# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'Lothar Weber' 'Andreas Brockhinke' 'Mark A Fox' 'Todd B. Marder' 'Beate Neumann' 'Stefanie Schwedler' 'Hans-Georg Stammler' 'Vanessa Werner' _publ_contact_author_name 'Lothar Weber' _publ_contact_author_email LOTHAR.WEBER@UNI-BIELEFELD.DE _publ_section_title ; Synthetic, Structural, Photophysical and Computational Studies on 2-Arylethynyl-1,3,2-Diazaboroles ; # Attachment 'Publikation.CIF' #============================================================================== data_compound2 _database_code_depnum_ccdc_archive 'CCDC 711345' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H21 B N2' _chemical_formula_sum 'C19 H21 B N2' _chemical_formula_weight 288.19 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 14.2697(3) _cell_length_b 8.3197(2) _cell_length_c 14.6128(2) _cell_angle_alpha 90.00 _cell_angle_beta 107.3256(11) _cell_angle_gamma 90.00 _cell_volume 1656.11(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 18862 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 30.034 _exptl_crystal_description fragment _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.156 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.067 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9828 _exptl_absorpt_correction_T_max 0.9841 _exptl_absorpt_process_details 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 35652 _diffrn_reflns_av_R_equivalents 0.038 _diffrn_reflns_av_sigmaI/netI 0.0254 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 29.99 _reflns_number_total 4828 _reflns_number_gt 3873 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect, Bruker AXS, 2004' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0562P)^2^+0.3835P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.017(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4828 _refine_ls_number_parameters 203 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0562 _refine_ls_R_factor_gt 0.0424 _refine_ls_wR_factor_ref 0.1162 _refine_ls_wR_factor_gt 0.1081 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _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 0.63459(6) 0.26631(9) 0.03733(6) 0.01871(17) Uani 1 1 d . . . N2 N 0.68686(6) 0.41110(10) 0.17754(5) 0.01869(17) Uani 1 1 d . . . B1 B 0.60672(8) 0.31929(13) 0.11861(7) 0.0187(2) Uani 1 1 d . . . C1 C 0.72875(7) 0.32333(11) 0.04699(6) 0.01883(19) Uani 1 1 d . . . C2 C 0.76107(7) 0.41251(11) 0.13300(7) 0.01871(19) Uani 1 1 d . . . C3 C 0.85335(7) 0.48419(12) 0.16022(7) 0.0232(2) Uani 1 1 d . . . H3 H 0.8755 0.5443 0.2179 0.028 Uiso 1 1 calc R . . C4 C 0.91221(7) 0.46488(14) 0.10010(8) 0.0285(2) Uani 1 1 d . . . H4 H 0.9752 0.5137 0.1170 0.034 Uiso 1 1 calc R . . C5 C 0.88068(8) 0.37559(15) 0.01583(8) 0.0293(2) Uani 1 1 d . . . H5 H 0.9228 0.3639 -0.0233 0.035 Uiso 1 1 calc R . . C6 C 0.78846(8) 0.30320(13) -0.01200(7) 0.0244(2) Uani 1 1 d . . . H6 H 0.7671 0.2421 -0.0694 0.029 Uiso 1 1 calc R . . C7 C 0.57824(8) 0.17395(12) -0.04569(7) 0.0224(2) Uani 1 1 d . . . H7A H 0.5228 0.1208 -0.0302 0.027 Uiso 1 1 calc R . . H7B H 0.6207 0.0889 -0.0594 0.027 Uiso 1 1 calc R . . C8 C 0.53832(9) 0.27653(14) -0.13462(8) 0.0313(3) Uani 1 1 d . . . H8A H 0.4933 0.3573 -0.1228 0.047 Uiso 1 1 calc R . . H8B H 0.5031 0.2081 -0.1885 0.047 Uiso 1 1 calc R . . H8C H 0.5928 0.3304 -0.1501 0.047 Uiso 1 1 calc R . . C9 C 0.69665(8) 0.49080(12) 0.26915(7) 0.0228(2) Uani 1 1 d . . . H9A H 0.6308 0.5018 0.2779 0.027 Uiso 1 1 calc R . . H9B H 0.7232 0.6003 0.2672 0.027 Uiso 1 1 calc R . . C10 C 0.76317(9) 0.40114(13) 0.35467(7) 0.0307(2) Uani 1 1 d . . . H10A H 0.7373 0.2927 0.3573 0.046 Uiso 1 1 calc R . . H10B H 0.7657 0.4590 0.4138 0.046 Uiso 1 1 calc R . . H10C H 0.8294 0.3940 0.3481 0.046 Uiso 1 1 calc R . . C11 C 0.50866(7) 0.27905(12) 0.13568(7) 0.0211(2) Uani 1 1 d . . . C12 C 0.42908(7) 0.24009(12) 0.14123(7) 0.0207(2) Uani 1 1 d . . . C13 C 0.33347(7) 0.19124(12) 0.14461(7) 0.01915(19) Uani 1 1 d . . . C14 C 0.24882(7) 0.25537(12) 0.07974(7) 0.0209(2) Uani 1 1 d . . . H14 H 0.2543 0.3352 0.0351 0.025 Uiso 1 1 calc R . . C15 C 0.15677(7) 0.20231(12) 0.08059(7) 0.0222(2) Uani 1 1 d . . . H15 