B3 B8 37.31(18) . . . . ? B7 B2 B3 B4 -63.2(2) . . . . ? B9 B5 B10 B7 -101.1(2) . . . . ? B9 B5 B10 B8 -38.01(18) . . . . ? B9 B5 B10 B6 -138.0(2) . . . . ? B9 B5 B6 C2 -96.49(19) . . . . ? B9 B5 B6 B1 -63.4(2) . . . . ? B9 B5 B6 B7 -0.1(2) . . . . ? B9 B5 B6 B10 37.68(18) . . . . ? B9 B5 B4 C2 134.0(2) . . . . ? B9 B5 B4 C1 98.8(2) . . . . ? B9 B5 B4 B3 38.42(19) . . . . ? B9 B10 B8 B7 -138.12(19) . . . . ? B9 B10 B8 B2 -100.6(2) . . . . ? B9 B10 B8 B3 -37.09(19) . . . . ? B9 B10 B6 C2 1.9(2) . . . . ? B9 B10 B6 B5 -37.46(19) . . . . ? B9 B10 B6 B1 63.6(2) . . . . ? B9 B10 B6 B7 101.0(2) . . . . ? B9 B8 B2 C1 -1.9(3) . . . . ? B9 B8 B2 B1 -63.7(3) . . . . ? B9 B8 B2 B7 -100.9(2) . . . . ? B9 B8 B2 B3 37.60(19) . . . . ? B9 B8 B3 C1 -98.3(2) . . . . ? B9 B8 B3 B2 -138.0(2) . . . . ? B9 B8 B3 B4 -36.60(18) . . . . ? B9 B4 B3 C1 133.3(2) . . . . ? B9 B4 B3 B8 36.96(19) . . . . ? B9 B4 B3 B2 100.4(2) . . . . ? B10 B5 B9 B8 37.66(18) . . . . ? B10 B5 B9 B4 138.80(19) . . . . ? B10 B5 B9 B3 100.6(2) . . . . ? B10 B5 B6 C2 -134.17(19) . . . . ? B10 B5 B6 B1 -101.1(2) . . . . ? B10 B5 B6 B7 -37.79(18) . . . . ? B10 B5 B4 C2 97.0(2) . . . . ? B10 B5 B4 C1 61.8(2) . . . . ? B10 B5 B4 B9 -36.99(18) . . . . ? B10 B5 B4 B3 1.4(2) . . . . ? B10 B7 B8 B9 -37.27(18) . . . . ? B10 B7 B8 B2 -138.0(2) . . . . ? B10 B7 B8 B3 -100.9(2) . . . . ? B10 B7 B6 C2 98.82(19) . . . . ? B10 B7 B6 B5 37.32(18) . . . . ? B10 B7 B6 B1 138.1(2) . . . . ? B10 B7 B2 C1 -60.9(2) . . . . ? B10 B7 B2 B1 -101.08(19) . . . . ? B10 B7 B2 B8 37.26(18) . . . . ? B10 B7 B2 B3 0.0(2) . . . . ? B10 B9 B8 B7 37.70(18) . . . . ? B10 B9 B8 B2 101.1(2) . . . . ? B10 B9 B8 B3 138.61(19) . . . . ? B10 B9 B4 C2 -2.1(2) . . . . ? B10 B9 B4 C1 -60.6(2) . . . . ? B10 B9 B4 B5 37.01(18) . . . . ? B10 B9 B4 B3 -100.2(2) . . . . ? B10 B9 B3 C1 61.7(2) . . . . ? B10 B9 B3 B8 -36.96(18) . . . . ? B10 B9 B3 B2 0.5(3) . . . . ? B10 B9 B3 B4 101.8(2) . . . . ? B10 B8 B2 C1 61.2(2) . . . . ? B10 B8 B2 B1 -0.6(3) . . . . ? B10 B8 B2 B7 -37.84(19) . . . . ? B10 B8 B2 B3 100.7(2) . . . . ? B10 B8 B3 C1 -61.5(2) . . . . ? B10 B8 B3 B9 36.84(18) . . . . ? B10 B8 B3 B2 -101.2(2) . . . . ? B10 B8 B3 B4 0.2(3) . . . . ? B8 B7 B10 B5 101.0(2) . . . . ? B8 B7 B10 B9 37.69(18) . . . . ? B8 B7 B10 B6 138.1(2) . . . . ? B8 B7 B6 C2 61.6(2) . . . . ? B8 B7 B6 B5 0.1(2) . . . . ? B8 B7 B6 B1 100.9(2) . . . . ? B8 B7 B6 B10 -37.17(18) . . . . ? B8 B7 B2 C1 -98.2(2) . . . . ? B8 B7 B2 B1 -138.3(2) . . . . ? B8 B7 B2 B3 -37.28(18) . . . . ? B8 B9 B10 B5 -137.72(19) . . . . ? B8 B9 B10 B7 -37.37(17) . . . . ? B8 B9 B10 B6 -100.2(2) . . . . ? B8 B9 B4 C2 61.5(2) . . . . ? B8 B9 B4 C1 2.9(2) . . . . ? B8 B9 B4 B5 100.5(2) . . . . ? B8 B9 B4 B3 -36.7(2) . . . . ? B8 B9 B3 C1 98.6(2) . . . . ? B8 B9 B3 B2 37.49(19) . . . . ? B8 B9 B3 B4 138.8(2) . . . . ? B8 B10 B6 C2 -61.9(2) . . . . ? B8 B10 B6 B5 -101.2(2) . . . . ? B8 B10 B6 B1 -0.2(3) . . . . ? B8 B10 B6 B7 37.20(19) . . . . ? B8 B2 B3 C1 -133.6(2) . . . . ? B8 B2 B3 B9 -37.63(19) . . . . ? B8 B2 B3 B4 -100.5(2) . . . . ? B6 C2 C3 N1 35.5(3) . . . . ? B6 C2 C3 O1 -143.8(3) . . . . ? B6 C2 C1 B1 39.70(17) . . . . ? B6 C2 C1 B2 0.8(2) . . . . ? B6 C2 C1 B4 -107.23(19) . . . . ? B6 C2 C1 B3 -67.8(2) . . . . ? B6 C2 B5 B9 102.6(2) . . . . ? B6 C2 B5 B10 40.07(18) . . . . ? B6 C2 B5 B4 142.50(19) . . . . ? B6 C2 B1 C1 -137.81(18) . . . . ? B6 C2 B1 B7 -39.60(17) . . . . ? B6 C2 B1 B2 -102.28(19) . . . . ? B6 C2 B4 C1 101.5(2) . . . . ? B6 C2 B4 B5 -36.36(18) . . . . ? B6 C2 B4 B9 3.5(2) . . . . ? B6 C2 B4 B3 66.2(2) . . . . ? B6 B5 B9 B10 -37.63(18) . . . . ? B6 B5 B9 B8 0.0(2) . . . . ? B6 B5 B9 B4 101.17(19) . . . . ? B6 B5 B9 B3 63.0(2) . . . . ? B6 B5 B10 B7 36.85(18) . . . . ? B6 B5 B10 B9 138.0(2) . . . . ? B6 B5 B10 B8 100.0(2) . . . . ? B6 B5 B4 C2 33.31(17) . . . . ? B6 B5 B4 C1 -1.9(2) . . . . ? B6 B5 B4 B9 -100.6(2) . . . . ? B6 B5 B4 B3 -62.2(2) . . . . ? B6 B1 B7 B10 -37.29(18) . . . . ? B6 B1 B7 B8 -100.3(2) . . . . ? B6 B1 B7 B2 -137.5(2) . . . . ? B6 B1 B2 C1 -95.61(19) . . . . ? B6 B1 B2 B7 37.87(18) . . . . ? B6 B1 B2 B8 0.5(3) . . . . ? B6 B1 B2 B3 -63.2(2) . . . . ? B6 B7 B10 B5 -37.10(18) . . . . ? B6 B7 B10 B9 -100.4(2) . . . . ? B6 B7 B10 B8 -138.1(2) . . . . ? B6 B7 B8 B9 -0.1(2) . . . . ? B6 B7 B8 B10 37.14(18) . . . . ? B6 B7 B8 B2 -100.9(2) . . . . ? B6 B7 B8 B3 -63.8(2) . . . . ? B6 B7 B2 C1 1.9(2) . . . . ? B6 B7 B2 B1 -38.21(18) . . . . ? B6 B7 B2 B8 100.1(2) . . . . ? B6 B7 B2 B3 62.8(2) . . . . ? B6 B10 B8 B7 -37.06(18) . . . . ? B6 B10 B8 B9 101.1(2) . . . . ? B6 B10 B8 B2 0.5(3) . . . . ? B6 B10 B8 B3 64.0(2) . . . . ? B2 C1 B1 C2 138.72(18) . . . . ? B2 C1 B1 B7 40.74(17) . . . . ? B2 C1 B1 B6 102.64(19) . . . . ? B2 C1 B4 C2 -102.0(2) . . . . ? B2 C1 B4 B5 -66.1(2) . . . . ? B2 C1 B4 B9 -4.4(3) . . . . ? B2 C1 B4 B3 36.5(2) . . . . ? B2 C1 B3 B9 -102.7(2) . . . . ? B2 C1 B3 B8 -40.31(18) . . . . ? B2 C1 B3 B4 -142.9(2) . . . . ? B2 B1 B7 B10 100.2(2) . . . . ? B2 B1 B7 B8 37.12(18) . . . . ? B2 B1 B7 B6 137.5(2) . . . . ? B2 B1 B6 C2 96.3(2) . . . . ? B2 B1 B6 B5 63.3(2) . . . . ? B2 B1 B6 B7 -38.17(18) . . . . ? B2 B1 B6 B10 -0.2(2) . . . . ? B2 B7 B10 B5 63.6(2) . . . . ? B2 B7 B10 B9 0.4(2) . . . . ? B2 B7 B10 B8 -37.34(18) . . . . ? B2 B7 B10 B6 100.7(2) . . . . ? B2 B7 B8 B9 100.8(2) . . . . ? B2 B7 B8 B10 138.0(2) . . . . ? B2 B7 B8 B3 37.12(19) . . . . ? B2 B7 B6 C2 -1.5(2) . . . . ? B2 B7 B6 B5 -63.0(2) . . . . ? B2 B7 B6 B1 37.81(17) . . . . ? B2 B7 B6 B10 -100.3(2) . . . . ? B2 B8 B3 C1 39.67(18) . . . . ? B2 B8 B3 B9 138.0(2) . . . . ? B2 B8 B3 B4 101.4(2) . . . . ? B4 C2 C3 N1 -114.9(2) . . . . ? B4 C2 C3 O1 65.8(3) . . . . ? B4 C2 C1 B1 146.94(19) . . . . ? B4 C2 C1 B2 108.1(2) . . . . ? B4 C2 C1 B3 39.4(2) . . . . ? B4 C2 B5 B9 -39.91(18) . . . . ? B4 C2 B5 B10 -102.4(2) . . . . ? B4 C2 B5 B6 -142.50(19) . . . . ? B4 C2 B1 C1 -31.82(18) . . . . ? B4 C2 B1 B7 66.4(2) . . . . ? B4 C2 B1 B6 106.0(2) . . . . ? B4 C2 B1 B2 3.7(2) . . . . ? B4 C2 B6 B5 36.49(18) . . . . ? B4 C2 B6 B1 -106.3(2) . . . . ? B4 C2 B6 B7 -66.7(2) . . . . ? B4 C2 B6 B10 -3.4(2) . . . . ? B4 C1 B1 C2 32.25(18) . . . . ? B4 C1 B1 B7 -65.7(2) . . . . ? B4 C1 B1 B6 -3.8(2) . . . . ? B4 C1 B1 B2 -106.5(2) . . . . ? B4 C1 B2 B1 106.8(2) . . . . ? B4 C1 B2 B7 66.4(2) . . . . ? B4 C1 B2 B8 4.0(3) . . . . ? B4 C1 B2 B3 -36.4(2) . . . . ? B4 C1 B3 B9 40.27(19) . . . . ? B4 C1 B3 B8 102.6(2) . . . . ? B4 C1 B3 B2 142.9(2) . . . . ? B4 B5 B9 B10 -138.80(19) . . . . ? B4 B5 B9 B8 -101.1(2) . . . . ? B4 B5 B9 B3 -38.17(19) . . . . ? B4 B5 B10 B7 -64.4(2) . . . . ? B4 B5 B10 B9 36.71(18) . . . . ? B4 B5 B10 B8 -1.3(2) . . . . ? B4 B5 B10 B6 -101.27(19) . . . . ? B4 B5 B6 C2 -33.38(17) . . . . ? B4 B5 B6 B1 -0.3(2) . . . . ? B4 B5 B6 B7 63.0(2) . . . . ? B4 B5 B6 B10 100.8(2) . . . . ? B4 B9 B10 B5 -37.37(18) . . . . ? B4 B9 B10 B7 63.0(2) . . . . ? B4 B9 B10 B8 100.3(2) . . . . ? B4 B9 B10 B6 0.1(3) . . . . ? B4 B9 B8 B7 -64.1(2) . . . . ? B4 B9 B8 B10 -101.8(2) . . . . ? B4 B9 B8 B2 -0.7(3) . . . . ? B4 B9 B8 B3 36.85(19) . . . . ? B4 B9 B3 C1 -40.15(18) . . . . ? B4 B9 B3 B8 -138.8(2) . . . . ? B4 B9 B3 B2 -101.3(2) . . . . ? B3 C1 B1 C2 102.7(2) . . . . ? B3 C1 B1 B7 4.7(3) . . . . ? B3 C1 B1 B6 66.6(2) . . . . ? B3 C1 B1 B2 -36.07(19) . . . . ? B3 C1 B2 B1 143.2(2) . . . . ? B3 C1 B2 B7 102.8(2) . . . . ? B3 C1 B2 B8 40.40(19) . . . . ? B3 C1 B4 C2 -138.5(2) . . . . ? B3 C1 B4 B5 -102.6(2) . . . . ? B3 C1 B4 B9 -40.93(18) . . . . ? B3 B9 B10 B5 -100.9(2) . . . . ? B3 B9 B10 B7 -0.5(2) . . . . ? B3 B9 B10 B8 36.82(18) . . . . ? B3 B9 B10 B6 -63.4(2) . . . . ? B3 B9 B8 B7 -100.9(2) . . . . ? B3 B9 B8 B10 -138.61(19) . . . . ? B3 B9 B8 B2 -37.52(19) . . . . ? B3 B9 B4 C2 98.2(2) . . . . ? B3 B9 B4 C1 39.59(18) . . . . ? B3 B9 B4 B5 137.2(2) . . . . ? B3 B8 B2 C1 -39.46(18) . . . . ? B3 B8 B2 B1 -101.3(2) . . . . ? B3 B8 B2 B7 -138.5(2) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 937468' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_130823_ny_wyf_65a _audit_creation_date 2013-08-24 _audit_creation_method ; Olex2 1.2 (compiled Apr 23 2013 17:54:37, GUI svn.r4466) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C9 H16 B10 I N O' _chemical_formula_sum 'C9 H16 B10 I N O' _chemical_formula_weight 389.23 _chemical_melting_point ? _chemical_oxdiff_formula 'C H N O B I' 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' I I -0.4742 1.8119 '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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.2249(2) _cell_length_b 22.8107(10) _cell_length_c 10.5504(4) _cell_angle_alpha 90.00 _cell_angle_beta 109.334(4) _cell_angle_gamma 90.00 _cell_volume 1640.71(11) _cell_formula_units_Z 4 _cell_measurement_reflns_used 5548 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 28.1990 _cell_measurement_theta_min 3.4690 _exptl_absorpt_coefficient_mu 1.941 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.57605 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.576 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.15 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0394 _diffrn_reflns_av_unetI/netI 0.0247 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 19725 _diffrn_reflns_theta_full 26.37 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_min 3.14 _diffrn_ambient_temperature 293.15 _diffrn_detector_area_resol_mean 16.0355 _diffrn_measured_fraction_theta_full 0.9977 _diffrn_measured_fraction_theta_max 0.9254 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -23.00 86.00 1.0000 7.5500 omega____ theta____ kappa____ phi______ frames - 17.7426 19.0000 90.0000 109 #__ type_ start__ end____ width___ exp.time_ 2 omega 9.00 47.00 1.0000 7.5500 omega____ theta____ kappa____ phi______ frames - -18.8363 57.0000 -180.0000 38 #__ type_ start__ end____ width___ exp.time_ 3 omega 32.00 57.00 1.0000 7.5500 omega____ theta____ kappa____ phi______ frames - 17.7426 -178.0000 120.0000 25 #__ type_ start__ end____ width___ exp.time_ 4 omega -50.00 -22.00 1.0000 7.5500 omega____ theta____ kappa____ phi______ frames - 17.5863 -57.0000 -30.0000 28 #__ type_ start__ end____ width___ exp.time_ 5 omega 36.00 91.00 1.0000 7.5500 omega____ theta____ kappa____ phi______ frames - 17.5863 178.0000 0.0000 55 #__ type_ start__ end____ width___ exp.time_ 6 omega 9.00 39.00 1.0000 7.5500 omega____ theta____ kappa____ phi______ frames - 17.5863 -57.0000 30.0000 30 #__ type_ start__ end____ width___ exp.time_ 7 omega 15.00 79.00 1.0000 7.5500 omega____ theta____ kappa____ phi______ frames - 17.5863 37.0000 150.0000 64 #__ type_ start__ end____ width___ exp.time_ 8 omega 47.00 87.00 1.0000 7.5500 omega____ theta____ kappa____ phi______ frames - 17.5863 178.0000 -120.0000 40 #__ type_ start__ end____ width___ exp.time_ 9 omega -21.00 19.00 1.0000 7.5500 omega____ theta____ kappa____ phi______ frames - -18.6801 -99.0000 -30.0000 40 #__ type_ start__ end____ width___ exp.time_ 10 omega -36.00 -4.00 1.0000 7.5500 omega____ theta____ kappa____ phi______ frames - -18.6801 -57.0000 -90.0000 32 #__ type_ start__ end____ width___ exp.time_ 11 omega -11.00 16.00 1.0000 7.5500 omega____ theta____ kappa____ phi______ frames - -18.6801 -99.0000 -150.0000 27 #__ type_ start__ end____ width___ exp.time_ 12 omega -25.00 6.00 1.0000 7.5500 omega____ theta____ kappa____ phi______ frames - -18.6801 -99.0000 -180.0000 31 #__ type_ start__ end____ width___ exp.time_ 13 omega -51.00 39.00 1.0000 7.5500 omega____ theta____ kappa____ phi______ frames - 17.5863 -57.0000 0.0000 90 #__ type_ start__ end____ width___ exp.time_ 14 omega -87.00 -42.00 1.0000 7.5500 omega____ theta____ kappa____ phi______ frames - -18.6801 -57.0000 -120.0000 45 ; _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0946145000 _diffrn_orient_matrix_UB_12 0.0061049000 _diffrn_orient_matrix_UB_13 -0.0460460000 _diffrn_orient_matrix_UB_21 -0.0038887000 _diffrn_orient_matrix_UB_22 0.0260806000 _diffrn_orient_matrix_UB_23 0.0356848000 _diffrn_orient_matrix_UB_31 0.0430491000 _diffrn_orient_matrix_UB_32 0.0158024000 _diffrn_orient_matrix_UB_33 -0.0410126000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2721 _reflns_number_total 3340 _reflns_odcompleteness_completeness 99.77 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.529 _refine_diff_density_min -0.880 _refine_diff_density_rms 0.068 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 199 _refine_ls_number_reflns 3340 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0456 _refine_ls_R_factor_gt 0.0340 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0310P)^2^+1.6385P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0744 _refine_ls_wR_factor_ref 0.0806 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All B(H) groups, All C(H) groups, All N(H) groups 2.a Aromatic/amide H refined with riding coordinates: N1(H1), C8(H8), C5(H5), C6(H6), C9(H9) 2.b Boron cage BH refined with riding coordinates: C1(H1A), B11(H11), B6(H6A), B12(H12), B7(H7), B5(H5A), B10(H10), B3(H3), B9(H9A), B4(H4), B8(H8A) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 I1 I 1.17755(3) 0.570780(12) 0.41617(2) 0.06076(11) Uani 1 1 d . . . N1 N 0.3058(3) 0.62851(11) 0.0839(2) 0.0400(6) Uani 1 1 d . . . H1 H 0.2700 0.6640 0.0904 0.048 Uiso 1 1 calc R . . C3 C 0.1742(4) 0.59437(14) -0.0038(3) 0.0405(7) Uani 1 1 d . . . O1 O 0.1897(4) 0.54212(11) -0.0161(3) 0.0815(10) Uani 1 1 d . . . C4 C 0.4972(4) 0.61318(13) 0.1674(3) 0.0352(6) Uani 1 1 d . . . C2 C -0.0050(4) 0.62646(12) -0.0946(3) 0.0321(6) Uani 1 1 d . . . C7 C 0.8808(4) 0.58910(14) 0.3167(3) 0.0382(7) Uani 1 1 d . . . C8 C 0.7511(5) 0.54381(14) 0.2677(3) 0.0431(7) Uani 1 1 d . . . H8 H 0.7931 0.5052 0.2848 0.052 Uiso 1 1 calc R . . C5 C 0.6265(5) 0.65822(14) 0.2206(3) 0.0445(8) Uani 1 1 d . . . H5 H 0.5837 0.6969 0.2058 0.053 Uiso 1 1 calc R . . C6 C 0.8190(5) 0.64648(15) 0.2958(3) 0.0459(8) Uani 1 1 d . . . H6 H 0.9060 0.6770 0.3318 0.055 Uiso 1 1 calc R . . C1 C -0.1676(5) 0.58392(13) -0.1963(3) 0.0449(8) Uani 1 1 d . . . H1A H -0.1444 0.5362 -0.1950 0.054 Uiso 1 1 calc R . . C9 C 0.5586(5) 0.55575(14) 0.1930(3) 0.0451(8) Uani 1 1 d . . . H9 H 0.4705 0.5252 0.1599 0.054 Uiso 1 1 calc R . . B11 B -0.1121(5) 0.68470(15) -0.0466(4) 0.0400(8) Uani 1 1 d . . . H11 H -0.0548 0.7065 0.0516 0.048 Uiso 1 1 calc R . . B6 B -0.2189(5) 0.61379(16) -0.0634(4) 0.0423(8) Uani 1 1 d . . . H6A H -0.2311 0.5890 0.0229 0.051 Uiso 1 1 calc R . . B12 B -0.2278(5) 0.72350(16) -0.1971(4) 0.0457(9) Uani 1 1 d . . . H12 H -0.2487 0.7713 -0.1980 0.055 Uiso 1 1 calc R . . B7 B 0.0053(5) 0.69220(15) -0.1684(4) 0.0429(8) Uani 1 1 d . . . H7 H 0.1387 0.7189 -0.1487 0.052 Uiso 1 1 calc R . . B5 B -0.3973(5) 0.60941(17) -0.2237(5) 0.0537(11) Uani 1 1 d . . . H5A H -0.5278 0.5816 -0.2416 0.064 Uiso 1 1 calc R . . B10 B -0.3659(6) 0.67547(18) -0.1313(4) 0.0488(9) Uani 1 1 d . . . H10 H -0.4763 0.6918 -0.0889 0.059 Uiso 1 1 calc R . . B3 B -0.0264(6) 0.62613(19) -0.2623(4) 0.0499(9) Uani 1 1 d . . . H3 H 0.0847 0.6093 -0.3034 0.060 Uiso 1 1 calc R . . B9 B -0.4059(6) 0.67704(17) -0.3066(4) 0.0511(10) Uani 1 1 d . . . H9A H -0.5427 0.6942 -0.3786 0.061 Uiso 1 1 calc R . . B4 B -0.2813(7) 0.61687(19) -0.3465(4) 0.0575(11) Uani 1 1 d . . . H4 H -0.3365 0.5941 -0.4438 0.069 Uiso 1 1 calc R . . B8 B -0.1744(6) 0.68747(19) -0.3286(4) 0.0533(10) Uani 1 1 d . . . H8A H -0.1598 0.7116 -0.4150 0.064 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 I1 0.03548(14) 0.0797(2) 0.05506(17) 0.00151(13) -0.00123(10) 0.01044(11) N1 0.0338(13) 0.0309(13) 0.0487(15) -0.0015(11) 0.0047(11) 0.0065(10) C3 0.0329(15) 0.0328(16) 0.0513(19) 0.0012(14) 0.0077(14) 0.0030(13) O1 0.0594(17) 0.0368(14) 0.110(2) -0.0114(15) -0.0240(15) 0.0140(12) C4 0.0305(14) 0.0363(15) 0.0350(15) 0.0025(13) 0.0060(12) 0.0056(12) C2 0.0287(14) 0.0267(14) 0.0382(15) 0.0001(12) 0.0073(12) 0.0004(11) C7 0.0313(15) 0.0497(18) 0.0302(15) 0.0027(13) 0.0056(12) 0.0060(13) C8 0.0401(16) 0.0347(16) 0.0496(19) 0.0108(14) 0.0080(14) 0.0059(14) C5 0.0438(18) 0.0340(16) 0.0473(18) -0.0081(14) 0.0039(14) 0.0060(14) C6 0.0387(17) 0.0442(18) 0.0461(18) -0.0127(15) 0.0022(14) -0.0028(14) C1 0.0413(18) 0.0314(16) 0.0512(19) -0.0037(14) 0.0007(15) -0.0024(13) C9 0.0354(16) 0.0382(17) 0.055(2) 0.0089(15) 0.0058(15) -0.0012(13) B11 0.0352(18) 0.0329(17) 0.047(2) -0.0046(15) 0.0065(15) 0.0072(14) B6 0.0336(18) 0.042(2) 0.052(2) 0.0120(17) 0.0152(16) 0.0003(15) B12 0.0383(18) 0.0310(18) 0.058(2) 0.0081(17) 0.0029(17) 0.0021(15) B7 0.0358(18) 0.0342(18) 0.054(2) 0.0105(16) 0.0089(16) -0.0024(15) B5 0.0318(18) 0.040(2) 0.074(3) 0.0116(19) -0.0035(18) -0.0055(16) B10 0.0344(19) 0.049(2) 0.063(2) 0.0125(19) 0.0164(17) 0.0094(16) B3 0.055(2) 0.056(2) 0.040(2) -0.0015(18) 0.0183(18) 0.0048(19) B9 0.038(2) 0.039(2) 0.061(2) 0.0083(18) -0.0049(17) 0.0002(16) B4 0.063(3) 0.048(2) 0.044(2) -0.0041(19) -0.0065(19) -0.001(2) B8 0.057(2) 0.054(2) 0.044(2) 0.0140(19) 0.0098(18) -0.001(2) _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 I1 C7 2.094(3) . ? N1 H1 0.8600 . ? N1 C3 1.336(4) . ? N1 C4 1.416(3) . ? C3 O1 1.208(4) . ? C3 C2 1.519(4) . ? C4 C5 1.377(4) . ? C4 C9 1.381(4) . ? C2 C1 1.624(4) . ? C2 B11 1.696(4) . ? C2 B6 1.708(4) . ? C2 B7 1.703(4) . ? C2 B3 1.725(5) . ? C7 C8 1.376(5) . ? C7 C6 1.377(5) . ? C8 H8 0.9300 . ? C8 C9 1.380(4) . ? C5 H5 0.9300 . ? C5 C6 1.380(4) . ? C6 H6 0.9300 . ? C1 H1A 1.1000 . ? C1 B6 1.706(5) . ? C1 B5 1.690(5) . ? C1 B3 1.710(5) . ? C1 B4 1.700(5) . ? C9 H9 0.9300 . ? B11 H11 1.1000 . ? B11 B6 1.776(5) . ? B11 B12 1.768(5) . ? B11 B7 1.766(5) . ? B11 B10 1.767(5) . ? B6 H6A 1.1000 . ? B6 B5 1.758(6) . ? B6 B10 1.766(5) . ? B12 H12 1.1000 . ? B12 B7 1.761(5) . ? B12 B10 1.771(5) . ? B12 B9 1.769(5) . ? B12 B8 1.761(6) . ? B7 H7 1.1000 . ? B7 B3 1.776(6) . ? B7 B8 1.761(6) . ? B5 H5A 1.1000 . ? B5 B10 1.768(6) . ? B5 B9 1.764(5) . ? B5 B4 1.769(7) . ? B10 H10 1.1000 . ? B10 B9 1.776(6) . ? B3 H3 1.1000 . ? B3 B4 1.773(6) . ? B3 B8 1.759(6) . ? B9 H9A 1.1000 . ? B9 B4 1.767(6) . ? B9 B8 1.778(6) . ? B4 H4 1.1000 . ? B4 B8 1.769(6) . ? B8 H8A 1.1000 . ? 