# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Roland Roesler' _publ_contact_author_email ROESLER@UCALGARY.CA _publ_section_title ; Tuning the electronic properties of cyclopentadienyl analogs with CB2N2 frameworks: 1,2-diphenyl-1,2-diaza-3,5-diborolyl ligands and their alkali metal salts ; loop_ _publ_author_name 'Roland Roesler' 'Jari Konu' 'Hanh V. Ly' 'Masood Parvez' # Attachment '1.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 678560' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H24 B2 N2' _chemical_formula_sum 'C26 H24 B2 N2' _chemical_formula_weight 386.09 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.274(5) _cell_length_b 10.117(7) _cell_length_c 12.837(8) _cell_angle_alpha 106.43(3) _cell_angle_beta 91.33(3) _cell_angle_gamma 110.43(3) _cell_volume 1072.6(12) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7063 _cell_measurement_theta_min 2.60 _cell_measurement_theta_max 25.27 _exptl_crystal_description ? _exptl_crystal_colour colorless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.195 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.068 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9905 _exptl_absorpt_correction_T_max 0.9966 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enraf Nonius FR590D, fine-focus sealed tube' _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_device_type 'KappaCCD (Nonius, FR540C)' _diffrn_measurement_method 'phi\omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7063 _diffrn_reflns_av_R_equivalents 0.0268 _diffrn_reflns_av_sigmaI/netI 0.0414 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.60 _diffrn_reflns_theta_max 25.27 _reflns_number_total 3854 _reflns_number_gt 2815 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0910P)^2^+0.5000P] 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 0.072(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3854 _refine_ls_number_parameters 272 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0871 _refine_ls_R_factor_gt 0.0605 _refine_ls_wR_factor_ref 0.1801 _refine_ls_wR_factor_gt 0.1591 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _refine_ls_shift/su_max 0.004 _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 0.1909(2) 0.4611(2) 0.26724(15) 0.0409(5) Uani 1 1 d . . . N2 N 0.1782(2) 0.39903(19) 0.35725(15) 0.0396(5) Uani 1 1 d . . . C1 C 0.3287(3) 0.6624(3) 0.4319(2) 0.0575(7) Uani 1 1 d . . . H1 H 0.2530 0.7099 0.4595 0.069 Uiso 1 1 calc R . . C2 C 0.4763(4) 0.7816(3) 0.4858(3) 0.0859(12) Uani 1 1 d . . . H2A H 0.4853 0.7958 0.5648 0.129 Uiso 0.50 1 calc PR . . H2B H 0.4802 0.8737 0.4730 0.129 Uiso 0.50 1 calc PR . . H2C H 0.5623 0.7552 0.4558 0.129 Uiso 0.50 1 calc PR . . H2D H 0.5332 0.8207 0.4309 0.129 Uiso 0.50 1 calc PR . . H2E H 0.5383 0.7428 0.5227 0.129 Uiso 0.50 1 calc PR . . H2F H 0.4563 0.8613 0.5399 0.129 Uiso 0.50 1 calc PR . . C3 C 0.1457(2) 0.3607(2) 0.15805(18) 0.0387(5) Uani 1 1 d . . . C4 C 0.2023(3) 0.2474(2) 0.12295(19) 0.0447(6) Uani 1 1 d . . . H4 H 0.2683 0.2324 0.1736 0.054 Uiso 1 1 d R . . C5 C 0.1626(3) 0.1557(3) 0.0150(2) 0.0515(6) Uani 1 1 d . . . H5 H 0.2026 0.0782 -0.0097 0.062 Uiso 1 1 d R . . C6 C 0.0658(3) 0.1763(3) -0.0574(2) 0.0520(7) Uani 1 1 d . . . H6 H 0.0384 0.1125 -0.1320 0.062 Uiso 1 1 d R . . C7 C 0.0086(3) 0.2877(3) -0.0218(2) 0.0498(6) Uani 1 1 d . . . H7 H -0.0578 0.3029 -0.0720 0.060 Uiso 1 1 d R . . C8 C 0.0470(3) 0.3792(3) 0.08614(19) 0.0455(6) Uani 1 1 d . . . H8 H 0.0050 0.4552 0.1115 0.055 Uiso 1 1 d R . . C9 C 0.0584(3) 0.2561(2) 0.34137(18) 0.0402(5) Uani 1 1 d . . . C10 C -0.0920(3) 0.2263(3) 0.2978(2) 0.0502(6) Uani 1 1 d . . . H10 H -0.1142 0.2996 0.2737 0.060 Uiso 1 1 d R . . C11 C -0.2068(3) 0.0905(3) 0.2895(2) 0.0649(8) Uani 1 1 d . . . H11 H -0.3106 0.0674 0.2573 0.078 Uiso 1 1 d R . . C12 C -0.1730(4) -0.0135(3) 0.3249(2) 0.0697(9) Uani 1 1 d . . . H12 H -0.2542 -0.1059 0.3207 0.084 Uiso 1 1 d R . . C13 C -0.0235(4) 0.0167(3) 0.3673(2) 0.0616(8) Uani 1 1 d . . . H13 H 0.0009 -0.0546 0.3927 0.074 Uiso 1 1 d R . . C14 C 0.0935(3) 0.1507(2) 0.37459(19) 0.0479(6) Uani 1 1 d . . . H14 H 0.1988 0.1706 0.4017 0.057 Uiso 1 1 d R . . C15 C 0.3251(3) 0.7170(2) 0.22943(19) 0.0445(6) Uani 1 1 d . . . C16 C 0.3751(3) 0.6814(3) 0.1267(2) 0.0545(7) Uani 1 1 d . . . H16 H 0.3871 0.5880 0.0976 0.065 Uiso 1 1 d R . . C17 C 0.4102(3) 0.7797(3) 0.0663(2) 0.0623(8) Uani 1 1 d . . . H17 H 0.4441 0.7534 -0.0041 0.075 Uiso 1 1 d R . . C18 C 0.3942(3) 0.9152(3) 0.1059(2) 0.0615(8) Uani 1 1 d . . . H18 H 0.4167 0.9826 0.0635 0.074 Uiso 1 1 d R . . C19 C 0.3463(3) 0.9536(3) 0.2069(2) 0.0543(7) Uani 1 1 d . . . H19 H 0.3353 1.0478 0.2342 0.065 Uiso 1 1 d R . . C20 C 0.3141(3) 0.8565(3) 0.2679(2) 0.0470(6) Uani 1 1 d . . . H20 H 0.2845 0.8871 0.3393 0.056 Uiso 1 1 d R . . C21 C 0.2555(3) 0.4829(2) 0.57120(18) 0.0406(6) Uani 1 1 d . . . C22 C 0.1206(3) 0.4016(2) 0.60647(19) 0.0439(6) Uani 1 1 d . . . H22 H 0.0235 0.3575 0.5590 0.053 Uiso 1 1 d R . . C23 C 0.1224(3) 0.3821(3) 0.70850(19) 0.0499(6) Uani 1 1 d . . . H23 H 0.0278 0.3268 0.7306 0.060 Uiso 1 1 d R . . C24 C 0.2589(3) 0.4411(3) 0.7787(2) 0.0590(7) Uani 1 1 d . . . H24 H 0.2595 0.4261 0.8493 0.071 Uiso 1 1 d R . . C25 C 0.3938(3) 0.5216(3) 0.7467(2) 0.0626(8) Uani 1 1 d . . . H25 H 0.4901 0.5635 0.7948 0.075 Uiso 1 1 d R . . C26 C 0.3916(3) 0.5437(3) 0.6454(2) 0.0509(6) Uani 1 1 d . . . H26 H 0.4869 0.6027 0.6264 0.061 Uiso 1 1 d R . . B1 B 0.2820(3) 0.6144(3) 0.3044(2) 0.0460(7) Uani 1 1 d . . . B2 B 0.2572(3) 0.5099(3) 0.4570(2) 0.0414(6) 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 0.0453(11) 0.0337(10) 0.0394(10) 0.0137(8) -0.0013(8) 0.0082(8) N2 0.0411(10) 0.0315(10) 0.0420(10) 0.0152(8) 0.0011(8) 0.0058(8) C1 0.0675(17) 0.0395(14) 0.0465(14) 0.0132(11) -0.0047(12) -0.0018(12) C2 0.105(3) 0.0499(17) 0.071(2) 0.0237(15) -0.0267(18) -0.0107(17) C3 0.0387(12) 0.0302(11) 0.0407(12) 0.0123(9) 0.0011(9) 0.0046(9) C4 0.0420(13) 0.0400(13) 0.0493(14) 0.0158(11) 0.0030(10) 0.0106(10) C5 0.0567(15) 0.0378(13) 0.0546(15) 0.0106(11) 0.0107(12) 0.0139(11) C6 0.0572(15) 0.0445(14) 0.0411(13) 0.0093(11) 0.0044(11) 0.0067(12) C7 0.0520(14) 0.0456(14) 0.0450(14) 0.0165(11) -0.0016(11) 0.0088(11) C8 0.0495(14) 0.0378(12) 0.0458(13) 0.0133(10) -0.0011(11) 0.0123(11) C9 0.0415(12) 0.0328(12) 0.0384(12) 0.0082(9) 0.0051(9) 0.0068(9) C10 0.0436(13) 0.0433(14) 0.0555(15) 0.0118(11) 0.0036(11) 0.0092(11) C11 0.0458(15) 0.0539(17) 0.0712(19) 0.0073(14) 0.0072(13) -0.0001(13) C12 0.074(2) 0.0406(15) 0.0674(18) 0.0098(13) 0.0197(15) -0.0052(14) C13 0.094(2) 0.0346(13) 0.0490(15) 0.0141(11) 0.0151(15) 0.0136(14) C14 0.0641(15) 0.0345(12) 0.0418(13) 0.0108(10) 0.0046(11) 0.0155(11) C15 0.0427(12) 0.0349(12) 0.0474(14) 0.0140(10) -0.0029(10) 0.0038(10) C16 0.0577(16) 0.0464(14) 0.0568(16) 0.0198(12) 0.0094(12) 0.0130(12) C17 0.0623(17) 0.0685(19) 0.0591(16) 0.0318(14) 0.0171(13) 0.0178(15) C18 0.0609(17) 0.0552(17) 0.0714(19) 0.0377(15) 0.0073(14) 0.0110(13) C19 0.0548(15) 0.0425(14) 0.0657(17) 0.0245(12) -0.0004(13) 0.0124(12) C20 0.0460(13) 0.0383(13) 0.0511(14) 0.0154(11) -0.0021(11) 0.0083(10) C21 0.0423(12) 0.0322(11) 0.0430(13) 0.0102(10) 0.0023(10) 0.0100(10) C22 0.0418(12) 0.0364(12) 0.0459(13) 0.0088(10) 0.0049(10) 0.0087(10) C23 0.0552(15) 0.0364(13) 0.0476(14) 0.0101(11) 0.0145(12) 0.0063(11) C24 0.0695(18) 0.0539(16) 0.0456(14) 0.0206(12) 0.0046(13) 0.0098(14) C25 0.0551(16) 0.0698(18) 0.0516(16) 0.0237(14) -0.0079(12) 0.0068(14) C26 0.0420(13) 0.0534(15) 0.0501(14) 0.0207(12) 0.0010(11) 0.0058(11) B1 0.0460(15) 0.0372(14) 0.0484(16) 0.0141(12) -0.0008(12) 0.0077(12) B2 0.0372(13) 0.0375(14) 0.0459(15) 0.0124(11) 0.0015(11) 0.0104(11) _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 B1 1.412(3) . ? N1 C3 1.429(3) . ? N1 N2 1.452(3) . ? N2 B2 1.416(3) . ? N2 C9 1.438(3) . ? C1 C2 1.462(4) . ? C1 B1 1.572(4) . ? C1 B2 1.581(4) . ? C1 H1 1.0000 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C2 H2D 0.9800 . ? C2 H2E 0.9800 . ? C2 H2F 0.9800 . ? C3 C8 1.379(3) . ? C3 C4 1.390(3) . ? C4 C5 1.388(4) . ? C4 H4 0.9599 . ? C5 C6 1.384(4) . ? C5 H5 0.9600 . ? C6 C7 1.378(4) . ? C6 H6 0.9599 . ? C7 C8 1.387(3) . ? C7 H7 0.9600 . ? C8 H8 0.9600 . ? C9 C14 1.385(3) . ? C9 C10 1.387(3) . ? C10 C11 1.387(4) . ? C10 H10 0.9600 . ? C11 C12 1.380(4) . ? C11 H11 0.9600 . ? C12 C13 1.374(5) . ? C12 H12 0.9600 . ? C13 C14 1.386(4) . ? C13 H13 0.9600 . ? C14 H14 0.9600 . ? C15 C20 1.398(4) . ? C15 C16 1.401(4) . ? C15 B1 1.568(4) . ? C16 C17 1.384(4) . ? C16 H16 0.9600 . ? C17 C18 1.383(4) . ? C17 H17 0.9600 . ? C18 C19 1.375(4) . ? C18 H18 0.9600 . ? C19 C20 1.381(3) . ? C19 H19 0.9600 . ? C20 H20 0.9600 . ? C21 C26 1.396(3) . ? C21 C22 1.402(3) . ? C21 B2 1.565(4) . ? C22 C23 1.379(3) . ? C22 H22 0.9600 . ? C23 C24 1.374(4) . ? C23 H23 0.9600 . ? C24 C25 1.378(4) . ? C24 H24 0.9600 . ? C25 C26 1.381(4) . ? C25 H25 0.9600 . ? C26 H26 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag B1 N1 C3 129.66(19) . . ? B1 N1 N2 110.44(18) . . ? C3 N1 N2 118.05(17) . . ? B2 N2 C9 128.48(19) . . ? B2 N2 N1 111.11(18) . . ? C9 N2 N1 117.56(17) . . ? C2 C1 B1 121.0(2) . . ? C2 C1 B2 125.3(2) . . ? B1 C1 B2 102.3(2) . . ? C2 C1 H1 101.2 . . ? B1 C1 H1 101.2 . . ? B2 C1 H1 101.2 . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C1 C2 H2D 109.5 . . ? H2A C2 H2D 141.1 . . ? H2B C2 H2D 56.3 . . ? H2C C2 H2D 56.3 . . ? C1 C2 H2E 109.5 . . ? H2A C2 H2E 56.3 . . ? H2B C2 H2E 141.1 . . ? H2C C2 H2E 56.3 . . ? H2D C2 H2E 109.5 . . ? C1 C2 H2F 109.5 . . ? H2A C2 H2F 56.3 . . ? H2B C2 H2F 56.3 . . ? H2C C2 H2F 141.1 . . ? H2D C2 H2F 109.5 . . ? H2E C2 H2F 109.5 . . ? C8 C3 C4 119.8(2) . . ? C8 C3 N1 119.2(2) . . ? C4 C3 N1 121.0(2) . . ? C5 C4 C3 120.0(2) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 119.9 . . ? C6 C5 C4 120.1(2) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 120.2 . . ? C7 C6 C5 119.7(2) . . ? C7 C6 H6 120.4 . . ? C5 C6 H6 119.9 . . ? C6 C7 C8 120.5(2) . . ? C6 C7 H7 119.9 . . ? C8 C7 H7 119.6 . . ? C3 C8 C7 119.9(2) . . ? C3 C8 H8 119.5 . . ? C7 C8 H8 120.6 . . ? C14 C9 C10 120.3(2) . . ? C14 C9 N2 119.1(2) . . ? C10 C9 N2 120.5(2) . . ? C11 C10 C9 119.1(3) . . ? C11 C10 H10 121.5 . . ? C9 C10 H10 119.4 . . ? C12 C11 C10 120.7(3) . . ? C12 C11 H11 119.5 . . ? C10 C11 H11 119.8 . . ? C13 C12 C11 119.7(3) . . ? C13 C12 H12 120.3 . . ? C11 C12 H12 119.9 . . ? C12 C13 C14 120.4(3) . . ? C12 C13 H13 120.3 . . ? C14 C13 H13 119.3 . . ? C9 C14 C13 119.7(3) . . ? C9 C14 H14 119.8 . . ? C13 C14 H14 120.6 . . ? C20 C15 C16 116.7(2) . . ? C20 C15 B1 117.8(2) . . ? C16 C15 B1 125.5(2) . . ? C17 C16 C15 121.3(3) . . ? C17 C16 H16 119.0 . . ? C15 C16 H16 119.8 . . ? C18 C17 C16 120.3(3) . . ? C18 C17 H17 119.5 . . ? C16 C17 H17 120.2 . . ? C19 C18 C17 119.7(2) . . ? C19 C18 H18 119.9 . . ? C17 C18 H18 120.4 . . ? C18 C19 C20 119.9(3) . . ? C18 C19 H19 119.5 . . ? C20 C19 H19 120.7 . . ? C19 C20 C15 122.1(3) . . ? C19 C20 H20 118.4 . . ? C15 C20 H20 119.4 . . ? C26 C21 C22 116.3(2) . . ? C26 C21 B2 120.5(2) . . ? C22 C21 B2 123.2(2) . . ? C23 C22 C21 121.9(2) . . ? C23 C22 H22 118.2 . . ? C21 C22 H22 120.0 . . ? C24 C23 C22 120.4(2) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 119.9 . . ? C23 C24 C25 119.3(2) . . ? C23 C24 H24 119.9 . . ? C25 C24 H24 120.8 . . ? C24 C25 C26 120.4(2) . . ? C24 C25 H25 120.3 . . ? C26 C25 H25 119.3 . . ? C25 C26 C21 121.8(2) . . ? C25 C26 H26 118.3 . . ? C21 C26 H26 119.8 . . ? N1 B1 C15 124.7(2) . . ? N1 B1 C1 108.4(2) . . ? C15 B1 C1 126.8(2) . . ? N2 B2 C21 124.2(2) . . ? N2 B2 C1 107.6(2) . . ? C21 B2 C1 127.9(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag B1 N1 N2 B2 1.4(3) . . . . ? C3 N1 N2 B2 167.4(2) . . . . ? B1 N1 N2 C9 163.9(2) . . . . ? C3 N1 N2 C9 -30.1(3) . . . . ? B1 N1 C3 C8 -66.1(3) . . . . ? N2 N1 C3 C8 131.0(2) . . . . ? B1 N1 C3 C4 112.5(3) . . . . ? N2 N1 C3 C4 -50.4(3) . . . . ? C8 C3 C4 C5 1.7(3) . . . . ? N1 C3 C4 C5 -176.9(2) . . . . ? C3 C4 C5 C6 -0.5(4) . . . . ? C4 C5 C6 C7 -0.2(4) . . . . ? C5 C6 C7 C8 -0.2(4) . . . . ? C4 C3 C8 C7 -2.1(3) . . . . ? N1 C3 C8 C7 176.5(2) . . . . ? C6 C7 C8 C3 1.4(4) . . . . ? B2 N2 C9 C14 -65.2(3) . . . . ? N1 N2 C9 C14 135.7(2) . . . . ? B2 N2 C9 C10 111.9(3) . . . . ? N1 N2 C9 C10 -47.1(3) . . . . ? C14 C9 C10 C11 0.9(4) . . . . ? N2 C9 C10 C11 -176.3(2) . . . . ? C9 C10 C11 C12 0.7(4) . . . . ? C10 C11 C12 C13 -1.1(4) . . . . ? C11 C12 C13 C14 0.0(4) . . . . ? C10 C9 C14 C13 -2.0(4) . . . . ? N2 C9 C14 C13 175.2(2) . . . . ? C12 C13 C14 C9 1.6(4) . . . . ? C20 C15 C16 C17 -0.6(4) . . . . ? B1 C15 C16 C17 179.9(2) . . . . ? C15 C16 C17 C18 -1.0(4) . . . . ? C16 C17 C18 C19 1.4(4) . . . . ? C17 C18 C19 C20 -0.2(4) . . . . ? C18 C19 C20 C15 -1.5(4) . . . . ? C16 C15 C20 C19 1.9(3) . . . . ? B1 C15 C20 C19 -178.6(2) . . . . ? C26 C21 C22 C23 -0.4(3) . . . . ? B2 C21 C22 C23 -178.7(2) . . . . ? C21 C22 C23 C24 -0.8(4) . . . . ? C22 C23 C24 C25 0.8(4) . . . . ? C23 C24 C25 C26 0.5(4) . . . . ? C24 C25 C26 C21 -1.7(4) . . . . ? C22 C21 C26 C25 1.6(4) . . . . ? B2 C21 C26 C25 -179.9(2) . . . . ? C3 N1 B1 C15 14.1(4) . . . . ? N2 N1 B1 C15 177.9(2) . . . . ? C3 N1 B1 C1 -166.8(2) . . . . ? N2 N1 B1 C1 -2.9(3) . . . . ? C20 C15 B1 N1 136.3(3) . . . . ? C16 C15 B1 N1 -44.2(4) . . . . ? C20 C15 B1 C1 -42.7(4) . . . . ? C16 C15 B1 C1 136.8(3) . . . . ? C2 C1 B1 N1 148.3(3) . . . . ? B2 C1 B1 N1 3.1(3) . . . . ? C2 C1 B1 C15 -32.5(5) . . . . ? B2 C1 B1 C15 -177.8(3) . . . . ? C9 N2 B2 C21 15.0(4) . . . . ? N1 N2 B2 C21 175.1(2) . . . . ? C9 N2 B2 C1 -159.4(2) . . . . ? N1 N2 B2 C1 0.7(3) . . . . ? C26 C21 B2 N2 137.6(3) . . . . ? C22 C21 B2 N2 -44.1(4) . . . . ? C26 C21 B2 C1 -49.2(4) . . . . ? C22 C21 B2 C1 129.1(3) . . . . ? C2 C1 B2 N2 -145.4(3) . . . . ? B1 C1 B2 N2 -2.3(3) . . . . ? C2 C1 B2 C21 40.5(5) . . . . ? B1 C1 B2 C21 -176.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.27 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.665 _refine_diff_density_min -0.379 _refine_diff_density_rms 0.041 # Attachment '2.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 678561' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H26 B2 N4' _chemical_formula_sum 'C18 H26 B2 N4' _chemical_formula_weight 320.05 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 triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.751(3) _cell_length_b 10.426(3) _cell_length_c 10.457(3) _cell_angle_alpha 117.055(15) _cell_angle_beta 90.450(18) _cell_angle_gamma 101.589(17) _cell_volume 921.4(5) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6410 _cell_measurement_theta_min 3.82 _cell_measurement_theta_max 25.31 _exptl_crystal_description ? _exptl_crystal_colour colorless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.154 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 0.068 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9905 _exptl_absorpt_correction_T_max 0.9959 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enraf Nonius FR590D, fine-focus sealed tube' _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_device_type 'KappaCCD (Nonius, FR540C)' _diffrn_measurement_method 'phi\omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6410 _diffrn_reflns_av_R_equivalents 0.0233 _diffrn_reflns_av_sigmaI/netI 0.0365 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.82 _diffrn_reflns_theta_max 25.31 _reflns_number_total 3333 _reflns_number_gt 2618 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0510P)^2^+0.3000P] 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 3333 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0612 _refine_ls_R_factor_gt 0.0436 _refine_ls_wR_factor_ref 0.1148 _refine_ls_wR_factor_gt 0.1035 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.001 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 0.69334(13) 0.16261(14) 0.38178(13) 0.0237(3) Uani 1 1 d . . . N2 N 0.68559(13) 0.23312(14) 0.29025(13) 0.0232(3) Uani 1 1 d . . . N3 N 0.81874(13) -0.04083(14) 0.33856(14) 0.0264(3) Uani 1 1 d . . . N4 N 0.86532(13) 0.37546(14) 0.20128(14) 0.0286(3) Uani 1 1 d . . . C1 C 0.92755(15) 0.18687(16) 0.28825(16) 0.0240(3) Uani 1 1 d . . . H1 H 0.9700 0.1270 0.2060 0.029 Uiso 1 1 d R . . C2 C 1.04361(17) 0.29674(18) 0.41376(18) 0.0331(4) Uani 1 1 d . . . H2A H 1.1098 0.3528 0.3800 0.040 Uiso 1 1 d R . . H2B H 1.0915 0.2427 0.4457 0.040 Uiso 1 1 d R . . H2C H 1.0019 0.3627 0.4927 0.040 Uiso 1 1 d R . . C3 C 0.67579(15) 0.25043(17) 0.52809(16) 0.0248(3) Uani 1 1 d . . . C4 C 0.70631(17) 0.20734(19) 0.63221(17) 0.0307(4) Uani 1 1 d . . . H4 H 0.7436 0.1210 0.6041 0.037 Uiso 