# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2008 data_global _journal_name_full 'New J.Chem.' _journal_coden_Cambridge 0440 _publ_contact_author_name 'Tony D James' _publ_contact_author_email T.D.JAMES@BATH.AC.UK _publ_section_title ; Dynamic Covalent Self-Assembled Macrocycles Prepared >From 2-Formyl-Aryl-Boronic acids and 1,2-Amino Alcohols. ; loop_ _publ_author_name 'Tony D James' 'Steven Bull' 'M Davidson' 'John Fossey' 'Ewan Galbraith' 'Andrew M Kelly' ; G.Kociok-Kohn ; # Attachment 'h06tdj1.cif' data_h06tdj1 _database_code_depnum_ccdc_archive 'CCDC 694358' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C33 H30 B N O3' _chemical_formula_sum 'C33 H30 B N O3' _chemical_formula_weight 499.39 _chemical_absolute_configuration syn 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.1770(2) _cell_length_b 14.8410(5) _cell_length_c 10.5950(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.8390(10) _cell_angle_gamma 90.00 _cell_volume 1281.17(6) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 12737 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.295 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9720 _exptl_absorpt_correction_T_max 0.9799 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method '148 2.0 degree images with \w scans' _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 15517 _diffrn_reflns_av_R_equivalents 0.0875 _diffrn_reflns_av_sigmaI/netI 0.0853 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 6.27 _diffrn_reflns_theta_max 27.51 _reflns_number_total 5671 _reflns_number_gt 4650 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinski & Minor, 1997)' _computing_data_reduction ; DENZO-SCALEPACK Z. Otwinowski and W. Minor, " Processing of X-ray Diffraction Data Collected in Oscillation Mode ", Methods in Enzymology, Volume 276: Macromolecular Crystallography, part A, p.307-326, 1997,C.W. Carter, Jr. & R. M. Sweet, Eds., Academic Press. ; _computing_structure_solution ; SIR97- Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C. , Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. (1999) J. Appl. Cryst. 32, 115-119 ; _computing_structure_refinement ; SHELXL97 -Program for Crystal Structure Analysis (Release 97-2). Sheldrick, G.M., Instit\"ut f\"ur Anorganische Chemie der Universit\"at, Tammanstrasse 4, D-3400 G\"ottingen, Germany, 1998 ; _computing_molecular_graphics 'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565' _computing_publication_material ; 'WinGX publication routines, Farrugia, L. J., J. Appl. Crystallogr., 1999, 32, 837-838 ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0765P)^2^+0.0329P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.3(11) _refine_ls_number_reflns 5671 _refine_ls_number_parameters 347 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0681 _refine_ls_R_factor_gt 0.0514 _refine_ls_wR_factor_ref 0.1329 _refine_ls_wR_factor_gt 0.1221 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group B B 0.4797(3) 0.10323(17) 0.7371(2) 0.0275(5) Uani 1 1 d . . . N N 0.2785(2) 0.08864(13) 0.74260(17) 0.0277(4) Uani 1 1 d . . . O1 O 0.55508(18) 0.14995(11) 0.84713(13) 0.0289(3) Uani 1 1 d . . . O2 O 0.48509(16) 0.15519(10) 0.61932(13) 0.0279(3) Uani 1 1 d . . . O3 O 0.10583(19) -0.03638(12) 0.73352(16) 0.0372(4) Uani 1 1 d . . . C1 C 0.5442(2) 0.24211(15) 0.85298(19) 0.0269(4) Uani 1 1 d . . . C2 C 0.4685(3) 0.27869(17) 0.9566(2) 0.0318(5) Uani 1 1 d . . . H2 H 0.4310 0.2396 1.0191 0.038 Uiso 1 1 calc R . . C3 C 0.4490(3) 0.36895(17) 0.9678(2) 0.0329(5) Uani 1 1 d . . . H3 H 0.3996 0.3927 1.0386 0.039 Uiso 1 1 calc R . . C4 C 0.5018(3) 0.42820(16) 0.8746(2) 0.0292(4) Uani 1 1 d . . . C5 C 0.4691(3) 0.52196(17) 0.8785(2) 0.0345(5) Uani 1 1 d . . . H5 H 0.4164 0.5462 0.9475 0.041 Uiso 1 1 calc R . . C6 C 0.5125(3) 0.57802(17) 0.7846(2) 0.0364(5) Uani 1 1 d . . . H6 H 0.4896 0.6407 0.7886 0.044 Uiso 1 1 calc R . . C7 C 0.5911(3) 0.54293(16) 0.6818(2) 0.0343(5) Uani 1 1 d . . . H7 H 0.6210 0.5820 0.6166 0.041 Uiso 1 1 calc R . . C8 C 0.6245(3) 0.45255(16) 0.6756(2) 0.0299(4) Uani 1 1 d . . . H8 H 0.6769 0.4299 0.6055 0.036 Uiso 1 1 calc R . . C9 C 0.5823(2) 0.39197(15) 0.77181(19) 0.0264(4) Uani 1 1 d . . . C10 C 0.6115(2) 0.29748(15) 0.76542(19) 0.0253(4) Uani 1 1 d . . . C11 C 0.7089(2) 0.25496(15) 0.66807(18) 0.0256(4) Uani 1 1 d . . . C12 C 0.8740(3) 0.28154(15) 0.6498(2) 0.0283(4) Uani 1 1 d . . . C13 C 0.9574(3) 0.35152(16) 0.7204(2) 0.0318(5) Uani 1 1 d . . . H13 H 0.9027 0.3830 0.7826 0.038 Uiso 1 1 calc R . . C14 C 1.1161(3) 0.37442(18) 0.7003(2) 0.0362(5) Uani 1 1 d . . . H14 H 1.1696 0.4213 0.7488 0.043 Uiso 1 1 calc R . . C15 C 1.2004(3) 0.3290(2) 0.6081(2) 0.0385(5) Uani 1 1 d . . . H15 H 1.3087 0.3464 0.5928 0.046 Uiso 1 1 calc R . . C16 C 1.1248(3) 0.26000(19) 0.5415(2) 0.0353(5) Uani 1 1 d . . . H16 H 1.1831 0.2280 0.4819 0.042 Uiso 1 1 calc R . . C17 C 0.9611(2) 0.23491(16) 0.55924(19) 0.0287(4) Uani 1 1 d . . . C18 C 0.8838(3) 0.16090(17) 0.4914(2) 0.0327(5) Uani 1 1 d . . . H18 H 0.9414 0.1294 0.4309 0.039 Uiso 1 1 calc R . . C19 C 0.7291(3) 0.13504(16) 0.5124(2) 0.0302(4) Uani 1 1 d . . . H19 H 0.6799 0.0851 0.4678 0.036 Uiso 1 1 calc R . . C20 C 0.6413(2) 0.18236(14) 0.60055(19) 0.0260(4) Uani 1 1 d . . . C21 C 0.5313(2) 0.00082(16) 0.72471(19) 0.0285(4) Uani 1 1 d . . . C22 C 0.6860(3) -0.04001(17) 0.7341(2) 0.0319(5) Uani 1 1 d . . . H22 H 0.7811 -0.0055 0.7593 0.038 Uiso 1 1 calc R . . C23 C 0.7006(3) -0.13115(18) 0.7064(2) 0.0368(5) Uani 1 1 d . . . H23 H 0.8057 -0.1588 0.7133 0.044 Uiso 1 1 calc R . . C24 C 0.5620(3) -0.18190(18) 0.6687(2) 0.0397(5) Uani 1 1 d . . . H24 H 0.5735 -0.2440 0.6496 0.048 Uiso 1 1 calc R . . C25 C 0.4074(3) -0.14315(17) 0.6587(2) 0.0365(5) Uani 1 1 d . . . H25 H 0.3126 -0.1779 0.6336 0.044 Uiso 1 1 calc R . . C26 C 0.3951(3) -0.05189(16) 0.6864(2) 0.0302(5) Uani 1 1 d . . . C27 C 0.2371(3) 0.00083(16) 0.6732(2) 0.0311(5) Uani 1 1 d . . . H27 H 0.2031 0.0128 0.5818 0.037 Uiso 1 1 calc R . . C28 C 0.1474(3) -0.02072(17) 0.8653(2) 0.0350(5) Uani 1 1 d . . . H28A H 0.2309 -0.0645 0.8998 0.042 Uiso 1 1 calc R . . H28B H 0.0491 -0.0260 0.9134 0.042 Uiso 1 1 calc R . . C29 C 0.2162(3) 0.07613(16) 0.8731(2) 0.0289(4) Uani 1 1 d . . . H29 H 0.3109 0.0788 0.9393 0.035 Uiso 1 1 calc R . . C30 C 0.0921(3) 0.14911(17) 0.8991(2) 0.0325(5) Uani 1 1 d . . . H30A H -0.0152 0.1328 0.8547 0.039 Uiso 1 1 calc R . . H30B H 0.1276 0.2065 0.8624 0.039 Uiso 1 1 calc R . . C31 C 0.0683(3) 0.16460(19) 1.0397(2) 0.0370(5) Uani 1 1 d . . . H31 H 0.1777 0.1814 1.0824 0.044 Uiso 1 1 calc R . . C32 C 0.0101(4) 0.0813(3) 1.1070(3) 0.0579(8) Uani 1 1 d . . . H32A H 0.0863 0.0314 1.0965 0.087 Uiso 1 1 calc R . . H32B H -0.0997 0.0645 1.0704 0.087 Uiso 1 1 calc R . . H32C H 0.0063 0.0944 1.1974 0.087 Uiso 1 1 calc R . . C33 C -0.0452(4) 0.2440(3) 1.0535(3) 0.0606(9) Uani 1 1 d . . . H33A H -0.0042 0.2964 1.0094 0.091 Uiso 1 1 calc R . . H33B H -0.0493 0.2583 1.1435 0.091 Uiso 1 1 calc R . . H33C H -0.1557 0.2288 1.0165 0.091 Uiso 1 1 calc R . . H H 0.217(3) 0.133(2) 0.707(3) 0.035(7) Uiso 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 B 0.0279(11) 0.0260(13) 0.0290(11) 0.0025(9) 0.0039(8) -0.0025(9) N 0.0279(9) 0.0257(10) 0.0295(9) 0.0027(7) 0.0031(7) 0.0002(7) O1 0.0339(7) 0.0240(8) 0.0288(7) 0.0016(6) 0.0020(5) -0.0036(6) O2 0.0291(7) 0.0267(8) 0.0280(7) 0.0024(6) 0.0033(5) -0.0028(6) O3 0.0318(8) 0.0344(10) 0.0461(9) -0.0020(7) 0.0072(6) -0.0071(6) C1 0.0290(10) 0.0227(11) 0.0287(10) 0.0005(8) -0.0004(7) -0.0039(8) C2 0.0334(11) 0.0345(13) 0.0280(10) 