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 C3 N1 H1 116.1 . . ? C3 N1 C4 127.7(3) . . ? C4 N1 H1 116.1 . . ? N1 C3 C2 114.7(3) . . ? O1 C3 N1 125.4(3) . . ? O1 C3 C2 119.8(3) . . ? C5 C4 N1 117.4(3) . . ? C5 C4 C9 119.9(3) . . ? C9 C4 N1 122.7(3) . . ? C3 C2 C1 114.1(2) . . ? C3 C2 B11 124.5(2) . . ? C3 C2 B6 115.7(2) . . ? C3 C2 B7 123.7(2) . . ? C3 C2 B3 114.4(2) . . ? C1 C2 B11 111.3(2) . . ? C1 C2 B6 61.5(2) . . ? C1 C2 B7 110.8(2) . . ? C1 C2 B3 61.3(2) . . ? B11 C2 B6 62.9(2) . . ? B11 C2 B7 62.6(2) . . ? B11 C2 B3 114.5(2) . . ? B6 C2 B3 114.7(2) . . ? B7 C2 B6 114.6(2) . . ? B7 C2 B3 62.4(2) . . ? C8 C7 I1 119.7(2) . . ? C8 C7 C6 120.6(3) . . ? C6 C7 I1 119.6(2) . . ? C7 C8 H8 120.0 . . ? C7 C8 C9 119.9(3) . . ? C9 C8 H8 120.0 . . ? C4 C5 H5 119.7 . . ? C4 C5 C6 120.5(3) . . ? C6 C5 H5 119.7 . . ? C7 C6 C5 119.2(3) . . ? C7 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? C2 C1 H1A 120.6 . . ? C2 C1 B6 61.63(19) . . ? C2 C1 B5 111.2(3) . . ? C2 C1 B3 62.2(2) . . ? C2 C1 B4 111.9(2) . . ? B6 C1 H1A 117.3 . . ? B6 C1 B3 115.5(2) . . ? B5 C1 H1A 118.7 . . ? B5 C1 B6 62.3(2) . . ? B5 C1 B3 114.9(3) . . ? B5 C1 B4 62.9(3) . . ? B3 C1 H1A 116.9 . . ? B4 C1 H1A 118.2 . . ? B4 C1 B6 114.9(3) . . ? B4 C1 B3 62.6(2) . . ? C4 C9 H9 120.1 . . ? C8 C9 C4 119.8(3) . . ? C8 C9 H9 120.1 . . ? C2 B11 H11 124.7 . . ? C2 B11 B6 58.87(18) . . ? C2 B11 B12 104.5(3) . . ? C2 B11 B7 58.86(19) . . ? C2 B11 B10 104.8(3) . . ? B6 B11 H11 121.5 . . ? B12 B11 H11 122.6 . . ? B12 B11 B6 107.8(3) . . ? B7 B11 H11 121.3 . . ? B7 B11 B6 108.3(3) . . ? B7 B11 B12 59.8(2) . . ? B7 B11 B10 108.2(3) . . ? B10 B11 H11 122.3 . . ? B10 B11 B6 59.8(2) . . ? B10 B11 B12 60.1(2) . . ? C2 B6 B11 58.25(18) . . ? C2 B6 H6A 124.9 . . ? C2 B6 B5 104.3(3) . . ? C2 B6 B10 104.4(2) . . ? C1 B6 C2 56.82(18) . . ? C1 B6 B11 103.9(2) . . ? C1 B6 H6A 125.0 . . ? C1 B6 B5 58.4(2) . . ? C1 B6 B10 104.5(3) . . ? B11 B6 H6A 122.5 . . ? B5 B6 B11 107.7(3) . . ? B5 B6 H6A 122.2 . . ? B5 B6 B10 60.2(2) . . ? B10 B6 B11 59.9(2) . . ? B10 B6 H6A 122.9 . . ? B11 B12 H12 121.8 . . ? B11 B12 B10 59.9(2) . . ? B11 B12 B9 108.2(3) . . ? B7 B12 B11 60.1(2) . . ? B7 B12 H12 121.6 . . ? B7 B12 B10 108.2(2) . . ? B7 B12 B9 108.5(3) . . ? B7 B12 B8 60.0(2) . . ? B10 B12 H12 121.5 . . ? B9 B12 H12 121.3 . . ? B9 B12 B10 60.2(2) . . ? B8 B12 B11 108.2(3) . . ? B8 B12 H12 121.4 . . ? B8 B12 B10 108.6(3) . . ? B8 B12 B9 60.5(2) . . ? C2 B7 B11 58.52(19) . . ? C2 B7 B12 104.6(2) . . ? C2 B7 H7 124.7 . . ? C2 B7 B3 59.4(2) . . ? C2 B7 B8 104.8(3) . . ? B11 B7 H7 121.2 . . ? B11 B7 B3 108.6(3) . . ? B12 B7 B11 60.2(2) . . ? B12 B7 H7 122.4 . . ? B12 B7 B3 108.0(3) . . ? B12 B7 B8 60.0(2) . . ? B3 B7 H7 121.2 . . ? B8 B7 B11 108.3(3) . . ? B8 B7 H7 122.5 . . ? B8 B7 B3 59.6(2) . . ? C1 B5 B6 59.3(2) . . ? C1 B5 H5A 124.6 . . ? C1 B5 B10 105.0(3) . . ? C1 B5 B9 104.9(3) . . ? C1 B5 B4 58.8(2) . . ? B6 B5 H5A 120.8 . . ? B6 B5 B10 60.1(2) . . ? B6 B5 B9 108.8(3) . . ? B6 B5 B4 109.0(3) . . ? B10 B5 H5A 122.2 . . ? B10 B5 B4 108.5(3) . . ? B9 B5 H5A 122.1 . . ? B9 B5 B10 60.4(2) . . ? B9 B5 B4 60.0(2) . . ? B4 B5 H5A 121.1 . . ? B11 B10 B12 60.0(2) . . ? B11 B10 B5 107.6(3) . . ? B11 B10 H10 121.7 . . ? B11 B10 B9 107.9(3) . . ? B6 B10 B11 60.4(2) . . ? B6 B10 B12 108.1(3) . . ? B6 B10 B5 59.7(2) . . ? B6 B10 H10 121.6 . . ? B6 B10 B9 107.9(3) . . ? B12 B10 H10 121.9 . . ? B12 B10 B9 59.8(2) . . ? B5 B10 B12 107.3(3) . . ? B5 B10 H10 122.3 . . ? B5 B10 B9 59.7(2) . . ? B9 B10 H10 121.8 . . ? C2 B3 B7 58.17(19) . . ? C2 B3 H3 125.2 . . ? C2 B3 B4 103.9(3) . . ? C2 B3 B8 103.9(3) . . ? C1 B3 C2 56.45(19) . . ? C1 B3 B7 103.6(3) . . ? C1 B3 H3 125.2 . . ? C1 B3 B4 58.4(2) . . ? C1 B3 B8 104.1(3) . . ? B7 B3 H3 122.6 . . ? B4 B3 B7 107.5(3) . . ? B4 B3 H3 122.3 . . ? B8 B3 B7 59.7(2) . . ? B8 B3 H3 123.2 . . ? B8 B3 B4 60.1(2) . . ? B12 B9 B10 60.0(2) . . ? B12 B9 H9A 122.1 . . ? B12 B9 B8 59.5(2) . . ? B5 B9 B12 107.5(3) . . ? B5 B9 B10 59.9(2) . . ? B5 B9 H9A 121.9 . . ? B5 B9 B4 60.1(3) . . ? B5 B9 B8 107.5(3) . . ? B10 B9 H9A 121.7 . . ? B10 B9 B8 107.6(3) . . ? B4 B9 B12 107.7(3) . . ? B4 B9 B10 108.2(3) . . ? B4 B9 H9A 121.6 . . ? B4 B9 B8 59.9(2) . . ? B8 B9 H9A 122.1 . . ? C1 B4 B5 58.3(2) . . ? C1 B4 B3 58.9(2) . . ? C1 B4 B9 104.4(3) . . ? C1 B4 H4 125.1 . . ? C1 B4 B8 104.1(3) . . ? B5 B4 B3 108.0(3) . . ? B5 B4 H4 121.7 . . ? B5 B4 B8 107.8(3) . . ? B3 B4 H4 121.3 . . ? B9 B4 B5 59.9(2) . . ? B9 B4 B3 108.3(3) . . ? B9 B4 H4 122.2 . . ? B9 B4 B8 60.4(2) . . ? B8 B4 B3 59.6(2) . . ? B8 B4 H4 122.6 . . ? B12 B8 B9 60.0(2) . . ? B12 B8 B4 107.9(3) . . ? B12 B8 H8A 121.6 . . ? B7 B8 B12 60.0(2) . . ? B7 B8 B9 108.0(3) . . ? B7 B8 B4 108.4(3) . . ? B7 B8 H8A 121.5 . . ? B3 B8 B12 108.7(3) . . ? B3 B8 B7 60.6(2) . . ? B3 B8 B9 108.4(3) . . ? B3 B8 B4 60.3(2) . . ? B3 B8 H8A 121.0 . . ? B9 B8 H8A 121.8 . . ? B4 B8 B9 59.7(2) . . ? B4 B8 H8A 121.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag I1 C7 C8 C9 -174.9(2) . . . . ? I1 C7 C6 C5 174.7(2) . . . . ? N1 C3 C2 C1 -177.6(3) . . . . ? N1 C3 C2 B11 -35.4(4) . . . . ? N1 C3 C2 B6 -109.0(3) . . . . ? N1 C3 C2 B7 42.4(4) . . . . ? N1 C3 C2 B3 114.4(3) . . . . ? N1 C4 C5 C6 -175.8(3) . . . . ? N1 C4 C9 C8 175.5(3) . . . . ? C3 N1 C4 C5 161.8(3) . . . . ? C3 N1 C4 C9 -16.1(5) . . . . ? C3 C2 C1 B6 107.3(3) . . . . ? C3 C2 C1 B5 146.4(3) . . . . ? C3 C2 C1 B3 -105.7(3) . . . . ? C3 C2 C1 B4 -145.3(3) . . . . ? C3 C2 B11 B6 -103.8(3) . . . . ? C3 C2 B11 B12 153.9(3) . . . . ? C3 C2 B11 B7 113.8(3) . . . . ? C3 C2 B11 B10 -143.7(3) . . . . ? C3 C2 B6 C1 -104.7(3) . . . . ? C3 C2 B6 B11 117.4(3) . . . . ? C3 C2 B6 B5 -140.4(3) . . . . ? C3 C2 B6 B10 157.2(3) . . . . ? C3 C2 B7 B11 -114.9(3) . . . . ? C3 C2 B7 B12 -155.3(3) . . . . ? C3 C2 B7 B3 102.2(3) . . . . ? C3 C2 B7 B8 142.5(3) . . . . ? C3 C2 B3 C1 105.2(3) . . . . ? C3 C2 B3 B7 -116.8(3) . . . . ? C3 C2 B3 B4 140.9(3) . . . . ? C3 C2 B3 B8 -156.9(3) . . . . ? O1 C3 C2 C1 3.5(4) . . . . ? O1 C3 C2 B11 145.7(3) . . . . ? O1 C3 C2 B6 72.1(4) . . . . ? O1 C3 C2 B7 -136.5(4) . . . . ? O1 C3 C2 B3 -64.5(4) . . . . ? C4 N1 C3 O1 8.5(6) . . . . ? C4 N1 C3 C2 -170.4(3) . . . . ? C4 C5 C6 C7 0.2(5) . . . . ? C2 C1 B6 B11 36.0(2) . . . . ? C2 C1 B6 B5 138.4(3) . . . . ? C2 C1 B6 B10 97.9(3) . . . . ? C2 C1 B5 B6 -38.8(2) . . . . ? C2 C1 B5 B10 1.7(4) . . . . ? C2 C1 B5 B9 64.5(4) . . . . ? C2 C1 B5 B4 104.5(3) . . . . ? C2 C1 B3 B7 -35.8(2) . . . . ? C2 C1 B3 B4 -138.3(3) . . . . ? C2 C1 B3 B8 -97.5(3) . . . . ? C2 C1 B4 B5 -103.4(3) . . . . ? C2 C1 B4 B3 39.4(3) . . . . ? C2 C1 B4 B9 -63.6(4) . . . . ? C2 C1 B4 B8 -1.1(4) . . . . ? C2 B11 B6 C1 -35.3(2) . . . . ? C2 B11 B6 B5 -96.1(3) . . . . ? C2 B11 B6 B10 -134.2(3) . . . . ? C2 B11 B12 B7 -39.7(2) . . . . ? C2 B11 B12 B10 98.9(3) . . . . ? C2 B11 B12 B9 61.6(3) . . . . ? C2 B11 B12 B8 -2.5(3) . . . . ? C2 B11 B7 B12 133.7(3) . . . . ? C2 B11 B7 B3 33.3(2) . . . . ? C2 B11 B7 B8 96.5(3) . . . . ? C2 B11 B10 B6 39.4(2) . . . . ? C2 B11 B10 B12 -98.5(3) . . . . ? C2 B11 B10 B5 1.7(3) . . . . ? C2 B11 B10 B9 -61.4(3) . . . . ? C2 B6 B5 C1 35.0(2) . . . . ? C2 B6 B5 B10 -98.6(3) . . . . ? C2 B6 B5 B9 -61.5(3) . . . . ? C2 B6 B5 B4 2.3(3) . . . . ? C2 B6 B10 B11 -39.0(2) . . . . ? C2 B6 B10 B12 -1.4(4) . . . . ? C2 B6 B10 B5 98.4(3) . . . . ? C2 B6 B10 B9 61.8(3) . . . . ? C2 B7 B3 C1 35.0(2) . . . . ? C2 B7 B3 B4 95.8(3) . . . . ? C2 B7 B3 B8 133.6(3) . . . . ? C2 B7 B8 B12 98.5(3) . . . . ? C2 B7 B8 B3 -40.1(2) . . . . ? C2 B7 B8 B9 61.3(3) . . . . ? C2 B7 B8 B4 -1.9(4) . . . . ? C2 B3 B4 C1 -34.9(2) . . . . ? C2 B3 B4 B5 -2.2(4) . . . . ? C2 B3 B4 B9 61.2(4) . . . . ? C2 B3 B4 B8 98.3(3) . . . . ? C2 B3 B8 B12 2.2(4) . . . . ? C2 B3 B8 B7 39.3(2) . . . . ? C2 B3 B8 B9 -61.5(3) . . . . ? C2 B3 B8 B4 -98.2(3) . . . . ? C7 C8 C9 C4 0.2(5) . . . . ? C8 C7 C6 C5 -2.3(5) . . . . ? C5 C4 C9 C8 -2.3(5) . . . . ? C6 C7 C8 C9 2.1(5) . . . . ? C1 C2 B11 B6 39.3(2) . . . . ? C1 C2 B11 B12 -63.0(3) . . . . ? C1 C2 B11 B7 -103.2(3) . . . . ? C1 C2 B11 B10 -0.6(3) . . . . ? C1 C2 B6 B11 -137.9(3) . . . . ? C1 C2 B6 B5 -35.7(2) . . . . ? C1 C2 B6 B10 -98.1(3) . . . . ? C1 C2 B7 B11 103.9(3) . . . . ? C1 C2 B7 B12 63.6(3) . . . . ? C1 C2 B7 B3 -38.9(3) . . . . ? C1 C2 B7 B8 1.3(3) . . . . ? C1 C2 B3 B7 138.0(3) . . . . ? C1 C2 B3 B4 35.7(2) . . . . ? C1 C2 B3 B8 97.9(3) . . . . ? C1 B6 B5 B10 -133.6(3) . . . . ? C1 B6 B5 B9 -96.5(3) . . . . ? C1 B6 B5 B4 -32.7(3) . . . . ? C1 B6 B10 B11 -97.9(3) . . . . ? C1 B6 B10 B12 -60.3(3) . . . . ? C1 B6 B10 B5 39.6(2) . . . . ? C1 B6 B10 B9 3.0(3) . . . . ? C1 B5 B10 B11 -2.1(4) . . . . ? C1 B5 B10 B6 -40.1(2) . . . . ? C1 B5 B10 B12 61.1(3) . . . . ? C1 B5 B10 B9 98.8(3) . . . . ? C1 B5 B9 B12 -61.2(4) . . . . ? C1 B5 B9 B10 -99.1(3) . . . . ? C1 B5 B9 B4 39.5(3) . . . . ? C1 B5 B9 B8 1.5(4) . . . . ? C1 B5 B4 B3 -33.0(3) . . . . ? C1 B5 B4 B9 -134.1(3) . . . . ? C1 B5 B4 B8 -95.9(3) . . . . ? C1 B3 B4 B5 32.7(3) . . . . ? C1 B3 B4 B9 96.1(3) . . . . ? C1 B3 B4 B8 133.1(3) . . . . ? C1 B3 B8 B12 60.5(3) . . . . ? C1 B3 B8 B7 97.7(3) . . . . ? C1 B3 B8 B9 -3.1(4) . . . . ? C1 B3 B8 B4 -39.9(3) . . . . ? C1 B4 B8 B12 -61.6(4) . . . . ? C1 B4 B8 B7 1.8(4) . . . . ? C1 B4 B8 B3 40.2(3) . . . . ? C1 B4 B8 B9 -98.7(3) . . . . ? C9 C4 C5 C6 2.1(5) . . . . ? B11 C2 C1 B6 -39.8(2) . . . . ? B11 C2 C1 B5 -0.7(4) . . . . ? B11 C2 C1 B3 107.1(3) . . . . ? B11 C2 C1 B4 67.5(3) . . . . ? B11 C2 B6 C1 137.9(3) . . . . ? B11 C2 B6 B5 102.2(3) . . . . ? B11 C2 B6 B10 39.8(3) . . . . ? B11 C2 B7 B12 -40.4(2) . . . . ? B11 C2 B7 B3 -142.9(3) . . . . ? B11 C2 B7 B8 -102.6(3) . . . . ? B11 C2 B3 C1 -101.9(3) . . . . ? B11 C2 B3 B7 36.1(3) . . . . ? B11 C2 B3 B4 -66.1(3) . . . . ? B11 C2 B3 B8 -4.0(4) . . . . ? B11 B6 B5 C1 95.7(3) . . . . ? B11 B6 B5 B10 -37.9(3) . . . . ? B11 B6 B5 B9 -0.8(4) . . . . ? B11 B6 B5 B4 63.0(3) . . . . ? B11 B6 B10 B12 37.6(3) . . . . ? B11 B6 B10 B5 137.4(3) . . . . ? B11 B6 B10 B9 100.9(3) . . . . ? B11 B12 B7 C2 39.5(2) . . . . ? B11 B12 B7 B3 101.6(3) . . . . ? B11 B12 B7 B8 138.4(3) . . . . ? B11 B12 B10 B6 -37.8(3) . . . . ? B11 B12 B10 B5 -100.7(3) . . . . ? B11 B12 B10 B9 -138.4(3) . . . . ? B11 B12 B9 B5 -0.6(4) . . . . ? B11 B12 B9 B10 37.2(3) . . . . ? B11 B12 B9 B4 -64.0(4) . . . . ? B11 B12 B9 B8 -101.0(3) . . . . ? B11 B12 B8 B7 -37.3(2) . . . . ? B11 B12 B8 B3 0.2(4) . . . . ? B11 B12 B8 B9 101.1(3) . . . . ? B11 B12 B8 B4 64.1(3) . . . . ? B11 B7 B3 C2 -32.9(2) . . . . ? B11 B7 B3 C1 2.1(3) . . . . ? B11 B7 B3 B4 62.8(3) . . . . ? B11 B7 B3 B8 100.7(3) . . . . ? B11 B7 B8 B12 37.3(2) . . . . ? B11 B7 B8 B3 -101.3(3) . . . . ? B11 B7 B8 B9 0.1(4) . . . . ? B11 B7 B8 B4 -63.2(4) . . . . ? B11 B10 B9 B12 -37.2(2) . . . . ? B11 B10 B9 B5 100.3(3) . . . . ? B11 B10 B9 B4 63.1(3) . . . . ? B11 B10 B9 B8 -0.1(4) . . . . ? B6 C2 C1 B5 39.1(3) . . . . ? B6 C2 C1 B3 146.9(3) . . . . ? B6 C2 C1 B4 107.3(3) . . . . ? B6 C2 B11 B12 -102.3(3) . . . . ? B6 C2 B11 B7 -142.4(3) . . . . ? B6 C2 B11 B10 -39.9(2) . . . . ? B6 C2 B7 B11 36.7(3) . . . . ? B6 C2 B7 B12 -3.7(4) . . . . ? B6 C2 B7 B3 -106.2(3) . . . . ? B6 C2 B7 B8 -65.9(3) . . . . ? B6 C2 B3 C1 -31.9(2) . . . . ? B6 C2 B3 B7 106.1(3) . . . . ? B6 C2 B3 B4 3.9(4) . . . . ? B6 C2 B3 B8 66.0(3) . . . . ? B6 C1 B5 B10 40.6(3) . . . . ? B6 C1 B5 B9 103.3(3) . . . . ? B6 C1 B5 B4 143.3(3) . . . . ? B6 C1 B3 C2 32.2(2) . . . . ? B6 C1 B3 B7 -3.6(4) . . . . ? B6 C1 B3 B4 -106.1(3) . . . . ? B6 C1 B3 B8 -65.4(3) . . . . ? B6 C1 B4 B5 -35.7(3) . . . . ? B6 C1 B4 B3 107.2(3) . . . . ? B6 C1 B4 B9 4.2(4) . . . . ? B6 C1 B4 B8 66.7(4) . . . . ? B6 B11 B12 B7 -101.2(3) . . . . ? B6 B11 B12 B10 37.5(3) . . . . ? B6 B11 B12 B9 0.1(4) . . . . ? B6 B11 B12 B8 -63.9(3) . . . . ? B6 B11 B7 C2 -33.4(2) . . . . ? B6 B11 B7 B12 100.4(3) . . . . ? B6 B11 B7 B3 -0.1(3) . . . . ? B6 B11 B7 B8 63.1(3) . . . . ? B6 B11 B10 B12 -137.9(3) . . . . ? B6 B11 B10 B5 -37.8(3) . . . . ? B6 B11 B10 B9 -100.8(3) . . . . ? B6 B5 B10 B11 38.1(3) . . . . ? B6 B5 B10 B12 101.2(3) . . . . ? B6 B5 B10 B9 139.0(3) . . . . ? B6 B5 B9 B12 0.9(4) . . . . ? B6 B5 B9 B10 -37.0(3) . . . . ? B6 B5 B9 B4 101.6(3) . . . . ? B6 B5 B9 B8 63.6(4) . . . . ? B6 B5 B4 C1 32.9(2) . . . . ? B6 B5 B4 B3 0.0(4) . . . . ? B6 B5 B4 B9 -101.2(3) . . . . ? B6 B5 B4 B8 -63.0(4) . . . . ? B6 B10 B9 B12 -100.9(3) . . . . ? B6 B10 B9 B5 36.6(3) . . . . ? B6 B10 B9 B4 -0.6(4) . . . . ? B6 B10 B9 B8 -63.9(3) . . . . ? B12 B11 B6 C2 96.5(3) . . . . ? B12 B11 B6 C1 61.2(3) . . . . ? B12 B11 B6 B5 0.4(3) . . . . ? B12 B11 B6 B10 -37.6(3) . . . . ? B12 B11 B7 C2 -133.7(3) . . . . ? B12 B11 B7 B3 -100.5(3) . . . . ? B12 B11 B7 B8 -37.3(3) . . . . ? B12 B11 B10 B6 137.9(3) . . . . ? B12 B11 B10 B5 100.2(3) . . . . ? B12 B11 B10 B9 37.1(3) . . . . ? B12 B7 B3 C2 -96.6(3) . . . . ? B12 B7 B3 C1 -61.6(3) . . . . ? B12 B7 B3 B4 -0.9(4) . . . . ? B12 B7 B3 B8 37.0(3) . . . . ? B12 B7 B8 B3 -138.7(3) . . . . ? B12 B7 B8 B9 -37.2(3) . . . . ? B12 B7 B8 B4 -100.5(3) . . . . ? B12 B10 B9 B5 137.5(3) . . . . ? B12 B10 B9 B4 100.3(3) . . . . ? B12 B10 B9 B8 37.0(3) . . . . ? B12 B9 B4 C1 61.4(3) . . . . ? B12 B9 B4 B5 100.5(3) . . . . ? B12 B9 B4 B3 -0.2(4) . . . . ? B12 B9 B4 B8 -36.9(3) . . . . ? B12 B9 B8 B7 37.3(2) . . . . ? B12 B9 B8 B3 101.4(3) . . . . ? B12 B9 B8 B4 138.5(3) . . . . ? B7 C2 C1 B6 -107.5(3) . . . . ? B7 C2 C1 B5 -68.4(3) . . . . ? B7 C2 C1 B3 39.4(3) . . . . ? B7 C2 C1 B4 -0.2(4) . . . . ? B7 C2 B11 B6 142.4(3) . . . . ? B7 C2 B11 B12 40.1(2) . . . . ? B7 C2 B11 B10 102.5(3) . . . . ? B7 C2 B6 C1 101.3(3) . . . . ? B7 C2 B6 B11 -36.6(3) . . . . ? B7 C2 B6 B5 65.6(3) . . . . ? B7 C2 B6 B10 3.3(4) . . . . ? B7 C2 B3 C1 -138.0(3) . . . . ? B7 C2 B3 B4 -102.2(3) . . . . ? B7 C2 B3 B8 -40.1(3) . . . . ? B7 B11 B6 C2 33.4(2) . . . . ? B7 B11 B6 C1 -2.0(3) . . . . ? B7 B11 B6 B5 -62.8(3) . . . . ? B7 B11 B6 B10 -100.8(3) . . . . ? B7 B11 B12 B10 138.6(3) . . . . ? B7 B11 B12 B9 101.3(3) . . . . ? B7 B11 B12 B8 37.2(3) . . . . ? B7 B11 B10 B6 101.0(3) . . . . ? B7 B11 B10 B12 -36.9(3) . . . . ? B7 B11 B10 B5 63.2(3) . . . . ? B7 B11 B10 B9 0.2(3) . . . . ? B7 B12 B10 B11 37.1(3) . . . . ? B7 B12 B10 B6 -0.7(4) . . . . ? B7 B12 B10 B5 -63.6(3) . . . . ? B7 B12 B10 B9 -101.3(3) . . . . ? B7 B12 B9 B5 63.0(4) . . . . ? B7 