H 0.0999 0.2469 0.0363 0.027 Uiso 1 1 calc R . . C16 C 0.14594(7) 0.08522(12) 0.14494(7) 0.0218(2) Uani 1 1 d . . . C17 C 0.23045(8) 0.02428(13) 0.21038(7) 0.0261(2) Uani 1 1 d . . . H17 H 0.2247 -0.0541 0.2556 0.031 Uiso 1 1 calc R . . C18 C 0.32303(8) 0.07606(13) 0.21064(7) 0.0250(2) Uani 1 1 d . . . H18 H 0.3797 0.0330 0.2560 0.030 Uiso 1 1 calc R . . C19 C 0.04576(8) 0.02310(15) 0.14198(8) 0.0296(2) Uani 1 1 d . . . H19A H 0.0230 -0.0532 0.0889 0.044 Uiso 1 1 calc R . . H19B H -0.0004 0.1132 0.1325 0.044 Uiso 1 1 calc R . . H19C H 0.0496 -0.0310 0.2026 0.044 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0188(4) 0.0173(4) 0.0195(4) -0.0006(3) 0.0051(3) -0.0011(3) N2 0.0187(4) 0.0183(4) 0.0192(4) -0.0006(3) 0.0057(3) -0.0006(3) B1 0.0190(5) 0.0162(5) 0.0204(5) 0.0009(4) 0.0050(4) 0.0009(4) C1 0.0187(4) 0.0175(4) 0.0202(4) 0.0030(3) 0.0056(3) 0.0018(3) C2 0.0182(4) 0.0169(4) 0.0207(4) 0.0042(3) 0.0053(3) 0.0013(3) C3 0.0195(4) 0.0237(5) 0.0236(4) 0.0053(4) 0.0022(4) -0.0017(4) C4 0.0171(4) 0.0358(6) 0.0313(5) 0.0113(4) 0.0054(4) -0.0009(4) C5 0.0223(5) 0.0381(6) 0.0303(5) 0.0101(4) 0.0120(4) 0.0056(4) C6 0.0246(5) 0.0270(5) 0.0232(4) 0.0034(4) 0.0095(4) 0.0051(4) C7 0.0268(5) 0.0183(4) 0.0204(4) -0.0025(3) 0.0046(4) -0.0024(4) C8 0.0341(6) 0.0295(6) 0.0235(5) 0.0019(4) -0.0016(4) -0.0037(5) C9 0.0252(5) 0.0222(5) 0.0214(4) -0.0051(4) 0.0074(4) -0.0024(4) C10 0.0436(6) 0.0251(5) 0.0200(4) -0.0008(4) 0.0043(4) -0.0059(5) C11 0.0216(4) 0.0198(5) 0.0216(4) -0.0009(3) 0.0059(3) -0.0005(4) C12 0.0216(4) 0.0191(4) 0.0217(4) -0.0019(3) 0.0071(4) 0.0001(4) C13 0.0192(4) 0.0197(4) 0.0199(4) -0.0035(3) 0.0078(3) -0.0013(3) C14 0.0226(5) 0.0211(5) 0.0198(4) 0.0006(3) 0.0074(4) -0.0017(4) C15 0.0194(4) 0.0254(5) 0.0208(4) 0.0016(4) 0.0046(3) -0.0003(4) C16 0.0215(4) 0.0255(5) 0.0195(4) -0.0016(4) 0.0078(4) -0.0035(4) C17 0.0249(5) 0.0306(5) 0.0231(5) 0.0068(4) 0.0074(4) -0.0033(4) C18 0.0216(5) 0.0288(5) 0.0230(4) 0.0050(4) 0.0043(4) 0.0007(4) C19 0.0238(5) 0.0391(6) 0.0269(5) 0.0016(4) 0.0090(4) -0.0073(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.3918(12) . ? N1 B1 1.4299(13) . ? N1 C7 1.4587(12) . ? N2 C2 1.3984(12) . ? N2 B1 1.4305(13) . ? N2 C9 1.4628(12) . ? B1 C11 1.5298(14) . ? C1 C6 1.3909(13) . ? C1 C2 1.4134(13) . ? C2 C3 1.3913(13) . ? C3 C4 1.3937(15) . ? C3 H3 0.9500 . ? C4 C5 1.3931(17) . ? C4 H4 0.9500 . ? C5 C6 1.3933(15) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.5169(14) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.5208(14) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.2067(14) . ? C12 C13 1.4384(13) . ? C13 C18 1.3990(14) . ? C13 C14 1.4002(13) . ? C14 C15 1.3892(13) . ? C14 H14 0.9500 . ? C15 C16 1.3942(14) . ? C15 H15 0.9500 . ? C16 C17 1.3925(14) . ? C16 C19 1.5085(14) . ? C17 C18 1.3884(14) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 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 C1 N1 B1 108.04(8) . . ? C1 N1 C7 122.71(8) . . ? B1 N1 C7 129.22(8) . . ? C2 N2 B1 107.74(8) . . ? C2 N2 C9 122.88(8) . . ? B1 N2 C9 129.37(8) . . ? N1 B1 N2 107.12(8) . . ? N1 B1 C11 124.21(9) . . ? N2 B1 C11 128.67(9) . . ? C6 C1 N1 130.33(9) . . ? C6 C1 C2 121.09(9) . . ? N1 C1 C2 108.58(8) . . ? C3 C2 N2 130.84(9) . . ? C3 C2 C1 120.64(9) . . ? N2 C2 C1 108.52(8) . . ? C2 C3 C4 117.84(10) . . ? C2 C3 H3 121.1 . . ? C4 C3 H3 121.1 . . ? C5 C4 C3 121.47(10) . . ? C5 C4 H4 119.3 . . ? C3 C4 H4 119.3 . . ? C4 C5 C6 121.12(10) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C1 C6 C5 117.83(10) . . ? C1 C6 H6 121.1 . . ? C5 C6 H6 121.1 . . ? N1 C7 C8 112.92(8) . . ? N1 C7 H7A 109.0 . . ? C8 C7 H7A 109.0 . . ? N1 C7 H7B 109.0 . . ? C8 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N2 C9 C10 113.32(8) . . ? N2 C9 H9A 108.9 . . ? C10 C9 H9A 108.9 . . ? N2 C9 H9B 108.9 . . ? C10 C9 H9B 108.9 . . ? H9A C9 H9B 107.7 . . ? 