0.0007(8) 0.0052(8) -0.0063(9) C3 0.0323(10) 0.0363(13) 0.0307(10) -0.0077(9) 0.0061(8) -0.0033(9) C4 0.0270(10) 0.0305(12) 0.0298(10) -0.0062(8) 0.0013(8) -0.0020(8) C5 0.0338(11) 0.0324(13) 0.0366(11) -0.0079(9) -0.0004(8) 0.0017(9) C6 0.0421(12) 0.0238(12) 0.0420(12) -0.0027(9) -0.0036(9) 0.0031(9) C7 0.0388(12) 0.0271(13) 0.0364(12) 0.0033(9) -0.0003(9) -0.0010(9) C8 0.0297(10) 0.0295(12) 0.0302(10) -0.0005(8) 0.0014(8) 0.0004(8) C9 0.0268(9) 0.0247(11) 0.0273(10) -0.0016(8) 0.0000(7) -0.0019(7) C10 0.0255(10) 0.0255(11) 0.0247(9) -0.0008(7) 0.0012(7) -0.0015(7) C11 0.0283(9) 0.0235(10) 0.0251(9) 0.0011(8) 0.0028(7) -0.0012(8) C12 0.0308(10) 0.0269(11) 0.0271(10) 0.0050(8) 0.0021(8) 0.0013(8) C13 0.0315(11) 0.0303(12) 0.0333(11) 0.0023(9) 0.0003(8) -0.0018(9) C14 0.0313(11) 0.0356(14) 0.0409(12) 0.0010(10) -0.0026(9) -0.0068(9) C15 0.0271(10) 0.0474(16) 0.0412(12) 0.0069(10) 0.0045(9) -0.0041(9) C16 0.0311(11) 0.0400(14) 0.0357(11) 0.0061(10) 0.0085(8) 0.0022(9) C17 0.0282(10) 0.0299(12) 0.0282(10) 0.0040(8) 0.0040(8) 0.0023(8) C18 0.0349(11) 0.0348(13) 0.0291(10) 0.0001(9) 0.0075(8) 0.0034(9) C19 0.0349(11) 0.0278(12) 0.0281(10) -0.0029(8) 0.0037(8) -0.0006(8) C20 0.0288(9) 0.0237(11) 0.0260(9) 0.0027(8) 0.0044(7) 0.0010(8) C21 0.0311(10) 0.0271(12) 0.0276(10) 0.0006(8) 0.0050(8) -0.0016(8) C22 0.0304(10) 0.0337(12) 0.0320(10) 0.0018(9) 0.0048(8) 0.0026(9) C23 0.0395(12) 0.0351(13) 0.0372(11) 0.0025(10) 0.0118(9) 0.0074(10) C24 0.0531(14) 0.0279(13) 0.0404(12) -0.0017(9) 0.0164(10) 0.0033(10) C25 0.0438(12) 0.0299(13) 0.0369(11) -0.0046(9) 0.0102(9) -0.0085(10) C26 0.0322(10) 0.0293(12) 0.0298(10) -0.0005(8) 0.0064(8) -0.0028(8) C27 0.0319(10) 0.0276(12) 0.0338(10) -0.0013(9) 0.0030(8) -0.0055(8) C28 0.0335(11) 0.0307(13) 0.0418(12) 0.0048(9) 0.0081(9) -0.0007(9) C29 0.0274(10) 0.0300(12) 0.0296(10) 0.0034(8) 0.0049(7) 0.0004(8) C30 0.0317(11) 0.0302(12) 0.0356(11) 0.0026(9) 0.0040(8) 0.0038(9) C31 0.0362(11) 0.0397(14) 0.0355(11) 0.0004(10) 0.0051(9) 0.0036(10) C32 0.074(2) 0.057(2) 0.0457(15) 0.0025(13) 0.0230(13) -0.0123(15) C33 0.0661(19) 0.070(2) 0.0468(16) -0.0108(15) 0.0098(13) 0.0259(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 B O1 1.448(3) . ? B O2 1.471(3) . ? B C21 1.586(3) . ? B N 1.665(3) . ? N C27 1.521(3) . ? N C29 1.525(3) . ? N H 0.90(3) . ? O1 C1 1.372(3) . ? O2 C20 1.370(2) . ? O3 C27 1.408(3) . ? O3 C28 1.428(3) . ? C1 C10 1.388(3) . ? C1 C2 1.413(3) . ? C2 C3 1.355(3) . ? C2 H2 0.9500 . ? C3 C4 1.416(3) . ? C3 H3 0.9500 . ? C4 C5 1.418(4) . ? C4 C9 1.425(3) . ? C5 C6 1.366(4) . ? C5 H5 0.9500 . ? C6 C7 1.411(3) . ? C6 H6 0.9500 . ? C7 C8 1.372(3) . ? C7 H7 0.9500 . ? C8 C9 1.424(3) . ? C8 H8 0.9500 . ? C9 C10 1.425(3) . ? C10 C11 1.495(3) . ? C11 C20 1.383(3) . ? C11 C12 1.435(3) . ? C12 C13 1.421(3) . ? C12 C17 1.422(3) . ? C13 C14 1.375(3) . ? C13 H13 0.9500 . ? C14 C15 1.413(4) . ? C14 H14 0.9500 . ? C15 C16 1.362(4) . ? C15 H15 0.9500 . ? C16 C17 1.418(3) . ? C16 H16 0.9500 . ? C17 C18 1.430(3) . ? C18 C19 1.358(3) . ? C18 H18 0.9500 . ? C19 C20 1.412(3) . ? C19 H19 0.9500 . ? C21 C26 1.393(3) . ? C21 C22 1.399(3) . ? C22 C23 1.391(4) . ? C22 H22 0.9500 . ? C23 C24 1.391(4) . ? C23 H23 0.9500 . ? C24 C25 1.384(4) . ? C24 H24 0.9500 . ? C25 C26 1.391(3) . ? C25 H25 0.9500 . ? C26 C27 1.507(3) . ? C27 H27 1.0000 . ? C28 C29 1.543(3) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 C30 1.525(3) . ? C29 H29 1.0000 . ? C30 C31 1.536(3) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C31 C33 1.515(4) . ? C31 C32 1.523(4) . ? C31 H31 1.0000 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? 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 O1 B O2 112.99(18) . . ? O1 B C21 115.30(18) . . ? O2 B C21 113.87(18) . . ? O1 B N 112.90(17) . . ? O2 B N 101.44(16) . . ? C21 B N 98.55(16) . . ? C27 N C29 104.85(16) . . ? C27 N B 105.97(16) . . ? C29 N B 117.00(16) . . ? C27 N H 109.8(19) . . ? C29 N H 104.7(17) . . ? B N H 114.1(18) . . ? C1 O1 B 119.24(16) . . ? C20 O2 B 111.88(15) . . ? C27 O3 C28 104.63(17) . . ? O1 C1 C10 121.94(18) . . ? O1 C1 C2 116.89(19) . . ? C10 C1 C2 121.1(2) . . ? C3 C2 C1 120.6(2) . . ? C3 C2 H2 119.7 . . ? C1 C2 H2 119.7 . . ? C2 C3 C4 120.6(2) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C3 C4 C5 121.3(2) . . ? C3 C4 C9 119.1(2) . . ? C5 C4 C9 119.5(2) . . ? C6 C5 C4 121.0(2) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C5 C6 C7 120.0(2) . . ? C5 C6 H6 120.0 . . ? C7 C6 H6 120.0 . . ? C8 C7 C6 120.3(2) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C7 C8 C9 121.5(2) . . ? C7 C8 H8 119.3 . . ? C9 C8 H8 119.3 . . ? C8 C9 C4 117.7(2) . . ? C8 C9 C10 122.37(19) . . ? C4 C9 C10 119.87(19) . . ? C1 C10 C9 118.24(18) . . ? C1 C10 C11 118.41(19) . . ? C9 C10 C11 123.34(18) . . ? C20 C11 C12 118.93(19) . . ? C20 C11 C10 118.24(18) . . ? C12 C11 C10 122.62(18) . . ? C13 C12 C17 117.73(18) . . ? C13 C12 C11 123.04(19) . . ? C17 C12 C11 119.21(19) . . ? C14 C13 C12 121.1(2) . . ? C14 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? C13 C14 C15 120.7(2) . . ? C13 C14 H14 119.6 . . ? C15 C14 H14 119.6 . . ? C16 C15 C14 119.4(2) . . ? C16 C15 H15 120.3 . . ? C14 C15 H15 120.3 . . ? C15 C16 C17 121.4(2) . . ? C15 C16 H16 119.3 . . ? C17 C16 H16 119.3 . . ? C16 C17 C12 119.6(2) . . ? C16 C17 C18 121.2(2) . . ? C12 C17 C18 119.17(18) . . ? C19 C18 C17 120.84(19) . . ? C19 C18 H18 119.6 . . ? C17 C18 H18 119.6 . . ? C18 C19 C20 120.0(2) . . ? C18 C19 H19 120.0 . . ? C20 C19 H19 120.0 . . ? O2 C20 C11 119.42(18) . . ? O2 C20 C19 118.81(19) . . ? C11 C20 C19 121.77(19) . . ? C26 C21 C22 118.2(2) . . ? C26 C21 B 110.54(18) . . ? C22 C21 B 130.9(2) . . ? C23 C22 C21 120.0(2) . . ? C23 C22 H22 120.0 . . ? C21 C22 H22 120.0 . . ? C24 C23 C22 120.3(2) . . ? C24 C23 H23 119.9 . . ? C22 C23 H23 119.9 . . ? C25 C24 C23 120.9(2) . . ? C25 C24 H24 119.5 . . ? C23 C24 H24 119.5 . . ? C24 C25 C26 118.0(2) . . ? C24 C25 H25 121.0 . . ? C26 C25 H25 121.0 . . ? C25 C26 C21 122.6(2) . . ? C25 C26 C27 124.2(2) . . ? C21 C26 C27 113.2(2) . . ? O3 C27 C26 115.8(2) . . ? O3 C27 N 105.30(17) . . ? C26 C27 N 104.23(17) . . ? O3 C27 H27 110.4 . . ? C26 C27 H27 110.4 . . ? N C27 H27 110.4 . . ? O3 C28 C29 105.06(18) . . ? O3 C28 H28A 110.7 . . ? C29 C28 H28A 110.7 . . ? O3 C28 H28B 110.7 . . ? C29 C28 H28B 110.7 . . ? H28A C28 H28B 108.8 . . ? N C29 C30 110.82(17) . . ? N C29 C28 102.29(17) . . ? C30 C29 C28 115.19(18) . . ? N C29 H29 109.4 . . ? C30 C29 H29 109.4 . . ? C28 C29 H29 109.4 . . ? C29 C30 C31 114.96(18) . . ? C29 C30 H30A 108.5 . . ? C31 C30 H30A 108.5 . . ? C29 C30 H30B 108.5 . . ? C31 C30 H30B 108.5 . . ? H30A C30 H30B 107.5 . . ? C33 C31 C32 111.6(2) . . ? C33 C31 C30 109.8(2) . . ? C32 C31 C30 113.7(2) . . ? C33 C31 H31 107.1 . . ? C32 C31 H31 107.1 . . ? C30 C31 H31 107.1 . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C31 C33 H33A 109.5 . . ? C31 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C31 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.230 _refine_diff_density_min -0.232 _refine_diff_density_rms 0.049 # Attachment 'k07tdj1.cif' data_k07tdj1 _database_code_depnum_ccdc_archive 'CCDC 694359' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H30 B2 N2 O3, 2(C H Cl3)' _chemical_formula_sum 'C26 H32 B2 Cl6 N2 O3' _chemical_formula_weight 654.86 _chemical_absolute_configuration unk loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 12.8270(2) _cell_length_b 9.1145(2) _cell_length_c 13.5149(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.4398(10) _cell_angle_gamma 90.00 _cell_volume 1580.10(6) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 13932 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.376 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 676 _exptl_absorpt_coefficient_mu 0.574 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7622 _exptl_absorpt_correction_T_max 0.8697 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method '167 2.0 degree images with \w scans' _diffrn_standards_number none _diffrn_standards_decay_% 0 _diffrn_reflns_number 17416 _diffrn_reflns_av_R_equivalents 0.0302 _diffrn_reflns_av_sigmaI/netI 0.0352 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 4.16 _diffrn_reflns_theta_max 27.48 _reflns_number_total 6826 _reflns_number_gt 6398 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect, Nonius program suite version 1.9 (1997)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution ; SIR97- Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C. , Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. (1999) J. Appl. Cryst. 32, 115-119. ; _computing_structure_refinement ; SHELX97-2 Program for Crystal Structure Analysis. G. M. Sheldrick, Institut f. Anorg. Chemie der Universit\"at, Tammanstrasse 4, D-3400 G\"ottingen, Germany, 1998. ; _computing_molecular_graphics 'ORTEP3 for Windows - L. J. Farrugia, J. Appl. Crystallogr. 1997, 30, 565' _computing_publication_material 'SHELX97-2, G. M. Sheldrick' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0380P)^2^+1.0797P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.45(5) _refine_ls_number_reflns 6826 _refine_ls_number_parameters 372 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0475 _refine_ls_R_factor_gt 0.0437 _refine_ls_wR_factor_ref 0.1059 _refine_ls_wR_factor_gt 0.1027 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group B1 B 0.0773(2) 0.4849(3) 0.17007(18) 0.0265(5) Uani 1 1 d . . . B2 B 0.2107(2) 0.5704(3) 0.29049(18) 0.0267(5) Uani 1 1 d . . . N1 N 0.10825(16) 0.5931(2) 0.07371(13) 0.0286(4) Uani 1 1 d . . . N2 N 0.24392(16) 0.4122(2) 0.34239(14) 0.0291(4) Uani 1 1 d . . . O1 O 0.13086(13) 0.34625(19) 0.15487(11) 0.0289(4) Uani 1 1 d . . . O2 O 0.28834(13) 0.5933(2) 0.21331(12) 0.0296(3) Uani 1 1 d . . . O3 O 0.10477(12) 0.56318(18) 0.25777(11) 0.0265(3) Uani 1 1 d . . . C1 C -0.04757(19) 0.4841(3) 0.14700(17) 0.0284(5) Uani 1 1 d . . . C2 C -0.13127(19) 0.4109(3) 0.18986(17) 0.0305(5) Uani 1 1 d . . . H2 H -0.1195 0.3453 0.2435 0.037 Uiso 1 1 calc R . . C3 C -0.2326(2) 0.4339(3) 0.15395(18) 0.0368(6) Uani 1 1 d . . . H3 H -0.2892 0.3837 0.1836 0.044 Uiso 1 1 calc R . . C4 C -0.2516(2) 0.5292(4) 0.0755(2) 0.0402(6) Uani 1 1 d . . . H4 H -0.3210 0.5441 0.0524 0.048 Uiso 1 1 calc R . . C5 C -0.1700(2) 0.6026(3) 0.03077(18) 0.0370(6) Uani 1 1 d . . . H5 H -0.1819 0.6682 -0.0227 0.044 Uiso 1 1 calc R . . C6 C -0.0703(2) 0.5766(3) 0.06695(17) 0.0316(5) Uani 1 1 d . . . C7 C 0.0261(2) 0.6405(3) 0.02942(17) 0.0331(5) Uani 1 1 d . . . H7 H 0.0278 0.7103 -0.0227 0.040 Uiso 1 1 calc R . . C8 C 0.2139(2) 0.6470(3) 0.04947(18) 0.0322(5) Uani 1 1 d . . . H8 H 0.2060 0.7309 0.0023 0.039 Uiso 1 1 calc R . . C9 C 0.2749(2) 0.5252(3) -0.00321(19) 0.0386(6) Uani 1 1 d . . . H9 H 0.2742 0.4358 0.0396 0.046 Uiso 1 1 calc R . . C10 C 0.2243(3) 0.4864(4) -0.1024(2) 0.0497(8) Uani 1 1 d . . . H10A H 0.1519 0.4563 -0.0918 0.075 Uiso 1 1 calc R . . H10B H 0.2628 0.4057 -0.1331 0.075 Uiso 1 1 calc R . . H10C H 0.2257 0.5723 -0.1460 0.075 Uiso 1 1 calc R . . C11 C 0.3881(3) 0.5705(5) -0.0187(2) 0.0568(9) Uani 1 1 d . . . H11A H 0.4255 0.4911 -0.0520 0.085 Uiso 1 1 calc R . . H11B H 0.4210 0.5904 0.0455 0.085 Uiso 1 1 calc R . . H11C H 0.3903 0.6592 -0.0597 0.085 Uiso 1 1 calc R . . C12 C 0.26436(19) 0.7055(3) 0.14423(18) 0.0327(5) Uani 1 1 d . . . H12A H 0.3292 0.7582 0.1271 0.039 Uiso 1 1 calc R . . H12B H 0.2165 0.7768 0.1754 0.039 Uiso 1 1 calc R . . C13 C 0.22704(18) 0.6715(3) 0.38864(18) 0.0314(5) Uani 1 1 d . . . C14 C 0.2186(2) 0.8218(3) 0.4061(2) 0.0394(6) Uani 1 1 d . . . H14 H 0.1994 0.8860 0.3537 0.047 Uiso 1 1 calc R . . C15 C 0.2383(2) 0.8782(4) 0.5004(2) 0.0501(8) Uani 1 1 d . . . H15 H 0.2314 0.9805 0.5121 0.060 Uiso 1 1 calc R . . C16 C 0.2680(2) 0.7856(4) 0.5771(2) 0.0549(9) Uani 1 1 d . . . H16 H 0.2820 0.8257 0.6408 0.066 Uiso 1 1 calc R . . C17 C 0.2778(2) 0.6346(4) 0.5625(2) 0.0486(8) Uani 1 1 d . . . H17 H 0.2970 0.5707 0.6151 0.058 Uiso 1 1 calc R . . C18 C 0.25810(19) 0.5817(3) 0.46765(18) 0.0350(6) Uani 1 1 d . . . C19 C 0.26387(19) 0.4291(3) 0.43486(18) 0.0344(6) Uani 1 1 d . . . H19 H 0.2808 0.3501 0.4779 0.041 Uiso 1 1 calc R . . C20 C 0.24083(19) 0.2677(3) 0.29505(18) 0.0316(5) Uani 1 1 d . . . H20 H 0.2423 0.1916 0.3484 0.038 Uiso 1 1 calc R . . C21 C 0.3367(2) 0.2436(3) 0.2288(2) 0.0372(6) Uani 1 1 d . . . H21 H 0.3313 0.3106 0.1704 0.045 Uiso 1 1 calc R . . C22 C 0.3389(2) 0.0849(3) 0.1916(2) 0.0436(6) Uani 1 1 d . . . H22A H 0.3998 0.0707 0.1493 0.065 Uiso 1 1 calc R . . H22B H 0.2752 0.0646 0.1536 0.065 Uiso 1 1 calc R . . H22C H 0.3432 0.0180 0.2483 0.065 Uiso 1 1 calc R . . C23 C 0.4386(2) 0.2769(4) 0.2844(3) 0.0543(8) Uani 1 1 d . . . H23A H 0.4373 0.3783 0.3084 0.082 Uiso 1 1 calc R . . H23B H 0.4976 0.2639 0.2396 0.082 Uiso 1 1 calc R . . H23C H 0.4459 0.2098 0.3407 0.082 Uiso 1 1 calc R . . C24 C 0.13721(19) 0.2526(3) 0.23855(17) 0.0307(5) Uani 1 1 d . . . H24A H 0.1288 0.1497 0.2166 0.037 Uiso 1 1 calc R . . H24B H 0.0792 0.2757 0.2838 0.037 Uiso 1 1 calc R . . C30 C -0.0560(2) 0.7703(3) 0.3613(2) 0.0376(6) Uani 1 1 d . . . H30 H -0.0085 0.6950 0.3323 0.045 Uiso 1 1 calc R A 1 Cl1 Cl -0.18595(5) 0.72597(9) 0.32922(5) 0.04356(16) Uani 1 1 d . B . Cl2 Cl -0.0252(3) 0.9444(4) 0.3101(2) 0.0680(10) Uani 0.683(18) 1 d P B 1 Cl3 Cl -0.0371(3) 0.7745(9) 0.4883(3) 0.0654(10) Uani 0.683(18) 1 d P B 1 Cl2A Cl -0.0357(6) 0.9521(8) 0.352(2) 0.124(5) Uani 0.317(18) 1 d P B 2 Cl3A Cl -0.0396(7) 0.708(2) 0.4882(6) 0.070(3) Uani 0.317(18) 1 d P B 2 C40 C 0.49768(18) 0.7163(3) 0.33085(18) 0.0341(5) Uani 1 1 d . . . H40 H 0.4228 0.6894 0.3206 0.041 Uiso 1 1 calc R . . Cl4 Cl 0.55369(9) 0.59435(12) 0.41391(9) 0.0859(4) Uani 1 1 d . . . Cl5 Cl 0.55995(7) 0.7114(2) 0.21896(7) 0.1036(5) Uani 1 1 d . . . Cl6 Cl 0.50451(10) 0.89079(12) 0.38327(13) 0.1030(5) 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 B1 0.0330(13) 0.0265(13) 0.0200(11) -0.0012(9) 0.0051(9) -0.0047(10) B2 0.0282(12) 0.0302(13) 0.0218(11) -0.0039(10) 0.0049(9) -0.0017(10) N1 0.0386(11) 0.0258(10) 0.0216(9) -0.0025(8) 0.0050(8) -0.0061(9) N2 0.0277(9) 0.0340(10) 0.0258(9) 0.0015(8) 0.0041(7) -0.0029(8) O1 0.0366(9) 0.0273(8) 0.0228(8) -0.0020(6) 0.0045(6) -0.0021(7) O2 0.0296(8) 0.0313(9) 0.0281(8) -0.0033(7) 0.0081(6) -0.0043(7) O3 0.0308(8) 0.0286(8) 0.0201(7) -0.0047(6) 0.0027(6) -0.0023(7) C1 0.0340(12) 0.0298(12) 0.0215(10) -0.0054(9) 0.0000(9) -0.0024(10) C2 0.0342(12) 0.0341(12) 0.0231(10) -0.0026(9) 0.0012(9) -0.0051(10) C3 0.0344(12) 0.0500(16) 0.0260(11) -0.0068(11) 0.0004(9) -0.0075(12) C4 0.0352(13) 0.0531(17) 0.0323(13) -0.0070(12) -0.0043(10) 0.0010(12) C5 0.0436(14) 0.0400(14) 0.0272(11) 0.0013(11) -0.0027(10) 0.0037(12) C6 0.0399(13) 0.0289(12) 0.0260(11) -0.0024(10) 0.0001(9) -0.0013(10) C7 0.0440(14) 0.0324(13) 0.0227(11) 0.0012(9) 0.0021(10) -0.0012(11) C8 0.0387(13) 0.0313(12) 0.0268(11) 0.0016(9) 0.0079(10) -0.0092(10) C9 0.0453(15) 0.0426(15) 0.0281(12) -0.0034(11) 0.0129(11) -0.0055(12) C10 0.0635(19) 0.0545(19) 0.0312(14) -0.0094(13) 0.0068(13) -0.0051(15) C11 0.0497(17) 0.071(2) 0.0496(17) -0.0163(17) 0.0215(14) -0.0128(17) C12 