B12 B9 B10 100.9(3) . . . . ? B7 B12 B9 B4 -0.4(4) . . . . ? B7 B12 B9 B8 -37.4(3) . . . . ? B7 B12 B8 B3 37.4(3) . . . . ? B7 B12 B8 B9 138.3(3) . . . . ? B7 B12 B8 B4 101.3(3) . . . . ? B7 B3 B4 C1 -95.4(3) . . . . ? B7 B3 B4 B5 -62.7(4) . . . . ? B7 B3 B4 B9 0.7(4) . . . . ? B7 B3 B4 B8 37.7(3) . . . . ? B7 B3 B8 B12 -37.1(3) . . . . ? B7 B3 B8 B9 -100.8(3) . . . . ? B7 B3 B8 B4 -137.5(3) . . . . ? B5 C1 B6 C2 -138.4(3) . . . . ? B5 C1 B6 B11 -102.4(3) . . . . ? B5 C1 B6 B10 -40.5(2) . . . . ? B5 C1 B3 C2 101.9(3) . . . . ? B5 C1 B3 B7 66.1(3) . . . . ? B5 C1 B3 B4 -36.3(3) . . . . ? B5 C1 B3 B8 4.4(4) . . . . ? B5 C1 B4 B3 142.9(3) . . . . ? B5 C1 B4 B9 39.9(3) . . . . ? B5 C1 B4 B8 102.4(3) . . . . ? B5 B6 B10 B11 -137.4(3) . . . . ? B5 B6 B10 B12 -99.8(3) . . . . ? B5 B6 B10 B9 -36.6(3) . . . . ? B5 B10 B9 B12 -137.5(3) . . . . ? B5 B10 B9 B4 -37.2(3) . . . . ? B5 B10 B9 B8 -100.5(3) . . . . ? B5 B9 B4 C1 -39.1(3) . . . . ? B5 B9 B4 B3 -100.7(3) . . . . ? B5 B9 B4 B8 -137.3(3) . . . . ? B5 B9 B8 B12 -100.4(3) . . . . ? B5 B9 B8 B7 -63.2(4) . . . . ? B5 B9 B8 B3 1.0(4) . . . . ? B5 B9 B8 B4 38.0(3) . . . . ? B5 B4 B8 B12 -0.9(4) . . . . ? B5 B4 B8 B7 62.6(4) . . . . ? B5 B4 B8 B3 100.9(3) . . . . ? B5 B4 B8 B9 -38.0(3) . . . . ? B10 B11 B6 C2 134.2(3) . . . . ? B10 B11 B6 C1 98.8(3) . . . . ? B10 B11 B6 B5 38.0(3) . . . . ? B10 B11 B12 B7 -138.6(3) . . . . ? B10 B11 B12 B9 -37.3(3) . . . . ? B10 B11 B12 B8 -101.4(3) . . . . ? B10 B11 B7 C2 -96.6(3) . . . . ? B10 B11 B7 B12 37.1(2) . . . . ? B10 B11 B7 B3 -63.4(3) . . . . ? B10 B11 B7 B8 -0.2(3) . . . . ? B10 B6 B5 C1 133.6(3) . . . . ? B10 B6 B5 B9 37.1(3) . . . . ? B10 B6 B5 B4 100.9(3) . . . . ? B10 B12 B7 C2 2.5(4) . . . . ? B10 B12 B7 B11 -37.0(3) . . . . ? B10 B12 B7 B3 64.6(3) . . . . ? B10 B12 B7 B8 101.4(3) . . . . ? B10 B12 B9 B5 -37.8(3) . . . . ? B10 B12 B9 B4 -101.2(3) . . . . ? B10 B12 B9 B8 -138.2(3) . . . . ? B10 B12 B8 B7 -100.8(3) . . . . ? B10 B12 B8 B3 -63.3(3) . . . . ? B10 B12 B8 B9 37.6(3) . . . . ? B10 B12 B8 B4 0.6(4) . . . . ? B10 B5 B9 B12 37.8(3) . . . . ? B10 B5 B9 B4 138.5(3) . . . . ? B10 B5 B9 B8 100.6(3) . . . . ? B10 B5 B4 C1 96.8(3) . . . . ? B10 B5 B4 B3 63.8(4) . . . . ? B10 B5 B4 B9 -37.4(3) . . . . ? B10 B5 B4 B8 0.9(4) . . . . ? B10 B9 B4 C1 -2.0(4) . . . . ? B10 B9 B4 B5 37.1(3) . . . . ? B10 B9 B4 B3 -63.6(4) . . . . ? B10 B9 B4 B8 -100.2(3) . . . . ? B10 B9 B8 B12 -37.2(3) . . . . ? B10 B9 B8 B7 0.0(4) . . . . ? B10 B9 B8 B3 64.2(4) . . . . ? B10 B9 B8 B4 101.2(3) . . . . ? B3 C2 C1 B6 -146.9(3) . . . . ? B3 C2 C1 B5 -107.8(3) . . . . ? B3 C2 C1 B4 -39.6(3) . . . . ? B3 C2 B11 B6 106.4(3) . . . . ? B3 C2 B11 B12 4.1(3) . . . . ? B3 C2 B11 B7 -36.0(3) . . . . ? B3 C2 B11 B10 66.5(3) . . . . ? B3 C2 B6 C1 31.8(3) . . . . ? B3 C2 B6 B11 -106.1(3) . . . . ? B3 C2 B6 B5 -3.9(3) . . . . ? B3 C2 B6 B10 -66.3(3) . . . . ? B3 C2 B7 B11 142.9(3) . . . . ? B3 C2 B7 B12 102.5(3) . . . . ? B3 C2 B7 B8 40.2(3) . . . . ? B3 C1 B6 C2 -32.4(3) . . . . ? B3 C1 B6 B11 3.6(3) . . . . ? B3 C1 B6 B5 106.0(3) . . . . ? B3 C1 B6 B10 65.5(3) . . . . ? B3 C1 B5 B6 -107.1(3) . . . . ? B3 C1 B5 B10 -66.5(4) . . . . ? B3 C1 B5 B9 -3.8(4) . . . . ? B3 C1 B5 B4 36.2(3) . . . . ? B3 C1 B4 B5 -142.9(3) . . . . ? B3 C1 B4 B9 -103.0(3) . . . . ? B3 C1 B4 B8 -40.5(3) . . . . ? B3 B7 B8 B12 138.7(3) . . . . ? B3 B7 B8 B9 101.4(3) . . . . ? B3 B7 B8 B4 38.2(3) . . . . ? B3 B4 B8 B12 -101.8(3) . . . . ? B3 B4 B8 B7 -38.3(3) . . . . ? B3 B4 B8 B9 -138.9(3) . . . . ? B9 B12 B7 C2 -61.3(3) . . . . ? B9 B12 B7 B11 -100.8(3) . . . . ? B9 B12 B7 B3 0.8(4) . . . . ? B9 B12 B7 B8 37.6(3) . . . . ? B9 B12 B10 B11 138.4(3) . . . . ? B9 B12 B10 B6 100.6(3) . . . . ? B9 B12 B10 B5 37.7(3) . . . . ? B9 B12 B8 B7 -138.3(3) . . . . ? B9 B12 B8 B3 -100.9(3) . . . . ? B9 B12 B8 B4 -37.0(3) . . . . ? B9 B5 B10 B11 -100.9(3) . . . . ? B9 B5 B10 B6 -139.0(3) . . . . ? B9 B5 B10 B12 -37.7(3) . . . . ? B9 B5 B4 C1 134.1(3) . . . . ? B9 B5 B4 B3 101.2(3) . . . . ? B9 B5 B4 B8 38.2(3) . . . . ? B9 B4 B8 B12 37.1(3) . . . . ? B9 B4 B8 B7 100.6(3) . . . . ? B9 B4 B8 B3 138.9(3) . . . . ? B4 C1 B6 C2 -102.5(3) . . . . ? B4 C1 B6 B11 -66.5(3) . . . . ? B4 C1 B6 B5 35.9(3) . . . . ? B4 C1 B6 B10 -4.6(4) . . . . ? B4 C1 B5 B6 -143.3(3) . . . . ? B4 C1 B5 B10 -102.7(3) . . . . ? B4 C1 B5 B9 -40.0(3) . . . . ? B4 C1 B3 C2 138.3(3) . . . . ? B4 C1 B3 B7 102.5(3) . . . . ? B4 C1 B3 B8 40.7(3) . . . . ? B4 B5 B10 B11 -63.7(3) . . . . ? B4 B5 B10 B6 -101.8(3) . . . . ? B4 B5 B10 B12 -0.5(4) . . . . ? B4 B5 B10 B9 37.2(3) . . . . ? B4 B5 B9 B12 -100.7(3) . . . . ? B4 B5 B9 B10 -138.5(3) . . . . ? B4 B5 B9 B8 -37.9(3) . . . . ? B4 B3 B8 B12 100.4(3) . . . . ? B4 B3 B8 B7 137.5(3) . . . . ? B4 B3 B8 B9 36.8(3) . . . . ? B4 B9 B8 B12 -138.5(3) . . . . ? B4 B9 B8 B7 -101.2(3) . . . . ? B4 B9 B8 B3 -37.0(3) . . . . ? B8 B12 B7 C2 -98.9(3) . . . . ? B8 B12 B7 B11 -138.4(3) . . . . ? B8 B12 B7 B3 -36.8(3) . . . . ? B8 B12 B10 B11 100.7(3) . . . . ? B8 B12 B10 B6 62.9(4) . . . . ? B8 B12 B10 B5 0.0(3) . . . . ? B8 B12 B10 B9 -37.7(3) . . . . ? B8 B12 B9 B5 100.4(3) . . . . ? B8 B12 B9 B10 138.2(3) . . . . ? B8 B12 B9 B4 37.0(3) . . . . ? B8 B7 B3 C2 -133.6(3) . . . . ? B8 B7 B3 C1 -98.6(3) . . . . ? B8 B7 B3 B4 -37.9(3) . . . . ? B8 B3 B4 C1 -133.1(3) . . . . ? B8 B3 B4 B5 -100.4(3) . . . . ? B8 B3 B4 B9 -37.0(3) . . . . ? B8 B9 B4 C1 98.2(3) . . . . ? B8 B9 B4 B5 137.3(3) . . . . ? B8 B9 B4 B3 36.7(3) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 958414' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_130830_ny_wyf_67b _audit_creation_date 2013-08-31 _audit_creation_method ; Olex2 1.2 (compiled Apr 23 2013 17:54:37, GUI svn.r4466) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C10 H16 B10 N2 O' _chemical_formula_sum 'C10 H16 B10 N2 O' _chemical_formula_weight 288.35 _chemical_absolute_configuration unk _chemical_melting_point ? _chemical_oxdiff_formula 'C H N O B' 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_H-M_alt 'P 21 21 21' _space_group_name_Hall 'P 2ac 2ab' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, -y, z+1/2' 3 'x+1/2, -y+1/2, -z' 4 '-x, y+1/2, -z+1/2' _cell_length_a 7.1169(6) _cell_length_b 8.6634(5) _cell_length_c 25.2552(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1557.14(19) _cell_formula_units_Z 4 _cell_measurement_reflns_used 1054 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 24.9000 _cell_measurement_theta_min 3.7110 _exptl_absorpt_coefficient_mu 0.068 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.83226 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.230 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.12 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0429 _diffrn_reflns_av_unetI/netI 0.0792 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_number 5365 _diffrn_reflns_theta_full 26.37 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_min 2.97 _diffrn_ambient_temperature 293.15 _diffrn_detector_area_resol_mean 16.0355 _diffrn_measured_fraction_theta_full 0.9957 _diffrn_measured_fraction_theta_max 0.8358 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -42.00 -8.00 1.0000 150.0000 omega____ theta____ kappa____ phi______ frames - 17.5863 -57.0000 120.0000 34 #__ type_ start__ end____ width___ exp.time_ 2 omega -36.00 84.00 1.0000 150.0000 omega____ theta____ kappa____ phi______ frames - 17.5863 0.0000 120.0000 120 #__ type_ start__ end____ width___ exp.time_ 3 omega -4.00 21.00 1.0000 150.0000 omega____ theta____ kappa____ phi______ frames - 17.5863 57.0000 -180.0000 25 ; _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0798736000 _diffrn_orient_matrix_UB_12 -0.0451580000 _diffrn_orient_matrix_UB_13 0.0064586000 _diffrn_orient_matrix_UB_21 -0.0196685000 _diffrn_orient_matrix_UB_22 -0.0496520000 _diffrn_orient_matrix_UB_23 -0.0216200000 _diffrn_orient_matrix_UB_31 0.0562997000 _diffrn_orient_matrix_UB_32 0.0468528000 _diffrn_orient_matrix_UB_33 -0.0167271000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2049 _reflns_number_total 3104 _reflns_odcompleteness_completeness 99.57 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.156 _refine_diff_density_min -0.175 _refine_diff_density_rms 0.036 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -6(2) _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 208 _refine_ls_number_reflns 3104 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1019 _refine_ls_R_factor_gt 0.0606 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0459P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1135 _refine_ls_wR_factor_ref 0.1320 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All B(H) groups, All C(H) groups, All N(H) groups 2.a Aromatic/amide H refined with riding coordinates: N1(H1), C9(H9), C7(H7), C5(H5), C6(H6) 2.b Boron cage BH refined with riding coordinates: C1(H1A), B4(H4), B12(H12), B10(H10), B7(H7A), B9(H9A), B5(H5A), B3(H3), B8(H8), B11(H11), B6(H6A) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 C4 C 0.2793(4) 0.6066(3) 0.00843(9) 0.0356(6) Uani 1 1 d . . . N1 N 0.2779(3) 0.4955(2) 0.04993(8) 0.0426(6) Uani 1 1 d . . . H1 H 0.2607 0.4010 0.0407 0.051 Uiso 1 1 calc R . . C9 C 0.2712(4) 0.7647(3) 0.01714(10) 0.0382(7) Uani 1 1 d . . . H9 H 0.2659 0.8041 0.0514 0.046 Uiso 1 1 calc R . . C8 C 0.2713(4) 0.8625(3) -0.02628(10) 0.0391(7) Uani 1 1 d . . . C3 C 0.3003(5) 0.5220(3) 0.10212(11) 0.0430(7) Uani 1 1 d . . . O1 O 0.3294(4) 0.6444(2) 0.12192(8) 0.0743(8) Uani 1 1 d . . . C10 C 0.2572(5) 1.0278(3) -0.01776(10) 0.0462(8) Uani 1 1 d . . . C7 C 0.2812(5) 0.8077(3) -0.07741(11) 0.0497(8) Uani 1 1 d . . . H7 H 0.2833 0.8754 -0.1060 0.060 Uiso 1 1 calc R . . N2 N 0.2450(5) 1.1575(3) -0.01189(10) 0.0709(9) Uani 1 1 d . . . C1 C 0.3186(5) 0.4099(3) 0.19964(10) 0.0490(8) Uani 1 1 d . . . H1A H 0.3520 0.5266 0.2140 0.059 Uiso 1 1 calc R . . C5 C 0.2876(5) 0.5509(3) -0.04304(10) 0.0490(8) Uani 1 1 d . . . H5 H 0.2929 0.4451 -0.0489 0.059 Uiso 1 1 calc R . . C2 C 0.2857(4) 0.3775(3) 0.13636(9) 0.0378(7) Uani 1 1 d . . . C6 C 0.2879(5) 0.6497(3) -0.08521(11) 0.0577(9) Uani 1 1 d . . . H6 H 0.2927 0.6104 -0.1195 0.069 Uiso 1 1 calc R . . B4 B 0.4207(6) 0.2586(4) 0.23060(15) 0.0514(10) Uani 1 1 d . . . H4 H 0.5171 0.2671 0.2645 0.062 Uiso 1 1 calc R . . B12 B 0.2229(6) 0.0701(4) 0.15621(13) 0.0504(9) Uani 1 1 d . . . H12 H 0.1903 -0.0463 0.1415 0.060 Uiso 1 1 calc R . . B10 B 0.0556(6) 0.1811(5) 0.19221(15) 0.0574(11) Uani 1 1 d . . . H10 H -0.0861 0.1373 0.2010 0.069 Uiso 1 1 calc R . . B7 B 0.3676(5) 0.1996(4) 0.12039(15) 0.0466(10) Uani 1 1 d . . . H7A H 0.4301 0.1693 0.0819 0.056 Uiso 1 1 calc R . . B9 B 0.2563(5) 0.1090(4) 0.22426(12) 0.0465(9) Uani 1 1 d . . . H9A H 0.2458 0.0168 0.2541 0.056 Uiso 1 1 calc R . . B5 B 0.1780(6) 0.2963(4) 0.23756(15) 0.0575(11) Uani 1 1 d . . . H5A H 0.1173 0.3298 0.2759 0.069 Uiso 1 1 calc R . . B3 B 0.4907(5) 0.3158(4) 0.16598(14) 0.0501(10) Uani 1 1 d . . . H3 H 0.6311 0.3630 0.1575 0.060 Uiso 1 1 calc R . . B8 B 0.4495(5) 0.1202(4) 0.18010(13) 0.0459(9) Uani 1 1 d . . . H8 H 0.5653 0.0361 0.1809 0.055 Uiso 1 1 calc R . . B11 B 0.1241(6) 0.2364(4) 0.12682(16) 0.0499(10) Uani 1 1 d . . . H11 H 0.0285 0.2296 0.0927 0.060 Uiso 1 1 calc R . . B6 B 0.0943(6) 0.3774(5) 0.17734(15) 0.0535(11) Uani 1 1 d . . . H6A H -0.0188 0.4638 0.1762 0.064 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 C4 0.0368(16) 0.0315(14) 0.0385(14) 0.0048(12) 0.0034(14) 0.0035(15) N1 0.0585(17) 0.0283(11) 0.0411(12) 0.0033(10) 0.0009(13) -0.0021(13) C9 0.0467(19) 0.0329(14) 0.0351(14) 0.0016(12) 0.0019(14) -0.0001(15) C8 0.0403(17) 0.0330(14) 0.0440(15) 0.0036(13) 0.0006(15) -0.0011(15) C3 0.055(2) 0.0321(15) 0.0419(16) 0.0036(13) 0.0011(16) 0.0015(17) O1 0.137(2) 0.0351(12) 0.0514(13) 0.0004(11) -0.0127(13) -0.0137(15) C10 0.055(2) 0.0398(17) 0.0438(16) 0.0104(14) -0.0026(16) -0.0044(17) C7 0.062(2) 0.0453(16) 0.0413(16) 0.0126(14) 0.0010(17) -0.0004(18) N2 0.108(3) 0.0361(14) 0.0689(18) 0.0097(13) -0.002(2) -0.0001(18) C1 0.071(2) 0.0369(16) 0.0387(15) -0.0006(14) -0.0068(16) 0.0003(18) C5 0.068(2) 0.0363(15) 0.0426(16) -0.0018(13) 0.0004(17) 0.0047(16) C2 0.0447(17) 0.0324(14) 0.0364(14) 0.0016(13) -0.0010(14) -0.0028(16) C6 0.086(3) 0.0523(19) 0.0352(15) -0.0029(14) -0.0025(17) 0.004(2) B4 0.066(3) 0.043(2) 0.045(2) 0.0133(17) -0.0093(19) -0.004(2) B12 0.064(3) 0.0313(16) 0.056(2) 0.0024(15) -0.001(2) -0.004(2) B10 0.042(2) 0.054(2) 0.076(3) 0.019(2) 0.009(2) 0.000(2) B7 0.060(3) 0.0360(19) 0.044(2) -0.0007(17) 0.0063(18) 0.0067(19) B9 0.050(2) 0.0396(18) 0.0499(18) 0.0098(16) 0.0058(19) 0.004(2) B5 0.074(3) 0.053(2) 0.045(2) 0.0089(18) 0.017(2) 0.013(2) B3 0.041(2) 0.054(2) 0.055(2) 0.012(2) -0.0060(18) -0.0019(19) B8 0.047(2) 0.041(2) 0.049(2) 0.0078(18) 0.0034(17) 0.008(2) B11 0.051(2) 0.042(2) 0.057(2) 0.0070(19) -0.0095(19) -0.0071(19) B6 0.050(2) 0.054(2) 0.057(2) 0.009(2) 0.0135(19) 0.016(2) _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 C4 N1 1.423(3) . ? C4 C9 1.388(3) . ? C4 C5 1.388(3) . ? N1 H1 0.8600 . ? N1 C3 1.347(3) . ? C9 H9 0.9300 . ? C9 C8 1.386(3) . ? C8 C10 1.452(4) . ? C8 C7 1.377(4) . ? C3 O1 1.191(3) . ? C3 C2 1.525(3) . ? C10 N2 1.136(3) . ? C7 H7 0.9300 . ? C7 C6 1.384(4) . ? C1 H1A 1.1000 . ? C1 C2 1.639(3) . ? C1 B4 1.690(4) . ? C1 B5 1.699(5) . ? C1 B3 1.699(5) . ? C1 B6 1.716(5) . ? C5 H5 0.9300 . ? C5 C6 1.366(4) . ? C2 B7 1.696(4) . ? C2 B3 1.724(4) . ? C2 B11 1.696(4) . ? C2 B6 1.711(5) . ? C6 H6 0.9300 . ? B4 H4 1.1000 . ? B4 B9 1.753(5) . ? B4 B5 1.767(6) . ? B4 B3 1.777(5) . ? B4 B8 1.763(5) . ? B12 H12 1.1000 . ? B12 B10 1.780(5) . ? B12 B7 1.771(5) . ? B12 B9 1.767(5) . ? B12 B8 1.776(5) . ? B12 B11 1.767(5) . ? B10 H10 1.1000 . ? B10 B9 1.757(5) . ? B10 B5 1.751(6) . ? B10 B11 1.787(5) . ? B10 B6 1.763(6) . ? B7 H7A 1.1000 . ? B7 B3 1.763(5) . ? B7 B8 1.757(5) . ? B7 B11 1.770(5) . ? B9 H9A 1.1000 . ? B9 B5 1.748(5) . ? B9 B8 1.773(5) . ? B5 H5A 1.1000 . ? B5 B6 1.778(5) . ? B3 H3 1.1000 . ? B3 B8 1.757(5) . ? B8 H8 1.1000 . ? B11 H11 1.1000 . ? B11 B6 1.779(5) . ? B6 H6A 1.1000 . ? 