1 1 d R . . C5 C 0.68479(18) 0.2897(2) 0.77481(18) 0.0365(4) Uani 1 1 d . . . H5 H 0.7039 0.2583 0.8450 0.044 Uiso 1 1 d R . . C6 C 0.63470(18) 0.4168(2) 0.81854(18) 0.0389(4) Uani 1 1 d . . . H6 H 0.6199 0.4730 0.9176 0.047 Uiso 1 1 d R . . C7 C 0.60653(18) 0.4610(2) 0.71684(18) 0.0366(4) Uani 1 1 d . . . H7 H 0.5727 0.5495 0.7457 0.044 Uiso 1 1 d R . . C8 C 0.62595(16) 0.37915(17) 0.57294(17) 0.0295(4) Uani 1 1 d . . . H8 H 0.6061 0.4117 0.5038 0.035 Uiso 1 1 d R . . C9 C 0.55273(15) 0.19324(16) 0.21150(15) 0.0227(3) Uani 1 1 d . . . C10 C 0.42952(16) 0.14683(18) 0.26058(17) 0.0302(4) Uani 1 1 d . . . H10 H 0.4346 0.1399 0.3489 0.036 Uiso 1 1 d R . . C11 C 0.29995(18) 0.1088(2) 0.18094(19) 0.0382(4) Uani 1 1 d . . . H11 H 0.2148 0.0780 0.2150 0.046 Uiso 1 1 d R . . C12 C 0.28971(18) 0.11605(19) 0.05262(19) 0.0372(4) Uani 1 1 d . . . H12 H 0.1986 0.0909 0.0008 0.045 Uiso 1 1 d R . . C13 C 0.41155(18) 0.15900(18) 0.00223(17) 0.0331(4) Uani 1 1 d . . . H13 H 0.4063 0.1626 -0.0878 0.040 Uiso 1 1 d R . . C14 C 0.54173(17) 0.19630(16) 0.07955(16) 0.0264(4) Uani 1 1 d . . . H14 H 0.6251 0.2248 0.0416 0.032 Uiso 1 1 d R . . C15 C 0.70114(17) -0.13376(19) 0.36537(19) 0.0346(4) Uani 1 1 d . . . H15A H 0.6248 -0.0845 0.3913 0.041 Uiso 1 1 d R . . H15B H 0.7316 -0.1499 0.4433 0.041 Uiso 1 1 d R . . H15C H 0.6701 -0.2271 0.2802 0.041 Uiso 1 1 d R . . C16 C 0.93936(18) -0.10834(19) 0.2980(2) 0.0371(4) Uani 1 1 d . . . H16A H 1.0127 -0.0434 0.2807 0.045 Uiso 1 1 d R . . H16B H 0.9118 -0.2014 0.2118 0.045 Uiso 1 1 d R . . H16C H 0.9733 -0.1241 0.3749 0.045 Uiso 1 1 d R . . C17 C 0.78582(19) 0.48410(18) 0.21424(19) 0.0348(4) Uani 1 1 d . . . H17A H 0.6975 0.4645 0.2495 0.042 Uiso 1 1 d R . . H17B H 0.7687 0.4785 0.1211 0.042 Uiso 1 1 d R . . H17C H 0.8393 0.5813 0.2803 0.042 Uiso 1 1 d R . . C18 C 1.00043(19) 0.3990(2) 0.1476(2) 0.0426(5) Uani 1 1 d . . . H18A H 1.0487 0.3248 0.1411 0.051 Uiso 1 1 d R . . H18B H 1.0563 0.4952 0.2130 0.051 Uiso 1 1 d R . . H18C H 0.9857 0.3924 0.0538 0.051 Uiso 1 1 d R . . B1 B 0.81582(18) 0.09153(19) 0.33796(18) 0.0234(4) Uani 1 1 d . . . B2 B 0.82667(18) 0.27095(18) 0.25123(18) 0.0234(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0258(7) 0.0284(7) 0.0241(7) 0.0166(6) 0.0064(5) 0.0102(5) N2 0.0229(7) 0.0285(7) 0.0255(7) 0.0179(6) 0.0034(5) 0.0077(5) N3 0.0241(7) 0.0265(7) 0.0341(7) 0.0183(6) 0.0050(6) 0.0066(5) N4 0.0274(7) 0.0286(7) 0.0348(8) 0.0195(6) 0.0034(6) 0.0049(6) C1 0.0218(8) 0.0239(8) 0.0256(8) 0.0109(7) 0.0034(6) 0.0052(6) C2 0.0289(9) 0.0331(9) 0.0376(9) 0.0181(8) -0.0020(7) 0.0042(7) C3 0.0191(8) 0.0304(8) 0.0248(8) 0.0139(7) 0.0035(6) 0.0031(6) C4 0.0284(9) 0.0378(9) 0.0305(9) 0.0198(8) 0.0053(7) 0.0074(7) C5 0.0338(10) 0.0515(11) 0.0276(9) 0.0229(8) 0.0052(7) 0.0058(8) C6 0.0320(10) 0.0497(11) 0.0259(9) 0.0108(8) 0.0068(7) 0.0075(8) C7 0.0315(9) 0.0367(10) 0.0343(9) 0.0093(8) 0.0038(7) 0.0110(7) C8 0.0292(9) 0.0310(9) 0.0288(8) 0.0136(7) 0.0028(7) 0.0086(7) C9 0.0238(8) 0.0205(7) 0.0234(8) 0.0083(6) 0.0030(6) 0.0090(6) C10 0.0271(9) 0.0359(9) 0.0282(8) 0.0148(7) 0.0056(7) 0.0087(7) C11 0.0236(9) 0.0432(10) 0.0402(10) 0.0133(8) 0.0045(7) 0.0069(7) C12 0.0280(9) 0.0378(10) 0.0350(9) 0.0069(8) -0.0068(7) 0.0104(7) C13 0.0398(10) 0.0294(9) 0.0266(8) 0.0090(7) -0.0039(7) 0.0111(7) C14 0.0295(8) 0.0240(8) 0.0247(8) 0.0102(7) 0.0025(6) 0.0071(6) C15 0.0317(9) 0.0329(9) 0.0456(10) 0.0253(8) 0.0042(8) 0.0035(7) C16 0.0359(10) 0.0323(9) 0.0536(11) 0.0256(9) 0.0132(8) 0.0155(8) C17 0.0433(10) 0.0256(9) 0.0373(10) 0.0174(8) -0.0055(8) 0.0052(7) C18 0.0383(10) 0.0477(11) 0.0526(11) 0.0344(10) 0.0119(9) 0.0050(8) B1 0.0236(9) 0.0256(9) 0.0198(8) 0.0096(7) -0.0011(7) 0.0055(7) B2 0.0253(9) 0.0225(9) 0.0199(8) 0.0082(7) 0.0020(7) 0.0046(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 N1 C3 1.4146(19) . ? N1 N2 1.4572(17) . ? N1 B1 1.497(2) . ? N2 C9 1.4087(19) . ? N2 B2 1.467(2) . ? N3 B1 1.389(2) . ? N3 C16 1.459(2) . ? N3 C15 1.462(2) . ? N4 B2 1.399(2) . ? N4 C17 1.455(2) . ? N4 C18 1.455(2) . ? C1 C2 1.550(2) . ? C1 B1 1.578(2) . ? C1 B2 1.592(2) . ? C1 H1 0.9600 . ? C2 H2A 0.9601 . ? C2 H2B 0.9601 . ? C2 H2C 0.9599 . ? C3 C8 1.397(2) . ? C3 C4 1.403(2) . ? C4 C5 1.385(2) . ? C4 H4 0.9599 . ? C5 C6 1.384(3) . ? C5 H5 0.9601 . ? C6 C7 1.382(3) . ? C6 H6 0.9600 . ? C7 C8 1.389(2) . ? C7 H7 0.9600 . ? C8 H8 0.9600 . ? C9 C10 1.394(2) . ? C9 C14 1.398(2) . ? C10 C11 1.389(2) . ? C10 H10 0.9600 . ? C11 C12 1.382(3) . ? C11 H11 0.9600 . ? C12 C13 1.379(2) . ? C12 H12 0.9599 . ? C13 C14 1.384(2) . ? C13 H13 0.9601 . ? C14 H14 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9599 . ? C16 H16A 0.9600 . ? C16 H16B 0.9599 . ? C16 H16C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9599 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 N1 N2 114.43(12) . . ? C3 N1 B1 122.49(12) . . ? N2 N1 B1 104.46(11) . . ? C9 N2 N1 114.45(11) . . ? C9 N2 B2 129.60(12) . . ? N1 N2 B2 109.05(11) . . ? B1 N3 C16 121.82(13) . . ? B1 N3 C15 125.27(13) . . ? C16 N3 C15 112.68(13) . . ? B2 N4 C17 124.51(14) . . ? B2 N4 C18 122.46(14) . . ? C17 N4 C18 112.57(13) . . ? C2 C1 B1 111.18(13) . . ? C2 C1 B2 111.33(13) . . ? B1 C1 B2 98.87(12) . . ? C2 C1 H1 109.8 . . ? B1 C1 H1 112.6 . . ? B2 C1 H1 112.7 . . ? C1 C2 H2A 109.1 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.8 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C8 C3 C4 118.22(14) . . ? C8 C3 N1 121.84(14) . . ? C4 C3 N1 119.93(14) . . ? C5 C4 C3 120.38(16) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 119.5 . . ? C6 C5 C4 121.15(16) . . ? C6 C5 H5 119.0 . . ? C4 C5 H5 119.9 . . ? C7 C6 C5 118.71(16) . . ? C7 C6 H6 120.8 . . ? C5 C6 H6 120.5 . . ? C6 C7 C8 121.07(17) . . ? C6 C7 H7 119.7 . . ? C8 C7 H7 119.2 . . ? C7 C8 C3 120.46(15) . . ? C7 C8 H8 119.9 . . ? C3 C8 H8 119.6 . . ? C10 C9 C14 118.20(14) . . ? C10 C9 N2 121.36(13) . . ? C14 C9 N2 120.43(13) . . ? C11 C10 C9 120.08(15) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 119.8 . . ? C12 C11 C10 121.32(16) . . ? C12 C11 H11 118.4 . . ? C10 C11 H11 120.3 . . ? C13 C12 C11 118.77(15) . . ? C13 C12 H12 121.8 . . ? C11 C12 H12 119.5 . . ? C12 C13 C14 120.74(15) . . ? C12 C13 H13 119.7 . . ? C14 C13 H13 119.5 . . ? C13 C14 C9 120.85(15) . . ? C13 C14 H14 119.1 . . ? C9 C14 H14 120.0 . . ? N3 C15 H15A 109.3 . . ? N3 C15 H15B 109.0 . . ? H15A C15 H15B 109.5 . . ? N3 C15 H15C 110.1 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N3 C16 H16A 109.2 . . ? N3 C16 H16B 109.7 . . ? H16A C16 H16B 109.5 . . ? N3 C16 H16C 109.6 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N4 C17 H17A 109.9 . . ? N4 C17 H17B 109.2 . . ? H17A C17 H17B 109.5 . . ? N4 C17 H17C 109.3 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N4 C18 H18A 109.4 . . ? N4 C18 H18B 109.4 . . ? H18A C18 H18B 109.5 . . ? N4 C18 H18C 109.7 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N3 B1 N1 122.07(14) . . ? N3 B1 C1 128.92(14) . . ? N1 B1 C1 108.95(13) . . ? N4 B2 N2 123.51(14) . . ? N4 B2 C1 126.75(14) . . ? N2 B2 C1 109.52(13) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 N1 N2 C9 -97.20(14) . . . . ? B1 N1 N2 C9 126.20(13) . . . . ? C3 N1 N2 B2 108.94(14) . . . . ? B1 N1 N2 B2 -27.66(15) . . . . ? N2 N1 C3 C8 12.84(19) . . . . ? B1 N1 C3 C8 140.76(15) . . . . ? N2 N1 C3 C4 -168.36(13) . . . . ? B1 N1 C3 C4 -40.4(2) . . . . ? C8 C3 C4 C5 1.1(2) . . . . ? N1 C3 C4 C5 -177.72(14) . . . . ? C3 C4 C5 C6 -0.8(3) . . . . ? C4 C5 C6 C7 -0.2(3) . . . . ? C5 C6 C7 C8 0.9(3) . . . . ? C6 C7 C8 C3 -0.6(2) . . . . ? C4 C3 C8 C7 -0.4(2) . . . . ? N1 C3 C8 C7 178.38(14) . . . . ? N1 N2 C9 C10 26.38(19) . . . . ? B2 N2 C9 C10 173.67(15) . . . . ? N1 N2 C9 C14 -152.21(13) . . . . ? B2 N2 C9 C14 -4.9(2) . . . . ? C14 C9 C10 C11 -1.6(2) . . . . ? N2 C9 C10 C11 179.73(14) . . . . ? C9 C10 C11 C12 -0.1(3) . . . . ? C10 C11 C12 C13 1.4(3) . . . . ? C11 C12 C13 C14 -0.9(2) . . . . ? C12 C13 C14 C9 -0.9(2) . . . . ? C10 C9 C14 C13 2.1(2) . . . . ? N2 C9 C14 C13 -179.23(14) . . . . ? C16 N3 B1 N1 -178.98(14) . . . . ? C15 N3 B1 N1 7.0(2) . . . . ? C16 N3 B1 C1 4.0(2) . . . . ? C15 N3 B1 C1 -170.02(15) . . . . ? C3 N1 B1 N3 81.56(19) . . . . ? N2 N1 B1 N3 -146.32(14) . . . . ? C3 N1 B1 C1 -100.92(15) . . . . ? N2 N1 B1 C1 31.19(15) . . . . ? C2 C1 B1 N3 -87.22(19) . . . . ? B2 