0.0364(12) 0.0284(12) 0.0334(12) -0.0029(10) 0.0067(10) -0.0095(10) C13 0.0225(10) 0.0430(14) 0.0288(11) -0.0113(10) 0.0038(9) -0.0027(10) C14 0.0286(12) 0.0434(15) 0.0462(15) -0.0200(12) 0.0034(11) -0.0036(11) C15 0.0381(14) 0.061(2) 0.0510(17) -0.0315(16) 0.0026(13) -0.0012(14) C16 0.0393(14) 0.085(3) 0.0403(15) -0.0372(17) 0.0051(12) -0.0080(16) C17 0.0411(15) 0.079(2) 0.0256(13) -0.0153(14) 0.0017(11) -0.0062(15) C18 0.0266(11) 0.0510(16) 0.0275(11) -0.0090(11) 0.0049(9) -0.0068(11) C19 0.0293(12) 0.0459(16) 0.0281(11) 0.0003(11) 0.0020(9) -0.0043(11) C20 0.0356(12) 0.0285(12) 0.0307(11) 0.0044(9) 0.0020(9) -0.0010(10) C21 0.0392(13) 0.0331(13) 0.0394(13) 0.0025(11) 0.0084(10) 0.0063(11) C22 0.0445(15) 0.0426(16) 0.0437(15) -0.0141(13) -0.0052(12) 0.0088(13) C23 0.0368(14) 0.0455(17) 0.081(2) -0.0196(17) 0.0090(14) -0.0052(13) C24 0.0380(12) 0.0256(12) 0.0287(11) 0.0006(9) 0.0039(9) -0.0052(10) C30 0.0333(12) 0.0411(15) 0.0384(13) -0.0002(12) 0.0025(10) 0.0040(11) Cl1 0.0387(3) 0.0485(4) 0.0435(3) -0.0069(3) -0.0009(3) -0.0034(3) Cl2 0.0467(13) 0.0590(14) 0.098(2) 0.0303(12) -0.0216(11) -0.0151(10) Cl3 0.0368(9) 0.125(3) 0.0341(8) -0.0077(16) 0.0031(6) 0.0050(16) Cl2A 0.049(2) 0.032(2) 0.293(15) 0.002(5) 0.014(6) 0.0003(16) Cl3A 0.0413(18) 0.135(7) 0.0329(17) -0.003(4) -0.0033(13) -0.006(4) C40 0.0257(10) 0.0385(13) 0.0381(12) 0.0010(11) -0.0028(9) -0.0023(11) Cl4 0.0840(7) 0.0652(6) 0.1077(8) 0.0442(6) -0.0523(6) -0.0250(5) Cl5 0.0507(5) 0.2165(16) 0.0439(4) -0.0183(7) 0.0138(4) -0.0369(8) Cl6 0.0766(7) 0.0604(6) 0.1711(13) -0.0523(8) -0.0544(8) 0.0295(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B1 O3 1.425(3) . ? B1 O1 1.454(3) . ? B1 C1 1.629(4) . ? B1 N1 1.684(3) . ? B2 O3 1.427(3) . ? B2 O2 1.463(3) . ? B2 C13 1.627(3) . ? B2 N2 1.658(3) . ? N1 C7 1.282(3) . ? N1 C8 1.480(3) . ? N2 C19 1.283(3) . ? N2 C20 1.465(3) . ? O1 C24 1.419(3) . ? O2 C12 1.417(3) . ? C1 C2 1.394(3) . ? C1 C6 1.401(3) . ? C2 C3 1.400(4) . ? C2 H2 0.9500 . ? C3 C4 1.391(4) . ? C3 H3 0.9500 . ? C4 C5 1.385(4) . ? C4 H4 0.9500 . ? C5 C6 1.385(4) . ? C5 H5 0.9500 . ? C6 C7 1.462(4) . ? C7 H7 0.9500 . ? C8 C12 1.527(3) . ? C8 C9 1.536(4) . ? C8 H8 1.0000 . ? C9 C11 1.525(4) . ? C9 C10 1.527(4) . ? C9 H9 1.0000 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.395(4) . ? C13 C18 1.401(4) . ? C14 C15 1.395(4) . ? C14 H14 0.9500 . ? C15 C16 1.389(5) . ? C15 H15 0.9500 . ? C16 C17 1.396(5) . ? C16 H16 0.9500 . ? C17 C18 1.391(4) . ? C17 H17 0.9500 . ? C18 C19 1.462(4) . ? C19 H19 0.9500 . ? C20 C24 1.534(3) . ? C20 C21 1.543(3) . ? C20 H20 1.0000 . ? C21 C22 1.531(4) . ? C21 C23 1.533(4) . ? C21 H21 1.0000 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C30 Cl2A 1.681(8) . ? C30 Cl3 1.732(5) . ? C30 Cl1 1.766(3) . ? C30 Cl2 1.777(4) . ? C30 Cl3A 1.815(10) . ? C30 H30 1.0000 . ? C40 Cl5 1.716(3) . ? C40 Cl4 1.732(3) . ? C40 Cl6 1.743(3) . ? C40 H40 1.0000 . ? 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 O3 B1 O1 116.0(2) . . ? O3 B1 C1 113.44(19) . . ? O1 B1 C1 115.72(19) . . ? O3 B1 N1 106.95(18) . . ? O1 B1 N1 106.58(18) . . ? C1 B1 N1 95.28(18) . . ? O3 B2 O2 115.94(19) . . ? O3 B2 C13 113.28(19) . . ? O2 B2 C13 114.6(2) . . ? O3 B2 N2 109.42(19) . . ? O2 B2 N2 104.57(18) . . ? C13 B2 N2 96.69(18) . . ? C7 N1 C8 122.3(2) . . ? C7 N1 B1 111.13(19) . . ? C8 N1 B1 125.97(19) . . ? C19 N2 C20 122.6(2) . . ? C19 N2 B2 110.9(2) . . ? C20 N2 B2 126.25(18) . . ? C24 O1 B1 115.76(17) . . ? C12 O2 B2 115.30(18) . . ? B1 O3 B2 120.63(18) . . ? C2 C1 C6 116.9(2) . . ? C2 C1 B1 133.0(2) . . ? C6 C1 B1 110.1(2) . . ? C1 C2 C3 120.0(2) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C4 C3 C2 121.0(3) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C5 C4 C3 120.3(3) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 C6 117.5(2) . . ? C4 C5 H5 121.2 . . ? C6 C5 H5 121.2 . . ? C5 C6 C1 124.2(2) . . ? C5 C6 C7 126.2(2) . . ? C1 C6 C7 109.6(2) . . ? N1 C7 C6 113.5(2) . . ? N1 C7 H7 123.3 . . ? C6 C7 H7 123.3 . . ? N1 C8 C12 108.26(19) . . ? N1 C8 C9 109.5(2) . . ? C12 C8 C9 115.3(2) . . ? N1 C8 H8 107.9 . . ? C12 C8 H8 107.9 . . ? C9 C8 H8 107.9 . . ? C11 C9 C10 109.9(2) . . ? C11 C9 C8 110.9(2) . . ? C10 C9 C8 111.1(3) . . ? C11 C9 H9 108.3 . . ? C10 C9 H9 108.3 . . ? C8 C9 H9 108.3 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O2 C12 C8 112.9(2) . . ? O2 C12 H12A 109.0 . . ? C8 C12 H12A 109.0 . . ? O2 C12 H12B 109.0 . . ? C8 C12 H12B 109.0 . . ? H12A C12 H12B 107.8 . . ? C14 C13 C18 117.8(2) . . ? C14 C13 B2 133.2(3) . . ? C18 C13 B2 109.0(2) . . ? C15 C14 C13 120.2(3) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C16 C15 C14 120.3(3) . . ? C16 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C15 C16 C17 121.2(3) . . ? C15 C16 H16 119.4 . . ? C17 C16 H16 119.4 . . ? C18 C17 C16 117.2(3) . . ? C18 C17 H17 121.4 . . ? C16 C17 H17 121.4 . . ? C17 C18 C13 123.3(3) . . ? C17 C18 C19 126.9(3) . . ? C13 C18 C19 109.8(2) . . ? N2 C19 C18 113.5(2) . . ? N2 C19 H19 123.2 . . ? C18 C19 H19 123.2 . . ? N2 C20 C24 108.6(2) . . ? N2 C20 C21 111.3(2) . . ? C24 C20 C21 112.9(2) . . ? N2 C20 H20 108.0 . . ? C24 C20 H20 108.0 . . ? C21 C20 H20 108.0 . . ? C22 C21 C23 109.3(2) . . ? C22 C21 C20 110.0(2) . . ? C23 C21 C20 111.5(2) . . ? C22 C21 H21 108.7 . . ? C23 C21 H21 108.7 . . ? C20 C21 H21 108.7 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? O1 C24 C20 112.79(19) . . ? O1 C24 H24A 109.0 . . ? C20 C24 H24A 109.0 . . ? O1 C24 H24B 109.0 . . ? C20 C24 H24B 109.0 . . ? H24A C24 H24B 107.8 . . ? Cl2A C30 Cl3 91.6(8) . . ? Cl2A C30 Cl1 110.7(4) . . ? Cl3 C30 Cl1 111.9(2) . . ? Cl3 C30 Cl2 109.7(3) . . ? Cl1 C30 Cl2 108.73(17) . . ? Cl2A C30 Cl3A 110.9(6) . . ? Cl1 C30 Cl3A 105.3(3) . . ? Cl2 C30 Cl3A 128.4(5) . . ? Cl2A C30 H30 123.6 . . ? Cl3 C30 H30 108.8 . . ? Cl1 C30 H30 108.8 . . ? Cl2 C30 H30 108.8 . . ? Cl3A C30 H30 95.2 . . ? Cl5 C40 Cl4 111.15(16) . . ? Cl5 C40 Cl6 111.08(17) . . ? Cl4 C40 Cl6 107.63(14) . . ? Cl5 C40 H40 109.0 . . ? Cl4 C40 H40 109.0 . . ? Cl6 C40 H40 109.0 . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.613 _refine_diff_density_min -0.649 _refine_diff_density_rms 0.049 # Attachment 'k07tdj2.cif' data_k07tdj2 _database_code_depnum_ccdc_archive 'CCDC 694360' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H22 B2 N2 O3, 2(C H Cl3)' _chemical_formula_sum 'C30 H24 B2 Cl6 N2 O3' _chemical_formula_weight 694.83 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.9035(1) _cell_length_b 12.1380(2) _cell_length_c 13.9067(2) _cell_angle_alpha 78.842(1) _cell_angle_beta 72.3618(10) _cell_angle_gamma 83.1794(10) _cell_volume 1559.72(4) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 18962 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 30.034 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.479 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 708 _exptl_absorpt_coefficient_mu 0.587 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7579 _exptl_absorpt_correction_T_max 0.8671 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method '261 2.0 degree images with \w scans' _diffrn_standards_number none _diffrn_standards_decay_% 0 _diffrn_reflns_number 37035 _diffrn_reflns_av_R_equivalents 0.0450 _diffrn_reflns_av_sigmaI/netI 0.0462 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 30.11 _reflns_number_total 9137 _reflns_number_gt 6248 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect, Nonius program suite version 1.9 (1997)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution ; SIR97- Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C. , Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. (1999) J. Appl. Cryst. 