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 C9 C4 N1 123.4(2) . . ? C5 C4 N1 117.0(2) . . ? C5 C4 C9 119.6(2) . . ? C4 N1 H1 116.4 . . ? C3 N1 C4 127.2(2) . . ? C3 N1 H1 116.4 . . ? C4 C9 H9 120.7 . . ? C8 C9 C4 118.5(2) . . ? C8 C9 H9 120.7 . . ? C9 C8 C10 119.1(2) . . ? C7 C8 C9 122.1(2) . . ? C7 C8 C10 118.8(2) . . ? N1 C3 C2 114.0(2) . . ? O1 C3 N1 125.7(3) . . ? O1 C3 C2 120.3(2) . . ? N2 C10 C8 178.9(3) . . ? C8 C7 H7 120.8 . . ? C8 C7 C6 118.4(2) . . ? C6 C7 H7 120.8 . . ? C2 C1 H1A 120.6 . . ? C2 C1 B4 112.3(2) . . ? C2 C1 B5 111.5(2) . . ? C2 C1 B3 62.15(18) . . ? C2 C1 B6 61.26(19) . . ? B4 C1 H1A 117.9 . . ? B4 C1 B5 62.8(2) . . ? B4 C1 B3 63.2(2) . . ? B4 C1 B6 115.1(3) . . ? B5 C1 H1A 118.3 . . ? B5 C1 B3 115.4(2) . . ? B5 C1 B6 62.8(2) . . ? B3 C1 H1A 116.7 . . ? B3 C1 B6 115.3(2) . . ? B6 C1 H1A 117.4 . . ? C4 C5 H5 119.6 . . ? C6 C5 C4 120.8(2) . . ? C6 C5 H5 119.6 . . ? C3 C2 C1 113.7(2) . . ? C3 C2 B7 126.0(2) . . ? C3 C2 B3 116.3(2) . . ? C3 C2 B11 123.9(2) . . ? C3 C2 B6 113.4(2) . . ? C1 C2 B7 109.8(2) . . ? C1 C2 B3 60.62(19) . . ? C1 C2 B11 111.0(2) . . ? C1 C2 B6 61.57(19) . . ? B7 C2 B3 62.0(2) . . ? B7 C2 B6 114.7(2) . . ? B11 C2 B7 62.9(2) . . ? B11 C2 B3 114.4(2) . . ? B11 C2 B6 63.0(2) . . ? B6 C2 B3 114.3(2) . . ? C7 C6 H6 119.7 . . ? C5 C6 C7 120.6(3) . . ? C5 C6 H6 119.7 . . ? C1 B4 H4 125.2 . . ? C1 B4 B9 104.1(3) . . ? C1 B4 B5 58.8(2) . . ? C1 B4 B3 58.62(19) . . ? C1 B4 B8 104.1(2) . . ? B9 B4 H4 122.5 . . ? B9 B4 B5 59.6(2) . . ? B9 B4 B3 108.0(3) . . ? B9 B4 B8 60.6(2) . . ? B5 B4 H4 121.3 . . ? B5 B4 B3 108.3(3) . . ? B3 B4 H4 121.5 . . ? B8 B4 H4 122.5 . . ? B8 B4 B5 108.2(3) . . ? B8 B4 B3 59.5(2) . . ? B10 B12 H12 121.8 . . ? B7 B12 H12 122.1 . . ? B7 B12 B10 107.9(2) . . ? B7 B12 B8 59.4(2) . . ? B9 B12 H12 122.1 . . ? B9 B12 B10 59.4(2) . . ? B9 B12 B7 107.3(3) . . ? B9 B12 B8 60.1(2) . . ? B8 B12 H12 122.0 . . ? B8 B12 B10 107.6(3) . . ? B11 B12 H12 121.5 . . ? B11 B12 B10 60.5(2) . . ? B11 B12 B7 60.0(2) . . ? B11 B12 B9 107.9(2) . . ? B11 B12 B8 107.8(2) . . ? B12 B10 H10 122.0 . . ? B12 B10 B11 59.4(2) . . ? B9 B10 B12 60.0(2) . . ? B9 B10 H10 122.0 . . ? B9 B10 B11 107.4(3) . . ? B9 B10 B6 108.3(3) . . ? B5 B10 B12 108.0(3) . . ? B5 B10 H10 121.3 . . ? B5 B10 B9 59.8(2) . . ? B5 B10 B11 108.4(3) . . ? B5 B10 B6 60.8(2) . . ? B11 B10 H10 122.0 . . ? B6 B10 B12 107.9(3) . . ? B6 B10 H10 121.3 . . ? B6 B10 B11 60.1(2) . . ? C2 B7 B12 104.7(2) . . ? C2 B7 H7A 124.4 . . ? C2 B7 B3 59.76(19) . . ? C2 B7 B8 105.4(2) . . ? C2 B7 B11 58.52(19) . . ? B12 B7 H7A 122.3 . . ? B3 B7 B12 108.5(3) . . ? B3 B7 H7A 120.8 . . ? B3 B7 B11 108.9(3) . . ? B8 B7 B12 60.4(2) . . ? B8 B7 H7A 122.0 . . ? B8 B7 B3 59.9(2) . . ? B8 B7 B11 108.5(3) . . ? B11 B7 B12 59.8(2) . . ? B11 B7 H7A 121.3 . . ? B4 B9 B12 108.6(2) . . ? B4 B9 B10 108.8(2) . . ? B4 B9 H9A 121.3 . . ? B4 B9 B8 60.0(2) . . ? B12 B9 H9A 121.2 . . ? B12 B9 B8 60.2(2) . . ? B10 B9 B12 60.7(2) . . ? B10 B9 H9A 121.2 . . ? B10 B9 B8 108.8(2) . . ? B5 B9 B4 60.6(2) . . ? B5 B9 B12 108.7(2) . . ? B5 B9 B10 60.0(2) . . ? B5 B9 H9A 121.4 . . ? B5 B9 B8 108.5(2) . . ? B8 B9 H9A 121.5 . . ? C1 B5 B4 58.3(2) . . ? C1 B5 B10 104.7(3) . . ? C1 B5 B9 104.0(3) . . ? C1 B5 H5A 125.1 . . ? C1 B5 B6 59.08(19) . . ? B4 B5 H5A 121.3 . . ? B4 B5 B6 108.4(3) . . ? B10 B5 B4 108.4(3) . . ? B10 B5 H5A 122.1 . . ? B10 B5 B6 60.0(2) . . ? B9 B5 B4 59.8(2) . . ? B9 B5 B10 60.3(2) . . ? B9 B5 H5A 122.7 . . ? B9 B5 B6 108.0(3) . . ? B6 B5 H5A 121.2 . . ? C1 B3 C2 57.22(17) . . ? C1 B3 B4 58.1(2) . . ? C1 B3 B7 104.0(3) . . ? C1 B3 H3 125.0 . . ? C1 B3 B8 103.9(3) . . ? C2 B3 B4 104.3(3) . . ? C2 B3 B7 58.21(19) . . ? C2 B3 H3 124.7 . . ? C2 B3 B8 104.2(3) . . ? B4 B3 H3 122.4 . . ? B7 B3 B4 107.5(3) . . ? B7 B3 H3 122.5 . . ? B8 B3 B4 59.84(19) . . ? B8 B3 B7 59.9(2) . . ? B8 B3 H3 123.3 . . ? B4 B8 B12 107.8(3) . . ? B4 B8 B9 59.5(2) . . ? B4 B8 H8 121.6 . . ? B12 B8 H8 121.7 . . ? B7 B8 B4 108.4(2) . . ? B7 B8 B12 60.2(2) . . ? B7 B8 B9 107.7(3) . . ? B7 B8 H8 121.6 . . ? B9 B8 B12 59.7(2) . . ? B9 B8 H8 122.2 . . ? B3 B8 B4 60.65(19) . . ? B3 B8 B12 108.5(3) . . ? B3 B8 B7 60.22(19) . . ? B3 B8 B9 108.0(2) . . ? B3 B8 H8 121.2 . . ? C2 B11 B12 104.9(3) . . ? C2 B11 B10 104.3(3) . . ? C2 B11 B7 58.56(19) . . ? C2 B11 H11 124.7 . . ? C2 B11 B6 58.9(2) . . ? B12 B11 B10 60.1(2) . . ? B12 B11 B7 60.1(2) . . ? B12 B11 H11 122.1 . . ? B12 B11 B6 107.8(3) . . ? B10 B11 H11 122.8 . . ? B7 B11 B10 107.7(3) . . ? B7 B11 H11 121.6 . . ? B7 B11 B6 107.8(3) . . ? B6 B11 B10 59.3(2) . . ? B6 B11 H11 121.7 . . ? C1 B6 B10 103.5(3) . . ? C1 B6 B5 58.2(2) . . ? C1 B6 B11 103.7(2) . . ? C1 B6 H6A 125.3 . . ? C2 B6 C1 57.17(17) . . ? C2 B6 B10 104.7(3) . . ? C2 B6 B5 104.5(2) . . ? C2 B6 B11 58.10(19) . . ? C2 B6 H6A 124.5 . . ? B10 B6 B5 59.3(2) . . ? B10 B6 B11 60.6(2) . . ? B10 B6 H6A 123.2 . . ? B5 B6 B11 107.6(3) . . ? B5 B6 H6A 122.5 . . ? B11 B6 H6A 122.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N1 C3 O1 -1.7(5) . . . . ? C4 N1 C3 C2 178.4(3) . . . . ? C4 C9 C8 C10 178.2(3) . . . . ? C4 C9 C8 C7 -0.7(4) . . . . ? C4 C5 C6 C7 0.4(5) . . . . ? N1 C4 C9 C8 -179.2(3) . . . . ? N1 C4 C5 C6 179.4(3) . . . . ? N1 C3 C2 C1 178.5(2) . . . . ? N1 C3 C2 B7 37.6(4) . . . . ? N1 C3 C2 B3 110.9(3) . . . . ? N1 C3 C2 B11 -41.4(4) . . . . ? N1 C3 C2 B6 -113.6(3) . . . . ? C9 C4 N1 C3 -12.0(5) . . . . ? C9 C4 C5 C6 0.0(5) . . . . ? C9 C8 C10 N2 -157(22) . . . . ? C9 C8 C7 C6 1.2(5) . . . . ? C8 C7 C6 C5 -1.0(5) . . . . ? C3 C2 B7 B12 -153.4(3) . . . . ? C3 C2 B7 B3 103.5(3) . . . . ? C3 C2 B7 B8 143.8(3) . . . . ? C3 C2 B7 B11 -113.7(3) . . . . ? C3 C2 B3 C1 103.7(3) . . . . ? C3 C2 B3 B4 139.4(2) . . . . ? C3 C2 B3 B7 -118.7(3) . . . . ? C3 C2 B3 B8 -158.7(2) . . . . ? C3 C2 B11 B12 156.7(2) . . . . ? C3 C2 B11 B10 -141.0(3) . . . . ? C3 C2 B11 B7 116.8(3) . . . . ? C3 C2 B11 B6 -101.2(3) . . . . ? C3 C2 B6 C1 -105.3(2) . . . . ? C3 C2 B6 B10 157.9(2) . . . . ? C3 C2 B6 B5 -140.6(3) . . . . ? C3 C2 B6 B11 117.4(3) . . . . ? O1 C3 C2 C1 -1.4(4) . . . . ? O1 C3 C2 B7 -142.3(3) . . . . ? O1 C3 C2 B3 -69.1(4) . . . . ? O1 C3 C2 B11 138.7(3) . . . . ? O1 C3 C2 B6 66.5(4) . . . . ? C10 C8 C7 C6 -177.8(3) . . . . ? C7 C8 C10 N2 22(23) . . . . ? C1 C2 B7 B12 64.5(3) . . . . ? C1 C2 B7 B3 -38.6(2) . . . . ? C1 C2 B7 B8 1.6(3) . . . . ? C1 C2 B7 B11 104.1(3) . . . . ? C1 C2 B3 B4 35.7(2) . . . . ? C1 C2 B3 B7 137.6(2) . . . . ? C1 C2 B3 B8 97.6(3) . . . . ? C1 C2 B11 B12 -62.3(3) . . . . ? C1 C2 B11 B10 0.0(3) . . . . ? C1 C2 B11 B7 -102.2(3) . . . . ? C1 C2 B11 B6 39.8(2) . . . . ? C1 C2 B6 B10 -96.8(3) . . . . ? C1 C2 B6 B5 -35.3(2) . . . . ? C1 C2 B6 B11 -137.3(3) . . . . ? C1 B4 B9 B12 61.5(3) . . . . ? C1 B4 B9 B10 -2.9(3) . . . . ? C1 B4 B9 B5 -39.9(2) . . . . ? C1 B4 B9 B8 98.4(3) . . . . ? C1 B4 B5 B10 96.3(3) . . . . ? C1 B4 B5 B9 133.3(2) . . . . ? C1 B4 B5 B6 32.8(2) . . . . ? C1 B4 B3 C2 -35.2(2) . . . . ? C1 B4 B3 B7 -95.9(3) . . . . ? C1 B4 B3 B8 -133.6(3) . . . . ? C1 B4 B8 B12 -62.1(3) . . . . ? C1 B4 B8 B7 1.6(3) . . . . ? C1 B4 B8 B9 -98.5(3) . . . . ? C1 B4 B8 B3 39.6(2) . . . . ? C1 B5 B6 C2 34.9(2) . . . . ? C1 B5 B6 B10 133.6(3) . . . . ? C1 B5 B6 B11 95.5(3) . . . . ? C1 B3 B8 B4 -39.3(2) . . . . ? C1 B3 B8 B12 61.1(3) . . . . ? C1 B3 B8 B7 98.3(3) . . . . ? C1 B3 B8 B9 -2.1(3) . . . . ? C5 C4 N1 C3 168.6(3) . . . . ? C5 C4 C9 C8 0.1(4) . . . . ? C2 C1 B4 B9 -63.3(3) . . . . ? C2 C1 B4 B5 -103.6(3) . . . . ? C2 C1 B4 B3 39.4(2) . . . . ? C2 C1 B4 B8 -0.6(3) . . . . ? C2 C1 B5 B4 104.8(3) . . . . ? C2 C1 B5 B10 2.0(3) . . . . ? C2 C1 B5 B9 64.5(3) . . . . ? C2 C1 B5 B6 -38.4(2) . . . . ? C2 C1 B3 B4 -138.3(3) . . . . ? C2 C1 B3 B7 -36.2(2) . . . . ? C2 C1 B3 B8 -98.1(2) . . . . ? C2 C1 B6 B10 98.9(3) . . . . ? C2 C1 B6 B5 138.8(2) . . . . ? C2 C1 B6 B11 36.4(2) . . . . ? C2 B7 B3 C1 35.7(2) . . . . ? C2 B7 B3 B4 96.3(3) . . . . ? C2 B7 B3 B8 133.9(2) . . . . ? C2 B7 B8 B4 -2.0(3) . . . . ? C2 B7 B8 B12 98.4(3) . . . . ? C2 B7 B8 B9 60.9(3) . . . . ? C2 B7 B8 B3 -40.2(2) . . . . ? C2 B7 B11 B12 -134.4(2) . . . . ? C2 B7 B11 B10 -96.3(3) . . . . ? C2 B7 B11 B6 -33.7(2) . . . . ? C2 B3 B8 B4 -98.5(3) . . . . ? C2 B3 B8 B12 2.0(3) . . . . ? C2 B3 B8 B7 39.2(2) . . . . ? C2 B3 B8 B9 -61.3(3) . . . . ? C2 B11 B6 C1 -36.0(2) . . . . ? C2 B11 B6 B10 -133.9(3) . . . . ? C2 B11 B6 B5 -96.5(3) . . . . ? B4 C1 C2 C3 -147.8(3) . . . . ? B4 C1 C2 B7 -0.7(3) . . . . ? B4 C1 C2 B3 -39.9(3) . . . . ? B4 C1 C2 B11 67.0(3) . . . . ? B4 C1 C2 B6 107.4(3) . . . . ? B4 C1 B5 B10 -102.8(3) . . . . ? B4 C1 B5 B9 -40.4(2) . . . . ? B4 C1 B5 B6 -143.2(3) . . . . ? B4 C1 B3 C2 138.3(3) . . . . ? B4 C1 B3 B7 102.1(3) . . . . ? B4 C1 B3 B8 40.2(2) . . . . ? B4 C1 B6 C2 -102.7(3) . . . . ? B4 C1 B6 B10 -3.8(3) . . . . ? B4 C1 B6 B5 36.0(3) . . . . ? B4 C1 B6 B11 -66.4(3) . . . . ? B4 B9 B5 C1 39.6(2) . . . . ? B4 B9 B5 B10 138.8(3) . . . . ? B4 B9 B5 B6 101.2(3) . . . . ? B4 B9 B8 B12 -139.1(2) . . . . ? B4 B9 B8 B7 -101.4(3) . . . . ? B4 B9 B8 B3 -37.8(2) . . . . ? B4 B5 B6 C1 -32.5(2) . . . . ? B4 B5 B6 C2 2.4(3) . . . . ? B4 B5 B6 B10 101.1(3) . . . . ? B4 B5 B6 B11 63.1(3) . . . . ? B4 B3 B8 B12 100.5(3) . . . . ? B4 B3 B8 B7 137.7(3) . . . . ? B4 B3 B8 B9 37.2(2) . . . . ? B12 B10 B9 B4 101.3(3) . . . . ? B12 B10 B9 B5 138.6(3) . . . . ? B12 B10 B9 B8 37.6(2) . . . . ? B12 B10 B5 C1 60.9(3) . . . . ? B12 B10 B5 B4 -0.2(3) . . . . ? B12 B10 B5 B9 -37.0(2) . . . . ? B12 B10 B5 B6 100.9(3) . . . . ? B12 B10 B11 C2 -99.2(3) . . . . ? B12 B10 B11 B7 -38.2(3) . . . . ? B12 B10 B11 B6 -138.8(3) . . . . ? B12 B10 B6 C1 -61.8(3) . . . . ? B12 B10 B6 C2 -2.6(3) . . . . ? B12 B10 B6 B5 -101.0(3) . . . . ? B12 B10 B6 B11 36.6(3) . . . . ? B12 B7 B3 C1 -60.9(3) . . . . ? B12 B7 B3 C2 -96.6(3) . . . . ? B12 B7 B3 B4 -0.3(3) . . . . ? B12 B7 B3 B8 37.3(2) . . . . ? B12 B7 B8 B4 -100.4(3) . . . . ? B12 B7 B8 B9 -37.6(2) . . . . ? B12 B7 B8 B3 -138.6(3) . . . . ? B12 B7 B11 C2 134.4(2) . . . . ? B12 B7 B11 B10 38.2(3) . . . . ? B12 B7 B11 B6 100.7(3) . . . . ? B12 B9 B5 C1 -61.7(3) . . . . ? B12 B9 B5 B4 -101.3(3) . . . . ? B12 B9 B5 B10 37.5(3) . . . . ? B12 B9 B5 B6 -0.1(4) . . . . ? B12 B9 B8 B4 139.1(2) . . . . ? B12 B9 B8 B7 37.8(2) . . . . ? B12 B9 B8 B3 101.4(3) . . . . ? B12 B11 B6 C1 61.1(3) . . . . ? B12 B11 B6 C2 97.0(3) . . . . ? B12 B11 B6 B10 -36.9(3) . . . . ? B12 B11 B6 B5 0.6(3) . . . . ? B10 B12 B7 C2 0.6(4) . . . . ? B10 B12 B7 B3 63.1(3) . . . . ? B10 B12 B7 B8 100.2(3) . . . . ? B10 B12 B7 B11 -38.4(3) . . . . ? B10 B12 B9 B4 -101.6(3) . . . . ? B10 B12 B9 B5 -37.2(3) . . . . ? B10 B12 B9 B8 -138.3(3) . . . . ? B10 B12 B8 B4 0.6(3) . . . . ? B10 B12 B8 B7 -100.8(3) . . . . ? B10 B12 B8 B9 36.9(2) . . . . ? B10 B12 B8 B3 -63.6(3) . . . . ? B10 B12 B11 C2 98.1(3) . . . . ? B10 B12 B11 B7 137.2(3) . . . . ? B10 B12 B11 B6 36.5(3) . . . . ? B10 B9 B5 C1 -99.2(3) . . . . ? B10 B9 B5 B4 -138.8(3) . . . . ? B10 B9 B5 B6 -37.6(2) . . . . ? B10 B9 B8 B4 101.3(3) . . . . ? B10 B9 B8 B12 -37.8(2) . . . . ? B10 B9 B8 B7 0.0(3) . . . . ? B10 B9 B8 B3 63.6(3) . . . . ? B10 B5 B6 C1 -133.6(3) . . . . ? B10 B5 B6 C2 -98.7(3) . . . . ? B10 B5 B6 B11 -38.0(3) . . . . ? B10 B11 B6 C1 98.0(3) . . . . ? B10 B11 B6 C2 133.9(3) . . . . ? B10 B11 B6 B5 37.4(3) . . . . ? B7 C2 B3 C1 -137.6(2) . . . . ? B7 C2 B3 B4 -102.0(3) . . . . ? B7 C2 B3 B8 -40.0(2) . . . . ? B7 C2 B11 B12 39.9(2) . . . . ? B7 C2 B11 B10 102.2(3) . . . . ? B7 C2 B11 B6 141.9(3) . . . . ? B7 C2 B6 C1 100.1(3) . . . . ? B7 C2 B6 B10 3.3(3) . . . . ? B7 C2 B6 B5 64.7(3) . . . . ? B7 C2 B6 B11 -37.2(3) . . . . ? B7 B12 B10 B9 -99.9(3) . . . . ? B7 B12 B10 B5 -63.0(3) . . . . ? B7 B12 B10 B11 38.2(3) . . . . ? B7 B12 B10 B6 1.3(4) . . . . ? B7 B12 B9 B4 -0.6(3) . . . . ? B7 B12 B9 B10 101.0(3) . . . . ? B7 B12 B9 B5 63.8(3) . . . . ? B7 B12 B9 B8 -37.3(2) . . . . ? B7 B12 B8 B4 101.4(3) . . . . ? B7 B12 B8 B9 137.7(2) . . . . ? B7 B12 B8 B3 37.2(2) . . . . ? B7 B12 B11 C2 -39.1(2) . . . . ? B7 B12 B11 B10 -137.2(3) . . . . ? B7 B12 B11 B6 -100.7(3) . . . . ? B7 B3 B8 B4 -137.7(3) . . . . ? B7 B3 B8 B12 -37.2(2) . . . . ? B7 B3 B8 B9 -100.5(3) . . . . ? B7 B11 B6 C1 -2.4(3) . . . . ? B7 B11 B6 C2 33.6(2) . . . . ? B7 B11 B6 B10 -100.4(3) . . . . ? B7 B11 B6 B5 -62.9(3) . . . . ? B9 B4 B5 C1 -133.3(2) . . . . ? B9 B4 B5 B10 -37.0(2) . . . . ? B9 B4 B5 B6 -100.6(3) . . . . ? B9 B4 B3 C1 95.9(3) . . . . ? B9 B4 B3 C2 60.6(3) . . . . ? B9 B4 B3 B7 -0.1(3) . . . . ? B9 B4 B3 B8 -37.7(3) . . . . ? B9 B4 B8 B12 36.4(2) . . . . ? B9 B4 B8 B7 100.1(3) . . . . ? B9 B4 B8 B3 138.1(3) . . . . ? B9 B12 B10 B5 36.9(2) . . . . ? B9 B12 B10 B11 138.1(3) . . . . ? B9 B12 B10 B6 101.2(3) . . . . ? B9 B12 B7 C2 -62.0(3) . . . . ? B9 B12 B7 B3 0.5(3) . . . . ? B9 B12 B7 B8 37.6(2) . . . . ? B9 B12 B7 B11 -101.0(3) . . . . ? B9 B12 B8 B4 -36.3(2) . . . . ? B9 B12 B8 B7 -137.7(2) . . . . ? B9 B12 B8 B3 -100.5(3) . . . . ? B9 B12 B11 C2 61.0(3) . . . . ? B9 B12 B11 B10 -37.1(3) . . . . ? B9 B12 B11 B7 100.1(3) . . . . ? B9 B12 B11 B6 -0.6(4) . . . . ? B9 B10 B5 C1 97.9(3) . . . . ? B9 B10 B5 B4 36.9(2) . . . . ? B9 B10 B5 B6 137.9(3) . . . . ? B9 B10 B11 C2 -61.9(3) . . . . ? B9 B10 B11 B12 37.3(2) . . . . ? B9 B10 B11 B7 -0.9(4) . . . . ? B9 B10 B11 B6 -101.5(3) . . . . ? B9 B10 B6 C1 1.7(3) . . . . ? B9 B10 B6 C2 60.8(3) . . . . ? B9 B10 B6 B5 -37.6(2) . . . . ? B9 B10 B6 B11 100.0(3) . . . . ? B9 B5 B6 C1 -95.8(3) . . . . ? B9 B5 B6 C2 -60.9(3) . . . . ? B9 B5 B6 B10 37.8(2) . . . . ? B9 B5 B6 B11 -0.3(4) . . . . ? B5 C1 C2 C3 143.9(3) . . . . ? B5 C1 C2 B7 -69.0(3) . . . . ? B5 C1 C2 B3 -108.3(3) . . . . ? B5 C1 C2 B11 -1.3(3) . . . . ? B5 C1 C2 B6 39.0(2) . . . . ? B5 C1 B4 B9 40.3(2) . . . . ? B5 C1 B4 B3 143.0(3) . . . . ? B5 C1 B4 B8 102.9(3) . . . . ? B5 C1 B3 C2 102.0(3) . . . . ? B5 C1 B3 B4 -36.3(3) . . . . ? B5 C1 B3 B7 65.8(3) . . . . ? B5 C1 B3 B8 3.9(3) . . . . ? B5 C1 B6 C2 -138.8(2) . . . . ? B5 C1 B6 B10 -39.8(2) . . . . ? B5 C1 B6 B11 -102.4(3) . . . . ? B5 B4 B9 B12 101.5(3) . . . . ? B5 B4 B9 B10 37.0(3) . . . . ? B5 B4 B9 B8 138.3(3) . . . . ? B5 B4 B3 C1 32.8(2) . . . . ? B5 B4 B3 C2 -2.4(3) . . . . ? B5 B4 B3 B7 -63.1(3) . . . . ? B5 B4 B3 B8 -100.7(3) . . . . ? B5 B4 B8 B12 -0.7(3) . . . . ? B5 B4 B8 B7 63.0(3) . . . . ? B5 B4 B8 B9 -37.1(2) . . . . ? B5 B4 B8 B3 101.0(3) . . . . ? B5 B10 B9 B4 -37.3(3) . . . . ? B5 B10 B9 B12 -138.6(3) . . . . ? B5 B10 B9 B8 -101.0(3) . . . . ? B5 B10 B11 C2 1.2(3) . . . . ? B5 B10 B11 B12 100.5(3) . . . . ? B5 B10 B11 B7 62.3(3) . . . . ? B5 B10 B11 B6 -38.3(3) . . . . ? B5 B10 B6 C1 39.3(2) . . . . ? B5 B10 B6 C2 98.4(3) . . . . ? B5 B10 B6 B11 137.6(3) . . . . ? B5 B9 B8 B4 37.7(3) . . . . ? B5 B9 B8 B12 -101.4(3) . . . . ? B5 B9 B8 B7 -63.7(3) . . . . ? B5 B9 B8 B3 -0.1(4) . . . . ? B3 C1 C2 C3 -107.9(3) . . . . ? B3 C1 C2 B7 39.2(2) . . . . ? B3 C1 C2 B11 106.9(3) . . . . ? B3 C1 C2 B6 147.3(3) . . . . ? B3 C1 B4 B9 -102.7(3) . . . . ? B3 C1 B4 B5 -143.0(3) . . . . ? B3 C1 B4 B8 -40.1(2) . . . . ? B3 C1 B5 B4 36.5(3) . . . . ? B3 C1 B5 B10 -66.3(3) . . . . ? B3 C1 B5 B9 -3.9(4) . . . . ? B3 C1 B5 B6 -106.7(3) . . . . ? B3 C1 B6 C2 -31.9(2) . . . . ? B3 C1 B6 B10 67.0(3) . . . . ? B3 C1 B6 B5 106.8(3) . . . . ? B3 C1 B6 B11 4.5(3) . . . . ? B3 C2 B7 B12 103.1(3) . . . . ? B3 C2 B7 B8 40.3(2) . . . . ? B3 C2 B7 B11 142.8(3) . . . . ? B3 C2 B11 B12 3.9(3) . . . . ? B3 C2 B11 B10 66.3(3) . . . . ? B3 C2 B11 B7 -35.9(3) . . . . ? B3 C2 B11 B6 106.0(2) . . . . ? B3 C2 B6 C1 31.1(2) . . . . ? B3 C2 B6 B10 -65.7(3) . . . . ? B3 C2 B6 B5 -4.2(3) . . . . ? B3 C2 B6 B11 -106.1(3) . . . . ? B3 B4 B9 B12 0.4(3) . . . . ? B3 B4 B9 B10 -64.1(3) . . . . ? B3 B4 B9 B5 -101.1(3) . . . . ? B3 B4 B9 B8 37.2(2) . . . . ? B3 B4 B5 C1 -32.8(2) . . . . ? B3 B4 B5 B10 63.5(3) . . . . ? B3 B4 B5 B9 100.6(3) . . . . ? B3 B4 B5 B6 0.0(4) . . . . ? B3 B4 B8 B12 -101.7(3) . . . . ? B3 B4 B8 B7 -38.0(3) . . . . ? B3 B4 B8 B9 -138.1(3) . . . . ? B3 B7 B8 B4 38.2(3) . . . . ? B3 B7 B8 B12 138.6(3) . . . . ? B3 B7 B8 B9 101.1(3) . . . . ? B3 B7 B11 C2 33.5(2) . . . . ? B3 B7 B11 B12 -100.9(3) . . . . ? B3 B7 B11 B10 -62.7(3) . . . . ? B3 B7 B11 B6 -0.2(4) . . . . ? B8 B4 B9 B12 -36.8(2) . . . . ? B8 B4 B9 B10 -101.3(3) . . . . ? B8 B4 B9 B5 -138.3(3) . . . . ? B8 B4 B5 C1 -95.8(3) . . . . ? B8 B4 B5 B10 0.5(3) . . . . ? B8 B4 B5 B9 37.6(2) . . . . ? B8 B4 B5 B6 -63.0(3) . . . . ? B8 B4 B3 C1 133.6(3) . . . . ? B8 B4 B3 C2 98.3(3) . . . . ? B8 B4 B3 B7 37.6(2) . . . . ? B8 B12 B10 B9 -37.2(2) . . . . ? B8 B12 B10 B5 -0.3(3) . . . . ? B8 B12 B10 B11 100.9(3) . . . . ? B8 B12 B10 B6 64.0(3) . . . . ? B8 B12 B7 C2 -99.6(3) . . . . ? B8 B12 B7 B3 -37.1(2) . . . . ? B8 B12 B7 B11 -138.6(3) . . . . ? B8 B12 B9 B4 36.7(2) . . . . ? B8 B12 B9 B10 138.3(3) . . . . ? B8 B12 B9 B5 101.1(3) . . . . ? B8 B12 B11 C2 -2.4(3) . . . . ? B8 B12 B11 B10 -100.6(3) . . . . ? B8 B12 B11 B7 36.7(2) . . . . ? B8 B12 B11 B6 -64.0(3) . . . . ? B8 B7 B3 C1 -98.2(3) . . . . ? B8 B7 B3 C2 -133.9(2) . . . . ? B8 B7 B3 B4 -37.6(2) . . . . ? B8 B7 B11 C2 97.1(2) . . . . ? B8 B7 B11 B12 -37.3(2) . . . . ? B8 B7 B11 B10 0.9(3) . . . . ? B8 B7 B11 B6 63.4(3) . . . . ? B8 B9 B5 C1 2.2(4) . . . . ? B8 B9 B5 B4 -37.4(3) . . . . ? B8 B9 B5 B10 101.4(3) . . . . ? B8 B9 B5 B6 63.8(3) . . . . ? B11 C2 B7 B12 -39.7(2) . . . . ? B11 C2 B7 B3 -142.8(3) . . . . ? B11 C2 B7 B8 -102.5(3) . . . . ? B11 C2 B3 C1 -101.4(2) . . . . ? B11 C2 B3 B4 -65.7(3) . . . . ? B11 C2 B3 B7 36.3(3) . . . . ? B11 C2 B3 B8 -3.8(3) . . . . ? B11 C2 B6 C1 137.3(3) . . . . ? B11 C2 B6 B10 40.4(2) . . . . ? B11 C2 B6 B5 101.9(3) . . . . ? B11 B12 B10 B9 -138.1(3) . . . . ? B11 B12 B10 B5 -101.2(3) . . . . ? B11 B12 B10 B6 -36.9(3) . . . . ? B11 B12 B7 C2 39.0(2) . . . . ? B11 B12 B7 B3 101.6(3) . . . . ? B11 B12 B7 B8 138.6(3) . . . . ? B11 B12 B9 B4 -63.9(3) . . . . ? B11 B12 B9 B10 37.7(3) . . . . ? B11 B12 B9 B5 0.5(4) . . . . ? B11 B12 B9 B8 -100.6(3) . . . . ? B11 B12 B8 B4 64.5(3) . . . . ? B11 B12 B8 B7 -37.0(2) . . . . ? B11 B12 B8 B9 100.8(3) . . . . ? B11 B12 B8 B3 0.3(3) . . . . ? B11 B10 B9 B4 64.3(3) . . . . ? B11 B10 B9 B12 -37.0(2) . . . . ? B11 B10 B9 B5 101.6(3) . . . . ? B11 B10 B9 B8 0.6(4) . . . . ? B11 B10 B5 C1 -2.0(3) . . . . ? B11 B10 B5 B4 -63.0(3) . . . . ? B11 B10 B5 B9 -99.9(3) . . . . ? B11 B10 