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 . . ? C12 C11 B1 174.03(10) . . ? C11 C12 C13 178.03(10) . . ? C18 C13 C14 118.71(9) . . ? C18 C13 C12 120.94(9) . . ? C14 C13 C12 120.33(9) . . ? C15 C14 C13 120.02(9) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C14 C15 C16 121.54(9) . . ? C14 C15 H15 119.2 . . ? C16 C15 H15 119.2 . . ? C17 C16 C15 118.05(9) . . ? C17 C16 C19 120.96(9) . . ? C15 C16 C19 120.97(9) . . ? C18 C17 C16 121.18(9) . . ? C18 C17 H17 119.4 . . ? C16 C17 H17 119.4 . . ? C17 C18 C13 120.48(9) . . ? C17 C18 H18 119.8 . . ? C13 C18 H18 119.8 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 29.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.268 _refine_diff_density_min -0.198 _refine_diff_density_rms 0.041 #========================================================================= data_compound3 _database_code_depnum_ccdc_archive 'CCDC 711346' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H21 B N2 O' _chemical_formula_sum 'C19 H21 B N2 O' _chemical_formula_weight 304.19 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P b c a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 8.3709(3) _cell_length_b 16.8468(5) _cell_length_c 48.0255(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6772.7(4) _cell_formula_units_Z 16 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 50615 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description fragment _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.193 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2592 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9784 _exptl_absorpt_correction_T_max 0.9869 _exptl_absorpt_process_details 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28284 _diffrn_reflns_av_R_equivalents 0.055 _diffrn_reflns_av_sigmaI/netI 0.0681 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -62 _diffrn_reflns_limit_l_max 62 _diffrn_reflns_theta_min 2.95 _diffrn_reflns_theta_max 27.47 _reflns_number_total 7576 _reflns_number_gt 4774 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect, Bruker AXS, 2004' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0519P)^2^+0.0000P] 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 7576 _refine_ls_number_parameters 421 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0890 _refine_ls_R_factor_gt 0.0449 _refine_ls_wR_factor_ref 0.1087 _refine_ls_wR_factor_gt 0.0949 _refine_ls_goodness_of_fit_ref 0.969 _refine_ls_restrained_S_all 0.969 _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 O1 O 0.96340(12) 0.16347(6) 0.14261(2) 0.0276(3) Uani 1 1 d . . . N1 N 0.60071(14) -0.18480(6) 0.00360(3) 0.0195(3) Uani 1 1 d . . . N2 N 0.73320(13) -0.08446(6) -0.01911(3) 0.0201(3) Uani 1 1 d . . . B1 B 0.69136(19) -0.11364(9) 0.00784(4) 0.0208(4) Uani 1 1 d . . . C1 C 0.58897(16) -0.19777(8) -0.02504(3) 0.0194(3) Uani 1 1 d . . . C2 C 0.67042(16) -0.13607(8) -0.03904(3) 0.0203(3) Uani 1 1 d . . . C3 C 0.67942(17) -0.13480(8) -0.06777(3) 0.0249(4) Uani 1 1 d . . . H3 H 0.7352 -0.0936 -0.0772 0.030 Uiso 1 1 calc R . . C4 C 0.60461(18) -0.19553(9) -0.08267(3) 0.0279(4) Uani 1 1 d . . . H4 H 0.6091 -0.1956 -0.1024 0.033 Uiso 1 1 calc R . . C5 C 0.52369(17) -0.25580(8) -0.06881(3) 0.0268(4) Uani 1 1 d . . . H5 H 0.4733 -0.2965 -0.0793 0.032 Uiso 1 1 calc R . . C6 C 0.51487(16) -0.25786(8) -0.04001(3) 0.0227(3) Uani 1 1 d . . . H6 H 0.4595 -0.2994 -0.0307 0.027 Uiso 1 1 calc R . . C7 C 0.52411(18) -0.23661(8) 0.02398(3) 0.0256(4) Uani 1 1 d . . . H7A H 0.4113 -0.2448 0.0185 0.031 Uiso 1 1 calc R . . H7B H 0.5244 -0.2098 0.0423 0.031 Uiso 1 1 calc R . . C8 C 0.60454(19) -0.31701(9) 0.02689(4) 0.0331(4) Uani 1 1 d . . . H8A H 0.5983 -0.3455 0.0091 0.050 Uiso 1 1 calc R . . H8B H 0.5504 -0.3479 0.0414 0.050 Uiso 1 1 calc R . . H8C H 0.7168 -0.3095 0.0320 0.050 Uiso 1 1 calc R . . C9 C 0.81764(17) -0.01173(8) -0.02652(3) 0.0236(4) Uani 1 1 d . . . H9A H 0.8963 -0.0237 -0.0413 0.028 Uiso 1 1 calc R . . H9B H 0.8772 0.0077 -0.0101 0.028 Uiso 1 1 calc R . . C10 C 0.70577(19) 0.05330(8) -0.03663(4) 0.0346(4) Uani 1 1 d . . . H10A H 0.6421 0.0334 -0.0523 0.052 Uiso 1 1 calc R . . H10B H 0.7686 0.0992 -0.0427 0.052 Uiso 1 1 calc R . . H10C H 0.6346 0.0692 -0.0214 0.052 Uiso 1 1 calc R . . C11 C 0.73910(18) -0.07475(8) 0.03525(3) 0.0230(3) Uani 1 1 d . . . C12 C 0.78338(17) -0.03829(8) 0.05547(3) 0.0235(4) Uani 1 1 d . . . C13 C 0.83200(17) 0.01006(8) 0.07871(3) 0.0213(3) Uani 1 1 d . . . C14 C 0.96533(18) -0.00752(8) 