C1 B1 N3 155.69(16) . . . . ? C2 C1 B1 N1 95.48(15) . . . . ? B2 C1 B1 N1 -21.60(15) . . . . ? C17 N4 B2 N2 15.6(2) . . . . ? C18 N4 B2 N2 -172.78(15) . . . . ? C17 N4 B2 C1 -158.39(15) . . . . ? C18 N4 B2 C1 13.2(2) . . . . ? C9 N2 B2 N4 50.6(2) . . . . ? N1 N2 B2 N4 -160.78(14) . . . . ? C9 N2 B2 C1 -134.49(15) . . . . ? N1 N2 B2 C1 14.14(16) . . . . ? C2 C1 B2 N4 62.4(2) . . . . ? B1 C1 B2 N4 179.39(15) . . . . ? C2 C1 B2 N2 -112.28(14) . . . . ? B1 C1 B2 N2 4.68(15) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.31 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.187 _refine_diff_density_min -0.202 _refine_diff_density_rms 0.040 # Attachment '3a.cif' data_3a _database_code_depnum_ccdc_archive 'CCDC 678562' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C38 H47 B2 Li N2 O3' _chemical_formula_sum 'C38 H47 B2 Li N2 O3' _chemical_formula_weight 608.34 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' Li Li -0.0003 0.0001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 22.732(7) _cell_length_b 8.931(2) _cell_length_c 35.3500(11) _cell_angle_alpha 90.00 _cell_angle_beta 104.183(11) _cell_angle_gamma 90.00 _cell_volume 6958(3) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 13196 _cell_measurement_theta_min 3.26 _cell_measurement_theta_max 27.47 _exptl_crystal_description ? _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.161 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2608 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9859 _exptl_absorpt_correction_T_max 0.9915 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enraf Nonius FR590D, fine-focus sealed tube' _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_device_type 'KappaCCD (Nonius, FR540C)' _diffrn_measurement_method 'phi\omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13196 _diffrn_reflns_av_R_equivalents 0.0367 _diffrn_reflns_av_sigmaI/netI 0.0577 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -45 _diffrn_reflns_limit_l_max 45 _diffrn_reflns_theta_min 3.26 _diffrn_reflns_theta_max 27.47 _reflns_number_total 7828 _reflns_number_gt 5245 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0605P)^2^+7.0200P] 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 7828 _refine_ls_number_parameters 415 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0951 _refine_ls_R_factor_gt 0.0557 _refine_ls_wR_factor_ref 0.1540 _refine_ls_wR_factor_gt 0.1295 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _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 O1 O 0.09685(6) 0.28376(15) 0.07104(4) 0.0394(3) Uani 1 1 d . . . O2 O -0.02122(6) 0.41960(15) 0.08045(4) 0.0410(3) Uani 1 1 d . . . O3 O 0.07989(6) 0.36433(15) 0.15228(4) 0.0367(3) Uani 1 1 d . . . N1 N 0.15817(6) 0.76179(17) 0.15668(4) 0.0292(3) Uani 1 1 d . . . N2 N 0.20477(6) 0.68552(16) 0.14309(4) 0.0272(3) Uani 1 1 d . . . C1 C 0.11214(8) 0.67956(19) 0.09125(5) 0.0286(4) Uani 1 1 d . . . C2 C 0.06950(9) 0.6675(2) 0.05063(6) 0.0365(4) Uani 1 1 d . . . H2A H 0.0290 0.7029 0.0515 0.055 Uiso 1 1 calc R . . H2B H 0.0670 0.5628 0.0421 0.055 Uiso 1 1 calc R . . H2C H 0.0851 0.7290 0.0323 0.055 Uiso 1 1 calc R . . C3 C 0.17114(7) 0.78648(19) 0.19720(5) 0.0267(4) Uani 1 1 d . . . C4 C 0.21137(8) 0.6957(2) 0.22351(5) 0.0296(4) Uani 1 1 d . . . H4 H 0.2319 0.6149 0.2142 0.035 Uiso 1 1 d R . . C5 C 0.22213(8) 0.7202(2) 0.26329(6) 0.0350(4) Uani 1 1 d . . . H5 H 0.2499 0.6563 0.2810 0.042 Uiso 1 1 d R . . C6 C 0.19371(9) 0.8364(2) 0.27763(6) 0.0389(5) Uani 1 1 d . . . H6 H 0.2010 0.8513 0.3053 0.047 Uiso 1 1 d R . . C7 C 0.15463(9) 0.9291(2) 0.25175(6) 0.0390(5) Uani 1 1 d . . . H7 H 0.1343 1.0101 0.2611 0.047 Uiso 1 1 d R . . C8 C 0.14369(8) 0.9060(2) 0.21192(6) 0.0331(4) Uani 1 1 d . . . H8 H 0.1177 0.9736 0.1943 0.040 Uiso 1 1 d R . . C9 C 0.26206(8) 0.7609(2) 0.15274(5) 0.0270(4) Uani 1 1 d . . . C10 C 0.26635(9) 0.9162(2) 0.15570(6) 0.0385(5) Uani 1 1 d . . . H10 H 0.2299 0.9751 0.1510 0.046 Uiso 1 1 d R . . C11 C 0.32252(10) 0.9855(2) 0.16580(7) 0.0474(6) Uani 1 1 d . . . H11 H 0.3254 1.0927 0.1671 0.057 Uiso 1 1 d R . . C12 C 0.37525(9) 0.9022(2) 0.17353(6) 0.0421(5) Uani 1 1 d . . . H12 H 0.4139 0.9512 0.1813 0.051 Uiso 1 1 d R . . C13 C 0.37149(8) 0.7480(2) 0.17045(6) 0.0377(5) Uani 1 1 d . . . H13 H 0.4080 0.6895 0.1753 0.045 Uiso 1 1 d R . . C14 C 0.31520(8) 0.6784(2) 0.16027(6) 0.0321(4) Uani 1 1 d . . . H14 H 0.3132 0.5712 0.1582 0.039 Uiso 1 1 d R . . C15 C 0.03812(8) 0.7945(2) 0.13671(6) 0.0316(4) Uani 1 1 d . . . C16 C -0.00529(9) 0.8786(2) 0.11022(7) 0.0404(5) Uani 1 1 d . . . H16 H 0.0038 0.9147 0.0867 0.049 Uiso 1 1 d R . . C17 C -0.06210(9) 0.9094(2) 0.11683(9) 0.0559(7) Uani 1 1 d . . . H17 H -0.0908 0.9676 0.0981 0.067 Uiso 1 1 d R . . C18 C -0.07667(10) 0.8577(3) 0.14997(9) 0.0584(7) Uani 1 1 d . . . H18 H -0.1157 0.8790 0.1547 0.070 Uiso 1 1 d R . . C19 C -0.03515(10) 0.7746(3) 0.17662(8) 0.0505(6) Uani 1 1 d . . . H19 H -0.0454 0.7390 0.1998 0.061 Uiso 1 1 d R . . C20 C 0.02140(9) 0.7428(2) 0.16992(6) 0.0384(5) Uani 1 1 d . . . H20 H 0.0496 0.6838 0.1887 0.046 Uiso 1 1 d R . . C21 C 0.21803(8) 0.5504(2) 0.07925(5) 0.0310(4) Uani 1 1 d . . . C22 C 0.24665(9) 0.4159(2) 0.09352(6) 0.0382(5) Uani 1 1 d . . . H22 H 0.2438 0.3803 0.1186 0.046 Uiso 1 1 d R . . C23 C 0.27878(10) 0.3312(3) 0.07251(8) 0.0524(6) Uani 1 1 d . . . H23 H 0.2976 0.2387 0.0828 0.063 Uiso 1 1 d R . . C24 C 0.28376(10) 0.3790(3) 0.03638(8) 0.0582(7) Uani 1 1 d . . . H24 H 0.3061 0.3196 0.0221 0.070 Uiso 1 1 d R . . C25 C 0.25661(10) 0.5117(3) 0.02134(7) 0.0551(7) Uani 1 1 d . . . H25 H 0.2608 0.5450 -0.0037 0.066 Uiso 1 1 d R . . C26 C 0.22364(9) 0.5957(3) 0.04241(6) 0.0418(5) Uani 1 1 d . . . H26 H 0.2043 0.6868 0.0315 0.050 Uiso 1 1 d R . . C27 C 0.12728(10) 0.1502(2) 0.08945(7) 0.0424(5) Uani 1 1 d . . . H27A H 0.1636 0.1791 0.1083 0.051 Uiso 1 1 d R . . H27B H 0.1009 0.0974 0.1023 0.051 Uiso 1 1 d R . . C28 C 0.14141(11) 0.0568(2) 0.05715(7) 0.0493(6) Uani 1 1 d . . . H28A H 0.1818 0.0789 0.0551 0.059 Uiso 1 1 d R . . H28B H 0.1386 -0.0476 0.0630 0.059 Uiso 1 1 d R . . C29 C 0.09336(11) 0.1075(3) 0.02173(7) 0.0514(6) Uani 1 1 d . . . H29A H 0.1065 0.0854 -0.0015 0.062 Uiso 1 1 d R . . H29B H 0.0562 0.0552 0.0210 0.062 Uiso 1 1 d R . . C30 C 0.09076(11) 0.2727(2) 0.02963(6) 0.0447(5) Uani 1 1 d . . . H30A H 0.0524 0.3150 0.0164 0.054 Uiso 1 1 d R . . H30B H 0.1230 0.3276 0.0228 0.054 Uiso 1 1 d R . . C31 C -0.04683(10) 0.2795(2) 0.06458(7) 0.0474(5) Uani 1 1 d . . . H31A H -0.0416 0.2693 0.0386 0.057 Uiso 1 1 d R . . H31B H -0.0262 0.1991 0.0805 0.057 Uiso 1 1 d R . . C32 C -0.11205(10) 0.2841(3) 0.06502(9) 0.0593(7) Uani 1 1 d . . . H32A H -0.1355 0.2333 0.0424 0.071 Uiso 1 1 d R . . H32B H -0.1177 0.2355 0.0881 0.071 Uiso 1 1 d R . . C33 C -0.12752(10) 0.4464(3) 0.06369(8) 0.0579(6) Uani 1 1 d . . . H33A H -0.1428 0.4790 0.0372 0.069 Uiso 1 1 d R . . H33B H -0.1577 0.4630 0.0780 0.069 Uiso 1 1 d R . . C34 C -0.06940(9) 0.5215(2) 0.08277(8) 0.0480(6) Uani 1 1 d . . . H34A H -0.0676 0.5437 0.1096 0.058 Uiso 1 1 d R . . H34B H -0.0647 0.6124 0.0693 0.058 Uiso 1 1 d R . . C35 C 0.03611(10) 0.2876(3) 0.16807(7) 0.0511(6) Uani 1 1 d . . . H35A H -0.0031 0.3312 0.1578 0.061 Uiso 1 1 d R . . H35B H 0.0353 0.1839 0.1608 0.061 Uiso 1 1 d R . . C36 C 0.05578(10) 0.3044(3) 0.21158(7) 0.0563(6) Uani 1 1 d . . . H36A H 0.0297 0.3749 0.2199 0.068 Uiso 1 1 d R . . H36B H 0.0537 0.2097 0.2241 0.068 Uiso 1 1 d R . . C37 C 0.12050(10) 0.3630(3) 0.22008(7) 0.0493(5) Uani 1 1 d . . . H37A H 0.1219 0.4639 0.2296 0.059 Uiso 1 1 d R . . H37B H 0.1460 0.3005 0.2394 0.059 Uiso 1 1 d R . . C38 C 0.13653(9) 0.3547(3) 0.18114(6) 0.0423(5) Uani 1 1 d . . . H38A H 0.1557 0.2612 0.1781 0.051 Uiso 1 1 d R . . H38B H 0.1624 0.4358 0.1777 0.051 Uiso 1 1 d R . . B1 B 0.10056(9) 0.7508(2) 0.12717(6) 0.0279(4) Uani 1 1 d . . . B2 B 0.17753(9) 0.6373(2) 0.10248(6) 0.0279(4) Uani 1 1 d . . . Li1 Li 0.06881(14) 0.4471(4) 0.10006(10) 0.0356(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0431(8) 0.0383(7) 0.0378(8) 0.0004(6) 0.0121(6) 0.0050(6) O2 0.0304(7) 0.0341(7) 0.0538(9) -0.0022(6) 0.0015(6) -0.0022(6) O3 0.0279(6) 0.0468(8) 0.0348(8) 0.0067(6) 0.0067(6) -0.0028(6) N1 0.0225(7) 0.0356(8) 0.0299(8) -0.0048(7) 0.0068(6) 0.0039(6) N2 0.0193(7) 0.0332(8) 