B5 B6 38.0(2) . . . . ? B11 B10 B6 C1 -98.3(3) . . . . ? B11 B10 B6 C2 -39.2(2) . . . . ? B11 B10 B6 B5 -137.6(3) . . . . ? B11 B7 B3 C1 2.7(3) . . . . ? B11 B7 B3 C2 -33.0(2) . . . . ? B11 B7 B3 B4 63.3(3) . . . . ? B11 B7 B3 B8 100.9(3) . . . . ? B11 B7 B8 B4 -63.4(3) . . . . ? B11 B7 B8 B12 37.0(2) . . . . ? B11 B7 B8 B9 -0.5(3) . . . . ? B11 B7 B8 B3 -101.6(3) . . . . ? B6 C1 C2 C3 104.8(3) . . . . ? B6 C1 C2 B7 -108.0(3) . . . . ? B6 C1 C2 B3 -147.3(3) . . . . ? B6 C1 C2 B11 -40.4(3) . . . . ? B6 C1 B4 B9 4.3(3) . . . . ? B6 C1 B4 B5 -36.0(3) . . . . ? B6 C1 B4 B3 107.0(3) . . . . ? B6 C1 B4 B8 66.9(3) . . . . ? B6 C1 B5 B4 143.2(3) . . . . ? B6 C1 B5 B10 40.4(2) . . . . ? B6 C1 B5 B9 102.8(3) . . . . ? B6 C1 B3 C2 31.6(2) . . . . ? B6 C1 B3 B4 -106.7(3) . . . . ? B6 C1 B3 B7 -4.6(3) . . . . ? B6 C1 B3 B8 -66.5(3) . . . . ? B6 C2 B7 B12 -2.5(3) . . . . ? B6 C2 B7 B3 -105.6(3) . . . . ? B6 C2 B7 B8 -65.3(3) . . . . ? B6 C2 B7 B11 37.2(3) . . . . ? B6 C2 B3 C1 -31.4(3) . . . . ? B6 C2 B3 B4 4.2(3) . . . . ? B6 C2 B3 B7 106.2(3) . . . . ? B6 C2 B3 B8 66.2(3) . . . . ? B6 C2 B11 B12 -102.1(3) . . . . ? B6 C2 B11 B10 -39.7(2) . . . . ? B6 C2 B11 B7 -141.9(3) . . . . ? B6 B10 B9 B4 0.8(4) . . . . ? B6 B10 B9 B12 -100.5(3) . . . . ? B6 B10 B9 B5 38.1(2) . . . . ? B6 B10 B9 B8 -63.0(3) . . . . ? B6 B10 B5 C1 -40.0(2) . . . . ? B6 B10 B5 B4 -101.0(3) . . . . ? B6 B10 B5 B9 -137.9(3) . . . . ? B6 B10 B11 C2 39.5(2) . . . . ? B6 B10 B11 B12 138.8(3) . . . . ? B6 B10 B11 B7 100.6(3) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 958415' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_130130_ny_wyf_36c _audit_creation_date 2013-01-28 _audit_creation_method ; Olex2 1.2 (compiled Dec 5 2012 16:20:19, GUI svn.r4385) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C18 H26 B10 N2 O4' _chemical_formula_sum 'C18 H26 B10 N2 O4' _chemical_formula_weight 442.51 _chemical_melting_point ? _chemical_oxdiff_formula 'C H B N O' 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 10.9013(10) _cell_length_b 15.5194(10) _cell_length_c 14.2472(10) _cell_angle_alpha 90.00 _cell_angle_beta 98.225(7) _cell_angle_gamma 90.00 _cell_volume 2385.6(3) _cell_formula_units_Z 4 _cell_measurement_reflns_used 2257 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 28.9854 _cell_measurement_theta_min 2.5307 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.45335 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour ? _exptl_crystal_density_diffrn 1.232 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description ? _exptl_crystal_F_000 920 _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.43 _exptl_crystal_size_min 0.034 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0635 _diffrn_reflns_av_unetI/netI 0.0643 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 14790 _diffrn_reflns_theta_full 26.37 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_min 2.57 _diffrn_ambient_temperature 293.15 _diffrn_detector_area_resol_mean 16.0355 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -9.00 67.00 1.0000 10.0200 omega____ theta____ kappa____ phi______ frames - 17.7486 77.0000 -150.0000 76 #__ type_ start__ end____ width___ exp.time_ 2 omega -8.00 88.00 1.0000 10.0200 omega____ theta____ kappa____ phi______ frames - 17.7486 77.0000 -30.0000 96 #__ type_ start__ end____ width___ exp.time_ 3 omega -39.00 -2.00 1.0000 10.0200 omega____ theta____ kappa____ phi______ frames - -18.9986 77.0000 90.0000 37 #__ type_ start__ end____ width___ exp.time_ 4 omega 32.00 80.00 1.0000 10.0200 omega____ theta____ kappa____ phi______ frames - 17.7486 -179.0000 90.0000 48 #__ type_ start__ end____ width___ exp.time_ 5 omega -51.00 39.00 1.0000 10.0200 omega____ theta____ kappa____ phi______ frames - 17.7486 -57.0000 -150.0000 90 ; _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0595775000 _diffrn_orient_matrix_UB_12 0.0153957000 _diffrn_orient_matrix_UB_13 0.0062526000 _diffrn_orient_matrix_UB_21 0.0268760000 _diffrn_orient_matrix_UB_22 0.0244304000 _diffrn_orient_matrix_UB_23 0.0396647000 _diffrn_orient_matrix_UB_31 0.0072619000 _diffrn_orient_matrix_UB_32 0.0354728000 _diffrn_orient_matrix_UB_33 -0.0302120000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2825 _reflns_number_total 4877 _reflns_odcompleteness_completeness 99.78 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.366 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.048 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 309 _refine_ls_number_reflns 4877 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1235 _refine_ls_R_factor_gt 0.0704 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0882P)^2^+0.8060P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1693 _refine_ls_wR_factor_ref 0.2088 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: H1A of B1, H2A of B2, H5 of C5, H3 of B3, H10 of B10, H9 of B9, H14 of C14, H4A of B4, H6 of C6, H2 of N2, H1 of N1, H15 of C15, H5A of B5, H6A of B6, H8 of C8, H17 of C17, H4 of C4, H13 of C13, H8A of B8, H7 of B7 At 1.5 times of: {H18A,H18B,H18C} of C18, {H9A,H9B,H9C} of C9 2.a Aromatic/amide H refined with riding coordinates: N1(H1), N2(H2), C4(H4), C17(H17), C8(H8), C6(H6), C5(H5), C15(H15), C13(H13), C14(H14) 2.b Idealised Me refined as rotating group: C18(H18A,H18B,H18C), C9(H9A,H9B,H9C) 2.c Boron cage BH refined with riding coordinates: B4(H4A), B3(H3), B2(H2A), B6(H6A), B5(H5A), B1(H1A), B10(H10), B9(H9), B8(H8A), B7(H7) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.4452(2) 0.08813(14) 0.35078(15) 0.0466(6) Uani 1 1 d . . . H1 H 0.3948 0.0510 0.3688 0.056 Uiso 1 1 calc R . . O1 O 0.5132(2) 0.22517(14) 0.36894(16) 0.0724(7) Uani 1 1 d . . . C3 C 0.5178(3) 0.06261(16) 0.27940(18) 0.0425(6) Uani 1 1 d . . . C1 C 0.3602(2) 0.18178(17) 0.46226(17) 0.0416(6) Uani 1 1 d . . . N2 N 0.5992(2) 0.18182(15) 0.69072(15) 0.0485(6) Uani 1 1 d . . . H2 H 0.5614 0.2200 0.7198 0.058 Uiso 1 1 calc R . . C10 C 0.4093(2) 0.18336(17) 0.57799(17) 0.0425(6) Uani 1 1 d . . . C2 C 0.4508(3) 0.16583(17) 0.39118(18) 0.0433(7) Uani 1 1 d . . . O4 O 0.8672(2) 0.13133(16) 0.98429(16) 0.0738(7) Uani 1 1 d . . . O2 O 0.8349(2) 0.06837(16) 0.22291(17) 0.0740(7) Uani 1 1 d . . . C4 C 0.4594(3) 0.01761(18) 0.20248(19) 0.0498(7) Uani 1 1 d . . . H4 H 0.3750 0.0059 0.1964 0.060 Uiso 1 1 calc R . . C17 C 0.7350(3) 0.15920(18) 0.83621(19) 0.0468(7) Uani 1 1 d . . . H17 H 0.6761 0.1864 0.8672 0.056 Uiso 1 1 calc R . . C8 C 0.6423(3) 0.08174(18) 0.28921(19) 0.0476(7) Uani 1 1 d . . . H8 H 0.6798 0.1126 0.3415 0.057 Uiso 1 1 calc R . . C12 C 0.7153(3) 0.15121(18) 0.7381(2) 0.0472(7) Uani 1 1 d . . . O3 O 0.5920(2) 0.1106(2) 0.55264(18) 0.0993(10) Uani 1 1 d . . . C11 C 0.5441(3) 0.15677(19) 0.6058(2) 0.0519(7) Uani 1 1 d . . . C7 C 0.7116(3) 0.05429(19) 0.2198(2) 0.0524(7) Uani 1 1 d . . . C6 C 0.6533(3) 0.0085(2) 0.1421(2) 0.0600(9) Uani 1 1 d . . . H6 H 0.6989 -0.0096 0.0953 0.072 Uiso 1 1 calc R . . B4 B 0.3320(3) 0.2603(2) 0.6322(2) 0.0491(8) Uani 1 1 d . . . H4A H 0.3721 0.2968 0.6954 0.059 Uiso 1 1 calc R . . B3 B 0.2952(4) 0.1494(2) 0.6396(2) 0.0543(9) Uani 1 1 d . . . H3 H 0.3118 0.1144 0.7074 0.065 Uiso 1 1 calc R . . C5 C 0.5301(3) -0.0100(2) 0.1339(2) 0.0590(8) Uani 1 1 d . . . H5 H 0.4926 -0.0415 0.0821 0.071 Uiso 1 1 calc R . . B2 B 0.3163(3) 0.0990(2) 0.5311(2) 0.0477(8) Uani 1 1 d . . . H2A H 0.3471 0.0317 0.5277 0.057 Uiso 1 1 calc R . . B6 B 0.2494(3) 0.2578(2) 0.4323(2) 0.0567(9) Uani 1 1 d . . . H6A H 0.2353 0.2925 0.3643 0.068 Uiso 1 1 calc R . . B5 B 0.3782(3) 0.2805(2) 0.5195(2) 0.0495(8) Uani 1 1 d . . . H5A H 0.4485 0.3290 0.5089 0.059 Uiso 1 1 calc R . . C16 C 0.8421(3) 0.1267(2) 0.8879(2) 0.0551(8) Uani 1 1 d . . . B1 B 0.2124(3) 0.1469(2) 0.4398(2) 0.0547(9) Uani 1 1 d . . . H1A H 0.1742 0.1100 0.3764 0.066 Uiso 1 1 calc R . . B10 B 0.2274(4) 0.3077(2) 0.5402(3) 0.0598(10) Uani 1 1 d . . . H10 H 0.1980 0.3753 0.5430 0.072 Uiso 1 1 calc R . . C15 C 0.9287(3) 0.0851(3) 0.8421(3) 0.0759(11) Uani 1 1 d . . . H15 H 0.9994 0.0612 0.8768 0.091 Uiso 1 1 calc R . . B9 B 0.1766(4) 0.2265(3) 0.6148(3) 0.0641(10) Uani 1 1 d . . . H9 H 0.1136 0.2416 0.6663 0.077 Uiso 1 1 calc R . . C13 C 0.8036(3) 0.1116(2) 0.6913(2) 0.0649(9) Uani 1 1 d . . . H13 H 0.7921 0.1067 0.6256 0.078 Uiso 1 1 calc R . . C14 C 0.9094(3) 0.0794(3) 0.7456(3) 0.0798(11) Uani 1 1 d . . . H14 H 0.9694 0.0530 0.7151 0.096 Uiso 1 1 calc R . . C18 C 0.7967(4) 0.1909(3) 1.0307(2) 0.0816(11) Uani 1 1 d . . . H18A H 0.7972 0.2462 1.0004 0.122 Uiso 1 1 calc R . . H18B H 0.8325 0.1961 1.0960 0.122 Uiso 1 1 calc R . . H18C H 0.7129 0.1707 1.0269 0.122 Uiso 1 1 calc R . . B8 B 0.1671(4) 0.1267(3) 0.5526(3) 0.0631(10) Uani 1 1 d . . . H8A H 0.0984 0.0771 0.5634 0.076 Uiso 1 1 calc R . . B7 B 0.1247(4) 0.2256(3) 0.4908(3) 0.0675(11) Uani 1 1 d . . . H7 H 0.0280 0.2400 0.4615 0.081 Uiso 1 1 calc R . . C9 C 0.8954(3) 0.1225(3) 0.2947(3) 0.0909(13) Uani 1 1 d . . . H9A H 0.9799 0.1309 0.2849 0.136 Uiso 1 1 calc R . . H9B H 0.8937 0.0962 0.3555 0.136 Uiso 1 1 calc R . . H9C H 0.8539 0.1772 0.2926 0.136 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 0.0607(15) 0.0398(13) 0.0434(13) -0.0041(10) 0.0216(11) -0.0053(11) O1 0.0958(18) 0.0560(13) 0.0759(15) -0.0192(11) 0.0484(13) -0.0275(13) C3 0.0576(18) 0.0373(14) 0.0351(14) 0.0038(11) 0.0153(12) 0.0039(13) C1 0.0533(16) 0.0396(15) 0.0326(14) -0.0007(11) 0.0081(12) 0.0018(13) N2 0.0545(14) 0.0508(14) 0.0401(13) -0.0061(10) 0.0059(11) 0.0079(12) C10 0.0538(17) 0.0417(15) 0.0322(13) -0.0030(11) 0.0072(12) 0.0053(13) C2 0.0533(17) 0.0420(16) 0.0361(14) -0.0044(12) 0.0115(12) -0.0078(13) O4 0.0753(16) 0.0878(18) 0.0538(14) 0.0053(12) -0.0065(12) 0.0094(14) O2 0.0600(15) 0.0878(18) 0.0774(16) -0.0041(13) 0.0211(12) 0.0082(13) C4 0.0647(19) 0.0438(16) 0.0421(15) -0.0021(13) 0.0111(13) -0.0052(14) C17 0.0483(16) 0.0482(17) 0.0438(16) -0.0044(12) 0.0058(13) -0.0033(13) C8 0.0594(18) 0.0474(16) 0.0357(14) -0.0021(12) 0.0062(13) 0.0030(14) C12 0.0470(16) 0.0470(16) 0.0476(16) 0.0007(13) 0.0070(13) -0.0003(13) O3 0.0800(17) 0.142(2) 0.0691(16) -0.0588(16) -0.0106(13) 0.0462(17) C11 0.0597(18) 0.0528(18) 0.0426(16) -0.0097(13) 0.0049(14) 0.0082(15) C7 0.0546(18) 0.0525(18) 0.0524(18) 0.0030(14) 0.0154(14) 0.0047(15) C6 0.082(2) 0.0588(19) 0.0444(17) -0.0030(14) 0.0271(16) 0.0048(18) B4 0.066(2) 0.0456(18) 0.0367(16) -0.0047(14) 0.0124(15) 0.0120(17) B3 0.076(2) 0.050(2) 0.0414(18) 0.0023(15) 0.0233(17) 0.0065(18) C5 0.086(2) 0.0546(19) 0.0376(16) -0.0090(13) 0.0113(15) -0.0039(17) B2 0.065(2) 0.0406(17) 0.0401(17) -0.0005(14) 0.0166(15) -0.0043(16) B6 0.070(2) 0.055(2) 0.0447(19) 0.0016(16) 0.0046(17) 0.0158(19) B5 0.071(2) 0.0364(17) 0.0422(17) -0.0001(14) 0.0121(16) 0.0031(16) C16 0.0534(18) 0.0568(19) 0.0525(18) 0.0025(14) -0.0015(14) -0.0022(15) B1 0.050(2) 0.064(2) 0.050(2) -0.0095(17) 0.0053(15) 0.0030(18) B10 0.071(2) 0.054(2) 0.055(2) -0.0020(17) 0.0109(18) 0.0234(19) C15 0.056(2) 0.094(3) 0.074(2) -0.003(2) -0.0060(17) 0.0242(19) B9 0.070(2) 0.069(2) 0.058(2) -0.0055(19) 0.0279(19) 0.013(2) C13 0.060(2) 0.085(2) 0.0505(18) -0.0050(17) 0.0106(15) 0.0130(18) C14 0.060(2) 0.103(3) 0.077(3) -0.015(2) 0.0123(18) 0.023(2) C18 0.094(3) 0.102(3) 0.049(2) 0.0018(19) 0.0115(19) 0.000(2) B8 0.061(2) 0.067(2) 0.067(2) -0.0083(19) 0.0289(19) -0.005(2) B7 0.056(2) 0.084(3) 0.063(2) -0.009(2) 0.0106(18) 0.014(2) C9 0.056(2) 0.104(3) 0.111(3) -0.010(3) 0.009(2) 0.000(2) _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 H1 0.8600 . ? N1 C3 1.431(3) . ? N1 C2 1.334(3) . ? O1 C2 1.214(3) . ? C3 C4 1.376(4) . ? C3 C8 1.377(4) . ? C1 C10 1.659(3) . ? C1 C2 1.532(3) . ? C1 B2 1.725(4) . ? C1 B6 1.699(4) . ? C1 B5 1.733(4) . ? C1 B1 1.686(4) . ? N2 H2 0.8600 . ? N2 C12 1.428(3) . ? N2 C11 1.329(3) . ? C10 C11 1.523(4) . ? C10 B4 1.708(4) . ? C10 B3 1.706(4) . ? C10 B2 1.731(4) . ? C10 B5 1.732(4) . ? O4 C16 1.364(4) . ? O4 C18 1.424(4) . ? O2 C7 1.356(4) . ? O2 C9 1.413(4) . ? C4 H4 0.9300 . ? C4 C5 1.395(4) . ? C17 H17 0.9300 . ? C17 C12 1.389(4) . ? C17 C16 1.384(4) . ? C8 H8 0.9300 . ? C8 C7 1.394(4) . ? C12 C13 1.391(4) . ? O3 C11 1.214(3) . ? C7 C6 1.390(4) . ? C6 H6 0.9300 . ? C6 C5 1.363(4) . ? B4 H4A 1.1000 . ? B4 B3 1.774(5) . ? B4 B5 1.779(4) . ? B4 B10 1.770(5) . ? B4 B9 1.756(5) . ? B3 H3 1.1000 . ? B3 B2 1.777(4) . ? B3 B9 1.760(5) . ? B3 B8 1.765(6) . ? C5 H5 0.9300 . ? B2 H2A 1.1000 . ? B2 B1 1.762(5) . ? B2 B8 1.752(5) . ? B6 H6A 1.1000 . ? B6 B5 1.772(5) . ? B6 B1 1.775(5) . ? B6 B10 1.768(5) . ? B6 B7 1.765(5) . ? B5 H5A 1.1000 . ? B5 B10 1.762(5) . ? C16 C15 1.382(4) . ? B1 H1A 1.1000 . ? B1 B8 1.775(5) . ? B1 B7 1.770(5) . ? B10 H10 1.1000 . ? B10 B9 1.787(5) . ? B10 B7 1.774(6) . ? C15 H15 0.9300 . ? C15 C14 1.365(5) . ? B9 H9 1.1000 . ? B9 B8 1.780(5) . ? B9 B7 1.775(6) . ? C13 H13 0.9300 . ? C13 C14 1.386(5) . ? C14 H14 0.9300 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? B8 H8A 1.1000 . ? B8 B7 1.796(6) . ? B7 H7 1.1000 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? 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 C3 N1 H1 117.9 . . ? C2 N1 H1 117.9 . . ? C2 N1 C3 124.1(2) . . ? C4 C3 N1 117.8(3) . . ? C4 C3 C8 121.8(2) . . ? C8 C3 N1 120.4(2) . . ? C10 C1 B2 61.46(17) . . ? C10 C1 B6 110.9(2) . . ? C10 C1 B5 61.36(16) . . ? C10 C1 B1 110.9(2) . . ? C2 C1 C10 120.8(2) . . ? C2 C1 B2 120.8(2) . . ? C2 C1 B6 116.6(2) . . ? C2 C1 B5 114.4(2) . . ? C2 C1 B1 120.8(2) . . ? B2 C1 B5 114.4(2) . . ? B6 C1 B2 114.5(2) . . ? B6 C1 B5 62.18(19) . . ? B1 C1 B2 62.20(19) . . ? B1 C1 B6 63.2(2) . . ? B1 C1 B5 114.5(2) . . ? C12 N2 H2 117.0 . . ? C11 N2 H2 117.0 . . ? C11 N2 C12 126.0(2) . . ? C1 C10 B4 110.5(2) . . ? C1 C10 B3 110.6(2) . . ? C1 C10 B2 61.15(16) . . ? C1 C10 B5 61.42(16) . . ? C11 C10 C1 114.6(2) . . ? C11 C10 B4 126.3(2) . . ? C11 C10 B3 122.0(2) . . ? C11 C10 B2 112.7(2) . . ? C11 C10 B5 118.4(2) . . ? B4 C10 B2 113.8(2) . . ? B4 C10 B5 62.25(17) . . ? B3 C10 B4 62.59(19) . . ? B3 C10 B2 62.25(18) . . ? B3 C10 B5 114.2(2) . . ? B2 C10 B5 114.2(2) . . ? N1 C2 C1 115.9(2) . . ? O1 C2 N1 124.5(2) . . ? O1 C2 C1 119.2(2) . . ? C16 O4 C18 117.3(3) . . ? C7 O2 C9 118.5(3) . . ? C3 C4 H4 120.8 . . ? C3 C4 C5 118.4(3) . . ? C5 C4 H4 120.8 . . ? C12 C17 H17 120.0 . . ? C16 C17 H17 120.0 . . ? C16 C17 C12 120.0(3) . . ? C3 C8 H8 120.4 . . ? C3 C8 C7 119.2(3) . . ? C7 C8 H8 120.4 . . ? C17 C12 N2 116.4(2) . . ? C17 C12 C13 120.2(3) . . ? C13 C12 N2 123.3(3) . . ? N2 C11 C10 116.8(2) . . ? O3 C11 N2 124.2(3) . . ? O3 C11 C10 118.8(3) . . ? O2 C7 C8 124.2(3) . . ? O2 C7 C6 116.5(3) . . ? C6 C7 C8 119.3(3) . . ? C7 C6 H6 119.7 . . ? C5 C6 C7 120.5(3) . . ? C5 C6 H6 119.7 . . ? C10 B4 H4A 124.5 . . ? C10 B4 B3 58.63(18) . . ? C10 B4 B5 59.53(17) . . ? C10 B4 B10 105.2(2) . . ? C10 B4 B9 104.8(2) . . ? B3 B4 H4A 121.3 . . ? B3 B4 B5 108.7(2) . . ? B5 B4 H4A 121.1 . . ? B10 B4 H4A 122.0 . . ? B10 B4 B3 108.7(3) . . ? B10 B4 B5 59.54(19) . . ? B9 B4 H4A 122.1 . . ? B9 B4 B3 59.8(2) . . ? B9 B4 B5 108.4(2) . . ? B9 B4 B10 60.9(2) . . ? C10 B3 B4 58.77(17) . . ? C10 B3 H3 124.3 . . ? C10 B3 B2 59.55(17) . . ? C10 B3 B9 104.8(2) . . ? C10 B3 B8 105.2(2) . . ? B4 B3 H3 121.4 . . ? B4 B3 B2 108.5(2) . . ? B2 B3 H3 121.4 . . ? B9 B3 B4 59.6(2) . . ? B9 B3 H3 122.4 . . ? B9 B3 B2 107.9(2) . . ? B9 B3 B8 60.6(2) . . ? B8 B3 B4 108.3(3) . . ? B8 B3 H3 122.2 . . ? B8 B3 B2 59.28(19) . . ? C4 C5 H5 119.6 . . ? C6 C5 C4 120.8(3) . . ? C6 C5 H5 119.6 . . ? C1 B2 C10 57.39(16) . . ? C1 B2 B3 104.4(2) . . ? C1 B2 H2A 124.8 . . ? C1 B2 B1 57.81(18) . . ? C1 B2 B8 104.8(2) . . ? C10 B2 B3 58.19(17) . . ? C10 B2 H2A 124.8 . . ? C10 B2 B1 104.2(2) . . ? C10 B2 B8 104.7(2) . . ? B3 B2 H2A 122.4 . . ? B1 B2 B3 107.9(2) . . ? B1 B2 H2A 122.4 . . ? B8 B2 B3 60.0(2) . . ? B8 B2 H2A 122.6 . . ? B8 B2 B1 60.7(2) . . ? C1 B6 H6A 124.5 . . ? C1 B6 B5 59.86(18) . . ? C1 B6 B1 58.03(18) . . ? C1 B6 B10 105.4(2) . . ? C1 B6 B7 104.6(3) . . ? B5 B6 H6A 121.1 . . ? B5 B6 B1 108.3(2) . . ? B1 B6 H6A 121.6 . . ? B10 B6 H6A 122.1 . . ? B10 B6 B5 59.7(2) . . ? B10 B6 B1 108.2(3) . . ? B7 B6 H6A 122.4 . . ? B7 B6 B5 108.1(2) . . ? B7 B6 B1 60.0(2) . . ? B7 B6 B10 60.3(2) . . ? C1 B5 B4 104.0(2) . . ? C1 B5 