32, 115-119. ; _computing_structure_refinement ; SHELX97-2 Program for Crystal Structure Analysis. G. M. Sheldrick, Institut f. Anorg. Chemie der Universit\"at, Tammanstrasse 4, D-3400 G\"ottingen, Germany, 1998. ; _computing_molecular_graphics 'ORTEP3 for Windows - L. J. Farrugia, J. Appl. Crystallogr. 1997, 30, 565' _computing_publication_material 'SHELX97-2, G. M. Sheldrick' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0682P)^2^+0.4876P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9137 _refine_ls_number_parameters 480 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0829 _refine_ls_R_factor_gt 0.0504 _refine_ls_wR_factor_ref 0.1427 _refine_ls_wR_factor_gt 0.1244 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group B1 B 0.63794(17) 0.18135(14) 0.28196(13) 0.0243(3) Uani 1 1 d . . . B2 B 0.64558(17) 0.21829(14) 0.44582(13) 0.0236(3) Uani 1 1 d . . . N1 N 0.51885(13) 0.08768(10) 0.31707(10) 0.0238(3) Uani 1 1 d . . . N2 N 0.66519(13) 0.35458(10) 0.42062(10) 0.0239(3) Uani 1 1 d . . . O1 O 0.73553(11) 0.13977(9) 0.18892(9) 0.0283(2) Uani 1 1 d . . . O2 O 0.73059(11) 0.18421(9) 0.52124(9) 0.0270(2) Uani 1 1 d . . . O3 O 0.70917(11) 0.17150(9) 0.35712(8) 0.0244(2) Uani 1 1 d . . . C1 C 0.67654(17) 0.05730(13) 0.16596(12) 0.0274(3) Uani 1 1 d . . . C2 C 0.7325(2) 0.00507(15) 0.08060(13) 0.0345(4) Uani 1 1 d . . . H2 H 0.8214 0.0238 0.0329 0.041 Uiso 1 1 calc R . . C3 C 0.6543(2) -0.07548(15) 0.06736(14) 0.0378(4) Uani 1 1 d . . . H3 H 0.6914 -0.1114 0.0090 0.045 Uiso 1 1 calc R . . C4 C 0.5235(2) -0.10632(14) 0.13582(13) 0.0333(4) Uani 1 1 d . . . C5 C 0.4408(2) -0.19047(16) 0.11420(16) 0.0439(5) Uani 1 1 d . . . H5A H 0.3779 -0.1510 0.0744 0.066 Uiso 1 1 calc R . . H5B H 0.3840 -0.2314 0.1790 0.066 Uiso 1 1 calc R . . H5C H 0.5068 -0.2438 0.0752 0.066 Uiso 1 1 calc R . . C6 C 0.47075(18) -0.05611(13) 0.22284(13) 0.0285(3) Uani 1 1 d . . . H6 H 0.3835 -0.0767 0.2719 0.034 Uiso 1 1 calc R . . C7 C 0.54818(16) 0.02451(12) 0.23650(12) 0.0256(3) Uani 1 1 d . . . C8 C 0.41951(16) 0.06857(12) 0.40192(12) 0.0248(3) Uani 1 1 d . . . H8 H 0.3614 0.0088 0.4092 0.030 Uiso 1 1 calc R . . C9 C 0.38707(16) 0.12911(12) 0.48788(12) 0.0245(3) Uani 1 1 d . . . C10 C 0.25248(17) 0.10831(14) 0.55798(13) 0.0300(3) Uani 1 1 d . . . H10 H 0.1952 0.0579 0.5461 0.036 Uiso 1 1 calc R . . C11 C 0.20208(17) 0.15973(15) 0.64361(13) 0.0337(4) Uani 1 1 d . . . H11 H 0.1100 0.1467 0.6891 0.040 Uiso 1 1 calc R . . C12 C 0.28764(18) 0.23047(15) 0.66208(13) 0.0333(4) Uani 1 1 d . . . H12 H 0.2544 0.2668 0.7204 0.040 Uiso 1 1 calc R . . C13 C 0.42233(17) 0.24844(14) 0.59527(12) 0.0291(3) Uani 1 1 d . . . H13 H 0.4797 0.2963 0.6103 0.035 Uiso 1 1 calc R . . C14 C 0.47798(15) 0.19942(12) 0.50663(11) 0.0237(3) Uani 1 1 d . . . C15 C 0.76801(15) 0.27621(13) 0.54578(12) 0.0254(3) Uani 1 1 d . . . C16 C 0.83594(17) 0.27669(15) 0.61958(13) 0.0309(3) Uani 1 1 d . . . H16 H 0.8632 0.2083 0.6574 0.037 Uiso 1 1 calc R . . C17 C 0.86299(18) 0.38000(15) 0.63660(13) 0.0326(4) Uani 1 1 d . . . H17 H 0.9097 0.3807 0.6869 0.039 Uiso 1 1 calc R . . C18 C 0.82465(17) 0.48310(14) 0.58309(12) 0.0291(3) Uani 1 1 d . . . C19 C 0.8514(2) 0.59319(16) 0.60646(14) 0.0364(4) Uani 1 1 d . . . H19A H 0.8573 0.6518 0.5462 0.055 Uiso 1 1 calc R . . H19B H 0.9409 0.5854 0.6243 0.055 Uiso 1 1 calc R . . H19C H 0.7733 0.6141 0.6641 0.055 Uiso 1 1 calc R . . C20 C 0.75892(16) 0.48165(13) 0.50773(12) 0.0273(3) Uani 1 1 d . . . H20 H 0.7333 0.5499 0.4689 0.033 Uiso 1 1 calc R . . C21 C 0.73165(16) 0.37856(13) 0.49047(11) 0.0245(3) Uani 1 1 d . . . C22 C 0.63243(17) 0.42768(13) 0.34939(12) 0.0263(3) Uani 1 1 d . . . H22 H 0.6536 0.5030 0.3454 0.032 Uiso 1 1 calc R . . C23 C 0.56663(16) 0.40793(13) 0.27427(12) 0.0254(3) Uani 1 1 d . . . C24 C 0.50760(19) 0.50718(13) 0.22669(13) 0.0315(3) Uani 1 1 d . . . H24 H 0.5171 0.5775 0.2437 0.038 Uiso 1 1 calc R . . C25 C 0.4365(2) 0.50434(14) 0.15602(14) 0.0343(4) Uani 1 1 d . . . H25 H 0.3965 0.5718 0.1250 0.041 Uiso 1 1 calc R . . C26 C 0.42422(19) 0.40157(14) 0.13099(13) 0.0323(3) Uani 1 1 d . . . H26 H 0.3740 0.3979 0.0835 0.039 Uiso 1 1 calc R . . C27 C 0.48547(17) 0.30406(14) 0.17546(12) 0.0296(3) Uani 1 1 d . . . H27 H 0.4773 0.2349 0.1560 0.036 Uiso 1 1 calc R . . C28 C 0.55890(16) 0.30241(12) 0.24764(12) 0.0243(3) Uani 1 1 d . . . C30 C 1.02436(19) 0.12242(19) 0.26135(14) 0.0423(4) Uani 1 1 d . . . H30 H 0.9184 0.1223 0.2851 0.051 Uiso 1 1 calc R A 1 Cl1 Cl 1.0888(6) 0.0163(5) 0.1760(3) 0.0500(6) Uani 0.50 1 d P B 1 Cl2 Cl 1.0812(2) 0.11091(17) 0.36953(16) 0.0634(5) Uani 0.50 1 d P B 1 Cl3 Cl 1.0698(8) 0.2682(4) 0.1937(4) 0.0820(14) Uani 0.50 1 d P B 1 Cl1A Cl 1.0903(8) 0.0352(6) 0.1808(4) 0.0766(18) Uani 0.50 1 d P B 2 Cl2A Cl 1.07568(18) 0.05337(17) 0.37296(14) 0.0575(4) Uani 0.50 1 d P B 2 Cl3A Cl 1.0940(8) 0.2428(5) 0.2048(5) 0.0942(15) Uani 0.50 1 d P B 2 C40 C 0.9622(6) 0.3113(5) -0.0275(4) 0.0542(12) Uani 0.60 1 d P . . H40 H 0.9603 0.2621 0.0394 0.065 Uiso 0.60 1 calc PR C 1 Cl4 Cl 0.9600(9) 0.2249(8) -0.1130(5) 0.0522(12) Uani 0.30 1 d P D 1 Cl5 Cl 1.1204(5) 0.3780(5) -0.0709(5) 0.0740(15) Uani 0.30 1 d P D 1 Cl6 Cl 0.8274(4) 0.4219(4) -0.0028(3) 0.0665(9) Uani 0.30 1 d P D 1 Cl4A Cl 0.9306(10) 0.2367(9) -0.1104(7) 0.090(3) Uani 0.30 1 d P D 2 Cl5A Cl 1.1422(7) 0.3575(6) -0.0723(4) 0.090(2) Uani 0.30 1 d P D 2 Cl6A Cl 0.8405(12) 0.4228(10) -0.0459(9) 0.224(6) Uani 0.30 1 d P D 2 C50 C 0.9741(9) 0.3588(6) -0.0559(5) 0.0464(16) Uani 0.40 1 d P D . H50 H 1.0265 0.3698 -0.0077 0.056 Uiso 0.40 1 calc PR . . Cl7 Cl 1.0217(6) 0.2241(3) -0.0867(3) 0.150(2) Uani 0.40 1 d P . . Cl8 Cl 1.0167(2) 0.46581(14) -0.16435(12) 0.0695(4) Uani 0.40 1 d P . . Cl9 Cl 0.7948(3) 0.3726(3) 0.00421(15) 0.0556(5) Uani 0.40 1 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 B1 0.0237(7) 0.0212(8) 0.0282(8) -0.0045(6) -0.0072(6) -0.0020(6) B2 0.0248(8) 0.0183(7) 0.0274(8) -0.0008(6) -0.0091(6) -0.0016(6) N1 0.0260(6) 0.0189(6) 0.0276(6) -0.0030(5) -0.0106(5) -0.0001(4) N2 0.0257(6) 0.0216(6) 0.0257(6) -0.0034(5) -0.0090(5) -0.0026(5) O1 0.0281(5) 0.0251(5) 0.0315(6) -0.0084(4) -0.0053(4) -0.0037(4) O2 0.0302(5) 0.0206(5) 0.0333(6) -0.0007(4) -0.0156(5) -0.0035(4) O3 0.0227(5) 0.0210(5) 0.0302(5) -0.0043(4) -0.0088(4) -0.0005(4) C1 0.0325(8) 0.0195(7) 0.0306(8) -0.0025(6) -0.0112(6) -0.0006(6) C2 0.0422(9) 0.0295(8) 0.0300(8) -0.0072(7) -0.0057(7) -0.0041(7) C3 0.0557(11) 0.0274(8) 0.0309(8) -0.0085(7) -0.0106(8) -0.0042(7) C4 0.0503(10) 0.0207(7) 0.0321(8) -0.0033(6) -0.0169(7) -0.0033(7) C5 0.0668(13) 0.0299(9) 0.0422(10) -0.0067(8) -0.0225(9) -0.0119(8) C6 0.0353(8) 0.0211(7) 0.0315(8) -0.0006(6) -0.0148(7) -0.0032(6) C7 0.0316(8) 0.0181(7) 0.0280(7) -0.0032(6) -0.0113(6) 0.0004(5) C8 0.0251(7) 0.0195(7) 0.0309(8) -0.0006(6) -0.0115(6) -0.0023(5) C9 0.0256(7) 0.0217(7) 0.0257(7) 0.0006(6) -0.0098(6) -0.0004(5) C10 0.0266(7) 0.0324(8) 0.0300(8) 0.0007(6) -0.0093(6) -0.0049(6) C11 0.0267(8) 0.0413(10) 0.0290(8) -0.0006(7) -0.0052(6) -0.0029(7) C12 0.0342(8) 0.0363(9) 0.0269(8) -0.0051(7) -0.0071(7) 0.0024(7) C13 0.0315(8) 0.0276(8) 0.0292(8) -0.0046(6) -0.0107(6) -0.0009(6) C14 0.0255(7) 0.0201(7) 0.0250(7) 0.0005(5) -0.0097(6) -0.0004(5) C15 0.0242(7) 0.0240(7) 0.0284(7) -0.0023(6) -0.0083(6) -0.0042(5) C16 0.0312(8) 0.0319(8) 0.0317(8) -0.0013(7) -0.0141(7) -0.0032(6) C17 0.0317(8) 0.0392(9) 0.0317(8) -0.0072(7) -0.0137(7) -0.0065(7) C18 0.0275(7) 0.0320(8) 