0.0298(8) -0.0035(6) 0.0073(6) 0.0029(6) C1 0.0275(9) 0.0282(9) 0.0280(10) 0.0019(7) 0.0029(7) -0.0016(7) C2 0.0355(10) 0.0377(10) 0.0329(11) 0.0041(8) 0.0020(8) -0.0029(9) C3 0.0215(8) 0.0298(9) 0.0293(10) -0.0029(7) 0.0072(7) -0.0036(7) C4 0.0253(9) 0.0307(9) 0.0326(10) -0.0026(8) 0.0068(8) -0.0014(7) C5 0.0320(10) 0.0389(10) 0.0318(11) 0.0012(8) 0.0037(8) -0.0026(8) C6 0.0434(11) 0.0435(11) 0.0298(11) -0.0048(9) 0.0087(9) -0.0053(9) C7 0.0416(11) 0.0377(10) 0.0400(12) -0.0086(9) 0.0146(9) 0.0003(9) C8 0.0291(9) 0.0328(9) 0.0368(11) -0.0028(8) 0.0068(8) 0.0030(8) C9 0.0244(8) 0.0327(9) 0.0246(9) -0.0005(7) 0.0076(7) 0.0001(7) C10 0.0361(10) 0.0305(10) 0.0526(13) 0.0000(9) 0.0176(10) 0.0037(8) C11 0.0484(12) 0.0337(10) 0.0671(16) -0.0105(10) 0.0277(12) -0.0097(10) C12 0.0329(10) 0.0485(12) 0.0493(13) -0.0126(10) 0.0184(10) -0.0139(9) C13 0.0238(9) 0.0481(12) 0.0425(12) 0.0002(9) 0.0101(8) -0.0019(8) C14 0.0268(9) 0.0321(9) 0.0382(11) 0.0006(8) 0.0093(8) 0.0008(8) C15 0.0240(9) 0.0265(9) 0.0426(12) -0.0049(8) 0.0050(8) -0.0012(7) C16 0.0280(9) 0.0288(10) 0.0600(14) 0.0016(9) 0.0021(9) 0.0004(8) C17 0.0260(10) 0.0317(11) 0.103(2) -0.0003(12) 0.0016(12) 0.0045(9) C18 0.0307(11) 0.0397(12) 0.110(2) -0.0147(14) 0.0269(13) 0.0019(10) C19 0.0400(12) 0.0491(13) 0.0698(17) -0.0144(12) 0.0275(12) -0.0071(10) C20 0.0287(10) 0.0413(11) 0.0464(13) -0.0061(9) 0.0115(9) -0.0014(8) C21 0.0243(8) 0.0378(10) 0.0302(10) -0.0071(8) 0.0057(8) -0.0062(8) C22 0.0347(10) 0.0379(11) 0.0420(12) -0.0088(9) 0.0093(9) -0.0003(9) C23 0.0346(11) 0.0495(13) 0.0722(18) -0.0244(12) 0.0114(11) 0.0007(10) C24 0.0350(12) 0.0783(18) 0.0660(17) -0.0412(15) 0.0215(12) -0.0104(12) C25 0.0421(12) 0.0911(19) 0.0366(13) -0.0207(13) 0.0186(10) -0.0203(13) C26 0.0345(10) 0.0576(13) 0.0343(12) -0.0057(10) 0.0100(9) -0.0096(10) C27 0.0442(12) 0.0348(11) 0.0488(13) 0.0050(9) 0.0124(10) 0.0028(9) C28 0.0539(13) 0.0360(11) 0.0634(16) -0.0055(11) 0.0244(12) -0.0019(10) C29 0.0572(14) 0.0501(13) 0.0505(14) -0.0135(11) 0.0203(12) -0.0130(11) C30 0.0502(13) 0.0478(12) 0.0375(12) -0.0003(10) 0.0132(10) -0.0008(10) C31 0.0437(12) 0.0413(12) 0.0543(14) -0.0082(10) 0.0062(10) -0.0065(10) C32 0.0404(12) 0.0517(14) 0.084(2) -0.0084(13) 0.0108(13) -0.0115(11) C33 0.0362(12) 0.0565(14) 0.0733(18) -0.0061(13) -0.0014(11) 0.0029(11) C34 0.0361(11) 0.0410(12) 0.0651(16) -0.0040(11) 0.0090(11) 0.0024(9) C35 0.0347(11) 0.0712(16) 0.0494(14) 0.0127(12) 0.0143(10) -0.0091(11) C36 0.0475(13) 0.0781(17) 0.0476(14) 0.0142(12) 0.0198(11) 0.0011(12) C37 0.0500(13) 0.0603(14) 0.0370(12) 0.0019(11) 0.0098(10) -0.0041(11) C38 0.0303(10) 0.0565(13) 0.0378(12) 0.0019(10) 0.0042(9) -0.0056(9) B1 0.0232(9) 0.0257(10) 0.0327(11) 0.0041(8) 0.0031(8) 0.0005(8) B2 0.0302(10) 0.0259(9) 0.0279(11) -0.0001(8) 0.0078(9) -0.0031(8) Li1 0.0334(17) 0.0356(17) 0.0374(19) 0.0013(14) 0.0076(14) -0.0014(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C30 1.439(2) . ? O1 C27 1.450(2) . ? O1 Li1 1.977(3) . ? O2 C31 1.435(2) . ? O2 C34 1.442(2) . ? O2 Li1 2.009(3) . ? O3 C35 1.430(2) . ? O3 C38 1.436(2) . ? O3 Li1 1.947(4) . ? N1 C3 1.407(2) . ? N1 N2 1.4374(19) . ? N1 B1 1.464(2) . ? N2 C9 1.431(2) . ? N2 B2 1.481(3) . ? C1 B2 1.490(3) . ? C1 B1 1.501(3) . ? C1 C2 1.527(3) . ? C1 Li1 2.351(4) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 C4 1.394(3) . ? C3 C8 1.399(2) . ? C4 C5 1.385(3) . ? C4 H4 0.9599 . ? C5 C6 1.382(3) . ? C5 H5 0.9599 . ? C6 C7 1.383(3) . ? C6 H6 0.9601 . ? C7 C8 1.384(3) . ? C7 H7 0.9600 . ? C8 H8 0.9600 . ? C9 C14 1.384(2) . ? C9 C10 1.392(3) . ? C10 C11 1.385(3) . ? C10 H10 0.9600 . ? C11 C12 1.380(3) . ? C11 H11 0.9600 . ? C12 C13 1.382(3) . ? C12 H12 0.9599 . ? C13 C14 1.389(3) . ? C13 H13 0.9599 . ? C14 H14 0.9600 . ? C15 C20 1.398(3) . ? C15 C16 1.400(3) . ? C15 B1 1.586(3) . ? C16 C17 1.395(3) . ? C16 H16 0.9601 . ? C17 C18 1.373(4) . ? C17 H17 0.9600 . ? C18 C19 1.376(4) . ? C18 H18 0.9601 . ? C19 C20 1.392(3) . ? C19 H19 0.9597 . ? C20 H20 0.9599 . ? C21 C26 1.399(3) . ? C21 C22 1.400(3) . ? C21 B2 1.579(3) . ? C22 C23 1.387(3) . ? C22 H22 0.9601 . ? C23 C24 1.377(4) . ? C23 H23 0.9601 . ? C24 C25 1.381(4) . ? C24 H24 0.9599 . ? C25 C26 1.397(3) . ? C25 H25 0.9601 . ? C26 H26 0.9599 . ? C27 C28 1.511(3) . ? C27 H27A 0.9600 . ? C27 H27B 0.9599 . ? C28 C29 1.515(3) . ? C28 H28A 0.9599 . ? C28 H28B 0.9601 . ? C29 C30 1.506(3) . ? C29 H29A 0.9599 . ? C29 H29B 0.9601 . ? C30 H30A 0.9599 . ? C30 H30B 0.9601 . ? C31 C32 1.487(3) . ? C31 H31A 0.9599 . ? C31 H31B 0.9601 . ? C32 C33 1.490(3) . ? C32 H32A 0.9598 . ? C32 H32B 0.9599 . ? C33 C34 1.488(3) . ? C33 H33A 0.9599 . ? C33 H33B 0.9601 . ? C34 H34A 0.9599 . ? C34 H34B 0.9602 . ? C35 C36 1.500(3) . ? C35 H35A 0.9599 . ? C35 H35B 0.9599 . ? C36 C37 1.521(3) . ? C36 H36A 0.9598 . ? C36 H36B 0.9601 . ? C37 C38 1.510(3) . ? C37 H37A 0.9600 . ? C37 H37B 0.9599 . ? C38 H38A 0.9600 . ? C38 H38B 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C30 O1 C27 108.44(15) . . ? C30 O1 Li1 127.98(15) . . ? C27 O1 Li1 123.58(15) . . ? C31 O2 C34 109.37(15) . . ? C31 O2 Li1 121.54(15) . . ? C34 O2 Li1 128.83(15) . . ? C35 O3 C38 106.41(15) . . ? C35 O3 Li1 127.71(16) . . ? C38 O3 Li1 125.57(15) . . ? C3 N1 N2 115.25(14) . . ? C3 N1 B1 131.56(14) . . ? N2 N1 B1 109.52(14) . . ? C9 N2 N1 113.54(13) . . ? C9 N2 B2 120.51(14) . . ? N1 N2 B2 107.11(13) . . ? B2 C1 B1 104.62(16) . . ? B2 C1 C2 126.50(17) . . ? B1 C1 C2 128.55(16) . . ? B2 C1 Li1 99.45(14) . . ? B1 C1 Li1 95.53(14) . . ? C2 C1 Li1 82.66(13) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C4 C3 C8 118.36(17) . . ? C4 C3 N1 121.86(15) . . ? C8 C3 N1 119.78(16) . . ? C5 C4 C3 120.64(17) . . ? C5 C4 H4 119.2 . . ? C3 C4 H4 120.2 . . ? C6 C5 C4 120.59(19) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.5 . . ? C5 C6 C7 119.26(19) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 120.9 . . ? C6 C7 C8 120.65(18) . . ? C6 C7 H7 120.6 . . ? C8 C7 H7 118.8 . . ? C7 C8 C3 120.45(18) . . ? C7 C8 H8 119.6 . . ? C3 C8 H8 120.0 . . ? C14 C9 C10 118.33(17) . . ? C14 C9 N2 119.68(16) . . ? C10 C9 N2 121.97(16) . . ? C11 C10 C9 120.49(18) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 119.4 . . ? C12 C11 C10 120.80(19) . . ? C12 C11 H11 118.9 . . ? C10 C11 H11 120.3 . . ? C11 C12 C13 119.15(19) . . ? C11 C12 H12 120.1 . . ? C13 C12 H12 120.7 . . ? C12 C13 C14 120.14(18) . . ? C12 C13 H13 119.7 . . ? C14 C13 H13 120.2 . . ? C9 C14 C13 121.09(18) . . ? C9 C14 H14 119.6 . . ? C13 C14 H14 119.3 . . ? C20 C15 C16 116.52(17) . . ? C20 C15 B1 122.61(17) . . ? C16 C15 B1 120.68(18) . . ? C17 C16 C15 121.6(2) . . ? C17 C16 H16 118.8 . . ? C15 C16 H16 119.6 . . ? C18 C17 C16 120.2(2) . . ? C18 C17 H17 120.4 . . ? C16 C17 H17 119.4 . . ? C17 C18 C19 119.8(2) . . ? C17 C18 H18 120.5 . . ? C19 C18 H18 119.7 . . ? C18 C19 C20 120.0(2) . . ? C18 C19 H19 119.6 . . ? C20 C19 H19 120.4 . . ? C19 C20 C15 121.9(2) . . ? C19 C20 H20 118.8 . . ? C15 C20 H20 119.4 . . ? C26 C21 C22 116.29(18) . . ? C26 C21 B2 122.66(18) . . ? C22 C21 B2 120.87(17) . . ? C23 C22 C21 122.3(2) . . ? C23 C22 H22 118.6 . . ? C21 C22 H22 119.1 . . ? C24 C23 C22 120.1(2) . . ? C24 C23 H23 119.2 . . ? C22 C23 H23 120.7 . . ? C23 C24 C25 119.5(2) . . ? C23 C24 H24 119.4 . . ? C25 C24 H24 121.1 . . ? C24 C25 C26 120.2(2) . . ? C24 C25 H25 119.0 . . ? C26 C25 H25 120.8 . . ? C25 C26 C21 121.6(2) . . ? C25 C26 H26 119.7 . . ? C21 C26 H26 118.7 . . ? O1 C27 C28 106.35(17) . . ? O1 C27 H27A 109.0 . . ? C28 C27 H27A 111.5 . . ? O1 C27 H27B 109.4 . . ? C28 C27 H27B 111.0 . . ? H27A C27 H27B 109.5 . . ? C27 C28 C29 102.45(18) . . ? C27 C28 H28A 109.2 . . ? C29 C28 H28A 112.6 . . ? C27 C28 H28B 109.6 . . ? C29 C28 H28B 113.3 . . ? H28A C28 H28B 109.5 . . ? C30 C29 C28 101.11(18) . . ? C30 C29 H29A 113.3 . . ? C28 C29 H29A 109.5 . . ? C30 C29 H29B 114.0 . . ? C28 C29 H29B 109.1 . . ? H29A C29 H29B 109.5 . . ? O1 C30 C29 104.93(17) . . ? O1 C30 H30A 108.6 . . ? C29 C30 H30A 111.6 . . ? O1 C30 H30B 109.3 . . ? C29 C30 H30B 112.8 . . ? H30A C30 H30B 109.5 . . ? O2 C31 C32 106.37(18) . . ? O2 C31 H31A 108.9 . . ? C32 C31 H31A 111.7 . . ? O2 C31 H31B 109.3 . . ? C32 C31 H31B 111.1 . . ? H31A C31 H31B 109.5 . . ? C31 C32 C33 104.76(19) . . ? C31 C32 H32A 109.2 . . ? C33 C32 H32A 110.8 . . ? C31 C32 H32B 109.8 . . ? C33 C32 H32B 112.7 . . ? H32A C32 H32B 109.5 . . ? C34 C33 C32 104.35(19) . . ? C34 C33 H33A 112.0 . . ? C32 C33 H33A 110.6 . . ? C34 C33 H33B 111.2 . . ? C32 C33 H33B 109.1 . . ? H33A C33 H33B 109.5 . . ? O2 C34 C33 106.99(17) . . ? O2 C34 H34A 109.7 . . ? C33 C34 H34A 111.0 . . ? O2 C34 H34B 109.1 . . ? C33 C34 H34B 110.5 . . ? H34A C34 H34B 109.5 . . ? O3 C35 C36 106.93(18) . . ? O3 C35 H35A 109.2 . . ? C36 C35 H35A 111.4 . . ? O3 C35 H35B 109.2 . . ? C36 C35 H35B 110.6 . . ? H35A C35 H35B 109.5 . . ? C35 C36 C37 105.54(17) . . ? C35 C36 H36A 109.2 . . ? C37 C36 H36A 110.7 . . ? C35 C36 H36B 110.3 . . ? C37 C36 H36B 111.5 . . ? H36A C36 H36B 109.5 . . ? C38 C37 C36 103.93(18) . . ? C38 C37 H37A 111.8 . . ? C36 C37 H37A 109.9 . . ? C38 C37 H37B 112.5 . . ? C36 C37 H37B 109.1 . . ? H37A C37 H37B 109.5 . . ? O3 C38 C37 105.68(16) . . ? O3 C38 H38A 109.0 . . ? C37 C38 H38A 111.3 . . ? O3 C38 H38B 109.6 . . ? C37 C38 H38B 111.7 . . ? H38A C38 H38B 109.5 . . ? N1 B1 C1 108.63(15) . . ? N1 B1 C15 121.54(17) . . ? C1 B1 C15 129.51(17) . . ? N2 B2 C1 109.73(15) . . ? N2 B2 C21 119.23(16) . . ? C1 B2 C21 131.02(17) . . ? O3 Li1 O1 103.20(16) . . ? O3 Li1 O2 99.48(15) . . ? O1 Li1 O2 99.29(16) . . ? O3 Li1 C1 120.00(17) . . ? O1 Li1 C1 112.59(15) . . ? O2 Li1 C1 119.15(16) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 N1 N2 C9 -58.10(19) . . . . ? B1 N1 N2 C9 140.91(15) . . . . ? C3 N1 N2 B2 166.37(14) . . . . ? B1 N1 N2 B2 5.38(18) . . . . ? N2 N1 C3 C4 -25.3(2) . . . . ? B1 N1 C3 C4 130.5(2) . . . . ? N2 N1 C3 C8 154.09(15) . . . . ? B1 N1 C3 C8 -50.1(3) . . . . ? C8 C3 C4 C5 2.3(3) . . . . ? N1 C3 C4 C5 -178.36(16) . . . . ? C3 C4 C5 C6 -0.8(3) . . . . ? C4 C5 C6 C7 -0.5(3) . . . . ? C5 C6 C7 C8 0.3(3) . . . . ? C6 C7 C8 C3 1.3(3) . . . . ? C4 C3 C8 C7 -2.5(3) . . . . ? N1 C3 C8 C7 178.11(16) . . . . ? N1 N2 C9 C14 147.31(16) . . . . ? B2 N2 C9 C14 -83.7(2) . . . . ? N1 N2 C9 C10 -31.3(2) . . . . ? B2 N2 C9 C10 97.7(2) . . . . ? C14 C9 C10 C11 0.2(3) . . . . ? N2 C9 C10 C11 178.81(19) . . . . ? C9 C10 C11 C12 -0.7(3) . . . . ? C10 C11 C12 C13 1.1(3) . . . . ? C11 C12 C13 C14 -1.0(3) . . . . ? C10 C9 C14 C13 -0.1(3) . . . . ? N2 C9 C14 C13 -178.74(17) . . . . ? C12 C13 C14 C9 0.5(3) . . . . ? C20 C15 C16 C17 0.3(3) . . . . ? B1 C15 C16 C17 175.55(18) . . . . ? C15 C16 C17 C18 0.2(3) . . . . ? C16 C17 C18 C19 -0.3(3) . . . . ? C17 C18 C19 C20 -0.2(3) . . . . ? C18 C19 C20 C15 0.7(3) . . . . ? C16 C15 C20 C19 -0.8(3) . . . . ? B1 C15 C20 C19 -175.93(18) . . . . ? C26 C21 C22 C23 -0.1(3) . . . . ? B2 C21 C22 C23 175.13(18) . . . . ? C21 C22 C23 C24 0.5(3) . . . . ? C22 C23 C24 C25 0.1(3) . . . . ? C23 C24 C25 C26 -0.9(3) . . . . ? C24 C25 C26 C21 1.2(3) . . . . ? C22 C21 C26 C25 -0.7(3) . . . . ? B2 C21 C26 C25 -175.87(18) . . . . ? C30 O1 C27 C28 1.5(2) . . . . ? Li1 O1 C27 C28 -179.30(17) . . . . ? O1 C27 C28 C29 -25.6(2) . . . . ? C27 C28 C29 C30 38.6(2) . . . . ? C27 O1 C30 C29 23.6(2) . . . . ? Li1 O1 C30 C29 -155.57(18) . . . . ? C28 C29 C30 O1 -38.7(2) . . . . ? C34 O2 C31 C32 -12.2(3) . . . . ? Li1 O2 C31 C32 162.48(19) . . . . ? O2 C31 C32 C33 25.4(3) . . . . ? C31 C32 C33 C34 -28.6(3) . . . . ? C31 O2 C34 C33 -6.0(3) . . . . ? Li1 O2 C34 C33 179.8(2) . . . . ? C32 C33 C34 O2 21.6(3) . . . . ? C38 O3 C35 C36 30.0(2) . . . . ? Li1 O3 C35 C36 -156.26(19) . . . . ? O3 C35 C36 C37 -12.9(3) . . . . ? C35 C36 C37 C38 -7.9(3) . . . . ? C35 O3 C38 C37 -35.1(2) . . . . ? Li1 O3 C38 C37 150.95(18) . . . . ? C36 C37 C38 O3 25.9(2) . . . . ? C3 N1 B1 C1 -163.43(17) . . . . ? N2 N1 B1 C1 -6.62(19) . . . . ? C3 N1 B1 C15 10.6(3) . . . . ? N2 N1 B1 C15 167.44(15) . . . . ? B2 C1 B1 N1 5.00(19) . . . . ? C2 C1 B1 N1 -168.70(17) . . . . ? Li1 C1 B1 N1 106.29(15) . . . . ? B2 C1 B1 C15 -168.43(18) . . . . ? C2 C1 B1 C15 17.9(3) . . . . ? Li1 C1 B1 C15 -67.1(2) . . . . ? C20 C15 B1 N1 -48.2(3) . . . . ? C16 C15 B1 N1 136.81(19) . . . . ? C20 C15 B1 C1 124.5(2) . . . . ? C16 C15 B1 C1 -50.5(3) . . . . ? C9 N2 B2 C1 -133.96(16) . . . . ? N1 N2 B2 C1 -2.17(19) . . . . ? C9 N2 B2 C21 47.8(2) . . . . ? N1 N2 B2 C21 179.62(15) . . . . ? B1 C1 B2 N2 -1.75(19) . . . . ? C2 C1 B2 N2 172.12(16) . . . . ? Li1 C1 B2 N2 -100.06(16) . . . . ? B1 C1 B2 C21 176.18(18) . . . . ? C2 C1 B2 C21 -9.9(3) . . . . ? Li1 C1 B2 C21 77.9(2) . . . . ? C26 C21 B2 N2 -127.1(2) . . . . ? C22 C21 B2 N2 58.0(2) . . . . ? C26 C21 B2 C1 55.2(3) . . . . ? C22 C21 B2 C1 -119.8(2) . . . . ? C35 O3 Li1 O1 -93.9(2) . . . . ? C38 O3 Li1 O1 78.7(2) . . . . ? C35 O3 Li1 O2 8.0(3) . . . . ? C38 O3 Li1 O2 -179.36(16) . . . . ? C35 O3 Li1 C1 139.83(19) . . . . ? C38 O3 Li1 C1 -47.6(3) . . . . ? C30 O1 Li1 O3 169.86(16) . . . . ? C27 O1 Li1 O3 -9.2(2) . . . . ? C30 O1 Li1 O2 67.7(2) . . . . ? C27 O1 Li1 O2 -111.29(18) . . . . ? C30 O1 Li1 C1 -59.3(2) . . . . ? C27 O1 Li1 C1 121.66(18) . . . . ? C31 O2 Li1 O3 -83.1(2) . . . . ? C34 O2 Li1 O3 90.5(2) . . . . ? C31 O2 Li1 O1 22.1(2) . . . . ? C34 O2 Li1 O1 -164.36(18) . . . . ? C31 O2 Li1 C1 144.56(18) . . . . ? C34 O2 Li1 C1 -41.9(3) . . . . ? B2 C1 Li1 O3 68.0(2) . . . . ? B1 C1 Li1 O3 -37.8(2) . . . . ? C2 C1 Li1 O3 -166.07(19) . . . . ? B2 C1 Li1 O1 -53.7(2) . . . . ? B1 C1 Li1 O1 -159.56(17) . . . . ? C2 C1 Li1 O1 72.20(18) . . . . ? B2 C1 Li1 O2 -169.31(18) . . . . ? B1 C1 Li1 O2 84.83(19) . . . . ? C2 C1 Li1 O2 -43.40(19) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.368 _refine_diff_density_min -0.378 _refine_diff_density_rms 0.040 # Attachment '3b.cif' data_3b _database_code_depnum_ccdc_archive 'CCDC 678563' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C38 H47 B2 N2 Na O3' _chemical_formula_sum 'C38 H47 B2 N2 Na O3' _chemical_formula_weight 624.39 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' Na Na 0.0362 0.0249 '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 monoclinic _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.154(5) _cell_length_b 14.153(5) _cell_length_c 13.912(7) _cell_angle_alpha 90.00 _cell_angle_beta 100.47(2) _cell_angle_gamma 90.00 _cell_volume 1772.4(15) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6923 _cell_measurement_theta_min 2.98 _cell_measurement_theta_max 27.47 _exptl_crystal_description ? _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.170 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 668 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9804 _exptl_absorpt_correction_T_max 0.9869 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enraf Nonius FR590D, fine-focus sealed tube' _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_device_type 'KappaCCD (Nonius, FR540C)' _diffrn_measurement_method 'phi\omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6923 _diffrn_reflns_av_R_equivalents 0.0471 _diffrn_reflns_av_sigmaI/netI 0.0776 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.98 _diffrn_reflns_theta_max 27.47 _reflns_number_total 4189 _reflns_number_gt 2653 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0630P)^2^+0.4000P] 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 0.032(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.4(6) _refine_ls_number_reflns 4189 _refine_ls_number_parameters 416 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1093 _refine_ls_R_factor_gt 0.0555 _refine_ls_wR_factor_ref 0.1440 _refine_ls_wR_factor_gt 0.1180 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 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 Na1 Na 0.57643(16) 0.44122(13) 0.83221(11) 0.0486(4) Uani 1 1 d . . . O1 O 0.7479(3) 0.3659(3) 0.7524(2) 0.0586(9) Uani 1 1 d . . . O2 O 0.6441(3) 0.4223(2) 1.00042(19) 0.0535(8) Uani 1 1 d . . . O3 O 0.7140(4) 0.5832(3) 0.8446(2) 0.0693(10) Uani 1 1 d . . . N1 N 0.2813(3) 0.4378(2) 0.6253(2) 0.0326(7) Uani 1 1 d . . . N2 N 0.2355(3) 0.5103(2) 0.6859(2) 0.0325(7) Uani 1 1 d . . . C1 C 0.3008(4) 0.3709(3) 0.7852(3) 0.0347(8) Uani 1 1 d . . . C2 C 0.3158(5) 0.2986(3) 0.8674(3) 0.0453(10) Uani 1 1 d . . . H2A H 0.2237 0.2649 0.8627 0.054 Uiso 1 1 d R . . H2B H 0.3379 0.3304 0.9293 0.054 Uiso 1 1 d R . . H2C H 0.3941 0.2550 0.8620 0.054 Uiso 1 1 d R . . C3 C 0.2330(4) 0.4487(2) 0.5233(2) 0.0311(8) Uani 1 1 d . . . C4 C 0.3173(4) 0.4077(3) 0.4604(3) 0.0347(8) Uani 1 1 d . . . H4 H 0.4077 0.3754 0.4874 0.042 Uiso 1 1 d R . . C5 C 0.2722(5) 