0.09490(3) 0.0232(4) Uani 1 1 d . . . H14 H 1.0246 -0.0543 0.0911 0.028 Uiso 1 1 calc R . . C15 C 1.01406(17) 0.04172(8) 0.11660(3) 0.0231(3) Uani 1 1 d . . . H15 H 1.1049 0.0284 0.1275 0.028 Uiso 1 1 calc R . . C16 C 0.92820(17) 0.11048(8) 0.12211(3) 0.0217(3) Uani 1 1 d . . . C17 C 0.79440(17) 0.12910(8) 0.10599(3) 0.0229(4) Uani 1 1 d . . . H17 H 0.7358 0.1762 0.1098 0.027 Uiso 1 1 calc R . . C18 C 0.74676(18) 0.07982(8) 0.08469(3) 0.0231(3) Uani 1 1 d . . . H18 H 0.6553 0.0931 0.0739 0.028 Uiso 1 1 calc R . . C19 C 1.10714(18) 0.15083(9) 0.15825(3) 0.0291(4) Uani 1 1 d . . . H19A H 1.0985 0.1010 0.1687 0.044 Uiso 1 1 calc R . . H19B H 1.1228 0.1950 0.1713 0.044 Uiso 1 1 calc R . . H19C H 1.1983 0.1479 0.1455 0.044 Uiso 1 1 calc R . . O2 O 0.14918(13) 0.32382(6) 0.12854(2) 0.0305(3) Uani 1 1 d . . . N3 N -0.09621(14) 0.81431(7) 0.19019(3) 0.0211(3) Uani 1 1 d . . . N4 N 0.06033(14) 0.79756(7) 0.22899(2) 0.0212(3) Uani 1 1 d . . . B2 B -0.00605(19) 0.75727(10) 0.20552(4) 0.0216(4) Uani 1 1 d . . . C20 C -0.08229(17) 0.88752(8) 0.20365(3) 0.0208(3) Uani 1 1 d . . . C21 C 0.01254(17) 0.87723(8) 0.22762(3) 0.0211(3) Uani 1 1 d . . . C22 C 0.04549(18) 0.94076(8) 0.24508(3) 0.0267(4) Uani 1 1 d . . . H22 H 0.1097 0.9340 0.2612 0.032 Uiso 1 1 calc R . . C23 C -0.01777(19) 1.01431(9) 0.23835(4) 0.0311(4) Uani 1 1 d . . . H23 H 0.0038 1.0586 0.2500 0.037 Uiso 1 1 calc R . . C24 C -0.11226(19) 1.02445(9) 0.21481(3) 0.0300(4) Uani 1 1 d . . . H24 H -0.1548 1.0754 0.2107 0.036 Uiso 1 1 calc R . . C25 C -0.14552(18) 0.96129(8) 0.19713(3) 0.0259(4) Uani 1 1 d . . . H25 H -0.2098 0.9684 0.1810 0.031 Uiso 1 1 calc R . . C26 C -0.18797(18) 0.80415(8) 0.16469(3) 0.0245(4) Uani 1 1 d . . . H26A H -0.2903 0.8332 0.1664 0.029 Uiso 1 1 calc R . . H26B H -0.2130 0.7472 0.1622 0.029 Uiso 1 1 calc R . . C27 C -0.0986(2) 0.83414(10) 0.13922(3) 0.0331(4) Uani 1 1 d . . . H27A H -0.0719 0.8903 0.1418 0.050 Uiso 1 1 calc R . . H27B H -0.1662 0.8281 0.1227 0.050 Uiso 1 1 calc R . . H27C H -0.0003 0.8034 0.1368 0.050 Uiso 1 1 calc R . . C28 C 0.14871(18) 0.76525(9) 0.25260(3) 0.0257(4) Uani 1 1 d . . . H28A H 0.2371 0.8019 0.2573 0.031 Uiso 1 1 calc R . . H28B H 0.1964 0.7138 0.2471 0.031 Uiso 1 1 calc R . . C29 C 0.04514(19) 0.75293(10) 0.27826(3) 0.0298(4) Uani 1 1 d . . . H29A H -0.0016 0.8038 0.2839 0.045 Uiso 1 1 calc R . . H29B H 0.1108 0.7319 0.2935 0.045 Uiso 1 1 calc R . . H29C H -0.0405 0.7152 0.2739 0.045 Uiso 1 1 calc R . . C30 C 0.01756(18) 0.67098(9) 0.19699(3) 0.0245(4) Uani 1 1 d . . . C31 C 0.03953(18) 0.60547(9) 0.18730(3) 0.0242(4) Uani 1 1 d . . . C32 C 0.06455(17) 0.53171(8) 0.17300(3) 0.0233(4) Uani 1 1 d . . . C33 C -0.00635(18) 0.52069(9) 0.14714(3) 0.0280(4) Uani 1 1 d . . . H33 H -0.0735 0.5611 0.1399 0.034 Uiso 1 1 calc R . . C34 C 0.01797(19) 0.45259(9) 0.13165(3) 0.0277(4) Uani 1 1 d . . . H34 H -0.0319 0.4464 0.1140 0.033 Uiso 1 1 calc R . . C35 C 0.11592(17) 0.39343(8) 0.14213(3) 0.0237(4) Uani 1 1 d . . . C36 C 0.18804(18) 0.40297(8) 0.16805(3) 0.0266(4) Uani 1 1 d . . . H36 H 0.2550 0.3623 0.1752 0.032 Uiso 1 1 calc R . . C37 C 0.16271(18) 0.47110(8) 0.18334(3) 0.0260(4) Uani 1 1 d . . . H37 H 0.2122 0.4770 0.2010 0.031 Uiso 1 1 calc R . . C38 C 0.06804(19) 0.31013(9) 0.10274(3) 0.0317(4) Uani 1 1 d . . . H38A H -0.0475 0.3142 0.1057 0.048 Uiso 1 1 calc R . . H38B H 0.0942 0.2569 0.0959 0.048 Uiso 1 1 calc R . . H38C H 0.1019 0.3499 0.0891 0.048 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 0.0294(6) 0.0277(6) 0.0256(7) -0.0073(5) -0.0052(5) 0.0024(5) N1 0.0221(7) 0.0180(6) 0.0185(8) 0.0008(5) 0.0016(5) -0.0023(5) N2 0.0202(7) 0.0167(6) 0.0233(8) -0.0001(6) -0.0008(5) -0.0021(5) B1 0.0182(9) 0.0188(8) 0.0255(11) -0.0010(8) 0.0007(7) 0.0030(7) C1 0.0177(8) 0.0198(7) 0.0208(9) -0.0021(6) -0.0005(6) 0.0032(6) C2 0.0179(8) 0.0185(7) 0.0244(10) 0.0008(7) 0.0001(7) 0.0023(6) C3 0.0234(8) 0.0242(8) 0.0273(10) 0.0026(7) 0.0013(7) -0.0002(6) C4 0.0291(9) 0.0330(9) 0.0217(10) -0.0032(7) -0.0017(7) 0.0047(7) C5 0.0273(9) 0.0235(8) 0.0297(11) -0.0076(7) -0.0044(7) 0.0027(7) C6 0.0207(8) 0.0190(7) 0.0283(10) -0.0023(7) -0.0011(7) 0.0005(6) C7 0.0283(9) 0.0250(8) 