0.0289(8) -0.0087(6) -0.0061(6) -0.0057(6) C19 0.0407(9) 0.0367(9) 0.0363(9) -0.0128(7) -0.0111(7) -0.0086(7) C20 0.0286(7) 0.0261(8) 0.0270(7) -0.0050(6) -0.0066(6) -0.0042(6) C21 0.0254(7) 0.0245(7) 0.0251(7) -0.0034(6) -0.0087(6) -0.0039(5) C22 0.0315(7) 0.0192(7) 0.0286(8) -0.0022(6) -0.0095(6) -0.0034(5) C23 0.0299(7) 0.0209(7) 0.0251(7) -0.0007(6) -0.0088(6) -0.0029(5) C24 0.0441(9) 0.0197(7) 0.0330(8) -0.0007(6) -0.0169(7) -0.0020(6) C25 0.0464(10) 0.0240(8) 0.0354(9) 0.0007(7) -0.0201(8) -0.0009(7) C26 0.0403(9) 0.0292(8) 0.0325(8) -0.0038(7) -0.0187(7) -0.0026(7) C27 0.0362(8) 0.0242(7) 0.0309(8) -0.0041(6) -0.0135(7) -0.0022(6) C28 0.0254(7) 0.0218(7) 0.0249(7) -0.0020(6) -0.0067(6) -0.0031(5) C30 0.0296(8) 0.0652(13) 0.0336(9) -0.0124(9) -0.0074(7) -0.0065(8) Cl1 0.0589(12) 0.0429(12) 0.0369(10) -0.0164(10) 0.0105(8) -0.0078(9) Cl2 0.0617(9) 0.0889(13) 0.0456(7) -0.0103(10) -0.0271(6) 0.0014(10) Cl3 0.127(3) 0.071(3) 0.0683(12) -0.0015(15) -0.0469(15) -0.050(2) Cl1A 0.0749(18) 0.070(3) 0.0737(19) -0.0386(13) 0.0104(11) 0.0012(15) Cl2A 0.0360(6) 0.1009(13) 0.0363(6) -0.0041(9) -0.0163(4) -0.0031(9) Cl3A 0.120(3) 0.0486(17) 0.110(3) -0.0165(17) -0.011(2) -0.0425(17) C40 0.055(2) 0.061(3) 0.051(3) -0.008(2) -0.023(2) -0.002(3) Cl4 0.066(2) 0.057(2) 0.0310(17) -0.0095(15) -0.0014(14) -0.0214(17) Cl5 0.0379(13) 0.0725(19) 0.116(3) -0.052(2) -0.0030(15) -0.0105(13) Cl6 0.0473(14) 0.0684(19) 0.090(2) -0.0226(16) -0.0184(13) -0.0139(12) Cl4A 0.130(7) 0.082(5) 0.072(4) 0.008(3) -0.041(3) -0.059(4) Cl5A 0.085(3) 0.127(4) 0.071(3) -0.016(2) -0.042(2) -0.010(3) Cl6A 0.222(10) 0.189(9) 0.347(13) -0.135(10) -0.210(11) 0.141(8) C50 0.053(3) 0.052(4) 0.035(3) -0.006(3) -0.016(3) 0.000(3) Cl7 0.209(4) 0.0732(18) 0.075(2) 0.0140(14) 0.050(2) 0.069(2) Cl8 0.0966(12) 0.0588(9) 0.0483(8) -0.0011(7) -0.0094(8) -0.0286(8) Cl9 0.0386(9) 0.0715(15) 0.0478(9) -0.0051(9) -0.0063(7) 0.0070(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B1 O3 1.408(2) . ? B1 O1 1.497(2) . ? B1 N1 1.636(2) . ? B1 C28 1.637(2) . ? B2 O3 1.399(2) . ? B2 O2 1.505(2) . ? B2 C14 1.639(2) . ? B2 N2 1.646(2) . ? N1 C8 1.288(2) . ? N1 C7 1.418(2) . ? N2 C22 1.288(2) . ? N2 C21 1.4157(19) . ? O1 C1 1.3494(19) . ? O2 C15 1.3503(19) . ? C1 C2 1.388(2) . ? C1 C7 1.396(2) . ? C2 C3 1.388(3) . ? C2 H2 0.9500 . ? C3 C4 1.397(3) . ? C3 H3 0.9500 . ? C4 C6 1.391(2) . ? C4 C5 1.507(3) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 C7 1.386(2) . ? C6 H6 0.9500 . ? C8 C9 1.457(2) . ? C8 H8 0.9500 . ? C9 C10 1.410(2) . ? C9 C14 1.421(2) . ? C10 C11 1.382(2) . ? C10 H10 0.9500 . ? C11 C12 1.383(3) . ? C11 H11 0.9500 . ? C12 C13 1.389(2) . ? C12 H12 0.9500 . ? C13 C14 1.404(2) . ? C13 H13 0.9500 . ? C15 C16 1.388(2) . ? C15 C21 1.399(2) . ? C16 C17 1.390(2) . ? C16 H16 0.9500 . ? C17 C18 1.401(2) . ? C17 H17 0.9500 . ? C18 C20 1.395(2) . ? C18 C19 1.505(2) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 C21 1.390(2) . ? C20 H20 0.9500 . ? C22 C23 1.456(2) . ? C22 H22 0.9500 . ? C23 C24 1.410(2) . ? C23 C28 1.417(2) . ? C24 C25 1.379(2) . ? C24 H24 0.9500 . ? C25 C26 1.386(2) . ? C25 H25 0.9500 . ? C26 C27 1.387(2) . ? C26 H26 0.9500 . ? C27 C28 1.403(2) . ? C27 H27 0.9500 . ? C30 Cl1A 1.628(7) . ? C30 Cl3A 1.641(6) . ? C30 Cl2 1.736(3) . ? C30 Cl2A 1.801(3) . ? C30 Cl1 1.847(7) . ? C30 Cl3 1.872(6) . ? C30 H30 1.0000 . ? C40 Cl4A 1.713(11) . ? C40 Cl5 1.736(7) . ? C40 Cl6A 1.737(9) . ? C40 Cl4 1.737(9) . ? C40 Cl6 1.782(7) . ? C40 Cl5A 1.819(9) . ? C40 H40 1.0000 . ? Cl4 Cl7 0.800(10) . ? Cl5 Cl8 1.973(7) . ? Cl5 Cl7 2.284(8) . ? Cl6 Cl9 0.690(3) . ? Cl6 Cl8 2.463(5) . ? Cl4A Cl7 1.036(13) . ? Cl5A Cl7 2.195(9) . ? Cl5A Cl8 2.200(6) . ? Cl6A Cl9 0.878(16) . ? Cl6A Cl8 2.043(14) . ? C50 Cl9 1.722(8) . ? C50 Cl7 1.745(9) . ? C50 Cl8 1.767(7) . ? C50 H50 1.0000 . ? 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 O3 B1 O1 109.65(12) . . ? O3 B1 N1 109.65(12) . . ? O1 B1 N1 99.75(12) . . ? O3 B1 C28 119.47(13) . . ? O1 B1 C28 109.52(12) . . ? N1 B1 C28 106.97(11) . . ? O3 B2 O2 110.80(12) . . ? O3 B2 C14 119.25(13) . . ? O2 B2 C14 108.50(12) . . ? O3 B2 N2 109.55(12) . . ? O2 B2 N2 99.21(11) . . ? C14 B2 N2 107.62(11) . . ? C8 N1 C7 124.54(13) . . ? C8 N1 B1 128.67(13) . . ? C7 N1 B1 106.73(12) . . ? C22 N2 C21 124.83(13) . . ? C22 N2 B2 128.08(13) . . ? C21 N2 B2 107.06(11) . . ? C1 O1 B1 110.01(12) . . ? C15 O2 B2 110.32(11) . . ? B2 O3 B1 119.98(12) . . ? O1 C1 C2 125.72(15) . . ? O1 C1 C7 114.80(14) . . ? C2 C1 C7 119.48(15) . . ? C3 C2 C1 117.78(16) . . ? C3 C2 H2 121.1 . . ? C1 C2 H2 121.1 . . ? C2 C3 C4 123.15(16) . . ? C2 C3 H3 118.4 . . ? C4 C3 H3 118.4 . . ? C6 C4 C3 118.56(16) . . ? C6 C4 C5 121.05(17) . . ? C3 C4 C5 120.39(16) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C7 C6 C4 118.60(15) . . ? C7 C6 H6 120.7 . . ? C4 C6 H6 120.7 . . ? C6 C7 C1 122.37(15) . . ? C6 C7 N1 129.91(14) . . ? C1 C7 N1 107.72(13) . . ? N1 C8 C9 126.72(14) . . ? N1 C8 H8 116.6 . . ? C9 C8 H8 116.6 . . ? C10 C9 C14 120.43(14) . . ? C10 C9 C8 113.03(14) . . ? C14 C9 C8 126.49(13) . . ? C11 C10 C9 121.42(16) . . ? C11 C10 H10 119.3 . . ? C9 C10 H10 119.3 . . ? C10 C11 C12 119.01(15) . . ? C10 C11 H11 120.5 . . ? C12 C11 H11 120.5 . . ? C11 C12 C13 119.94(16) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C12 C13 C14 123.35(15) . . ? C12 C13 H13 118.3 . . ? C14 C13 H13 118.3 . . ? C13 C14 C9 115.77(14) . . ? C13 C14 B2 115.76(13) . . ? C9 C14 B2 128.02(14) . . ? O2 C15 C16 126.02(14) . . ? O2 C15 C21 114.75(13) . . ? C16 C15 C21 119.23(14) . . ? C15 C16 C17 118.18(15) . . ? C15 C16 H16 120.9 . . ? C17 C16 H16 120.9 . . ? C16 C17 C18 123.11(15) . . ? C16 C17 H17 118.4 . . ? C18 C17 H17 118.4 . . ? C20 C18 C17 118.25(15) . . ? C20 C18 C19 120.34(15) . . ? C17 C18 C19 121.40(15) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C21 C20 C18 118.81(15) . . ? C21 C20 H20 120.6 . . ? C18 C20 H20 120.6 . . ? C20 C21 C15 122.39(14) . . ? C20 C21 N2 129.75(14) . . ? C15 C21 N2 107.86(13) . . ? N2 C22 C23 127.39(14) . . ? N2 C22 H22 116.3 . . ? C23 C22 H22 116.3 . . ? C24 C23 C28 120.57(14) . . ? C24 C23 C22 113.22(14) . . ? C28 C23 C22 126.20(13) . . ? C25 C24 C23 121.38(15) . . ? C25 C24 H24 119.3 . . ? C23 C24 H24 119.3 . . ? C24 C25 C26 118.94(15) . . ? C24 C25 H25 120.5 . . ? C26 C25 H25 120.5 . . ? C25 C26 C27 119.90(15) . . ? C25 C26 H26 120.1 . . ? C27 C26 H26 120.1 . . ? C26 C27 C28 123.37(15) . . ? C26 C27 H27 118.3 . . ? C28 C27 H27 118.3 . . ? C27 C28 C23 115.78(14) . . ? C27 C28 B1 115.95(14) . . ? C23 C28 B1 127.97(13) . . ? Cl1A C30 Cl3A 105.9(3) . . ? Cl1A C30 Cl2 120.2(3) . . ? Cl3A C30 Cl2 95.8(2) . . ? Cl1A C30 Cl2A 102.8(3) . . ? Cl3A C30 Cl2A 116.2(2) . . ? Cl3A C30 Cl1 110.1(3) . . ? Cl2 C30 Cl1 119.9(2) . . ? Cl2A C30 Cl1 101.4(2) . . ? Cl1A C30 Cl3 108.6(3) . . ? Cl2 C30 Cl3 102.67(18) . . ? Cl2A C30 Cl3 124.32(18) . . ? Cl1 C30 Cl3 112.5(3) . . ? Cl1A C30 H30 110.4 . . ? Cl3A C30 H30 117.3 . . ? Cl2 C30 H30 107.0 . . ? Cl2A C30 H30 103.2 . . ? Cl1 C30 H30 107.0 . . ? Cl3 C30 H30 107.0 . . ? Cl4A C40 Cl5 115.7(5) . . ? Cl4A C40 Cl6A 95.5(6) . . ? Cl5 C40 Cl6A 101.5(6) . . ? Cl5 C40 Cl4 109.1(4) . . ? Cl6A C40 Cl4 104.7(5) . . ? Cl4A C40 Cl6 109.6(5) . . ? Cl5 C40 Cl6 104.7(4) . . ? Cl4 C40 Cl6 119.5(5) . . ? Cl4A C40 Cl5A 111.4(5) . . ? Cl6A C40 Cl5A 110.9(6) . . ? Cl4 C40 Cl5A 103.7(4) . . ? Cl6 C40 Cl5A 114.3(4) . . ? Cl4A C40 H40 111.0 . . ? Cl5 C40 H40 107.7 . . ? Cl6A C40 H40 125.4 . . ? Cl4 C40 H40 107.7 . . ? Cl6 C40 H40 107.7 . . ? Cl5A C40 H40 102.6 . . ? Cl7 Cl4 C40 54.4(5) . . ? C40 Cl5 Cl8 79.6(3) . . ? Cl8 