B6 57.96(18) . . ? C1 B5 H5A 125.0 . . ? C1 B5 B10 104.2(2) . . ? C10 B5 C1 57.22(15) . . ? C10 B5 B4 58.22(17) . . ? C10 B5 B6 104.2(2) . . ? C10 B5 H5A 124.7 . . ? C10 B5 B10 104.6(2) . . ? B4 B5 H5A 122.5 . . ? B6 B5 B4 107.4(3) . . ? B6 B5 H5A 122.5 . . ? B10 B5 B4 60.0(2) . . ? B10 B5 B6 60.0(2) . . ? B10 B5 H5A 123.0 . . ? O4 C16 C17 123.3(3) . . ? O4 C16 C15 116.6(3) . . ? C15 C16 C17 120.1(3) . . ? C1 B1 B2 59.99(18) . . ? C1 B1 B6 58.73(19) . . ? C1 B1 H1A 124.2 . . ? C1 B1 B8 105.5(2) . . ? C1 B1 B7 104.9(3) . . ? B2 B1 B6 109.1(2) . . ? B2 B1 H1A 121.0 . . ? B2 B1 B8 59.4(2) . . ? B2 B1 B7 108.4(3) . . ? B6 B1 H1A 121.2 . . ? B6 B1 B8 108.7(2) . . ? B8 B1 H1A 122.0 . . ? B7 B1 B6 59.7(2) . . ? B7 B1 H1A 122.2 . . ? B7 B1 B8 60.9(2) . . ? B4 B10 H10 122.0 . . ? B4 B10 B9 59.2(2) . . ? B4 B10 B7 107.3(3) . . ? B6 B10 B4 108.0(2) . . ? B6 B10 H10 121.8 . . ? B6 B10 B9 107.5(3) . . ? B6 B10 B7 59.8(2) . . ? B5 B10 B4 60.47(19) . . ? B5 B10 B6 60.3(2) . . ? B5 B10 H10 121.3 . . ? B5 B10 B9 107.8(2) . . ? B5 B10 B7 108.2(2) . . ? B9 B10 H10 122.3 . . ? B7 B10 H10 121.9 . . ? B7 B10 B9 59.8(2) . . ? C16 C15 H15 120.4 . . ? C14 C15 C16 119.2(3) . . ? C14 C15 H15 120.4 . . ? B4 B9 B3 60.6(2) . . ? B4 B9 B10 59.9(2) . . ? B4 B9 H9 121.6 . . ? B4 B9 B8 108.5(2) . . ? B4 B9 B7 107.9(3) . . ? B3 B9 B10 108.5(2) . . ? B3 B9 H9 121.4 . . ? B3 B9 B8 59.8(2) . . ? B3 B9 B7 108.4(2) . . ? B10 B9 H9 121.6 . . ? B8 B9 B10 108.6(2) . . ? B8 B9 H9 121.3 . . ? B7 B9 B10 59.7(2) . . ? B7 B9 H9 121.7 . . ? B7 B9 B8 60.7(2) . . ? C12 C13 H13 121.0 . . ? C14 C13 C12 118.0(3) . . ? C14 C13 H13 121.0 . . ? C15 C14 C13 122.3(3) . . ? C15 C14 H14 118.8 . . ? C13 C14 H14 118.8 . . ? O4 C18 H18A 109.5 . . ? O4 C18 H18B 109.5 . . ? O4 C18 H18C 109.5 . . ? H18A C18 H18B 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? B3 B8 B1 107.8(2) . . ? B3 B8 B9 59.5(2) . . ? B3 B8 H8A 121.8 . . ? B3 B8 B7 107.2(3) . . ? B2 B8 B3 60.7(2) . . ? B2 B8 B1 59.96(19) . . ? B2 B8 B9 108.1(3) . . ? B2 B8 H8A 121.3 . . ? B2 B8 B7 107.7(3) . . ? B1 B8 B9 107.0(3) . . ? B1 B8 H8A 122.2 . . ? B1 B8 B7 59.4(2) . . ? B9 B8 H8A 122.2 . . ? B9 B8 B7 59.5(2) . . ? B7 B8 H8A 122.3 . . ? B6 B7 B1 60.3(2) . . ? B6 B7 B10 59.9(2) . . ? B6 B7 B9 108.1(3) . . ? B6 B7 B8 108.2(3) . . ? B6 B7 H7 121.6 . . ? B1 B7 B10 108.1(3) . . ? B1 B7 B9 107.5(3) . . ? B1 B7 B8 59.7(2) . . ? B1 B7 H7 121.9 . . ? B10 B7 B9 60.4(2) . . ? B10 B7 B8 108.4(3) . . ? B10 B7 H7 121.4 . . ? B9 B7 B8 59.8(2) . . ? B9 B7 H7 121.9 . . ? B8 B7 H7 121.7 . . ? O2 C9 H9A 109.5 . . ? O2 C9 H9B 109.5 . . ? O2 C9 H9C 109.5 . . ? H9A C9 H9B 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C3 C4 C5 -178.0(2) . . . . ? N1 C3 C8 C7 178.4(2) . . . . ? C3 N1 C2 O1 3.9(5) . . . . ? C3 N1 C2 C1 176.8(2) . . . . ? C3 C4 C5 C6 -1.2(5) . . . . ? C3 C8 C7 O2 -179.0(3) . . . . ? C3 C8 C7 C6 0.2(4) . . . . ? C1 C10 C11 N2 159.5(2) . . . . ? C1 C10 C11 O3 -24.7(4) . . . . ? C1 C10 B4 B3 103.2(2) . . . . ? C1 C10 B4 B5 -39.3(2) . . . . ? C1 C10 B4 B10 0.3(3) . . . . ? C1 C10 B4 B9 63.6(3) . . . . ? C1 C10 B3 B4 -103.1(2) . . . . ? C1 C10 B3 B2 38.8(2) . . . . ? C1 C10 B3 B9 -63.6(3) . . . . ? C1 C10 B3 B8 -0.6(3) . . . . ? C1 C10 B2 B3 -138.0(2) . . . . ? C1 C10 B2 B1 -35.53(19) . . . . ? C1 C10 B2 B8 -98.4(2) . . . . ? C1 C10 B5 B4 137.4(2) . . . . ? C1 C10 B5 B6 35.51(19) . . . . ? C1 C10 B5 B10 97.7(2) . . . . ? C1 B2 B1 B6 -33.5(2) . . . . ? C1 B2 B1 B8 -134.5(2) . . . . ? C1 B2 B1 B7 -97.0(3) . . . . ? C1 B2 B8 B3 -98.2(2) . . . . ? C1 B2 B8 B1 38.7(2) . . . . ? C1 B2 B8 B9 -61.0(3) . . . . ? C1 B2 B8 B7 2.0(3) . . . . ? C1 B6 B5 C10 -35.17(19) . . . . ? C1 B6 B5 B4 -95.8(2) . . . . ? C1 B6 B5 B10 -134.0(2) . . . . ? C1 B6 B1 B2 34.0(2) . . . . ? C1 B6 B1 B8 97.1(3) . . . . ? C1 B6 B1 B7 134.7(3) . . . . ? C1 B6 B10 B4 1.7(3) . . . . ? C1 B6 B10 B5 40.2(2) . . . . ? C1 B6 B10 B9 -60.8(3) . . . . ? C1 B6 B10 B7 -98.3(3) . . . . ? C1 B6 B7 B1 -38.5(2) . . . . ? C1 B6 B7 B10 99.6(2) . . . . ? C1 B6 B7 B9 61.7(3) . . . . ? C1 B6 B7 B8 -1.6(3) . . . . ? C1 B5 B10 B4 98.1(2) . . . . ? C1 B5 B10 B6 -39.0(2) . . . . ? C1 B5 B10 B9 61.4(3) . . . . ? C1 B5 B10 B7 -1.9(3) . . . . ? C1 B1 B8 B3 -1.1(3) . . . . ? C1 B1 B8 B2 -39.9(2) . . . . ? C1 B1 B8 B9 61.6(3) . . . . ? C1 B1 B8 B7 98.7(3) . . . . ? C1 B1 B7 B6 38.9(2) . . . . ? C1 B1 B7 B10 1.5(3) . . . . ? C1 B1 B7 B9 -62.3(3) . . . . ? C1 B1 B7 B8 -99.7(3) . . . . ? N2 C12 C13 C14 -175.8(3) . . . . ? C10 C1 C2 N1 105.5(3) . . . . ? C10 C1 C2 O1 -81.2(3) . . . . ? C10 C1 B2 B3 35.9(2) . . . . ? C10 C1 B2 B1 138.3(2) . . . . ? C10 C1 B2 B8 98.2(2) . . . . ? C10 C1 B6 B5 38.6(2) . . . . ? C10 C1 B6 B1 -103.6(2) . . . . ? C10 C1 B6 B10 -1.5(3) . . . . ? C10 C1 B6 B7 -64.1(3) . . . . ? C10 C1 B5 B4 -36.3(2) . . . . ? C10 C1 B5 B6 -138.4(2) . . . . ? C10 C1 B5 B10 -98.4(2) . . . . ? C10 C1 B1 B2 -38.8(2) . . . . ? C10 C1 B1 B6 103.6(2) . . . . ? C10 C1 B1 B8 0.8(3) . . . . ? C10 C1 B1 B7 64.1(3) . . . . ? C10 B4 B3 B2 -34.2(2) . . . . ? C10 B4 B3 B9 -134.5(2) . . . . ? C10 B4 B3 B8 -97.0(2) . . . . ? C10 B4 B5 C1 35.9(2) . . . . ? C10 B4 B5 B6 96.2(2) . . . . ? C10 B4 B5 B10 134.4(3) . . . . ? C10 B4 B10 B6 -1.2(3) . . . . ? C10 B4 B10 B5 -39.7(2) . . . . ? C10 B4 B10 B9 98.7(3) . . . . ? C10 B4 B10 B7 61.8(3) . . . . ? C10 B4 B9 B3 39.0(2) . . . . ? C10 B4 B9 B10 -99.4(2) . . . . ? C10 B4 B9 B8 1.9(3) . . . . ? C10 B4 B9 B7 -62.4(3) . . . . ? C10 B3 B2 C1 -35.6(2) . . . . ? C10 B3 B2 B1 -95.9(2) . . . . ? C10 B3 B2 B8 -134.6(3) . . . . ? C10 B3 B9 B4 -39.1(2) . . . . ? C10 B3 B9 B10 -1.8(3) . . . . ? C10 B3 B9 B8 99.4(2) . . . . ? C10 B3 B9 B7 61.5(3) . . . . ? C10 B3 B8 B2 39.5(2) . . . . ? C10 B3 B8 B1 1.0(3) . . . . ? C10 B3 B8 B9 -98.6(3) . . . . ? C10 B3 B8 B7 -61.6(3) . . . . ? C10 B2 B1 C1 35.34(18) . . . . ? C10 B2 B1 B6 1.8(3) . . . . ? C10 B2 B1 B8 -99.1(2) . . . . ? C10 B2 B1 B7 -61.6(3) . . . . ? C10 B2 B8 B3 -38.7(2) . . . . ? C10 B2 B8 B1 98.2(2) . . . . ? C10 B2 B8 B9 -1.4(3) . . . . ? C10 B2 B8 B7 61.5(3) . . . . ? C10 B5 B10 B4 38.9(2) . . . . ? C10 B5 B10 B6 -98.2(2) . . . . ? C10 B5 B10 B9 2.1(3) . . . . ? C10 B5 B10 B7 -61.1(3) . . . . ? C2 N1 C3 C4 -136.1(3) . . . . ? C2 N1 C3 C8 44.9(4) . . . . ? C2 C1 C10 C11 -7.4(3) . . . . ? C2 C1 C10 B4 142.6(2) . . . . ? C2 C1 C10 B3 -150.0(2) . . . . ? C2 C1 C10 B2 -110.8(3) . . . . ? C2 C1 C10 B5 102.9(3) . . . . ? C2 C1 B2 C10 110.7(3) . . . . ? C2 C1 B2 B3 146.7(2) . . . . ? C2 C1 B2 B1 -111.0(3) . . . . ? C2 C1 B2 B8 -151.1(2) . . . . ? C2 C1 B6 B5 -105.0(3) . . . . ? C2 C1 B6 B1 112.8(3) . . . . ? C2 C1 B6 B10 -145.1(3) . . . . ? C2 C1 B6 B7 152.3(2) . . . . ? C2 C1 B5 C10 -113.1(2) . . . . ? C2 C1 B5 B4 -149.5(2) . . . . ? C2 C1 B5 B6 108.5(3) . . . . ? C2 C1 B5 B10 148.5(2) . . . . ? C2 C1 B1 B2 111.1(3) . . . . ? C2 C1 B1 B6 -106.5(3) . . . . ? C2 C1 B1 B8 150.7(3) . . . . ? C2 C1 B1 B7 -145.9(3) . . . . ? O4 C16 C15 C14 -179.2(3) . . . . ? O2 C7 C6 C5 178.8(3) . . . . ? C4 C3 C8 C7 -0.5(4) . . . . ? C17 C12 C13 C14 1.1(5) . . . . ? C17 C16 C15 C14 2.5(6) . . . . ? C8 C3 C4 C5 1.0(4) . . . . ? C8 C7 C6 C5 -0.5(5) . . . . ? C12 N2 C11 C10 167.5(2) . . . . ? C12 N2 C11 O3 -8.1(5) . . . . ? C12 C17 C16 O4 -179.3(3) . . . . ? C12 C17 C16 C15 -1.0(5) . . . . ? C12 C13 C14 C15 0.4(6) . . . . ? C11 N2 C12 C17 -156.6(3) . . . . ? C11 N2 C12 C13 20.5(5) . . . . ? C11 C10 B4 B3 -111.1(3) . . . . ? C11 C10 B4 B5 106.3(3) . . . . ? C11 C10 B4 B10 146.0(3) . . . . ? C11 C10 B4 B9 -150.7(3) . . . . ? C11 C10 B3 B4 117.5(3) . . . . ? C11 C10 B3 B2 -100.7(3) . . . . ? C11 C10 B3 B9 157.0(2) . . . . ? C11 C10 B3 B8 -140.0(3) . . . . ? C11 C10 B2 C1 -106.6(2) . . . . ? C11 C10 B2 B3 115.4(3) . . . . ? C11 C10 B2 B1 -142.1(2) . . . . ? C11 C10 B2 B8 155.0(2) . . . . ? C11 C10 B5 C1 104.2(2) . . . . ? C11 C10 B5 B4 -118.4(3) . . . . ? C11 C10 B5 B6 139.7(2) . . . . ? C11 C10 B5 B10 -158.1(2) . . . . ? C7 C6 C5 C4 1.0(5) . . . . ? B4 C10 C11 N2 15.1(4) . . . . ? B4 C10 C11 O3 -169.1(3) . . . . ? B4 C10 B3 B2 141.8(2) . . . . ? B4 C10 B3 B9 39.5(2) . . . . ? B4 C10 B3 B8 102.5(3) . . . . ? B4 C10 B2 C1 101.2(2) . . . . ? B4 C10 B2 B3 -36.8(2) . . . . ? B4 C10 B2 B1 65.6(3) . . . . ? B4 C10 B2 B8 2.8(3) . . . . ? B4 C10 B5 C1 -137.4(2) . . . . ? B4 C10 B5 B6 -101.9(3) . . . . ? B4 C10 B5 B10 -39.8(2) . . . . ? B4 B3 B2 C1 -1.7(3) . . . . ? B4 B3 B2 C10 33.9(2) . . . . ? B4 B3 B2 B1 -62.0(3) . . . . ? B4 B3 B2 B8 -100.8(3) . . . . ? B4 B3 B9 B10 37.3(2) . . . . ? B4 B3 B9 B8 138.5(2) . . . . ? B4 B3 B9 B7 100.6(3) . . . . ? B4 B3 B8 B2 101.0(2) . . . . ? B4 B3 B8 B1 62.6(3) . . . . ? B4 B3 B8 B9 -37.1(2) . . . . ? B4 B3 B8 B7 0.0(3) . . . . ? B4 B5 B10 B6 -137.1(3) . . . . ? B4 B5 B10 B9 -36.8(2) . . . . ? B4 B5 B10 B7 -100.0(3) . . . . ? B4 B10 B9 B3 -37.6(2) . . . . ? B4 B10 B9 B8 -101.0(3) . . . . ? B4 B10 B9 B7 -138.4(3) . . . . ? B4 B10 B7 B6 -101.1(3) . . . . ? B4 B10 B7 B1 -63.6(3) . . . . ? B4 B10 B7 B9 36.6(2) . . . . ? B4 B10 B7 B8 -0.3(3) . . . . ? B4 B9 B8 B3 37.5(2) . . . . ? B4 B9 B8 B2 -0.3(3) . . . . ? B4 B9 B8 B1 -63.5(3) . . . . ? B4 B9 B8 B7 -100.6(3) . . . . ? B4 B9 B7 B6 0.6(4) . . . . ? B4 B9 B7 B1 64.2(3) . . . . ? B4 B9 B7 B10 -37.1(2) . . . . ? B4 B9 B7 B8 101.6(3) . . . . ? B3 C10 C11 N2 -62.5(4) . . . . ? B3 C10 C11 O3 113.3(4) . . . . ? B3 C10 B4 B5 -142.6(3) . . . . ? B3 C10 B4 B10 -102.9(3) . . . . ? B3 C10 B4 B9 -39.6(2) . . . . ? B3 C10 B2 C1 138.0(2) . . . . ? B3 C10 B2 B1 102.5(2) . . . . ? B3 C10 B2 B8 39.6(2) . . . . ? B3 C10 B5 C1 -101.2(2) . . . . ? B3 C10 B5 B4 36.3(2) . . . . ? B3 C10 B5 B6 -65.7(3) . . . . ? B3 C10 B5 B10 -3.5(3) . . . . ? B3 B4 B5 C1 2.6(3) . . . . ? B3 B4 B5 C10 -33.2(2) . . . . ? B3 B4 B5 B6 63.0(3) . . . . ? B3 B4 B5 B10 101.2(3) . . . . ? B3 B4 B10 B6 -62.7(3) . . . . ? B3 B4 B10 B5 -101.2(2) . . . . ? B3 B4 B10 B9 37.3(2) . . . . ? B3 B4 B10 B7 0.3(3) . . . . ? B3 B4 B9 B10 -138.4(2) . . . . ? B3 B4 B9 B8 -37.2(2) . . . . ? B3 B4 B9 B7 -101.4(3) . . . . ? B3 B2 B1 C1 96.0(2) . . . . ? B3 B2 B1 B6 62.5(3) . . . . ? B3 B2 B1 B8 -38.5(2) . . . . ? B3 B2 B1 B7 -1.0(3) . . . . ? B3 B2 B8 B1 136.9(3) . . . . ? B3 B2 B8 B9 37.3(2) . . . . ? B3 B2 B8 B7 100.2(3) . . . . ? B3 B9 B8 B2 -37.8(2) . . . . ? B3 B9 B8 B1 -101.0(3) . . . . ? B3 B9 B8 B7 -138.1(3) . . . . ? B3 B9 B7 B6 -63.5(3) . . . . ? B3 B9 B7 B1 0.1(4) . . . . ? B3 B9 B7 B10 -101.2(3) . . . . ? B3 B9 B7 B8 37.5(3) . . . . ? B3 B8 B7 B6 63.7(3) . . . . ? B3 B8 B7 B1 100.9(3) . . . . ? B3 B8 B7 B10 0.2(3) . . . . ? B3 B8 B7 B9 -37.1(2) . . . . ? B2 C1 C10 C11 103.4(3) . . . . ? B2 C1 C10 B4 -106.6(2) . . . . ? B2 C1 C10 B3 -39.2(2) . . . . ? B2 C1 C10 B5 -146.3(2) . . . . ? B2 C1 C2 N1 32.5(4) . . . . ? B2 C1 C2 O1 -154.2(3) . . . . ? B2 C1 B6 B5 105.8(2) . . . . ? B2 C1 B6 B1 -36.4(2) . . . . ? B2 C1 B6 B10 65.7(3) . . . . ? B2 C1 B6 B7 3.0(3) . . . . ? B2 C1 B5 C10 32.3(2) . . . . ? B2 C1 B5 B4 -4.0(3) . . . . ? B2 C1 B5 B6 -106.1(3) . . . . ? B2 C1 B5 B10 -66.1(3) . . . . ? B2 C1 B1 B6 142.3(2) . . . . ? B2 C1 B1 B8 39.6(2) . . . . ? B2 C1 B1 B7 102.9(3) . . . . ? B2 C10 C11 N2 -133.0(3) . . . . ? B2 C10 C11 O3 42.8(4) . . . . ? B2 C10 B4 B3 36.7(2) . . . . ? B2 C10 B4 B5 -105.9(2) . . . . ? B2 C10 B4 B10 -66.2(3) . . . . ? B2 C10 B4 B9 -2.9(3) . . . . ? B2 C10 B3 B4 -141.8(2) . . . . ? B2 C10 B3 B9 -102.3(3) . . . . ? B2 C10 B3 B8 -39.3(2) . . . . ? B2 C10 B5 C1 -32.2(2) . . . . ? B2 C10 B5 B4 105.3(2) . . . . ? B2 C10 B5 B6 3.4(3) . . . . ? B2 C10 B5 B10 65.5(3) . . . . ? B2 B3 B9 B4 -101.3(2) . . . . ? B2 B3 B9 B10 -64.1(3) . . . . ? B2 B3 B9 B8 37.1(2) . . . . ? B2 B3 B9 B7 -0.7(4) . . . . ? B2 B3 B8 B1 -38.4(2) . . . . ? B2 B3 B8 B9 -138.1(3) . . . . ? B2 B3 B8 B7 -101.0(3) . . . . ? B2 B1 B8 B3 38.7(2) . . . . ? B2 B1 B8 B9 101.5(3) . . . . ? B2 B1 B8 B7 138.6(3) . . . . ? B2 B1 B7 B6 101.8(3) . . . . ? B2 B1 B7 B10 64.3(3) . . . . ? B2 B1 B7 B9 0.5(4) . . . . ? B2 B1 B7 B8 -36.8(3) . . . . ? B2 B8 B7 B6 -0.3(3) . . . . ? B2 B8 B7 B1 36.9(2) . . . . ? B2 B8 B7 B10 -63.7(3) . . . . ? B2 B8 B7 B9 -101.0(3) . . . . ? B6 C1 C10 C11 -149.2(2) . . . . ? B6 C1 C10 B4 0.7(3) . . . . ? B6 C1 C10 B3 68.1(3) . . . . ? B6 C1 C10 B2 107.4(3) . . . . ? B6 C1 C10 B5 -39.0(2) . . . . ? B6 C1 C2 N1 -114.7(3) . . . . ? B6 C1 C2 O1 58.6(4) . . . . ? B6 C1 B2 C10 -101.4(2) . . . . ? B6 C1 B2 B3 -65.5(3) . . . . ? B6 C1 B2 B1 36.8(2) . . . . ? B6 C1 B2 B8 -3.2(3) . . . . ? B6 C1 B5 C10 138.4(2) . . . . ? B6 C1 B5 B4 102.1(3) . . . . ? B6 C1 B5 B10 40.0(2) . . . . ? B6 C1 B1 B2 -142.3(2) . . . . ? B6 C1 B1 B8 -102.8(3) . . . . ? B6 C1 B1 B7 -39.4(2) . . . . ? B6 B5 B10 B4 137.1(3) . . . . ? B6 B5 B10 B9 100.3(3) . . . . ? B6 B5 B10 B7 37.1(2) . . . . ? B6 B1 B8 B3 -62.8(3) . . . . ? B6 B1 B8 B2 -101.5(3) . . . . ? B6 B1 B8 B9 -0.1(3) . . . . ? B6 B1 B8 B7 37.1(3) . . . . ? B6 B1 B7 B10 -37.4(2) . . . . ? B6 B1 B7 B9 -101.2(3) . . . . ? B6 B1 B7 B8 -138.6(3) . . . . ? B6 B10 B9 B4 100.9(3) . . . . ? B6 B10 B9 B3 63.4(3) . . . . ? B6 B10 B9 B8 -0.1(4) . . . . ? B6 B10 B9 B7 -37.5(2) . . . . ? B6 B10 B7 B1 37.6(2) . . . . ? B6 B10 B7 B9 137.8(3) . . . . ? B6 B10 B7 B8 100.8(3) . . . . ? B5 C1 C10 C11 -110.3(3) . . . . ? B5 C1 C10 B4 39.7(2) . . . . ? B5 C1 C10 B3 107.1(2) . . . . ? B5 C1 C10 B2 146.3(2) . . . . ? B5 C1 C2 N1 175.5(2) . . . . ? B5 C1 C2 O1 -11.2(4) . . . . ? B5 C1 B2 C10 -32.3(2) . . . . ? B5 C1 B2 B3 3.7(3) . . . . ? B5 C1 B2 B1 106.0(3) . . . . ? B5 C1 B2 B8 65.9(3) . . . . ? B5 C1 B6 B1 -142.2(2) . . . . ? B5 C1 B6 B10 -40.1(2) . . . . ? B5 C1 B6 B7 -102.7(3) . . . . ? B5 C1 B1 B2 -105.8(2) . . . . ? B5 C1 B1 B6 36.5(2) . . . . ? B5 C1 B1 B8 -66.2(3) . . . . ? B5 C1 B1 B7 -2.9(3) . . . . ? B5 C10 C11 N2 90.0(3) . . . . ? B5 C10 C11 O3 -94.2(4) . . . . ? B5 C10 B4 B3 142.6(3) . . . . ? B5 C10 B4 B10 39.7(2) . . . . ? B5 C10 B4 B9 103.0(3) . . . . ? B5 C10 B3 B4 -36.1(2) . . . . ? B5 C10 B3 B2 105.7(2) . . . . ? B5 C10 B3 B9 3.4(3) . . . . ? B5 C10 B3 B8 66.4(3) . . . . ? B5 C10 B2 C1 32.3(2) . . . . ? B5 C10 B2 B3 -105.7(2) . . . . ? B5 C10 B2 B1 -3.3(3) . . . . ? B5 C10 B2 B8 -66.1(3) . . . . ? B5 B4 B3 C10 33.6(2) . . . . ? B5 B4 B3 B2 -0.6(3) . . . . ? B5 B4 B3 B9 -100.9(3) . . . . ? B5 B4 B3 B8 -63.4(3) . . . . ? B5 B4 B10 B6 38.4(2) . . . . ? B5 B4 B10 B9 138.4(3) . . . . ? B5 B4 B10 B7 101.5(3) . . . . ? B5 B4 B9 B3 101.3(2) . . . . ? B5 B4 B9 B10 -37.1(2) . . . . ? B5 B4 B9 B8 64.2(3) . . . . ? B5 B4 B9 B7 -0.1(3) . . . . ? B5 B6 B1 C1 -33.9(2) . . . . ? B5 B6 B1 B2 0.1(3) . . . . ? B5 B6 B1 B8 63.2(3) . . . . ? B5 B6 B1 B7 100.8(3) . . . . ? B5 B6 B10 B4 -38.5(2) . . . . ? B5 B6 B10 B9 -101.0(3) . . . . ? B5 B6 B10 B7 -138.5(3) . . . . ? B5 B6 B7 B1 -101.1(3) . . . . ? B5 B6 B7 B10 37.0(2) . . . . ? B5 B6 B7 B9 -0.9(3) . . . . ? B5 B6 B7 B8 -64.2(3) . . . . ? B5 B10 B9 B4 37.4(2) . . . . ? B5 B10 B9 B3 -0.2(3) . . . . ? B5 B10 B9 B8 -63.7(3) . . . . ? B5 B10 B9 B7 -101.1(3) . . . . ? B5 B10 B7 B6 -37.3(2) . . . . ? B5 B10 B7 B1 0.3(3) . . . . ? B5 B10 B7 B9 100.5(3) . . . . ? B5 B10 B7 B8 63.5(3) . . . . ? C16 C17 C12 N2 176.4(3) . . . . ? C16 C17 C12 C13 -0.8(4) . . . . ? C16 C15 C14 C13 -2.2(6) . . . . ? B1 C1 C10 C11 142.5(2) . . . . ? B1 C1 C10 B4 -67.5(3) . . . . ? B1 C1 C10 B3 -0.2(3) . . . . ? B1 C1 C10 B2 39.1(2) . . . . ? B1 C1 C10 B5 -107.2(2) . . . . ? B1 C1 C2 N1 -41.5(4) . . . . ? B1 C1 C2 O1 131.9(3) . . . . ? B1 C1 B2 C10 -138.3(2) . . . . ? B1 C1 B2 B3 -102.3(3) . . . . ? B1 C1 B2 B8 -40.1(2) . . . . ? B1 C1 B6 B5 142.2(2) . . . . ? B1 C1 B6 B10 102.1(3) . . . . ? B1 C1 B6 B7 39.5(2) . . . . ? B1 C1 B5 C10 101.4(2) . . . . ? B1 C1 B5 B4 65.1(3) . . . . ? B1 C1 B5 B6 -36.9(2) . . . . ? B1 C1 B5 B10 3.1(3) . . . . ? B1 B2 B8 B3 -136.9(3) . . . . ? B1 B2 B8 B9 -99.6(3) . . . . ? B1 B2 B8 B7 -36.7(2) . . . . ? B1 B6 B5 C1 33.2(2) . . . . ? B1 B6 B5 C10 -2.0(3) . . . . ? B1 B6 B5 B4 -62.7(3) . . . . ? B1 B6 B5 B10 -100.8(3) . . . . ? B1 B6 B10 B4 62.5(3) . . . . ? B1 B6 B10 B5 101.0(3) . . . . ? B1 B6 B10 B9 0.0(3) . . . . ? B1 B6 B10 B7 -37.5(2) . . . . ? B1 B6 B7 B10 138.1(3) . . . . ? B1 B6 B7 B9 100.2(3) . . . . ? B1 B6 B7 B8 36.9(2) . . . . ? B1 B8 B7 B6 -37.2(2) . . . . ? B1 B8 B7 B10 -100.7(3) . . . . ? B1 B8 B7 B9 -137.9(3) . . . . ? B10 B4 B3 C10 