0.0236(10) 0.0026(7) 0.0021(7) -0.0051(7) C8 0.0315(9) 0.0283(8) 0.0396(11) 0.0115(8) -0.0067(8) -0.0072(7) C9 0.0217(8) 0.0187(7) 0.0304(10) 0.0030(7) 0.0005(7) -0.0023(6) C10 0.0320(10) 0.0205(8) 0.0514(13) 0.0053(8) -0.0056(8) -0.0016(7) C11 0.0224(8) 0.0189(7) 0.0276(10) 0.0019(7) 0.0011(7) -0.0005(6) C12 0.0227(8) 0.0206(7) 0.0273(10) 0.0035(7) 0.0036(7) -0.0021(6) C13 0.0241(8) 0.0210(7) 0.0188(9) 0.0009(7) 0.0044(7) -0.0041(6) C14 0.0282(8) 0.0180(7) 0.0233(10) 0.0010(7) 0.0046(7) 0.0010(6) C15 0.0240(8) 0.0243(8) 0.0211(9) 0.0026(7) -0.0002(7) 0.0000(6) C16 0.0249(8) 0.0209(7) 0.0195(9) -0.0033(7) 0.0029(7) -0.0023(6) C17 0.0244(8) 0.0202(7) 0.0241(10) -0.0015(7) 0.0016(7) 0.0029(6) C18 0.0237(8) 0.0242(8) 0.0216(9) 0.0035(7) 0.0011(7) -0.0009(6) C19 0.0285(9) 0.0346(9) 0.0242(10) -0.0029(7) -0.0055(7) 0.0009(7) O2 0.0356(7) 0.0238(5) 0.0321(7) -0.0062(5) -0.0046(5) 0.0044(5) N3 0.0251(7) 0.0218(6) 0.0163(7) -0.0015(6) 0.0002(5) -0.0039(5) N4 0.0218(7) 0.0223(6) 0.0194(8) 0.0010(6) 0.0001(5) -0.0005(5) B2 0.0212(9) 0.0245(8) 0.0190(10) 0.0008(8) 0.0044(7) -0.0018(7) C20 0.0233(8) 0.0211(7) 0.0180(9) -0.0006(7) 0.0025(7) -0.0034(6) C21 0.0212(8) 0.0219(7) 0.0202(9) -0.0009(7) 0.0040(6) -0.0035(6) C22 0.0297(9) 0.0301(8) 0.0204(9) -0.0023(7) 0.0016(7) -0.0069(7) C23 0.0409(10) 0.0234(8) 0.0289(11) -0.0072(7) 0.0063(8) -0.0054(7) C24 0.0405(10) 0.0202(8) 0.0293(11) 0.0013(7) 0.0071(8) 0.0010(7) C25 0.0288(9) 0.0255(8) 0.0234(10) 0.0026(7) 0.0025(7) 0.0000(7) C26 0.0280(9) 0.0274(8) 0.0181(9) -0.0002(7) -0.0017(7) -0.0032(7) C27 0.0434(10) 0.0375(9) 0.0184(10) 0.0009(8) 0.0003(8) -0.0098(8) C28 0.0232(8) 0.0301(8) 0.0239(10) 0.0002(7) -0.0048(7) 0.0000(7) C29 0.0307(9) 0.0348(9) 0.0240(10) 0.0030(7) -0.0036(7) -0.0013(7) C30 0.0256(8) 0.0276(8) 0.0204(9) 0.0023(7) 0.0009(7) -0.0010(7) C31 0.0254(8) 0.0250(8) 0.0223(9) 0.0034(7) 0.0008(7) -0.0009(7) C32 0.0249(8) 0.0211(7) 0.0241(10) 0.0001(7) 0.0016(7) -0.0017(6) C33 0.0311(9) 0.0231(8) 0.0298(10) 0.0017(7) -0.0053(7) 0.0062(7) C34 0.0321(9) 0.0261(8) 0.0248(10) -0.0003(7) -0.0062(7) 0.0022(7) C35 0.0250(8) 0.0192(7) 0.0268(10) -0.0018(7) 0.0014(7) -0.0010(6) C36 0.0276(9) 0.0236(8) 0.0286(11) 0.0029(7) -0.0036(7) 0.0031(7) C37 0.0273(9) 0.0259(8) 0.0248(10) 0.0011(7) -0.0033(7) -0.0008(7) C38 0.0387(10) 0.0286(8) 0.0278(11) -0.0072(8) -0.0025(8) 0.0012(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C16 1.3611(16) . ? O1 C19 1.4344(17) . ? N1 C1 1.3963(18) . ? N1 B1 1.4333(19) . ? N1 C7 1.4597(17) . ? N2 C2 1.3956(17) . ? N2 B1 1.428(2) . ? N2 C9 1.4586(16) . ? B1 C11 1.524(2) . ? C1 C6 1.3878(19) . ? C1 C2 1.4132(19) . ? C2 C3 1.382(2) . ? C3 C4 1.397(2) . ? C3 H3 0.9500 . ? C4 C5 1.390(2) . ? C4 H4 0.9500 . ? C5 C6 1.386(2) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.519(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.5208(19) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.207(2) . ? C12 C13 1.440(2) . ? C13 C14 1.392(2) . ? C13 C18 1.4046(19) . ? C14 C15 1.393(2) . ? C14 H14 0.9500 . ? C15 C16 1.3887(19) . ? C15 H15 0.9500 . ? C16 C17 1.397(2) . ? C17 C18 1.376(2) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? O2 C35 1.3706(17) . ? O2 C38 1.4318(17) . ? N3 C20 1.3974(17) . ? N3 B2 1.426(2) . ? N3 C26 1.4556(18) . ? N4 C21 1.4022(17) . ? N4 B2 1.428(2) . ? N4 C28 1.4590(18) . ? B2 C30 1.523(2) . ? C20 C25 1.3866(19) . ? C20 C21 1.409(2) . ? C21 C22 1.3874(19) . ? C22 C23 1.386(2) . ? C22 H22 0.9500 . ? C23 C24 1.390(2) . ? C23 H23 0.9500 . ? C24 C25 1.389(2) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? C26 C27 1.520(2) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 C29 1.521(2) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 C31 1.212(2) . ? C31 C32 1.435(2) . ? C32 C33 1.389(2) . ? C32 C37 1.402(2) . ? C33 C34 1.382(2) . ? C33 H33 0.9500 . ? C34 C35 1.385(2) . ? C34 H34 0.9500 . ? C35 C36 1.393(2) . ? C36 C37 1.379(2) . ? C36 H36 0.9500 . ? C37 H37 0.9500 . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 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 C16 O1 C19 117.58(11) . . ? C1 N1 B1 107.95(12) . . ? C1 N1 C7 122.41(12) . . ? B1 N1 C7 129.60(13) . . ? C2 N2 B1 108.34(11) . . ? C2 N2 C9 122.59(12) . . ? B1 N2 C9 128.98(12) . . ? N2 B1 N1 106.80(13) . . ? N2 B1 C11 124.80(13) . . ? N1 B1 C11 128.40(14) . . ? C6 C1 N1 130.99(14) . . ? C6 C1 C2 120.39(14) . . ? N1 C1 C2 108.62(12) . . ? C3 C2 N2 130.87(13) . . ? C3 C2 C1 120.83(13) . . ? N2 C2 C1 108.29(13) . . ? C2 C3 C4 118.41(14) . . ? C2 C3 H3 120.8 . . ? C4 C3 H3 120.8 . . ? C5 C4 C3 120.54(15) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C6 C5 C4 121.47(14) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C5 C6 C1 118.36(14) . . ? C5 C6 H6 120.8 . . ? C1 C6 H6 120.8 . . ? N1 C7 C8 113.60(12) . . ? N1 C7 H7A 108.8 . . ? C8 C7 H7A 108.8 . . ? N1 C7 H7B 108.8 . . ? C8 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N2 C9 C10 112.62(12) . . ? N2 C9 H9A 109.1 . . ? C10 C9 H9A 109.1 . . ? N2 C9 H9B 109.1 . . ? C10 C9 H9B 109.1 . . ? H9A C9 H9B 107.8 . . ? 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 . . ? C12 C11 B1 173.77(15) . . ? C11 C12 C13 176.08(16) . . ? C14 C13 C18 118.09(13) . . ? C14 C13 C12 122.62(13) . . ? C18 C13 C12 119.23(14) . . ? C13 C14 C15 121.73(13) . . ? C13 C14 H14 119.1 . . ? C15 C14 H14 119.1 . . ? C16 C15 C14 119.19(14) . . ? C16 C15 H15 120.4 . . ? C14 C15 H15 120.4 . . ? O1 C16 C15 124.95(13) . . ? O1 C16 C17 115.28(12) . . ? C15 C16 C17 119.77(14) . . ? C18 C17 C16 120.58(14) . . ? C18 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? C17 C18 C13 120.63(14) . . ? C17 C18 H18 119.7 . . ? C13 C18 H18 119.7 . . ? O1 C19 H19A 109.5 . . ? O1 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? O1 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C35 O2 C38 116.97(12) . . ? C20 N3 B2 108.16(12) . . ? C20 N3 C26 122.49(12) . . ? B2 N3 C26 129.35(12) . . ? C21 N4 B2 107.86(12) . . ? C21 N4 C28 122.57(12) . . ? B2 N4 C28 129.29(12) . . ? N3 B2 N4 107.04(13) . . ? N3 B2 C30 124.95(15) . . ? N4 B2 C30 127.96(14) . . ? C25 C20 N3 130.89(14) . . ? C25 C20 C21 120.66(14) . . ? N3 C20 C21 108.45(12) . . ? C22 C21 N4 130.79(14) . . ? C22 C21 C20 120.73(13) . . ? N4 C21 C20 108.48(12) . . ? C23 C22 C21 118.22(15) . . ? C23 C22 H22 120.9 . . ? C21 C22 H22 120.9 . . ? C22 C23 C24 121.12(15) . . ? C22 C23 H23 119.4 . . ? C24 C23 H23 119.4 . . ? C25 C24 C23 121.12(14) . . ? C25 C24 H24 119.4 . . ? C23 C24 H24 119.4 . . ? C20 C25 C24 118.15(15) . . ? C20 C25 H25 120.9 . . ? C24 C25 H25 120.9 . . ? N3 C26 C27 112.22(12) . . ? N3 C26 H26A 109.2 . . ? C27 C26 H26A 109.2 . . ? N3 C26 H26B 109.2 . . ? C27 C26 H26B 109.2 . . ? H26A C26 H26B 107.9 . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? N4 C28 C29 113.04(12) . . ? N4 C28 H28A 109.0 . . ? C29 C28 H28A 109.0 . . ? N4 C28 H28B 109.0 . . ? C29 C28 H28B 109.0 . . ? H28A C28 H28B 107.8 . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C31 C30 B2 172.81(17) . . ? C30 C31 C32 174.02(17) . . ? C33 C32 C37 118.03(14) . . ? C33 C32 C31 118.76(14) . . ? C37 C32 C31 123.16(14) . . ? C34 C33 C32 121.94(14) . . ? C34 C33 H33 119.0 . . ? C32 C33 H33 119.0 . . ? C33 C34 C35 119.27(15) . . ? C33 C34 H34 120.4 . . ? C35 C34 H34 120.4 . . ? O2 C35 C34 124.25(15) . . ? O2 C35 C36 115.87(13) . . ? C34 C35 C36 119.88(14) . . ? C37 C36 C35 120.36(14) . . ? C37 C36 H36 119.8 . . ? C35 C36 H36 119.8 . . ? C36 C37 C32 120.52(15) . . ? C36 C37 H37 119.7 . . ? C32 C37 H37 119.7 . . ? O2 C38 H38A 109.5 . . ? O2 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? O2 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.181 _refine_diff_density_min -0.260 _refine_diff_density_rms 0.045 #========================================================================= data_compound5 _database_code_depnum_ccdc_archive 'CCDC 711347' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H24 B N3' _chemical_formula_sum 'C20 H24 B N3' _chemical_formula_weight 317.