Cl5 Cl7 86.4(2) . . ? Cl9 Cl6 C40 71.8(5) . . ? Cl9 Cl6 Cl8 116.3(5) . . ? C40 Cl6 Cl8 66.0(2) . . ? Cl7 Cl4A C40 56.3(5) . . ? C40 Cl5A Cl8 71.9(3) . . ? Cl7 Cl5A Cl8 83.4(2) . . ? Cl9 Cl6A C40 72.8(6) . . ? Cl9 Cl6A Cl8 149.8(8) . . ? C40 Cl6A Cl8 77.6(4) . . ? Cl9 C50 Cl7 110.3(5) . . ? Cl9 C50 Cl8 108.8(4) . . ? Cl7 C50 Cl8 112.7(4) . . ? Cl9 C50 H50 108.3 . . ? Cl7 C50 H50 108.3 . . ? Cl8 C50 H50 108.3 . . ? Cl4 Cl7 C50 94.7(7) . . ? Cl4A Cl7 C50 84.0(6) . . ? Cl4 Cl7 Cl5A 132.5(7) . . ? Cl4A Cl7 Cl5A 125.4(7) . . ? C50 Cl7 Cl5A 46.5(4) . . ? Cl4 Cl7 Cl5 126.0(7) . . ? Cl4A Cl7 Cl5 118.3(7) . . ? Cl5 Cl8 Cl6A 84.1(3) . . ? C50 Cl8 Cl5A 46.3(3) . . ? Cl6A Cl8 Cl5A 87.2(3) . . ? Cl5 Cl8 Cl6 77.0(2) . . ? Cl5A Cl8 Cl6 80.7(2) . . ? Cl6 Cl9 C50 67.9(5) . . ? Cl6A Cl9 C50 56.3(6) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 30.11 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.623 _refine_diff_density_min -0.445 _refine_diff_density_rms 0.059 # Attachment 'k07tdj7.cif' data_k07tdj7 _database_code_depnum_ccdc_archive 'CCDC 694361' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H31 B2 Cl3 N2 O3' _chemical_formula_weight 559.51 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.5230(2) _cell_length_b 11.6200(3) _cell_length_c 13.0520(4) _cell_angle_alpha 99.1380(10) _cell_angle_beta 110.4610(10) _cell_angle_gamma 106.6310(10) _cell_volume 1371.87(6) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 15563 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.354 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.366 _exptl_absorpt_correction_type none _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19446 _diffrn_reflns_av_R_equivalents 0.0476 _diffrn_reflns_av_sigmaI/netI 0.0447 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.25 _diffrn_reflns_theta_max 27.52 _reflns_number_total 6273 _reflns_number_gt 4946 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinski & Minor, 1997)' _computing_data_reduction ; DENZO-SCALEPACK Z. Otwinowski and W. Minor, " Processing of X-ray Diffraction Data Collected in Oscillation Mode ", Methods in Enzymology, Volume 276: Macromolecular Crystallography, part A, p.307-326, 1997,C.W. Carter, Jr. & R. M. Sweet, Eds., Academic Press. ; _computing_structure_solution ; SIR97- Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C. , Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. (1999) J. Appl. Cryst. 32, 115-119 ; _computing_structure_refinement ; SHELXL97 -Program for Crystal Structure Analysis (Release 97-2). Sheldrick, G.M., Instit\"ut f\"ur Anorganische Chemie der Universit\"at, Tammanstrasse 4, D-3400 G\"ottingen, Germany, 1998 ; _computing_molecular_graphics 'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565' _computing_publication_material ; 'WinGX publication routines, Farrugia, L. J., J. Appl. Crystallogr., 1999, 32, 837-838 ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0388P)^2^+1.0894P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6273 _refine_ls_number_parameters 334 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0670 _refine_ls_R_factor_gt 0.0495 _refine_ls_wR_factor_ref 0.1229 _refine_ls_wR_factor_gt 0.1125 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.96735(15) -0.03791(13) 0.83987(11) 0.0199(3) Uani 1 1 d . . . N2 N 0.68811(15) 0.12398(13) 0.63385(12) 0.0197(3) Uani 1 1 d . . . O1 O 0.70679(13) -0.08065(11) 0.63588(10) 0.0217(3) Uani 1 1 d . . . O2 O 0.86310(13) 0.12194(12) 0.86703(10) 0.0231(3) Uani 1 1 d . . . O3 O 0.93481(12) 0.10217(11) 0.70777(9) 0.0201(2) Uani 1 1 d . . . B1 B 0.7878(2) 0.03699(18) 0.62396(16) 0.0201(4) Uani 1 1 d . . . B2 B 0.9678(2) 0.10296(18) 0.82362(16) 0.0206(4) Uani 1 1 d . . . C1 C 0.77258(18) -0.17091(16) 0.65252(14) 0.0209(3) Uani 1 1 d . . . H1 H 0.8489 -0.1576 0.6220 0.025 Uiso 1 1 calc R . . C2 C 0.6522(2) -0.30012(17) 0.58707(16) 0.0273(4) Uani 1 1 d . . . H2A H 0.5685 -0.3052 0.6068 0.033 Uiso 1 1 calc R . . H2B H 0.6183 -0.3095 0.5042 0.033 Uiso 1 1 calc R . . C3 C 0.7003(2) -0.40861(17) 0.61196(17) 0.0302(4) Uani 1 1 d . . . H3A H 0.6166 -0.4892 0.5698 0.036 Uiso 1 1 calc R . . H3B H 0.7778 -0.4094 0.5859 0.036 Uiso 1 1 calc R . . C4 C 0.7571(2) -0.39442(18) 0.73912(17) 0.0306(4) Uani 1 1 d . . . H4A H 0.7897 -0.4642 0.7550 0.037 Uiso 1 1 calc R . . H4B H 0.6779 -0.3983 0.7643 0.037 Uiso 1 1 calc R . . C5 C 0.8844(2) -0.26962(17) 0.80526(15) 0.0262(4) Uani 1 1 d . . . H5A H 0.9663 -0.2692 0.7843 0.031 Uiso 1 1 calc R . . H5B H 0.9183 -0.2608 0.8881 0.031 Uiso 1 1 calc R . . C6 C 0.84229(18) -0.15824(16) 0.78095(14) 0.0206(3) Uani 1 1 d . . . H6 H 0.7679 -0.1552 0.8113 0.025 Uiso 1 1 calc R . . C7 C 1.09274(19) -0.02814(17) 0.91170(14) 0.0229(4) Uani 1 1 d . . . H7 H 1.1130 -0.0976 0.9332 0.027 Uiso 1 1 calc R . . C8 C 1.20110(19) 0.09898(17) 0.95727(14) 0.0226(4) Uani 1 1 d . . . C9 C 1.3462(2) 0.13634(19) 1.03462(15) 0.0282(4) Uani 1 1 d . . . H9 H 1.3839 0.0775 1.0638 0.034 Uiso 1 1 calc R . . C10 C 1.4338(2) 0.2622(2) 1.06765(16) 0.0321(4) Uani 1 1 d . . . H10 H 1.5332 0.2909 1.1203 0.039 Uiso 1 1 calc R . . C11 C 1.3756(2) 0.34625(19) 1.02344(16) 0.0310(4) Uani 1 1 d . . . H11 H 1.4361 0.4324 1.0467 0.037 Uiso 1 1 calc R . . C12 C 1.2302(2) 0.30658(18) 0.94565(15) 0.0278(4) Uani 1 1 d . . . H12 H 1.1931 0.3657 0.9164 0.033 Uiso 1 1 calc R . . C13 C 1.13915(19) 0.18140(17) 0.91058(14) 0.0225(3) Uani 1 1 d . . . C14 C 0.80725(19) 0.21710(16) 0.84357(14) 0.0215(3) Uani 1 1 d . . . H14 H 0.8800 0.2853 0.8326 0.026 Uiso 1 1 calc R . . C15 C 0.7836(2) 0.26925(18) 0.94771(15) 0.0278(4) Uani 1 1 d . . . H15A H 0.7249 0.1986 0.9654 0.033 Uiso 1 1 calc R . . H15B H 0.8796 0.3110 1.0141 0.033 Uiso 1 1 calc R . . C16 C 0.7072(2) 0.36244(19) 0.93149(16) 0.0300(4) Uani 1 1 d . . . H16A H 0.6930 0.3911 1.0009 0.036 Uiso 1 1 calc R . . H16B H 0.7680 0.4366 0.9190 0.036 Uiso 1 1 calc R . . C17 C 0.5602(2) 0.2999(2) 0.82915(17) 0.0345(5) Uani 1 1 d . . . H17A H 0.5109 0.3607 0.8177 0.041 Uiso 1 1 calc R . . H17B H 0.4977 0.2286 0.8437 0.041 Uiso 1 1 calc R . . C18 C 0.5797(2) 0.25275(18) 0.72160(15) 0.0268(4) Uani 1 1 d . . . H18A H 0.6339 0.3254 0.7032 0.032 Uiso 1 1 calc R . . H18B H 0.4825 0.2092 0.6568 0.032 Uiso 1 1 calc R . . C19 C 0.66218(18) 0.16293(16) 0.73564(14) 0.0203(3) Uani 1 1 d . . . H19 H 0.5988 0.0857 0.7439 0.024 Uiso 1 1 calc R . . C20 C 0.63634(18) 0.15143(16) 0.54019(14) 0.0228(4) Uani 1 1 d . . . H20 H 0.5762 0.1998 0.5290 0.027 Uiso 1 1 calc R . . C21 C 0.67840(18) 0.10151(17) 0.45276(14) 0.0230(4) Uani 1 1 d . . . C22 C 0.6408(2) 0.11741(19) 0.34377(15) 0.0296(4) Uani 1 1 d . . . H22 H 0.5809 0.1638 0.3185 0.036 Uiso 1 1 calc R . . C23 C 0.6938(2) 0.0634(2) 0.27349(16) 0.0346(5) Uani 1 1 d . . . H23 H 0.6717 0.0739 0.1993 0.042 Uiso 1 1 calc R . . C24 C 0.7792(2) -0.0062(2) 0.31102(16) 0.0330(4) Uani 1 1 d . . . H24 H 0.8133 -0.0442 0.2615 0.040 Uiso 1 1 calc R . . C25 C 0.8155(2) -0.02097(18) 0.42061(15) 0.0269(4) Uani 1 1 d . . . H25 H 0.8737 -0.0690 0.4449 0.032 Uiso 1 1 calc R . . C26 C 0.76679(18) 0.03425(16) 0.49407(14) 0.0221(3) Uani 1 1 d . . . C30 C 1.0787(2) 0.3577(2) 0.6508(2) 0.0404(5) Uani 1 1 d . . . H30 H 1.0474 0.2764 0.6687 0.048 Uiso 1 1 calc R . . Cl1 Cl 0.99856(8) 0.33121(8) 0.50337(6) 0.0752(3) Uani 1 1 d . . . Cl2 Cl 1.26798(8) 0.41578(11) 0.69867(8) 0.0872(3) Uani 1 1 d . . . Cl3 Cl 1.02555(12) 0.46361(9) 0.71987(8) 0.0834(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0215(7) 0.0251(7) 0.0162(6) 0.0071(5) 0.0084(6) 0.0115(6) N2 0.0192(7) 0.0211(7) 0.0180(7) 0.0061(5) 0.0062(5) 