96.8(2) . . . . ? B10 B4 B3 B2 62.6(3) . . . . ? B10 B4 B3 B9 -37.7(2) . . . . ? B10 B4 B3 B8 -0.2(3) . . . . ? B10 B4 B5 C1 -98.5(3) . . . . ? B10 B4 B5 C10 -134.4(3) . . . . ? B10 B4 B5 B6 -38.2(2) . . . . ? B10 B4 B9 B3 138.4(2) . . . . ? B10 B4 B9 B8 101.3(3) . . . . ? B10 B4 B9 B7 37.0(3) . . . . ? B10 B6 B5 C1 134.0(2) . . . . ? B10 B6 B5 C10 98.8(2) . . . . ? B10 B6 B5 B4 38.2(2) . . . . ? B10 B6 B1 C1 -97.1(3) . . . . ? B10 B6 B1 B2 -63.1(3) . . . . ? B10 B6 B1 B8 0.0(3) . . . . ? B10 B6 B1 B7 37.6(3) . . . . ? B10 B6 B7 B1 -138.1(3) . . . . ? B10 B6 B7 B9 -37.9(2) . . . . ? B10 B6 B7 B8 -101.2(3) . . . . ? B10 B9 B8 B3 101.1(3) . . . . ? B10 B9 B8 B2 63.3(3) . . . . ? B10 B9 B8 B1 0.1(4) . . . . ? B10 B9 B8 B7 -37.0(3) . . . . ? B10 B9 B7 B6 37.7(2) . . . . ? B10 B9 B7 B1 101.3(3) . . . . ? B10 B9 B7 B8 138.7(3) . . . . ? B9 B4 B3 C10 134.5(2) . . . . ? B9 B4 B3 B2 100.3(3) . . . . ? B9 B4 B3 B8 37.5(2) . . . . ? B9 B4 B5 C1 -60.8(3) . . . . ? B9 B4 B5 C10 -96.7(3) . . . . ? B9 B4 B5 B6 -0.5(3) . . . . ? B9 B4 B5 B10 37.7(2) . . . . ? B9 B4 B10 B6 -100.0(3) . . . . ? B9 B4 B10 B5 -138.4(3) . . . . ? B9 B4 B10 B7 -36.9(2) . . . . ? B9 B3 B2 C1 61.4(3) . . . . ? B9 B3 B2 C10 96.9(3) . . . . ? B9 B3 B2 B1 1.0(3) . . . . ? B9 B3 B2 B8 -37.7(3) . . . . ? B9 B3 B8 B2 138.1(3) . . . . ? B9 B3 B8 B1 99.7(3) . . . . ? B9 B3 B8 B7 37.1(2) . . . . ? B9 B10 B7 B6 -137.8(3) . . . . ? B9 B10 B7 B1 -100.2(3) . . . . ? B9 B10 B7 B8 -37.0(2) . . . . ? B9 B8 B7 B6 100.8(3) . . . . ? B9 B8 B7 B1 137.9(3) . . . . ? B9 B8 B7 B10 37.3(2) . . . . ? C18 O4 C16 C17 -16.7(5) . . . . ? C18 O4 C16 C15 165.0(3) . . . . ? B8 B3 B2 C1 99.1(3) . . . . ? B8 B3 B2 C10 134.6(3) . . . . ? B8 B3 B2 B1 38.8(2) . . . . ? B8 B3 B9 B4 -138.5(2) . . . . ? B8 B3 B9 B10 -101.2(3) . . . . ? B8 B3 B9 B7 -37.8(3) . . . . ? B8 B2 B1 C1 134.5(2) . . . . ? B8 B2 B1 B6 100.9(3) . . . . ? B8 B2 B1 B7 37.5(3) . . . . ? B8 B1 B7 B6 138.6(3) . . . . ? B8 B1 B7 B10 101.2(3) . . . . ? B8 B1 B7 B9 37.4(3) . . . . ? B8 B9 B7 B6 -101.0(3) . . . . ? B8 B9 B7 B1 -37.3(3) . . . . ? B8 B9 B7 B10 -138.7(3) . . . . ? B7 B6 B5 C1 96.7(3) . . . . ? B7 B6 B5 C10 61.5(3) . . . . ? B7 B6 B5 B4 0.9(3) . . . . ? B7 B6 B5 B10 -37.3(3) . . . . ? B7 B6 B1 C1 -134.7(3) . . . . ? B7 B6 B1 B2 -100.7(3) . . . . ? B7 B6 B1 B8 -37.6(3) . . . . ? B7 B6 B10 B4 100.0(3) . . . . ? B7 B6 B10 B5 138.5(3) . . . . ? B7 B6 B10 B9 37.5(3) . . . . ? B7 B1 B8 B3 -99.9(3) . . . . ? B7 B1 B8 B2 -138.6(3) . . . . ? B7 B1 B8 B9 -37.2(3) . . . . ? B7 B10 B9 B4 138.4(3) . . . . ? B7 B10 B9 B3 100.9(3) . . . . ? B7 B10 B9 B8 37.4(3) . . . . ? B7 B9 B8 B3 138.1(3) . . . . ? B7 B9 B8 B2 100.3(3) . . . . ? B7 B9 B8 B1 37.1(3) . . . . ? C9 O2 C7 C8 -7.6(5) . . . . ? C9 O2 C7 C6 173.2(3) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 937469' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_130924_ny_wyf_68b _audit_creation_date 2013-09-25 _audit_creation_method ; Olex2 1.2 (compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C11 H21 B10 N S' _chemical_formula_sum 'C11 H21 B10 N S' _chemical_formula_weight 307.45 _chemical_melting_point ? _chemical_oxdiff_formula 'C H N O B S' 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 11.4931(16) _cell_length_b 18.880(2) _cell_length_c 8.6737(10) _cell_angle_alpha 90.00 _cell_angle_beta 110.802(13) _cell_angle_gamma 90.00 _cell_volume 1759.4(4) _cell_formula_units_Z 4 _cell_measurement_reflns_used 2156 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 27.6530 _cell_measurement_theta_min 4.1150 _exptl_absorpt_coefficient_mu 0.172 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.81786 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.161 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.23 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0419 _diffrn_reflns_av_unetI/netI 0.0562 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 9305 _diffrn_reflns_theta_full 26.37 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_min 3.31 _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 16.0355 _diffrn_measured_fraction_theta_full 0.9960 _diffrn_measured_fraction_theta_max 0.8835 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -35.00 88.00 1.0000 42.3700 omega____ theta____ kappa____ phi______ frames - 17.7426 0.0000 150.0000 123 #__ type_ start__ end____ width___ exp.time_ 2 omega 35.00 94.00 1.0000 42.3700 omega____ theta____ kappa____ phi______ frames - 17.7426 -178.0000 -150.0000 59 #__ type_ start__ end____ width___ exp.time_ 3 omega -24.00 14.00 1.0000 42.3700 omega____ theta____ kappa____ phi______ frames - -18.8363 -99.0000 -150.0000 38 #__ type_ start__ end____ width___ exp.time_ 4 omega -55.00 7.00 1.0000 42.3700 omega____ theta____ kappa____ phi______ frames - 17.7426 -37.0000 -30.0000 62 ; _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0255922000 _diffrn_orient_matrix_UB_12 0.0284053000 _diffrn_orient_matrix_UB_13 -0.0311150000 _diffrn_orient_matrix_UB_21 -0.0603859000 _diffrn_orient_matrix_UB_22 0.0146587000 _diffrn_orient_matrix_UB_23 -0.0376745000 _diffrn_orient_matrix_UB_31 0.0079838000 _diffrn_orient_matrix_UB_32 0.0197643000 _diffrn_orient_matrix_UB_33 0.0724914000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2304 _reflns_number_total 3591 _reflns_odcompleteness_completeness 99.60 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELX, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution 'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790' _refine_diff_density_max 0.231 _refine_diff_density_min -0.201 _refine_diff_density_rms 0.043 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 209 _refine_ls_number_reflns 3591 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0939 _refine_ls_R_factor_gt 0.0601 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0786P)^2^+0.3422P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1508 _refine_ls_wR_factor_ref 0.1812 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All B(H) groups, All C(H) groups, All C(H,H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Secondary CH2 refined with riding coordinates: C10(H10A,H10B) 2.b Aromatic/amide H refined with riding coordinates: N1(H1), C5(H5), C8(H8), C6(H6), C9(H9) 2.c Idealised Me refined as rotating group: C11(H11A,H11B,H11C) 2.d Boron cage BH refined with riding coordinates: C1(H1A), B6(H6A), B3(H3), B7(H7), B11(H11), B10(H10), B5(H5A), B4(H4), B8(H8A), B12(H12), B9(H9A) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _atom_sites_solution_secondary difmap 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 S1 S 0.57141(8) 0.64608(4) -0.11955(8) 0.0702(3) Uani 1 1 d . . . N1 N 0.45435(19) 0.69415(11) 0.0715(2) 0.0570(6) Uani 1 1 d . . . H1 H 0.4551 0.6998 0.1702 0.068 Uiso 1 1 calc R . . C3 C 0.5462(2) 0.65667(11) 0.0530(3) 0.0478(6) Uani 1 1 d . . . C2 C 0.6298(2) 0.62213(11) 0.2118(3) 0.0455(5) Uani 1 1 d . . . C4 C 0.3540(2) 0.72606(12) -0.0597(3) 0.0497(6) Uani 1 1 d . . . C7 C 0.1523(3) 0.78765(14) -0.3058(3) 0.0593(7) Uani 1 1 d . . . C1 C 0.7650(2) 0.59247(12) 0.2153(3) 0.0511(6) Uani 1 1 d . . . H1A H 0.7922 0.5991 0.1067 0.061 Uiso 1 1 calc R . . C11 C 0.0380(4) 0.8942(2) -0.4687(4) 0.1193(15) Uani 1 1 d . . . H11A H -0.0390 0.9072 -0.5534 0.179 Uiso 1 1 calc R . . H11B H 0.1062 0.9062 -0.5032 0.179 Uiso 1 1 calc R . . H11C H 0.0463 0.9191 -0.3689 0.179 Uiso 1 1 calc R . . C5 C 0.3372(3) 0.79767(13) -0.0624(3) 0.0617(7) Uani 1 1 d . . . H5 H 0.3932 0.8260 0.0176 0.074 Uiso 1 1 calc R . . C8 C 0.1722(3) 0.71587(16) -0.2994(4) 0.0763(9) Uani 1 1 d . . . H8 H 0.1170 0.6872 -0.3793 0.092 Uiso 1 1 calc R . . C6 C 0.2367(3) 0.82797(15) -0.1845(3) 0.0700(8) Uani 1 1 d . . . H6 H 0.2258 0.8768 -0.1848 0.084 Uiso 1 1 calc R . . C10 C 0.0387(3) 0.81820(19) -0.4394(4) 0.0914(11) Uani 1 1 d . . . H10A H 0.0293 0.7942 -0.5420 0.110 Uiso 1 1 calc R . . H10B H -0.0338 0.8068 -0.4119 0.110 Uiso 1 1 calc R . . C9 C 0.2711(3) 0.68531(14) -0.1788(4) 0.0741(8) Uani 1 1 d . . . H9 H 0.2820 0.6365 -0.1780 0.089 Uiso 1 1 calc R . . B6 B 0.6512(3) 0.53177(14) 0.2006(4) 0.0546(7) Uani 1 1 d . . . H6A H 0.6036 0.4989 0.0916 0.065 Uiso 1 1 calc R . . B3 B 0.7633(3) 0.66674(15) 0.3273(4) 0.0595(8) Uani 1 1 d . . . H3 H 0.7874 0.7204 0.2996 0.071 Uiso 1 1 calc R . . B7 B 0.8773(3) 0.59964(17) 0.4045(4) 0.0644(8) Uani 1 1 d . . . H7 H 0.9763 0.6098 0.4280 0.077 Uiso 1 1 calc R . . B11 B 0.8076(3) 0.51733(15) 0.3275(4) 0.0616(8) Uani 1 1 d . . . H11 H 0.8623 0.4742 0.3015 0.074 Uiso 1 1 calc R . . B10 B 0.6871(3) 0.50079(16) 0.4016(4) 0.0659(9) Uani 1 1 d . . . H10 H 0.6626 0.4467 0.4259 0.079 Uiso 1 1 calc R . . B5 B 0.5723(3) 0.56746(15) 0.3237(4) 0.0571(7) Uani 1 1 d . . . H5A H 0.4726 0.5576 0.2958 0.069 Uiso 1 1 calc R . . B4 B 0.6422(3) 0.65020(15) 0.4034(3) 0.0585(8) Uani 1 1 d . . . H4 H 0.5873 0.6937 0.4276 0.070 Uiso 1 1 calc R . . B8 B 0.7987(3) 0.63534(16) 0.5290(4) 0.0658(9) Uani 1 1 d . . . H8A H 0.8466 0.6691 0.6363 0.079 Uiso 1 1 calc R . . B12 B 0.8267(3) 0.54296(16) 0.5292(4) 0.0667(9) Uani 1 1 d . . . H12 H 0.8933 0.5164 0.6376 0.080 Uiso 1 1 calc R . . B9 B 0.6817(4) 0.57350(17) 0.5284(4) 0.0699(9) Uani 1 1 d . . . H9A H 0.6535 0.5666 0.6361 0.084 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 S1 0.0780(6) 0.0782(5) 0.0521(4) 0.0065(3) 0.0205(4) 0.0199(4) N1 0.0567(14) 0.0592(13) 0.0491(11) 0.0021(10) 0.0115(10) 0.0167(10) C3 0.0517(15) 0.0345(11) 0.0509(13) -0.0018(10) 0.0104(11) -0.0010(10) C2 0.0444(14) 0.0373(11) 0.0501(13) -0.0017(10) 0.0112(10) 0.0021(10) C4 0.0477(14) 0.0475(13) 0.0469(13) -0.0022(11) 0.0082(10) 0.0067(11) C7 0.0535(16) 0.0653(17) 0.0486(14) -0.0036(12) 0.0052(12) 0.0070(12) C1 0.0403(14) 0.0490(13) 0.0576(14) -0.0090(11) 0.0094(11) -0.0002(10) C11 0.131(4) 0.114(3) 0.082(2) 0.022(2) 0.000(2) 0.040(3) C5 0.0586(17) 0.0507(14) 0.0571(15) -0.0131(12) -0.0023(12) 0.0071(12) C8 0.066(2) 0.0659(18) 0.0729(19) -0.0250(15) -0.0048(15) -0.0017(14) C6 0.069(2) 0.0512(15) 0.0719(18) -0.0073(13) 0.0034(15) 0.0125(13) C10 0.082(3) 0.101(3) 0.0651(19) -0.0003(18) -0.0062(16) 0.0190(19) C9 0.068(2) 0.0462(15) 0.088(2) -0.0114(14) 0.0026(16) 0.0040(13) B6 0.0497(17) 0.0348(13) 0.0654(18) -0.0046(12) 0.0034(13) 0.0012(11) B3 0.065(2) 0.0407(15) 0.0604(18) -0.0111(13) 0.0071(15) -0.0096(13) B7 0.0526(19) 0.0603(19) 0.0635(18) -0.0111(15) -0.0002(14) 0.0000(14) B11 0.0553(19) 0.0465(16) 0.0670(18) -0.0080(14) 0.0021(14) 0.0123(13) B10 0.071(2) 0.0420(15) 0.0704(19) 0.0076(15) 0.0081(16) 0.0006(14) B5 0.0515(18) 0.0513(16) 0.0666(18) 0.0129(14) 0.0185(14) 0.0027(13) B4 0.074(2) 0.0471(16) 0.0514(16) -0.0031(13) 0.0189(15) 0.0104(14) B8 0.076(2) 0.0557(18) 0.0510(17) -0.0120(14) 0.0046(15) 0.0055(15) B12 0.071(2) 0.0548(18) 0.0564(18) 0.0017(14) 0.0010(15) 0.0122(15) B9 0.083(3) 0.066(2) 0.0567(18) 0.0095(16) 0.0194(17) 0.0110(17) _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 S1 C3 1.635(2) . ? N1 H1 0.8600 . ? N1 C3 1.327(3) . ? N1 C4 1.434(3) . ? C3 C2 1.519(3) . ? C2 C1 1.641(3) . ? C2 B6 1.731(3) . ? C2 B3 1.724(4) . ? C2 B5 1.702(4) . ? C2 B4 1.701(3) . ? C4 C5 1.365(3) . ? C4 C9 1.367(3) . ? C7 C8 1.372(4) . ? C7 C6 1.379(4) . ? C7 C10 1.518(4) . ? C1 H1A 1.1000 . ? C1 B6 1.709(4) . ? C1 B3 1.710(4) . ? C1 B7 1.695(4) . ? C1 B11 1.691(4) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C11 C10 1.456(5) . ? C5 H5 0.9300 . ? C5 C6 1.384(3) . ? C8 H8 0.9300 . ? C8 C9 1.369(4) . ? C6 H6 0.9300 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C9 H9 0.9300 . ? B6 H6A 1.1000 . ? B6 B11 1.764(4) . ? B6 B10 1.743(4) . ? B6 B5 1.761(4) . ? B3 H3 1.1000 . ? B3 B7 1.774(4) . ? B3 B4 1.767(5) . ? B3 B8 1.753(4) . ? B7 H7 1.1000 . ? B7 B11 1.767(4) . ? B7 B8 1.768(5) . ? B7 B12 1.760(5) . ? B11 H11 1.1000 . ? B11 B10 1.749(5) . ? B11 B12 1.752(4) . ? B10 H10 1.1000 . ? B10 B5 1.775(4) . ? B10 B12 1.781(5) . ? B10 B9 1.774(5) . ? B5 H5A 1.1000 . ? B5 B4 1.780(4) . ? B5 B9 1.778(5) . ? B4 H4 1.1000 . ? B4 B8 1.763(5) . ? B4 B9 1.769(4) . ? B8 H8A 1.1000 . ? B8 B12 1.773(4) . ? B8 B9 1.780(5) . ? B12 H12 1.1000 . ? B12 B9 1.761(5) . ? B9 H9A 1.1000 . ? 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 C3 N1 H1 117.3 . . ? C3 N1 C4 125.3(2) . . ? C4 N1 H1 117.3 . . ? N1 C3 S1 125.66(18) . . ? N1 C3 C2 113.2(2) . . ? C2 C3 S1 121.13(18) . . ? C3 C2 C1 116.95(19) . . ? C3 C2 B6 115.39(18) . . ? C3 C2 B3 117.57(19) . . ? C3 C2 B5 121.9(2) . . ? C3 C2 B4 123.95(19) . . ? C1 C2 B6 60.85(15) . . ? C1 C2 B3 61.00(16) . . ? C1 C2 B5 109.82(18) . . ? C1 C2 B4 109.76(19) . . ? B3 C2 B6 113.55(19) . . ? B5 C2 B6 61.71(16) . . ? B5 C2 B3 114.24(19) . . ? B4 C2 B6 113.43(18) . . ? B4 C2 B3 62.11(18) . . ? B4 C2 B5 63.07(16) . . ? C5 C4 N1 119.9(2) . . ? C5 C4 C9 119.2(2) . . ? C9 C4 N1 120.8(2) . . ? C8 C7 C6 116.9(2) . . ? C8 C7 C10 119.5(3) . . ? C6 C7 C10 123.6(3) . . ? C2 C1 H1A 120.1 . . ? C2 C1 B6 62.18(15) . . ? C2 C1 B3 61.91(16) . . ? C2 C1 B7 112.4(2) . . ? C2 C1 B11 112.1(2) . . ? B6 C1 H1A 117.1 . . ? B6 C1 B3 115.4(2) . . ? B3 C1 H1A 117.2 . . ? B7 C1 H1A 118.0 . . ? B7 C1 B6 115.2(2) . . ? B7 C1 B3 62.79(17) . . ? B11 C1 H1A 118.4 . . ? B11 C1 B6 62.50(16) . . ? B11 C1 B3 114.9(2) . . ? B11 C1 B7 62.91(17) . . ? H11A C11 H11B 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? C4 C5 H5 120.1 . . ? C4 C5 C6 119.8(2) . . ? C6 C5 H5 120.1 . . ? C7 C8 H8 119.1 . . ? C9 C8 C7 121.9(3) . . ? C9 C8 H8 119.1 . . ? C7 C6 C5 121.7(2) . . ? C7 C6 H6 119.1 . . ? C5 C6 H6 119.1 . . ? C7 C10 H10A 108.0 . . ? C7 C10 H10B 108.0 . . ? C11 C10 C7 117.2(3) . . ? C11 C10 H10A 108.0 . . ? C11 C10 H10B 108.0 . . ? H10A C10 H10B 107.2 . . ? C4 C9 C8 120.5(2) . . ? C4 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C2 B6 H6A 124.5 . . ? C2 B6 B11 104.50(19) . . ? C2 B6 B10 105.2(2) . . ? C2 B6 B5 58.34(15) . . ? C1 B6 C2 56.98(14) . . ? C1 B6 H6A 125.1 . . ? C1 B6 B11 58.25(16) . . ? C1 B6 B10 104.3(2) . . ? C1 B6 B5 104.06(19) . . ? B11 B6 H6A 122.3 . . ? B10 B6 H6A 122.6 . . ? B10 B6 B11 59.81(19) . . ? B10 B6 B5 60.84(18) . . ? B5 B6 H6A 122.1 . . ? B5 B6 B11 108.1(2) . . ? C2 B3 H3 124.4 . . ? C2 B3 B7 104.82(19) . . ? C2 B3 B4 58.30(16) . . ? C2 B3 B8 104.9(2) . . ? C1 B3 C2 57.10(14) . . ? C1 B3 H3 125.3 . . ? C1 B3 B7 58.20(16) . . ? C1 B3 B4 103.7(2) . . ? C1 B3 B8 104.1(2) . . ? B7 B3 H3 122.1 . . ? B4 B3 H3 122.5 . . ? B4 B3 B7 107.9(2) . . ? B8 B3 H3 122.8 . . ? B8 B3 B7 60.18(19) . . ? B8 B3 B4 60.13(19) . . ? C1 B7 B3 59.00(15) . . ? C1 B7 H7 125.1 . . ? C1 B7 B11 58.44(16) . . ? C1 B7 B8 104.1(2) . . ? C1 B7 B12 104.0(2) . . ? B3 B7 H7 121.5 . . ? B11 B7 B3 108.1(2) . . ? B11 B7 H7 121.6 . . ? B11 B7 B8 107.8(2) . . ? B8 B7 B3 59.32(18) . . ? B8 B7 H7 122.7 . . ? B12 B7 B3 107.8(2) . . ? B12 B7 H7 122.6 . . ? B12 B7 B11 59.57(18) . . ? B12 B7 B8 60.35(19) . . ? C1 B11 B6 59.25(15) . . ? C1 B11 B7 58.65(16) . . ? C1 B11 H11 125.0 . . ? C1 B11 B10 104.8(2) . . ? C1 B11 B12 104.5(2) . . ? B6 B11 B7 108.9(2) . . ? B6 B11 H11 121.1 . . ? B7 B11 H11 120.9 . . ? B10 B11 B6 59.50(18) . . ? B10 B11 B7 109.3(2) . . ? B10 B11 H11 121.8 . . ? B10 B11 B12 61.15(19) . . ? B12 B11 B6 108.6(2) . . ? B12 B11 B7 60.02(18) . . ? B12 B11 H11 122.1 . . ? B6 B10 B11 60.69(18) . . ? B6 B10 H10 121.2 . . ? B6 B10 B5 60.07(17) . . ? B6 B10 B12 108.2(2) . . ? B6 B10 B9 108.2(2) . . ? B11 B10 H10 121.8 . . ? B11 B10 B5 108.2(2) . . ? B11 B10 B12 59.52(19) . . ? B11 B10 B9 107.2(2) . . ? B5 B10 H10 121.7 . . ? B5 B10 B12 107.7(2) . . ? B12 B10 H10 122.1 . . ? B9 B10 H10 122.1 . . ? B9 B10 B5 60.13(18) . . ? B9 B10 B12 59.39(19) . . ? C2 B5 B6 59.95(15) . . ? C2 B5 B10 105.1(2) . . ? C2 B5 H5A 124.2 . . ? C2 B5 B4 58.43(15) . . ? C2 B5 B9 104.5(2) . . ? B6 B5 B10 59.09(17) . . ? B6 B5 H5A 121.5 . . ? B6 B5 B4 108.2(2) . . ? B6 B5 B9 107.2(2) . . ? B10 B5 H5A 122.6 . . ? B10 B5 B4 107.6(2) . . ? B10 B5 B9 59.93(18) . . ? B4 B5 H5A 121.7 . . ? B9 B5 H5A 122.8 . . ? B9 B5 B4 59.63(17) . . ? C2 B4 B3 59.59(15) . . ? C2 B4 B5 58.50(15) . . ? C2 B4 H4 124.3 . . ? C2 B4 B8 105.5(2) . . ? C2 B4 B9 104.95(19) . . ? B3 B4 B5 108.4(2) . . ? B3 B4 H4 121.4 . . ? B3 B4 B9 108.0(2) . . ? B5 B4 H4 121.2 . . ? B8 B4 B3 59.53(19) . . ? B8 B4 B5 108.7(2) . . ? B8 B4 H4 122.0 . . ? B8 B4 B9 60.51(19) . . ? B9 B4 B5 60.13(17) . . ? B9 B4 H4 122.3 . . ? B3 B8 B7 60.50(18) . . ? B3 B8 B4 60.34(18) . . ? B3 B8 H8A 121.2 . . ? B3 B8 B12 108.2(2) . . ? B3 B8 B9 108.2(2) . . ? B7 B8 H8A 121.8 . . ? B7 B8 B12 59.61(19) . . ? B7 B8 B9 107.3(2) . . ? B4 B8 B7 108.3(2) . . ? B4 B8 H8A 121.6 . . ? B4 B8 B12 107.6(2) . . ? B4 B8 B9 59.90(19) . . ? B12 B8 H8A 122.1 . . ? B12 B8 B9 59.43(19) . . ? B9 B8 H8A 122.1 . . ? B7 B12 B10 108.1(2) . . ? B7 B12 B8 60.05(19) . . ? B7 B12 H12 121.4 . . ? B7 B12 B9 108.5(2) . . ? B11 B12 B7 60.41(18) . . ? B11 B12 B10 59.33(18) . . ? B11 B12 B8 108.2(2) . . ? B11 B12 H12 122.0 . . ? B11 B12 B9 107.7(2) . . ? B10 B12 H12 121.8 . . ? B8 B12 B10 108.4(2) . . ? B8 B12 H12 121.4 . . ? B9 B12 B10 60.1(2) . . ? B9 B12 B8 60.46(19) . . ? B9 B12 H12 121.5 . . ? B10 B9 B5 59.94(17) . . ? B10 B9 B8 108.4(2) . . ? B10 B9 H9A 121.4 . . ? B5 B9 B8 108.1(2) . . ? B5 B9 H9A 121.6 . . ? B4 B9 B10 108.1(2) . . ? B4 B9 B5 60.25(17) . . ? B4 B9 B8 59.59(18) . . ? B4 B9 H9A 121.9 . . ? B8 B9 H9A 121.7 . . ? B12 B9 B10 60.49(19) . . ? B12 B9 B5 108.4(2) . . ? B12 B9 B4 107.9(2) . . ? B12 B9 B8 60.1(2) . . ? B12 B9 H9A 121.