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.0573(2) _cell_length_b 11.5078(2) _cell_length_c 14.1544(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.3123(13) _cell_angle_gamma 90.00 _cell_volume 1795.98(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 15142 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description fragment _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.173 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 0.069 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9796 _exptl_absorpt_correction_T_max 0.9829 _exptl_absorpt_process_details 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27595 _diffrn_reflns_av_R_equivalents 0.032 _diffrn_reflns_av_sigmaI/netI 0.0260 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4108 _reflns_number_gt 3437 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect, Bruker AXS, 2004' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0533P)^2^+0.3482P] 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 4108 _refine_ls_number_parameters 221 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0473 _refine_ls_R_factor_gt 0.0385 _refine_ls_wR_factor_ref 0.1033 _refine_ls_wR_factor_gt 0.0973 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _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 0.46702(7) 0.32664(7) 0.29107(6) 0.02042(19) Uani 1 1 d . . . N2 N 0.46259(7) 0.13425(7) 0.24827(6) 0.01948(19) Uani 1 1 d . . . N3 N -0.31606(8) 0.34065(9) 0.00529(6) 0.0294(2) Uani 1 1 d . . . B1 B 0.39257(10) 0.23878(10) 0.24479(8) 0.0202(2) Uani 1 1 d . . . C1 C 0.57766(9) 0.27619(9) 0.32217(7) 0.0199(2) Uani 1 1 d . . . C2 C 0.57524(8) 0.15813(9) 0.29522(7) 0.0192(2) Uani 1 1 d . . . C3 C 0.67364(9) 0.08569(9) 0.31820(7) 0.0226(2) Uani 1 1 d . . . H3 H 0.6723 0.0063 0.2998 0.027 Uiso 1 1 calc R . . C4 C 0.77437(9) 0.13372(10) 0.36916(8) 0.0264(2) Uani 1 1 d . . . H4 H 0.8426 0.0859 0.3861 0.032 Uiso 1 1 calc R . . C5 C 0.77701(10) 0.25007(10) 0.39562(8) 0.0272(2) Uani 1 1 d . . . H5 H 0.8471 0.2802 0.4302 0.033 Uiso 1 1 calc R . . C6 C 0.67885(9) 0.32332(9) 0.37242(7) 0.0245(2) Uani 1 1 d . . . H6 H 0.6810 0.4029 0.3904 0.029 Uiso 1 1 calc R . . C7 C 0.42730(9) 0.01831(9) 0.21488(7) 0.0241(2) Uani 1 1 d . . . H7A H 0.3378 0.0122 0.2111 0.029 Uiso 1 1 calc R . . H7B H 0.4604 -0.0398 0.2615 0.029 Uiso 1 1 calc R . . C8 C 0.47145(11) -0.01005(11) 0.11896(9) 0.0351(3) Uani 1 1 d . . . H8A H 0.4356 0.0446 0.0717 0.053 Uiso 1 1 calc R . . H8B H 0.4474 -0.0895 0.1011 0.053 Uiso 1 1 calc R . . H8C H 0.5600 -0.0036 0.1220 0.053 Uiso 1 1 calc R . . C9 C 0.43349(10) 0.44438(9) 0.31744(7) 0.0247(2) Uani 1 1 d . . . H9A H 0.3747 0.4763 0.2679 0.030 Uiso 1 1 calc R . . H9B H 0.5066 0.4944 0.3207 0.030 Uiso 1 1 calc R . . C10 C 0.37779(11) 0.44751(10) 0.41235(8) 0.0293(2) Uani 1 1 d . . . H10A H 0.3036 0.4006 0.4087 0.044 Uiso 1 1 calc R . . H10B H 0.3582 0.5280 0.4280 0.044 Uiso 1 1 calc R . . H10C H 0.4357 0.4160 0.4616 0.044 Uiso 1 1 calc R . . C11 C 0.26368(9) 0.25304(9) 0.19991(7) 0.0220(2) Uani 1 1 d . . . C12 C 0.16167(9) 0.26336(9) 0.16381(7) 0.0207(2) Uani 1 1 d . . . C13 C 0.04043(9) 0.27910(8) 0.12205(7) 0.0195(2) Uani 1 1 d . . . C14 C 0.01866(9) 0.33755(8) 0.03568(7) 0.0205(2) Uani 1 1 d . . . H14 H 0.0854 0.3637 0.0029 0.025 Uiso 1 1 calc R . . C15 C -0.09772(9) 0.35788(9) -0.00270(7) 0.0211(2) Uani 1 1 d . . . H15 H -0.1096 0.3976 -0.0615 0.025 Uiso 1 1 calc R . . C16 C -0.19946(9) 0.32081(9) 0.04356(7) 0.0209(2) Uani 1 1 d . . . C17 C -0.17747(9) 0.26189(9) 0.13067(7) 0.0214(2) Uani 1 1 d . . . H17 H -0.2439 0.2355 0.1637 0.026 Uiso 1 1 calc R . . C18 C -0.06046(9) 0.24218(8) 0.16844(7) 0.0210(2) Uani 1 1 d . . . H18 H -0.0480 0.2026 0.2273 0.025 Uiso 1 1 calc R . . C19 C -0.33564(10) 0.41111(11) -0.07951(8) 0.0297(3) Uani 1 1 d . . . H19A H -0.3043 0.4896 -0.0667 0.045 Uiso 1 1 calc R . . H19B H -0.4227 0.4151 -0.0983 0.045 Uiso 1 1 calc R . . H19C H -0.2932 0.3761 -0.1308 0.045 Uiso 1 1 calc R . . C20 C -0.41735(9) 0.31988(11) 0.06178(8) 0.0299(3) Uani 1 1 d . . . H20A H -0.4203 0.2373 0.0782 0.045 Uiso 1 1 calc R . . H20B H -0.4929 0.3420 0.0256 0.045 Uiso 1 1 calc R . . H20C H -0.4076 0.3663 0.1199 0.045 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0184(4) 0.0215(4) 0.0212(4) 0.0011(3) 0.0005(3) 0.0019(3) N2 0.0178(4) 0.0213(4) 0.0193(4) 0.0005(3) 0.0015(3) -0.0003(3) N3 0.0180(4) 0.0452(6) 0.0247(5) 0.0087(4) 0.0004(4) 0.0017(4) B1 0.0193(5) 0.0241(5) 0.0174(5) 0.0017(4) 0.0037(4) -0.0004(4) C1 