0.0081(5) O1 0.0211(6) 0.0226(6) 0.0233(6) 0.0093(5) 0.0075(5) 0.0115(5) O2 0.0283(6) 0.0289(7) 0.0205(6) 0.0113(5) 0.0116(5) 0.0182(5) O3 0.0207(6) 0.0238(6) 0.0159(5) 0.0066(5) 0.0060(5) 0.0098(5) B1 0.0198(9) 0.0228(9) 0.0182(8) 0.0061(7) 0.0064(7) 0.0102(7) B2 0.0231(9) 0.0226(9) 0.0178(9) 0.0067(7) 0.0070(7) 0.0119(7) C1 0.0219(8) 0.0220(8) 0.0201(8) 0.0072(6) 0.0075(7) 0.0109(7) C2 0.0266(9) 0.0243(9) 0.0256(9) 0.0063(7) 0.0051(7) 0.0095(7) C3 0.0299(9) 0.0214(9) 0.0324(10) 0.0063(7) 0.0064(8) 0.0092(8) C4 0.0325(10) 0.0258(9) 0.0346(10) 0.0149(8) 0.0120(8) 0.0112(8) C5 0.0281(9) 0.0279(9) 0.0240(9) 0.0121(7) 0.0083(7) 0.0129(8) C6 0.0219(8) 0.0236(8) 0.0182(8) 0.0078(6) 0.0087(7) 0.0096(7) C7 0.0270(9) 0.0291(9) 0.0176(8) 0.0101(7) 0.0098(7) 0.0152(7) C8 0.0244(8) 0.0296(9) 0.0156(7) 0.0060(7) 0.0092(7) 0.0116(7) C9 0.0255(9) 0.0362(10) 0.0216(8) 0.0085(7) 0.0070(7) 0.0130(8) C10 0.0230(9) 0.0423(11) 0.0230(9) 0.0052(8) 0.0058(7) 0.0079(8) C11 0.0286(9) 0.0306(10) 0.0254(9) 0.0033(8) 0.0095(8) 0.0042(8) C12 0.0312(9) 0.0272(9) 0.0226(8) 0.0057(7) 0.0098(7) 0.0103(8) C13 0.0266(9) 0.0261(9) 0.0156(7) 0.0047(6) 0.0089(7) 0.0116(7) C14 0.0241(8) 0.0246(9) 0.0188(8) 0.0081(7) 0.0082(7) 0.0134(7) C15 0.0341(10) 0.0324(10) 0.0211(8) 0.0075(7) 0.0105(8) 0.0194(8) C16 0.0375(10) 0.0322(10) 0.0238(9) 0.0058(7) 0.0115(8) 0.0205(8) C17 0.0355(10) 0.0427(12) 0.0292(10) 0.0043(8) 0.0113(8) 0.0257(9) C18 0.0271(9) 0.0290(9) 0.0238(9) 0.0050(7) 0.0064(7) 0.0165(8) C19 0.0227(8) 0.0219(8) 0.0181(8) 0.0052(6) 0.0092(7) 0.0102(7) C20 0.0206(8) 0.0255(9) 0.0209(8) 0.0084(7) 0.0052(7) 0.0098(7) C21 0.0203(8) 0.0281(9) 0.0190(8) 0.0078(7) 0.0064(7) 0.0083(7) C22 0.0273(9) 0.0384(11) 0.0207(9) 0.0127(8) 0.0056(7) 0.0120(8) C23 0.0335(10) 0.0498(13) 0.0193(9) 0.0130(8) 0.0102(8) 0.0128(9) C24 0.0305(10) 0.0469(12) 0.0208(9) 0.0059(8) 0.0131(8) 0.0121(9) C25 0.0245(8) 0.0332(10) 0.0209(8) 0.0057(7) 0.0080(7) 0.0108(8) C26 0.0197(8) 0.0244(8) 0.0180(8) 0.0045(6) 0.0055(6) 0.0060(7) C30 0.0410(12) 0.0431(12) 0.0436(12) 0.0203(10) 0.0196(10) 0.0183(10) Cl1 0.0558(4) 0.0870(6) 0.0430(4) 0.0197(3) 0.0097(3) -0.0159(4) Cl2 0.0389(4) 0.1457(9) 0.0791(6) 0.0525(6) 0.0166(4) 0.0363(5) Cl3 0.1364(8) 0.0914(6) 0.1050(7) 0.0654(5) 0.0909(6) 0.0867(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C7 1.284(2) . ? N1 C6 1.475(2) . ? N1 B2 1.682(2) . ? N2 C20 1.285(2) . ? N2 C19 1.476(2) . ? N2 B1 1.673(2) . ? O1 C1 1.4175(19) . ? O1 B1 1.454(2) . ? O2 C14 1.4197(19) . ? O2 B2 1.456(2) . ? O3 B2 1.426(2) . ? O3 B1 1.430(2) . ? B1 C26 1.625(2) . ? B2 C13 1.634(3) . ? C1 C2 1.528(2) . ? C1 C6 1.539(2) . ? C1 H1 1.0000 . ? C2 C3 1.527(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.517(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.524(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.527(2) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6 1.0000 . ? C7 C8 1.456(3) . ? C7 H7 0.9500 . ? C8 C9 1.394(2) . ? C8 C13 1.407(2) . ? C9 C10 1.387(3) . ? C9 H9 0.9500 . ? C10 C11 1.392(3) . ? C10 H10 0.9500 . ? C11 C12 1.395(3) . ? C11 H11 0.9500 . ? C12 C13 1.388(3) . ? C12 H12 0.9500 . ? C14 C15 1.529(2) . ? C14 C19 1.541(2) . ? C14 H14 1.0000 . ? C15 C16 1.522(2) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.519(3) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.528(3) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.531(2) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 H19 1.0000 . ? C20 C21 1.457(3) . ? C20 H20 0.9500 . ? C21 C22 1.395(2) . ? C21 C26 1.402(2) . ? C22 C23 1.386(3) . ? C22 H22 0.9500 . ? C23 C24 1.392(3) . ? C23 H23 0.9500 . ? C24 C25 1.398(3) . ? C24 H24 0.9500 . ? C25 C26 1.389(3) . ? C25 H25 0.9500 . ? C30 Cl3 1.742(2) . ? C30 Cl1 1.743(2) . ? C30 Cl2 1.744(2) . ? C30 H30 1.0000 . ? 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 C7 N1 C6 123.20(15) . . ? C7 N1 B2 110.84(14) . . ? C6 N1 B2 125.95(13) . . ? C20 N2 C19 124.68(15) . . ? C20 N2 B1 110.58(14) . . ? C19 N2 B1 124.75(13) . . ? C1 O1 B1 118.77(13) . . ? C14 O2 B2 119.36(13) . . ? B2 O3 B1 118.88(14) . . ? O3 B1 O1 116.68(14) . . ? O3 B1 C26 114.09(15) . . ? O1 B1 C26 114.68(14) . . ? O3 B1 N2 109.42(13) . . ? O1 B1 N2 102.63(13) . . ? C26 B1 N2 96.40(12) . . ? O3 B2 O2 116.20(14) . . ? O3 B2 C13 113.91(15) . . ? O2 B2 C13 115.14(14) . . ? O3 B2 N1 110.40(13) . . ? O2 B2 N1 102.46(13) . . ? C13 B2 N1 95.88(12) . . ? O1 C1 C2 107.25(13) . . ? O1 C1 C6 109.30(13) . . ? C2 C1 C6 110.73(14) . . ? O1 C1 H1 109.8 . . ? C2 C1 H1 109.8 . . ? C6 C1 H1 109.8 . . ? C3 C2 C1 113.67(15) . . ? C3 C2 H2A 108.8 . . ? C1 C2 H2A 108.8 . . ? C3 C2 H2B 108.8 . . ? C1 C2 H2B 108.8 . . ? H2A C2 H2B 107.7 . . ? C4 C3 C2 109.91(16) . . ? C4 C3 H3A 109.7 . . ? C2 C3 H3A 109.7 . . ? C4 C3 H3B 109.7 . . ? C2 C3 H3B 109.7 . . ? H3A C3 H3B 108.2 . . ? C3 C4 C5 110.22(15) . . ? C3 C4 H4A 109.6 . . ? C5 C4 H4A 109.6 . . ? C3 C4 H4B 109.6 . . ? C5 C4 H4B 109.6 . . ? H4A C4 H4B 108.1 . . ? C4 C5 C6 112.11(15) . . ? C4 C5 H5A 109.2 . . ? C6 C5 H5A 109.2 . . ? C4 C5 H5B 109.2 . . ? C6 C5 H5B 109.2 . . ? H5A C5 H5B 107.9 . . ? N1 C6 C5 112.18(14) . . ? N1 C6 C1 109.36(13) . . ? C5 C6 C1 112.92(14) . . ? N1 C6 H6 107.4 . . ? C5 C6 H6 107.4 . . ? C1 C6 H6 107.4 . . ? N1 C7 C8 113.87(15) . . ? N1 C7 H7 123.1 . . ? C8 C7 H7 123.1 . . ? C9 C8 C13 123.73(17) . . ? C9 C8 C7 126.19(16) . . ? C13 C8 C7 110.08(15) . . ? C10 C9 C8 117.88(17) . . ? C10 C9 H9 121.1 . . ? C8 C9 H9 121.1 . . ? C9 C10 C11 119.80(17) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C10 C11 C12 121.31(18) . . ? C10 C11 H11 119.3 . . ? C12 C11 H11 119.3 . . ? C13 C12 C11 120.56(18) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C12 C13 C8 116.73(16) . . ? C12 C13 B2 133.96(16) . . ? C8 C13 B2 109.31(15) . . ? O2 C14 C15 106.71(13) . . ? O2 C14 C19 110.71(14) . . ? C15 C14 C19 110.43(14) . . ? O2 C14 H14 109.7 . . ? C15 C14 H14 109.7 . . ? C19 C14 H14 109.7 . . ? C16 C15 C14 113.70(15) . . ? C16 C15 H15A 108.8 . . ? C14 C15 H15A 108.8 . . ? C16 C15 H15B 108.8 . . ? C14 C15 H15B 108.8 . . ? H15A C15 H15B 107.7 . . ? C17 C16 C15 109.39(16) . . ? C17 C16 H16A 109.8 . . ? C15 C16 H16A 109.8 . . ? C17 C16 H16B 109.8 . . ? C15 C16 H16B 109.8 . . ? H16A C16 H16B 108.2 . . ? C16 C17 C18 110.53(17) . . ? C16 C17 H17A 109.5 . . ? C18 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? C18 C17 H17B 109.5 . . ? H17A C17 H17B 108.1 . . ? C17 C18 C19 112.28(15) . . ? C17 C18 H18A 109.1 . . ? C19 C18 H18A 109.1 . . ? C17 C18 H18B 109.1 . . ? C19 C18 H18B 109.1 . . ? H18A C18 H18B 107.9 . . ? N2 C19 C18 111.79(14) . . ? N2 C19 C14 110.12(13) . . ? C18 C19 C14 112.84(14) . . ? N2 C19 H19 107.3 . . ? C18 C19 H19 107.3 . . ? C14 C19 H19 107.3 . . ? N2 C20 C21 113.78(15) . . ? N2 C20 H20 123.1 . . ? C21 C20 H20 123.1 . . ? C22 C21 C26 123.23(17) . . ? C22 C21 C20 126.76(16) . . ? C26 C21 C20 110.00(15) . . ? C23 C22 C21 117.86(18) . . ? C23 C22 H22 121.1 . . ? C21 C22 H22 121.1 . . ? C22 C23 C24 120.33(17) . . ? C22 C23 H23 119.8 . . ? C24 C23 H23 119.8 . . ? C23 C24 C25 120.83(18) . . ? C23 C24 H24 119.6 . . ? C25 C24 H24 119.6 . . ? C26 C25 C24 120.27(18) . . ? C26 C25 H25 119.9 . . ? C24 C25 H25 119.9 . . ? C25 C26 C21 117.45(16) . . ? C25 C26 B1 133.30(16) . . ? C21 C26 B1 109.24(15) . . ? Cl3 C30 Cl1 110.91(13) . . ? Cl3 C30 Cl2 109.98(14) . . ? Cl1 C30 Cl2 108.99(13) . . ? Cl3 C30 H30 109.0 . . ? Cl1 C30 H30 109.0 . . ? Cl2 C30 H30 109.0 . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.583 _refine_diff_density_min -0.664 _refine_diff_density_rms 0.053