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag S1 C3 C2 C1 16.0(3) . . . . ? S1 C3 C2 B6 -52.7(3) . . . . ? S1 C3 C2 B3 85.6(2) . . . . ? S1 C3 C2 B5 -123.9(2) . . . . ? S1 C3 C2 B4 159.05(19) . . . . ? N1 C3 C2 C1 -164.46(19) . . . . ? N1 C3 C2 B6 126.9(2) . . . . ? N1 C3 C2 B3 -94.8(3) . . . . ? N1 C3 C2 B5 55.7(3) . . . . ? N1 C3 C2 B4 -21.4(3) . . . . ? N1 C4 C5 C6 -176.8(3) . . . . ? N1 C4 C9 C8 177.0(3) . . . . ? C3 N1 C4 C5 -119.8(3) . . . . ? C3 N1 C4 C9 63.1(4) . . . . ? C3 C2 C1 B6 -105.5(2) . . . . ? C3 C2 C1 B3 108.2(2) . . . . ? C3 C2 C1 B7 146.9(2) . . . . ? C3 C2 C1 B11 -144.50(19) . . . . ? C3 C2 B6 C1 108.0(2) . . . . ? C3 C2 B6 B11 143.3(2) . . . . ? C3 C2 B6 B10 -154.6(2) . . . . ? C3 C2 B6 B5 -114.1(2) . . . . ? C3 C2 B3 C1 -107.2(2) . . . . ? C3 C2 B3 B7 -142.0(2) . . . . ? C3 C2 B3 B4 115.9(2) . . . . ? C3 C2 B3 B8 155.5(2) . . . . ? C3 C2 B5 B6 103.8(2) . . . . ? C3 C2 B5 B10 143.4(2) . . . . ? C3 C2 B5 B4 -114.9(2) . . . . ? C3 C2 B5 B9 -154.4(2) . . . . ? C3 C2 B4 B3 -106.0(3) . . . . ? C3 C2 B4 B5 111.9(3) . . . . ? C3 C2 B4 B8 -145.4(2) . . . . ? C3 C2 B4 B9 151.7(2) . . . . ? C2 C1 B6 B11 -138.9(2) . . . . ? C2 C1 B6 B10 -99.1(2) . . . . ? C2 C1 B6 B5 -36.09(17) . . . . ? C2 C1 B3 B7 139.4(2) . . . . ? C2 C1 B3 B4 36.70(18) . . . . ? C2 C1 B3 B8 98.8(2) . . . . ? C2 C1 B7 B3 -38.3(2) . . . . ? C2 C1 B7 B11 104.2(2) . . . . ? C2 C1 B7 B8 1.8(3) . . . . ? C2 C1 B7 B12 64.2(2) . . . . ? C2 C1 B11 B6 38.86(19) . . . . ? C2 C1 B11 B7 -104.7(2) . . . . ? C2 C1 B11 B10 -0.9(3) . . . . ? C2 C1 B11 B12 -64.4(3) . . . . ? C2 B6 B11 C1 -34.71(18) . . . . ? C2 B6 B11 B7 -2.3(3) . . . . ? C2 B6 B11 B10 99.4(2) . . . . ? C2 B6 B11 B12 61.5(3) . . . . ? C2 B6 B10 B11 -98.2(2) . . . . ? C2 B6 B10 B5 39.24(19) . . . . ? C2 B6 B10 B12 -61.1(3) . . . . ? C2 B6 B10 B9 1.8(3) . . . . ? C2 B6 B5 B10 -134.2(2) . . . . ? C2 B6 B5 B4 -34.15(18) . . . . ? C2 B6 B5 B9 -97.1(2) . . . . ? C2 B3 B7 C1 34.39(18) . . . . ? C2 B3 B7 B11 1.4(3) . . . . ? C2 B3 B7 B8 -99.0(2) . . . . ? C2 B3 B7 B12 -61.6(2) . . . . ? C2 B3 B4 B5 33.45(18) . . . . ? C2 B3 B4 B8 134.8(2) . . . . ? C2 B3 B4 B9 97.1(2) . . . . ? C2 B3 B8 B7 98.8(2) . . . . ? C2 B3 B8 B4 -38.70(18) . . . . ? C2 B3 B8 B12 61.6(3) . . . . ? C2 B3 B8 B9 -1.3(3) . . . . ? C2 B5 B4 B3 -33.89(19) . . . . ? C2 B5 B4 B8 -97.1(2) . . . . ? C2 B5 B4 B9 -134.5(2) . . . . ? C2 B5 B9 B10 -99.3(2) . . . . ? C2 B5 B9 B4 38.89(19) . . . . ? C2 B5 B9 B8 2.0(3) . . . . ? C2 B5 B9 B12 -61.6(3) . . . . ? C2 B4 B8 B3 39.45(18) . . . . ? C2 B4 B8 B7 1.1(3) . . . . ? C2 B4 B8 B12 -61.8(3) . . . . ? C2 B4 B8 B9 -98.7(2) . . . . ? C2 B4 B9 B10 -1.6(3) . . . . ? C2 B4 B9 B5 -39.0(2) . . . . ? C2 B4 B9 B8 99.6(2) . . . . ? C2 B4 B9 B12 62.4(3) . . . . ? C4 N1 C3 S1 6.6(4) . . . . ? C4 N1 C3 C2 -172.9(2) . . . . ? C4 C5 C6 C7 -0.5(5) . . . . ? C7 C8 C9 C4 0.0(5) . . . . ? C1 C2 B6 B11 35.27(19) . . . . ? C1 C2 B6 B10 97.4(2) . . . . ? C1 C2 B6 B5 137.8(2) . . . . ? C1 C2 B3 B7 -34.87(19) . . . . ? C1 C2 B3 B4 -137.0(2) . . . . ? C1 C2 B3 B8 -97.4(2) . . . . ? C1 C2 B5 B6 -38.55(18) . . . . ? C1 C2 B5 B10 1.0(3) . . . . ? C1 C2 B5 B4 102.7(2) . . . . ? C1 C2 B5 B9 63.2(2) . . . . ? C1 C2 B4 B3 39.37(18) . . . . ? C1 C2 B4 B5 -102.8(2) . . . . ? C1 C2 B4 B8 0.0(3) . . . . ? C1 C2 B4 B9 -63.0(3) . . . . ? C1 B6 B11 B7 32.4(2) . . . . ? C1 B6 B11 B10 134.1(2) . . . . ? C1 B6 B11 B12 96.2(2) . . . . ? C1 B6 B10 B11 -39.06(18) . . . . ? C1 B6 B10 B5 98.3(2) . . . . ? C1 B6 B10 B12 -2.0(3) . . . . ? C1 B6 B10 B9 60.9(3) . . . . ? C1 B6 B5 C2 35.47(17) . . . . ? C1 B6 B5 B10 -98.7(2) . . . . ? C1 B6 B5 B4 1.3(2) . . . . ? C1 B6 B5 B9 -61.6(2) . . . . ? C1 B3 B7 B11 -33.0(2) . . . . ? C1 B3 B7 B8 -133.3(2) . . . . ? C1 B3 B7 B12 -96.0(2) . . . . ? C1 B3 B4 C2 -36.14(17) . . . . ? C1 B3 B4 B5 -2.7(3) . . . . ? C1 B3 B4 B8 98.6(2) . . . . ? C1 B3 B4 B9 61.0(3) . . . . ? C1 B3 B8 B7 39.6(2) . . . . ? C1 B3 B8 B4 -97.9(2) . . . . ? C1 B3 B8 B12 2.5(3) . . . . ? C1 B3 B8 B9 -60.4(3) . . . . ? C1 B7 B11 B6 -32.6(2) . . . . ? C1 B7 B11 B10 -96.0(2) . . . . ? C1 B7 B11 B12 -133.7(2) . . . . ? C1 B7 B8 B3 -39.99(19) . . . . ? C1 B7 B8 B4 -1.8(3) . . . . ? C1 B7 B8 B12 98.3(2) . . . . ? C1 B7 B8 B9 61.5(3) . . . . ? C1 B7 B12 B11 39.44(19) . . . . ? C1 B7 B12 B10 2.8(3) . . . . ? C1 B7 B12 B8 -98.4(2) . . . . ? C1 B7 B12 B9 -60.8(3) . . . . ? C1 B11 B10 B6 39.67(18) . . . . ? C1 B11 B10 B5 1.5(3) . . . . ? C1 B11 B10 B12 -98.7(2) . . . . ? C1 B11 B10 B9 -61.9(3) . . . . ? C1 B11 B12 B7 -39.6(2) . . . . ? C1 B11 B12 B10 99.1(2) . . . . ? C1 B11 B12 B8 -1.9(3) . . . . ? C1 B11 B12 B9 62.0(3) . . . . ? C5 C4 C9 C8 -0.1(5) . . . . ? C8 C7 C6 C5 0.3(5) . . . . ? C8 C7 C10 C11 -164.3(3) . . . . ? C6 C7 C8 C9 -0.1(5) . . . . ? C6 C7 C10 C11 17.8(5) . . . . ? C10 C7 C8 C9 -178.1(3) . . . . ? C10 C7 C6 C5 178.3(3) . . . . ? C9 C4 C5 C6 0.4(4) . . . . ? B6 C2 C1 B3 -146.3(2) . . . . ? B6 C2 C1 B7 -107.6(2) . . . . ? B6 C2 C1 B11 -38.99(19) . . . . ? B6 C2 B3 C1 31.88(19) . . . . ? B6 C2 B3 B7 -3.0(3) . . . . ? B6 C2 B3 B4 -105.1(2) . . . . ? B6 C2 B3 B8 -65.5(2) . . . . ? B6 C2 B5 B10 39.58(19) . . . . ? B6 C2 B5 B4 141.3(2) . . . . ? B6 C2 B5 B9 101.8(2) . . . . ? B6 C2 B4 B3 105.3(2) . . . . ? B6 C2 B4 B5 -36.9(2) . . . . ? B6 C2 B4 B8 65.8(3) . . . . ? B6 C2 B4 B9 2.9(3) . . . . ? B6 C1 B3 C2 -32.88(19) . . . . ? B6 C1 B3 B7 106.6(2) . . . . ? B6 C1 B3 B4 3.8(3) . . . . ? B6 C1 B3 B8 66.0(3) . . . . ? B6 C1 B7 B3 -107.0(2) . . . . ? B6 C1 B7 B11 35.6(2) . . . . ? B6 C1 B7 B8 -66.8(3) . . . . ? B6 C1 B7 B12 -4.4(3) . . . . ? B6 C1 B11 B7 -143.6(2) . . . . ? B6 C1 B11 B10 -39.80(19) . . . . ? B6 C1 B11 B12 -103.2(2) . . . . ? B6 B11 B10 B5 -38.13(19) . . . . ? B6 B11 B10 B12 -138.3(2) . . . . ? B6 B11 B10 B9 -101.6(2) . . . . ? B6 B11 B12 B7 -101.6(2) . . . . ? B6 B11 B12 B10 37.2(2) . . . . ? B6 B11 B12 B8 -63.9(3) . . . . ? B6 B11 B12 B9 0.0(3) . . . . ? B6 B10 B5 C2 -40.00(18) . . . . ? B6 B10 B5 B4 -101.1(2) . . . . ? B6 B10 B5 B9 -138.3(2) . . . . ? B6 B10 B12 B7 -0.6(3) . . . . ? B6 B10 B12 B11 -37.6(2) . . . . ? B6 B10 B12 B8 63.0(3) . . . . ? B6 B10 B12 B9 100.8(2) . . . . ? B6 B10 B9 B5 37.4(2) . . . . ? B6 B10 B9 B4 -0.1(3) . . . . ? B6 B10 B9 B8 -63.3(3) . . . . ? B6 B10 B9 B12 -100.9(3) . . . . ? B6 B5 B4 C2 34.78(18) . . . . ? B6 B5 B4 B3 0.9(3) . . . . ? B6 B5 B4 B8 -62.3(3) . . . . ? B6 B5 B4 B9 -99.7(2) . . . . ? B6 B5 B9 B10 -36.7(2) . . . . ? B6 B5 B9 B4 101.4(2) . . . . ? B6 B5 B9 B8 64.5(3) . . . . ? B6 B5 B9 B12 0.9(3) . . . . ? B3 C2 C1 B6 146.3(2) . . . . ? B3 C2 C1 B7 38.7(2) . . . . ? B3 C2 C1 B11 107.3(2) . . . . ? B3 C2 B6 C1 -31.93(19) . . . . ? B3 C2 B6 B11 3.3(3) . . . . ? B3 C2 B6 B10 65.4(3) . . . . ? B3 C2 B6 B5 105.9(2) . . . . ? B3 C2 B5 B6 -104.8(2) . . . . ? B3 C2 B5 B10 -65.2(2) . . . . ? B3 C2 B5 B4 36.5(2) . . . . ? B3 C2 B5 B9 -3.0(3) . . . . ? B3 C2 B4 B5 -142.2(2) . . . . ? B3 C2 B4 B8 -39.4(2) . . . . ? B3 C2 B4 B9 -102.4(3) . . . . ? B3 C1 B6 C2 32.79(19) . . . . ? B3 C1 B6 B11 -106.1(2) . . . . ? B3 C1 B6 B10 -66.3(3) . . . . ? B3 C1 B6 B5 -3.3(3) . . . . ? B3 C1 B7 B11 142.6(2) . . . . ? B3 C1 B7 B8 40.1(2) . . . . ? B3 C1 B7 B12 102.6(2) . . . . ? B3 C1 B11 B6 107.0(2) . . . . ? B3 C1 B11 B7 -36.6(2) . . . . ? B3 C1 B11 B10 67.2(3) . . . . ? B3 C1 B11 B12 3.8(3) . . . . ? B3 B7 B11 C1 33.2(2) . . . . ? B3 B7 B11 B6 0.6(3) . . . . ? B3 B7 B11 B10 -62.8(3) . . . . ? B3 B7 B11 B12 -100.4(3) . . . . ? B3 B7 B8 B4 38.2(2) . . . . ? B3 B7 B8 B12 138.3(2) . . . . ? B3 B7 B8 B9 101.5(2) . . . . ? B3 B7 B12 B11 100.9(2) . . . . ? B3 B7 B12 B10 64.3(3) . . . . ? B3 B7 B12 B8 -36.9(2) . . . . ? B3 B7 B12 B9 0.7(3) . . . . ? B3 B4 B8 B7 -38.3(2) . . . . ? B3 B4 B8 B12 -101.3(2) . . . . ? B3 B4 B8 B9 -138.1(2) . . . . ? B3 B4 B9 B10 -64.0(3) . . . . ? B3 B4 B9 B5 -101.4(2) . . . . ? B3 B4 B9 B8 37.2(2) . . . . ? B3 B4 B9 B12 0.0(3) . . . . ? B3 B8 B12 B7 37.5(2) . . . . ? B3 B8 B12 B11 -0.4(3) . . . . ? B3 B8 B12 B10 -63.2(3) . . . . ? B3 B8 B12 B9 -100.8(3) . . . . ? B3 B8 B9 B10 63.0(3) . . . . ? B3 B8 B9 B5 -0.5(3) . . . . ? B3 B8 B9 B4 -37.6(2) . . . . ? B3 B8 B9 B12 100.8(2) . . . . ? B7 C1 B6 C2 103.2(2) . . . . ? B7 C1 B6 B11 -35.7(2) . . . . ? B7 C1 B6 B10 4.1(3) . . . . ? B7 C1 B6 B5 67.1(2) . . . . ? B7 C1 B3 C2 -139.4(2) . . . . ? B7 C1 B3 B4 -102.7(2) . . . . ? B7 C1 B3 B8 -40.6(2) . . . . ? B7 C1 B11 B6 143.6(2) . . . . ? B7 C1 B11 B10 103.8(2) . . . . ? B7 C1 B11 B12 40.3(2) . . . . ? B7 B3 B4 C2 -96.7(2) . . . . ? B7 B3 B4 B5 -63.3(3) . . . . ? B7 B3 B4 B8 38.05(19) . . . . ? B7 B3 B4 B9 0.4(3) . . . . ? B7 B3 B8 B4 -137.5(2) . . . . ? B7 B3 B8 B12 -37.1(2) . . . . ? B7 B3 B8 B9 -100.0(2) . . . . ? B7 B11 B10 B6 101.1(2) . . . . ? B7 B11 B10 B5 63.0(3) . . . . ? B7 B11 B10 B12 -37.2(2) . . . . ? B7 B11 B10 B9 -0.4(3) . . . . ? B7 B11 B12 B10 138.8(2) . . . . ? B7 B11 B12 B8 37.7(2) . . . . ? B7 B11 B12 B9 101.6(2) . . . . ? B7 B8 B12 B11 -37.9(2) . . . . ? B7 B8 B12 B10 -100.7(2) . . . . ? B7 B8 B12 B9 -138.3(2) . . . . ? B7 B8 B9 B10 -0.8(3) . . . . ? B7 B8 B9 B5 -64.3(3) . . . . ? B7 B8 B9 B4 -101.5(2) . . . . ? B7 B8 B9 B12 36.9(2) . . . . ? B7 B12 B9 B10 100.7(2) . . . . ? B7 B12 B9 B5 63.3(3) . . . . ? B7 B12 B9 B4 -0.4(3) . . . . ? B7 B12 B9 B8 -37.4(2) . . . . ? B11 C1 B6 C2 138.9(2) . . . . ? B11 C1 B6 B10 39.8(2) . . . . ? B11 C1 B6 B5 102.8(2) . . . . ? B11 C1 B3 C2 -102.8(2) . . . . ? B11 C1 B3 B7 36.6(2) . . . . ? B11 C1 B3 B4 -66.1(3) . . . . ? B11 C1 B3 B8 -4.0(3) . . . . ? B11 C1 B7 B3 -142.6(2) . . . . ? B11 C1 B7 B8 -102.4(2) . . . . ? B11 C1 B7 B12 -40.0(2) . . . . ? B11 B6 B10 B5 137.4(2) . . . . ? B11 B6 B10 B12 37.1(2) . . . . ? B11 B6 B10 B9 100.0(3) . . . . ? B11 B6 B5 C2 96.2(2) . . . . ? B11 B6 B5 B10 -38.0(2) . . . . ? B11 B6 B5 B4 62.0(2) . . . . ? B11 B6 B5 B9 -0.9(3) . . . . ? B11 B7 B8 B3 -100.9(2) . . . . ? B11 B7 B8 B4 -62.7(3) . . . . ? B11 B7 B8 B12 37.4(2) . . . . ? B11 B7 B8 B9 0.6(3) . . . . ? B11 B7 B12 B10 -36.6(2) . . . . ? B11 B7 B12 B8 -137.9(2) . . . . ? B11 B7 B12 B9 -100.3(2) . . . . ? B11 B10 B5 C2 -1.6(3) . . . . ? B11 B10 B5 B6 38.4(2) . . . . ? B11 B10 B5 B4 -62.7(3) . . . . ? B11 B10 B5 B9 -99.8(2) . . . . ? B11 B10 B12 B7 37.1(2) . . . . ? B11 B10 B12 B8 100.7(2) . . . . ? B11 B10 B12 B9 138.4(2) . . . . ? B11 B10 B9 B5 101.5(2) . . . . ? B11 B10 B9 B4 63.9(3) . . . . ? B11 B10 B9 B8 0.8(3) . . . . ? B11 B10 B9 B12 -36.8(2) . . . . ? B11 B12 B9 B10 36.8(2) . . . . ? B11 B12 B9 B5 -0.6(3) . . . . ? B11 B12 B9 B4 -64.3(3) . . . . ? B11 B12 B9 B8 -101.3(2) . . . . ? B10 B6 B11 C1 -134.1(2) . . . . ? B10 B6 B11 B7 -101.7(2) . . . . ? B10 B6 B11 B12 -37.9(2) . . . . ? B10 B6 B5 C2 134.2(2) . . . . ? B10 B6 B5 B4 100.0(2) . . . . ? B10 B6 B5 B9 37.1(2) . . . . ? B10 B11 B12 B7 -138.8(2) . . . . ? B10 B11 B12 B8 -101.1(3) . . . . ? B10 B11 B12 B9 -37.2(2) . . . . ? B10 B5 B4 C2 97.2(2) . . . . ? B10 B5 B4 B3 63.3(3) . . . . ? B10 B5 B4 B8 0.2(3) . . . . ? B10 B5 B4 B9 -37.3(2) . . . . ? B10 B5 B9 B4 138.2(2) . . . . ? B10 B5 B9 B8 101.3(3) . . . . ? B10 B5 B9 B12 37.6(2) . . . . ? B10 B12 B9 B5 -37.4(2) . . . . ? B10 B12 B9 B4 -101.1(2) . . . . ? B10 B12 B9 B8 -138.1(2) . . . . ? B5 C2 C1 B6 38.93(19) . . . . ? B5 C2 C1 B3 -107.4(2) . . . . ? B5 C2 C1 B7 -68.7(2) . . . . ? B5 C2 C1 B11 -0.1(3) . . . . ? B5 C2 B6 C1 -137.8(2) . . . . ? B5 C2 B6 B11 -102.6(2) . . . . ? B5 C2 B6 B10 -40.5(2) . . . . ? B5 C2 B3 C1 100.1(2) . . . . ? B5 C2 B3 B7 65.2(3) . . . . ? B5 C2 B3 B4 -36.84(19) . . . . ? B5 C2 B3 B8 2.7(3) . . . . ? B5 C2 B4 B3 142.2(2) . . . . ? B5 C2 B4 B8 102.8(2) . . . . ? B5 C2 B4 B9 39.8(2) . . . . ? B5 B6 B11 C1 -95.6(2) . . . . ? B5 B6 B11 B7 -63.2(3) . . . . ? B5 B6 B11 B10 38.45(19) . . . . ? B5 B6 B11 B12 0.5(3) . . . . ? B5 B6 B10 B11 -137.4(2) . . . . ? B5 B6 B10 B12 -100.3(2) . . . . ? B5 B6 B10 B9 -37.4(2) . . . . ? B5 B10 B12 B7 -64.0(3) . . . . ? B5 B10 B12 B11 -101.1(2) . . . . ? B5 B10 B12 B8 -0.5(3) . . . . ? B5 B10 B12 B9 37.3(2) . . . . ? B5 B10 B9 B4 -37.5(2) . . . . ? B5 B10 B9 B8 -100.7(2) . . . . ? B5 B10 B9 B12 -138.3(2) . . . . ? B5 B4 B8 B3 100.9(2) . . . . ? B5 B4 B8 B7 62.6(3) . . . . ? B5 B4 B8 B12 -0.4(3) . . . . ? B5 B4 B8 B9 -37.3(2) . . . . ? B5 B4 B9 B10 37.4(2) . . . . ? B5 B4 B9 B8 138.6(2) . . . . ? B5 B4 B9 B12 101.4(2) . . . . ? B4 C2 C1 B6 106.5(2) . . . . ? B4 C2 C1 B3 -39.9(2) . . . . ? B4 C2 C1 B7 -1.2(3) . . . . ? B4 C2 C1 B11 67.5(2) . . . . ? B4 C2 B6 C1 -100.4(2) . . . . ? B4 C2 B6 B11 -65.1(3) . . . . ? B4 C2 B6 B10 -3.0(3) . . . . ? B4 C2 B6 B5 37.4(2) . . . . ? B4 C2 B3 C1 137.0(2) . . . . ? B4 C2 B3 B7 102.1(2) . . . . ? B4 C2 B3 B8 39.58(19) . . . . ? B4 C2 B5 B6 -141.3(2) . . . . ? B4 C2 B5 B10 -101.7(2) . . . . ? B4 C2 B5 B9 -39.5(2) . . . . ? B4 B3 B7 C1 95.3(2) . . . . ? B4 B3 B7 B11 62.3(3) . . . . ? B4 B3 B7 B8 -38.0(2) . . . . ? B4 B3 B7 B12 -0.7(3) . . . . ? B4 B3 B8 B7 137.5(2) . . . . ? B4 B3 B8 B12 100.3(3) . . . . ? B4 B3 B8 B9 37.4(2) . . . . ? B4 B5 B9 B10 -138.2(2) . . . . ? B4 B5 B9 B8 -36.9(2) . . . . ? B4 B5 B9 B12 -100.5(3) . . . . ? B4 B8 B12 B7 101.3(2) . . . . ? B4 B8 B12 B11 63.4(3) . . . . ? B4 B8 B12 B10 0.5(3) . . . . ? B4 B8 B12 B9 -37.0(2) . . . . ? B4 B8 B9 B10 100.6(2) . . . . ? B4 B8 B9 B5 37.2(2) . . . . ? B4 B8 B9 B12 138.4(2) . . . . ? B8 B3 B7 C1 133.3(2) . . . . ? B8 B3 B7 B11 100.3(3) . . . . ? B8 B3 B7 B12 37.4(2) . . . . ? B8 B3 B4 C2 -134.8(2) . . . . ? B8 B3 B4 B5 -101.3(2) . . . . ? B8 B3 B4 B9 -37.7(2) . . . . ? B8 B7 B11 C1 95.9(2) . . . . ? B8 B7 B11 B6 63.3(3) . . . . ? B8 B7 B11 B10 -0.1(3) . . . . ? B8 B7 B11 B12 -37.8(2) . . . . ? B8 B7 B12 B11 137.9(2) . . . . ? B8 B7 B12 B10 101.3(2) . . . . ? B8 B7 B12 B9 37.6(2) . . . . ? B8 B4 B9 B10 -101.2(3) . . . . ? B8 B4 B9 B5 -138.6(2) . . . . ? B8 B4 B9 B12 -37.2(2) . . . . ? B8 B12 B9 B10 138.1(2) . . . . ? B8 B12 B9 B5 100.7(2) . . . . ? B8 B12 B9 B4 37.0(2) . . . . ? B12 B7 B11 C1 133.7(2) . . . . ? B12 B7 B11 B6 101.0(3) . . . . ? B12 B7 B11 B10 37.7(2) . . . . ? B12 B7 B8 B3 -138.3(2) . . . . ? B12 B7 B8 B4 -100.1(2) . . . . ? B12 B7 B8 B9 -36.8(2) . . . . ? B12 B11 B10 B6 138.3(2) . . . . ? B12 B11 B10 B5 100.2(2) . . . . ? B12 B11 B10 B9 36.7(2) . . . . ? B12 B10 B5 C2 61.3(3) . . . . ? B12 B10 B5 B6 101.3(2) . . . . ? B12 B10 B5 B4 0.2(3) . . . . ? B12 B10 B5 B9 -37.0(2) . . . . ? B12 B10 B9 B5 138.3(2) . . . . ? B12 B10 B9 B4 100.7(3) . . . . ? B12 B10 B9 B8 37.6(2) . . . . ? B12 B8 B9 B10 -37.8(2) . . . . ? B12 B8 B9 B5 -101.2(2) . . . . ? B12 B8 B9 B4 -138.4(2) . . . . ? B9 B10 B5 C2 98.3(2) . . . . ? B9 B10 B5 B6 138.3(2) . . . . ? B9 B10 B5 B4 37.1(2) . . . . ? B9 B10 B12 B7 -101.3(2) . . . . ? B9 B10 B12 B11 -138.4(2) . . . . ? B9 B10 B12 B8 -37.7(2) . . . . ? B9 B5 B4 C2 134.5(2) . . . . ? B9 B5 B4 B3 100.6(3) . . . . ? B9 B5 B4 B8 37.4(2) . . . . ? B9 B4 B8 B3 138.1(2) . . . . ? B9 B4 B8 B7 99.8(2) . . . . ? B9 B4 B8 B12 36.8(2) . . . . ? B9 B8 B12 B7 138.3(2) . . . . ? B9 B8 B12 B11 100.4(3) . . . . ? B9 B8 B12 B10 37.6(2) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 963492'