0.0178(5) 0.0232(5) 0.0190(5) 0.0028(4) 0.0027(4) 0.0006(4) C2 0.0178(5) 0.0239(5) 0.0162(5) 0.0026(4) 0.0030(4) -0.0011(4) C3 0.0222(5) 0.0238(5) 0.0221(5) 0.0043(4) 0.0045(4) 0.0022(4) C4 0.0185(5) 0.0346(6) 0.0262(5) 0.0074(4) 0.0018(4) 0.0048(4) C5 0.0187(5) 0.0357(6) 0.0267(6) 0.0041(4) -0.0024(4) -0.0037(4) C6 0.0225(5) 0.0263(5) 0.0245(5) 0.0007(4) 0.0011(4) -0.0034(4) C7 0.0251(5) 0.0209(5) 0.0264(5) 0.0003(4) 0.0016(4) -0.0036(4) C8 0.0362(6) 0.0323(6) 0.0376(7) -0.0129(5) 0.0073(5) -0.0021(5) C9 0.0254(5) 0.0200(5) 0.0283(6) 0.0005(4) -0.0006(4) 0.0021(4) C10 0.0356(6) 0.0252(5) 0.0267(6) -0.0022(4) -0.0013(5) 0.0080(4) C11 0.0215(5) 0.0239(5) 0.0208(5) 0.0004(4) 0.0025(4) 0.0003(4) C12 0.0214(5) 0.0211(5) 0.0198(5) -0.0018(4) 0.0028(4) 0.0002(4) C13 0.0186(5) 0.0192(5) 0.0204(5) -0.0033(4) 0.0000(4) 0.0008(4) C14 0.0196(5) 0.0221(5) 0.0203(5) -0.0021(4) 0.0038(4) -0.0012(4) C15 0.0223(5) 0.0248(5) 0.0162(5) 0.0006(4) 0.0013(4) 0.0001(4) C16 0.0184(5) 0.0232(5) 0.0208(5) -0.0015(4) -0.0001(4) 0.0003(4) C17 0.0189(5) 0.0229(5) 0.0227(5) 0.0012(4) 0.0036(4) -0.0015(4) C18 0.0217(5) 0.0209(5) 0.0204(5) 0.0009(4) 0.0009(4) 0.0009(4) C19 0.0228(5) 0.0427(6) 0.0233(5) 0.0050(5) -0.0009(4) 0.0059(5) C20 0.0182(5) 0.0391(6) 0.0324(6) 0.0066(5) 0.0009(4) -0.0007(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.3952(12) . ? N1 B1 1.4311(14) . ? N1 C9 1.4606(13) . ? N2 C2 1.3943(12) . ? N2 B1 1.4293(14) . ? N2 C7 1.4588(13) . ? N3 C16 1.3795(12) . ? N3 C20 1.4441(14) . ? N3 C19 1.4512(14) . ? B1 C11 1.5250(15) . ? C1 C6 1.3900(14) . ? C1 C2 1.4109(14) . ? C2 C3 1.3898(14) . ? C3 C4 1.3948(15) . ? C3 H3 0.9500 . ? C4 C5 1.3900(16) . ? C4 H4 0.9500 . ? C5 C6 1.3939(15) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.5127(16) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.5197(15) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.2086(14) . ? C12 C13 1.4354(13) . ? C13 C14 1.4002(14) . ? C13 C18 1.4023(14) . ? C14 C15 1.3787(13) . ? C14 H14 0.9500 . ? C15 C16 1.4095(14) . ? C15 H15 0.9500 . ? C16 C17 1.4121(14) . ? C17 C18 1.3809(14) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 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 C1 N1 B1 108.12(8) . . ? C1 N1 C9 122.60(8) . . ? B1 N1 C9 128.62(8) . . ? C2 N2 B1 108.22(8) . . ? C2 N2 C7 122.84(8) . . ? B1 N2 C7 128.87(8) . . ? C16 N3 C20 119.74(9) . . ? C16 N3 C19 119.62(9) . . ? C20 N3 C19 118.47(9) . . ? N2 B1 N1 106.70(9) . . ? N2 B1 C11 126.28(9) . . ? N1 B1 C11 127.01(9) . . ? C6 C1 N1 130.70(10) . . ? C6 C1 C2 120.81(9) . . ? N1 C1 C2 108.48(8) . . ? C3 C2 N2 130.46(9) . . ? C3 C2 C1 121.05(9) . . ? N2 C2 C1 108.47(8) . . ? C2 C3 C4 117.64(10) . . ? C2 C3 H3 121.2 . . ? C4 C3 H3 121.2 . . ? C5 C4 C3 121.39(10) . . ? C5 C4 H4 119.3 . . ? C3 C4 H4 119.3 . . ? C4 C5 C6 121.25(10) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C1 C6 C5 117.85(10) . . ? C1 C6 H6 121.1 . . ? C5 C6 H6 121.1 . . ? N2 C7 C8 113.05(9) . . ? N2 C7 H7A 109.0 . . ? C8 C7 H7A 109.0 . . ? N2 C7 H7B 109.0 . . ? C8 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N1 C9 C10 112.05(8) . . ? N1 C9 H9A 109.2 . . ? C10 C9 H9A 109.2 . . ? N1 C9 H9B 109.2 . . ? C10 C9 H9B 109.2 . . ? H9A C9 H9B 107.9 . . ? 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 . . ? C12 C11 B1 179.35(12) . . ? C11 C12 C13 178.28(11) . . ? C14 C13 C18 117.63(9) . . ? C14 C13 C12 120.93(9) . . ? C18 C13 C12 121.35(9) . . ? C15 C14 C13 121.30(9) . . ? C15 C14 H14 119.3 . . ? C13 C14 H14 119.3 . . ? C14 C15 C16 121.30(9) . . ? C14 C15 H15 119.3 . . ? C16 C15 H15 119.3 . . ? N3 C16 C15 121.50(9) . . ? N3 C16 C17 121.12(9) . . ? C15 C16 C17 117.38(9) . . ? C18 C17 C16 120.78(9) . . ? C18 C17 H17 119.6 . . ? C16 C17 H17 119.6 . . ? C17 C18 C13 121.61(9) . . ? C17 C18 H18 119.2 . . ? C13 C18 H18 119.2 . . ? N3 C19 H19A 109.5 . . ? N3 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N3 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N3 C20 H20A 109.5 . . ? N3 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? N3 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.216 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.041 #===END