0.4137(3) 0.3604(3) 0.0409(9) Uani 1 1 d . . . H5 H 0.3294 0.3846 0.3170 0.049 Uiso 1 1 d R . . C6 C 0.1444(5) 0.4622(3) 0.3217(3) 0.0483(11) Uani 1 1 d . . . H6 H 0.1116 0.4653 0.2522 0.058 Uiso 1 1 d R . . C7 C 0.0610(5) 0.5048(3) 0.3832(3) 0.0480(10) Uani 1 1 d . . . H7 H -0.0263 0.5401 0.3559 0.058 Uiso 1 1 d R . . C8 C 0.1046(4) 0.4975(3) 0.4829(3) 0.0389(9) Uani 1 1 d . . . H8 H 0.0451 0.5270 0.5246 0.047 Uiso 1 1 d R . . C9 C 0.2685(4) 0.6042(2) 0.6615(3) 0.0316(8) Uani 1 1 d . . . C10 C 0.1700(5) 0.6753(3) 0.6738(3) 0.0421(10) Uani 1 1 d . . . H10 H 0.0790 0.6599 0.6954 0.051 Uiso 1 1 d R . . C11 C 0.2031(5) 0.7689(3) 0.6550(3) 0.0510(11) Uani 1 1 d . . . H11 H 0.1354 0.8183 0.6645 0.061 Uiso 1 1 d R . . C12 C 0.3315(6) 0.7912(3) 0.6222(3) 0.0540(12) Uani 1 1 d . . . H12 H 0.3552 0.8558 0.6107 0.065 Uiso 1 1 d R . . C13 C 0.4267(5) 0.7202(3) 0.6066(3) 0.0508(11) Uani 1 1 d . . . H13 H 0.5157 0.7344 0.5821 0.061 Uiso 1 1 d R . . C14 C 0.3955(5) 0.6267(3) 0.6256(3) 0.0399(9) Uani 1 1 d . . . H14 H 0.4613 0.5770 0.6138 0.048 Uiso 1 1 d R . . C15 C 0.3299(4) 0.2521(3) 0.6314(3) 0.0351(9) Uani 1 1 d . . . C16 C 0.4512(5) 0.1959(3) 0.6668(3) 0.0506(11) Uani 1 1 d . . . H16 H 0.5230 0.2169 0.7217 0.061 Uiso 1 1 d R . . C17 C 0.4726(6) 0.1082(3) 0.6275(4) 0.0602(13) Uani 1 1 d . . . H17 H 0.5598 0.0721 0.6529 0.072 Uiso 1 1 d R . . C18 C 0.3715(6) 0.0740(3) 0.5506(4) 0.0574(13) Uani 1 1 d . . . H18 H 0.3858 0.0133 0.5230 0.069 Uiso 1 1 d R . . C19 C 0.2453(5) 0.1271(3) 0.5137(3) 0.0505(12) Uani 1 1 d . . . H19 H 0.1727 0.1027 0.4611 0.061 Uiso 1 1 d R . . C20 C 0.2265(5) 0.2152(3) 0.5532(3) 0.0426(10) Uani 1 1 d . . . H20 H 0.1407 0.2519 0.5259 0.051 Uiso 1 1 d R . . C21 C 0.2399(4) 0.5353(3) 0.8790(3) 0.0344(8) Uani 1 1 d . . . C22 C 0.1680(5) 0.5003(3) 0.9504(3) 0.0484(11) Uani 1 1 d . . . H22 H 0.1166 0.4410 0.9404 0.058 Uiso 1 1 d R . . C23 C 0.1667(5) 0.5468(4) 1.0387(3) 0.0650(15) Uani 1 1 d . . . H23 H 0.1133 0.5205 1.0857 0.078 Uiso 1 1 d R . . C24 C 0.2438(6) 0.6316(4) 1.0568(4) 0.0718(16) Uani 1 1 d . . . H24 H 0.2450 0.6644 1.1173 0.086 Uiso 1 1 d R . . C25 C 0.3156(6) 0.6688(4) 0.9874(4) 0.0619(13) Uani 1 1 d . . . H25 H 0.3691 0.7272 0.9999 0.074 Uiso 1 1 d R . . C26 C 0.3129(5) 0.6224(3) 0.8999(3) 0.0486(11) Uani 1 1 d . . . H26 H 0.3640 0.6505 0.8526 0.058 Uiso 1 1 d R . . C27 C 0.7399(6) 0.3622(5) 0.6483(4) 0.0776(17) Uani 1 1 d . . . H27A H 0.6396 0.3495 0.6168 0.093 Uiso 1 1 d R . . H27B H 0.7703 0.4225 0.6270 0.093 Uiso 1 1 d R . . C28 C 0.8500(8) 0.2914(8) 0.6284(5) 0.143(4) Uani 1 1 d . . . H28A H 0.7929 0.2415 0.5929 0.172 Uiso 1 1 d R . . H28B H 0.9177 0.3167 0.5898 0.172 Uiso 1 1 d R . . C29 C 0.9242(5) 0.2549(4) 0.7247(3) 0.0594(12) Uani 1 1 d . . . H29A H 0.8849 0.1950 0.7400 0.071 Uiso 1 1 d R . . H29B H 1.0284 0.2486 0.7241 0.071 Uiso 1 1 d R . . C30 C 0.8918(5) 0.3299(3) 0.7936(3) 0.0514(11) Uani 1 1 d . . . H30A H 0.9637 0.3798 0.7979 0.062 Uiso 1 1 d R . . H30B H 0.8899 0.3056 0.8579 0.062 Uiso 1 1 d R . . C31 C 0.7957(5) 0.4319(5) 1.0493(4) 0.0754(16) Uani 1 1 d . . . H31A H 0.8333 0.3694 1.0654 0.090 Uiso 1 1 d R . . H31B H 0.8537 0.4617 1.0070 0.090 Uiso 1 1 d R . . C32 C 0.7901(7) 0.4879(6) 1.1398(5) 0.108(3) Uani 1 1 d . . . H32A H 0.8445 0.4562 1.1961 0.130 Uiso 1 1 d R . . H32B H 0.8340 0.5487 1.1331 0.130 Uiso 1 1 d R . . C33 C 0.6347(7) 0.4947(6) 1.1495(4) 0.097(2) Uani 1 1 d . . . H33A H 0.6208 0.4784 1.2142 0.116 Uiso 1 1 d R . . H33B H 0.6029 0.5586 1.1353 0.116 Uiso 1 1 d R . . C34 C 0.5549(5) 0.4320(5) 1.0738(3) 0.0706(14) Uani 1 1 d . . . H34A H 0.4593 0.4565 1.0447 0.085 Uiso 1 1 d R . . H34B H 0.5431 0.3710 1.1016 0.085 Uiso 1 1 d R . . C35 C 0.8096(6) 0.6100(4) 0.7786(4) 0.0649(13) Uani 1 1 d . . . H35A H 0.8842 0.5624 0.7782 0.078 Uiso 1 1 d R . . H35B H 0.7505 0.6157 0.7144 0.078 Uiso 1 1 d R . . C36 C 0.8740(8) 0.7042(4) 0.8133(5) 0.091(2) Uani 1 1 d . . . H36A H 0.9752 0.6945 0.8447 0.109 Uiso 1 1 d R . . H36B H 0.8711 0.7464 0.7589 0.109 Uiso 1 1 d R . . C37 C 0.7738(11) 0.7361(4) 0.8810(7) 0.126(3) Uani 1 1 d . . . H37A H 0.8341 0.7661 0.9363 0.152 Uiso 1 1 d R . . H37B H 0.7017 0.7803 0.8486 0.152 Uiso 1 1 d R . . C38 C 0.7141(10) 0.6581(6) 0.9093(6) 0.142(4) Uani 1 1 d . . . H38A H 0.6129 0.6733 0.9124 0.170 Uiso 1 1 d R . . H38B H 0.7653 0.6395 0.9729 0.170 Uiso 1 1 d R . . B1 B 0.3089(5) 0.3502(3) 0.6819(3) 0.0316(9) Uani 1 1 d . . . B2 B 0.2538(4) 0.4723(3) 0.7870(3) 0.0318(9) 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 Na1 0.0391(9) 0.0637(10) 0.0433(9) -0.0061(8) 0.0087(7) -0.0056(8) O1 0.0436(17) 0.084(2) 0.0483(19) -0.0092(17) 0.0085(14) 0.0027(17) O2 0.0477(17) 0.072(2) 0.0395(16) -0.0041(15) 0.0053(13) 0.0000(15) O3 0.067(2) 0.089(2) 0.059(2) -0.0208(19) 0.0321(17) -0.0277(19) N1 0.0424(17) 0.0300(14) 0.0275(15) -0.0021(14) 0.0121(13) 0.0058(14) N2 0.0404(17) 0.0286(15) 0.0306(17) -0.0024(13) 0.0120(14) 0.0047(14) C1 0.036(2) 0.0340(19) 0.033(2) 0.0022(16) 0.0041(16) -0.0011(17) C2 0.063(3) 0.037(2) 0.035(2) 0.0001(18) 0.007(2) 0.000(2) C3 0.0396(19) 0.0275(17) 0.0271(18) 0.0026(16) 0.0079(15) 0.0011(18) C4 0.039(2) 0.0323(18) 0.034(2) -0.0008(16) 0.0096(17) 0.0011(16) C5 0.052(2) 0.043(2) 0.030(2) -0.0052(17) 0.0139(18) -0.0052(19) C6 0.058(3) 0.054(3) 0.031(2) 0.0002(19) 0.002(2) -0.007(2) C7 0.050(2) 0.051(2) 0.039(2) 0.002(2) -0.002(2) 0.006(2) C8 0.041(2) 0.042(2) 0.035(2) -0.0014(18) 0.0095(17) 0.0041(18) C9 0.037(2) 0.0312(18) 0.0270(19) 0.0020(15) 0.0068(16) 0.0014(16) C10 0.050(2) 0.038(2) 0.041(2) 0.0039(18) 0.0161(19) 0.0085(19) C11 0.071(3) 0.033(2) 0.049(3) -0.0012(19) 0.011(2) 0.010(2) C12 0.079(3) 0.038(2) 0.047(3) 0.006(2) 0.015(2) -0.005(2) C13 0.058(3) 0.044(2) 0.055(3) -0.001(2) 0.022(2) -0.015(2) C14 0.044(2) 0.040(2) 0.038(2) -0.0002(18) 0.0138(18) 0.0001(19) C15 0.041(2) 0.0317(18) 0.035(2) -0.0004(16) 0.0125(18) -0.0010(17) C16 0.067(3) 0.040(2) 0.045(3) -0.001(2) 0.011(2) 0.013(2) C17 0.089(4) 0.039(2) 0.056(3) 0.004(2) 0.023(3) 0.025(2) C18 0.097(4) 0.030(2) 0.055(3) -0.003(2) 0.040(3) -0.008(3) C19 0.059(3) 0.047(2) 0.052(3) -0.015(2) 0.027(2) -0.024(2) C20 0.043(2) 0.043(2) 0.045(2) -0.0069(19) 0.0172(19) -0.0072(19) C21 0.0317(19) 0.041(2) 0.030(2) -0.0011(17) 0.0040(16) 0.0020(17) C22 0.041(2) 0.067(3) 0.038(2) -0.008(2) 0.0085(19) -0.008(2) C23 0.049(3) 0.111(5) 0.039(3) -0.018(3) 0.020(2) -0.003(3) C24 0.075(3) 0.092(4) 0.045(3) -0.035(3) 0.000(3) 0.021(3) C25 0.079(4) 0.054(3) 0.049(3) -0.022(2) 0.000(3) 0.001(3) C26 0.061(3) 0.042(2) 0.039(2) -0.0086(19) 0.001(2) -0.005(2) C27 0.064(3) 0.120(5) 0.050(3) 0.010(3) 0.013(3) 0.010(3) C28 0.107(5) 0.265(12) 0.058(4) -0.020(5) 0.012(4) 0.092(7) C29 0.053(3) 0.071(3) 0.055(3) -0.009(2) 0.014(2) -0.005(2) C30 0.049(3) 0.059(3) 0.046(3) -0.002(2) 0.007(2) -0.007(2) C31 0.042(3) 0.104(4) 0.073(3) -0.020(3) -0.010(2) 0.011(3) C32 0.073(4) 0.165(7) 0.076(4) -0.036(4) -0.012(3) -0.011(4) C33 0.105(5) 0.124(6) 0.061(4) -0.032(4) 0.016(3) 0.002(4) C34 0.060(3) 0.098(4) 0.054(3) -0.003(3) 0.012(2) 0.005(3) C35 0.064(3) 0.081(3) 0.058(3) 0.005(3) 0.030(2) 0.001(3) C36 0.122(5) 0.048(3) 0.126(5) 0.002(3) 0.085(4) 0.002(3) C37 0.195(8) 0.063(4) 0.162(7) -0.010(4) 0.137(7) 0.000(5) C38 0.166(8) 0.146(7) 0.146(7) -0.099(6) 0.116(6) -0.104(6) B1 0.031(2) 0.028(2) 0.035(2) -0.0033(18) 0.0051(18) 0.0000(18) B2 0.030(2) 0.038(2) 0.028(2) -0.0043(18) 0.0056(17) -0.0036(18) _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 Na1 O2 2.325(3) . ? Na1 O1 2.338(3) . ? Na1 O3 2.360(4) . ? Na1 C1 2.680(4) . ? Na1 B2 2.939(5) . ? O1 C30 1.432(5) . ? O1 C27 1.438(6) . ? O2 C34 1.426(5) . ? O2 C31 1.436(5) . ? O3 C38 1.391(7) . ? O3 C35 1.430(6) . ? N1 C3 1.415(4) . ? N1 N2 1.438(4) . ? N1 B1 1.466(5) . ? N2 C9 1.418(5) . ? N2 B2 1.486(5) . ? C1 B1 1.482(6) . ? C1 B2 1.499(6) . ? C1 C2 1.522(5) . ? C2 H2A 0.9600 . ? C2 H2B 0.9601 . ? C2 H2C 0.9600 . ? C3 C8 1.391(5) . ? C3 C4 1.395(5) . ? C4 C5 1.380(5) . ? C4 H4 0.9600 . ? C5 C6 1.378(6) . ? C5 H5 0.9600 . ? C6 C7 1.384(6) . ? C6 H6 0.9600 . ? C7 C8 1.376(6) . ? C7 H7 0.9600 . ? C8 H8 0.9601 . ? C9 C10 1.383(5) . ? C9 C14 1.383(5) . ? C10 C11 1.393(6) . ? C10 H10 0.9600 . ? C11 C12 1.373(7) . ? C11 H11 0.9600 . ? C12 C13 1.373(6) . ? C12 H12 0.9600 . ? C13 C14 1.388(6) . ? C13 H13 0.9599 . ? C14 H14 0.9600 . ? C15 C16 1.383(6) . ? C15 C20 1.407(6) . ? C15 B1 1.583(5) . ? C16 C17 1.384(6) . ? C16 H16 0.9600 . ? C17 C18 1.369(7) . ? C17 H17 0.9601 . ? C18 C19 1.396(7) . ? C18 H18 0.9599 . ? C19 C20 1.385(6) . ? C19 H19 0.9600 . ? C20 H20 0.9600 . ? C21 C22 1.380(6) . ? C21 C26 1.407(6) . ? C21 B2 1.584(5) . ? C22 C23 1.394(6) . ? C22 H22 0.9600 . ? C23 C24 1.393(8) . ? C23 H23 0.9600 . ? C24 C25 1.367(8) . ? C24 H24 0.9601 . ? C25 C26 1.379(6) . ? C25 H25 0.9599 . ? C26 H26 0.9601 . ? C27 C28 1.483(9) . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C28 C29 1.481(8) . ? C28 H28A 0.9600 . ? C28 H28B 0.9601 . ? C29 C30 1.496(6) . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C30 H30A 0.9599 . ? C30 H30B 0.9600 . ? C31 C32 1.497(8) . ? C31 H31A 0.9601 . ? C31 H31B 0.9600 . ? C32 C33 1.457(8) . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C33 C34 1.466(8) . ? C33 H33A 0.9600 . ? C33 H33B 0.9599 . ? C34 H34A 0.9600 . ? C34 H34B 0.9600 . ? C35 C36 1.501(8) . ? C35 H35A 0.9600 . ? C35 H35B 0.9601 . ? C36 C37 1.499(8) . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C37 C38 1.322(9) . ? C37 H37A 0.9601 . ? C37 H37B 0.9601 . ? C38 H38A 0.9601 . ? C38 H38B 0.9599 . ? 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 O2 Na1 O1 110.28(13) . . ? O2 Na1 O3 89.03(13) . . ? O1 Na1 O3 91.58(13) . . ? O2 Na1 C1 105.66(12) . . ? O1 Na1 C1 113.48(13) . . ? O3 Na1 C1 143.10(14) . . ? O2 Na1 B2 107.84(12) . . ? O1 Na1 B2 134.57(13) . . ? O3 Na1 B2 112.97(14) . . ? C1 Na1 B2 30.51(12) . . ? C30 O1 C27 105.4(3) . . ? C30 O1 Na1 128.3(3) . . ? C27 O1 Na1 125.4(3) . . ? C34 O2 C31 106.4(3) . . ? C34 O2 Na1 128.9(3) . . ? C31 O2 Na1 121.6(3) . . ? C38 O3 C35 106.5(4) . . ? C38 O3 Na1 129.4(3) . . ? C35 O3 Na1 124.1(3) . . ? C3 N1 N2 116.0(3) . . ? C3 N1 B1 128.5(3) . . ? N2 N1 B1 109.2(3) . . ? C9 N2 N1 115.5(3) . . ? C9 N2 B2 125.0(3) . . ? N1 N2 B2 107.6(3) . . ? B1 C1 B2 105.7(3) . . ? B1 C1 C2 125.6(3) . . ? B2 C1 C2 128.2(3) . . ? B1 C1 Na1 95.7(2) . . ? B2 C1 Na1 84.3(2) . . ? C2 C1 Na1 96.5(2) . . ? C1 C2 H2A 108.9 . . ? C1 C2 H2B 109.6 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.9 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C8 C3 C4 118.4(3) . . ? C8 C3 N1 123.1(3) . . ? C4 C3 N1 118.5(3) . . ? C5 C4 C3 120.6(4) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 119.2 . . ? C6 C5 C4 120.1(4) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 120.6 . . ? C5 C6 C7 120.0(4) . . ? C5 C6 H6 120.3 . . ? C7 C6 H6 119.7 . . ? C8 C7 C6 119.9(4) . . ? C8 C7 H7 120.4 . . ? C6 C7 H7 119.6 . . ? C7 C8 C3 121.0(4) . . ? C7 C8 H8 118.9 . . ? C3 C8 H8 120.1 . . ? C10 C9 C14 119.1(3) . . ? C10 C9 N2 118.7(3) . . ? C14 C9 N2 122.1(3) . . ? C9 C10 C11 120.0(4) . . ? C9 C10 H10 119.7 . . ? C11 C10 H10 120.4 . . ? C12 C11 C10 120.7(4) . . ? C12 C11 H11 119.4 . . ? C10 C11 H11 119.9 . . ? C11 C12 C13 119.4(4) . . ? C11 C12 H12 120.6 . . ? C13 C12 H12 120.1 . . ? C12 C13 C14 120.6(4) . . ? C12 C13 H13 120.4 . . ? C14 C13 H13 119.0 . . ? C9 C14 C13 120.2(4) . . ? C9 C14 H14 119.2 . . ? C13 C14 H14 120.6 . . ? C16 C15 C20 116.4(3) . . ? C16 C15 B1 120.1(4) . . ? C20 C15 B1 123.4(3) . . ? C15 C16 C17 122.5(5) . . ? C15 C16 H16 119.6 . . ? C17 C16 H16 117.8 . . ? C18 C17 C16 120.1(5) . . ? C18 C17 H17 119.9 . . ? C16 C17 H17 120.0 . . ? C17 C18 C19 119.5(4) . . ? C17 C18 H18 120.5 . . ? C19 C18 H18 119.9 . . ? C20 C19 C18 119.6(4) . . ? C20 C19 H19 120.5 . . ? C18 C19 H19 119.9 . . ? C19 C20 C15 121.8(4) . . ? C19 C20 H20 118.8 . . ? C15 C20 H20 119.4 . . ? C22 C21 C26 115.9(4) . . ? C22 C21 B2 119.9(4) . . ? C26 C21 B2 123.8(4) . . ? C21 C22 C23 123.1(4) . . ? C21 C22 H22 119.6 . . ? C23 C22 H22 117.3 . . ? C24 C23 C22 118.8(5) . . ? C24 C23 H23 121.0 . . ? C22 C23 H23 120.3 . . ? C25 C24 C23 119.8(4) . . ? C25 C24 H24 120.2 . . ? C23 C24 H24 120.0 . . ? C24 C25 C26 120.4(5) . . ? C24 C25 H25 119.9 . . ? C26 C25 H25 119.7 . . ? C25 C26 C21 122.1(4) . . ? C25 C26 H26 118.3 . . ? C21 C26 H26 119.6 . . ? O1 C27 C28 107.5(5) . . ? O1 C27 H27A 109.6 . . ? C28 C27 H27A 114.5 . . ? O1 C27 H27B 108.3 . . ? C28 C27 H27B 107.4 . . ? H27A C27 H27B 109.5 . . ? C29 C28 C27 106.4(5) . . ? C29 C28 H28A 109.0 . . ? C27 C28 H28A 105.5 . . ? C29 C28 H28B 113.6 . . ? C27 C28 H28B 112.4 . . ? H28A C28 H28B 109.5 . . ? C28 C29 C30 102.7(5) . . ? C28 C29 H29A 112.3 . . ? C30 C29 H29A 111.0 . . ? C28 C29 H29B 108.5 . . ? C30 C29 H29B 112.6 . . ? H29A C29 H29B 109.5 . . ? O1 C30 C29 105.7(4) . . ? O1 C30 H30A 109.5 . . ? C29 C30 H30A 110.3 . . ? O1 C30 H30B 109.3 . . ? C29 C30 H30B 112.5 . . ? H30A C30 H30B 109.5 . . ? O2 C31 C32 105.7(4) . . ? O2 C31 H31A 107.4 . . ? C32 C31 H31A 110.9 . . ? O2 C31 H31B 110.2 . . ? C32 C31 H31B 113.0 . . ? H31A C31 H31B 109.5 . . ? C33 C32 C31 107.2(5) . . ? C33 C32 H32A 109.0 . . ? C31 C32 H32A 110.3 . . ? C33 C32 H32B 112.5 . . ? C31 C32 H32B 108.3 . . ? H32A C32 H32B 109.5 . . ? C32 C33 C34 105.2(5) . . ? C32 C33 H33A 111.6 . . ? C34 C33 H33A 113.2 . . ? C32 C33 H33B 107.9 . . ? C34 C33 H33B 109.2 . . ? H33A C33 H33B 109.5 . . ? O2 C34 C33 107.3(4) . . ? O2 C34 H34A 109.2 . . ? C33 C34 H34A 112.5 . . ? O2 C34 H34B 108.9 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? O3 C35 C36 106.3(4) . . ? O3 C35 H35A 109.7 . . ? C36 C35 H35A 112.8 . . ? O3 C35 H35B 108.1 . . ? C36 C35 H35B 110.3 . . ? H35A C35 H35B 109.5 . . ? C37 C36 C35 102.7(5) . . ? C37 C36 H36A 114.0 . . ? C35 C36 H36A 108.0 . . ? C37 C36 H36B 112.1 . . ? C35 C36 H36B 110.2 . . ? H36A C36 H36B 109.5 . . ? C38 C37 C36 105.6(5) . . ? C38 C37 H37A 109.8 . . ? C36 C37 H37A 107.9 . . ? C38 C37 H37B 113.4 . . ? C36 C37 H37B 110.4 . . ? H37A C37 H37B 109.5 . . ? C37 C38 O3 113.3(6) . . ? C37 C38 H38A 106.4 . . ? O3 C38 H38A 108.2 . . ? C37 C38 H38B 110.1 . . ? O3 C38 H38B 109.3 . . ? H38A C38 H38B 109.5 . . ? N1 B1 C1 108.7(3) . . ? N1 B1 C15 121.8(3) . . ? C1 B1 C15 129.4(3) . . ? N2 B2 C1 108.3(3) . . ? N2 B2 C21 123.3(3) . . ? C1 B2 C21 128.1(4) . . ? N2 B2 Na1 101.1(2) . . ? C1 B2 Na1 65.2(2) . . ? C21 B2 Na1 97.8(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 Na1 O1 C30 -13.0(4) . . . . ? O3 Na1 O1 C30 76.5(4) . . . . ? C1 Na1 O1 C30 -131.3(3) . . . . ? B2 Na1 O1 C30 -158.4(3) . . . . ? O2 Na1 O1 C27 179.3(4) . . . . ? O3 Na1 O1 C27 -91.2(4) . . . . ? C1 Na1 O1 C27 60.9(4) . . . . ? B2 Na1 O1 C27 33.9(5) . . . . ? O1 Na1 O2 C34 -160.4(4) . . . . ? O3 Na1 O2 C34 108.3(4) . . . . ? C1 Na1 O2 C34 -37.4(4) . . . . ? B2 Na1 O2 C34 -5.6(4) . . . . ? O1 Na1 O2 C31 42.6(4) . . . . ? O3 Na1 O2 C31 -48.7(4) . . . . ? C1 Na1 O2 C31 165.6(4) . . . . ? B2 Na1 O2 C31 -162.6(4) . . . . ? O2 Na1 O3 C38 -47.6(7) . . . . ? O1 Na1 O3 C38 -157.8(7) . . . . ? C1 Na1 O3 C38 67.7(7) . . . . ? B2 Na1 O3 C38 61.4(7) . . . . ? O2 Na1 O3 C35 136.8(4) . . . . ? O1 Na1 O3 C35 26.5(4) . . . . ? C1 Na1 O3 C35 -107.9(4) . . . . ? B2 Na1 O3 C35 -114.2(4) . . . . ? C3 N1 N2 C9 -52.9(4) . . . . ? B1 N1 N2 C9 152.6(3) . . . . ? C3 N1 N2 B2 162.3(3) . . . . ? B1 N1 N2 B2 7.7(4) . . . . ? O2 Na1 C1 B1 -156.1(2) . . . . ? O1 Na1 C1 B1 -35.1(3) . . . . ? O3 Na1 C1 B1 93.8(3) . . . . ? B2 Na1 C1 B1 105.3(3) . . . . ? O2 Na1 C1 B2 98.7(2) . . . . ? O1 Na1 C1 B2 -140.4(2) . . . . ? O3 Na1 C1 B2 -11.4(3) . . . . ? O2 Na1 C1 C2 -29.2(3) . . . . ? O1 Na1 C1 C2 91.8(2) . . . . ? O3 Na1 C1 C2 -139.3(2) . . . . ? B2 Na1 C1 C2 -127.9(3) . . . . ? N2 N1 C3 C8 -26.8(5) . . . . ? B1 N1 C3 C8 122.0(4) . . . . ? N2 N1 C3 C4 153.9(3) . . . . ? B1 N1 C3 C4 -57.3(5) . . . . ? C8 C3 C4 C5 -1.5(5) . . . . ? N1 C3 C4 C5 177.9(3) . . . . ? C3 C4 C5 C6 1.4(6) . . . . ? C4 C5 C6 C7 -0.1(6) . . . . ? C5 C6 C7 C8 -1.0(6) . . . . ? C6 C7 C8 C3 0.8(6) . . . . ? C4 C3 C8 C7 0.4(6) . . . . ? N1 C3 C8 C7 -178.9(4) . . . . ? N1 N2 C9 C10 145.3(3) . . . . ? B2 N2 C9 C10 -76.7(5) . . . . ? N1 N2 C9 C14 -34.4(5) . . . . ? B2 N2 C9 C14 103.6(4) . . . . ? C14 C9 C10 C11 -3.4(6) . . . . ? N2 C9 C10 C11 176.8(4) . . . . ? C9 C10 C11 C12 1.5(7) . . . . ? C10 C11 C12 C13 0.9(7) . . . . ? C11 C12 C13 C14 -1.3(7) . . . . ? C10 C9 C14 C13 3.0(6) . . . . ? N2 C9 C14 C13 -177.2(4) . . . . ? C12 C13 C14 C9 -0.7(7) . . . . ? C20 C15 C16 C17 0.8(6) . . . . ? B1 C15 C16 C17 177.9(4) . . . . ? C15 C16 C17 C18 0.0(7) . . . . ? C16 C17 C18 C19 -1.4(7) . . . . ? C17 C18 C19 C20 2.1(6) . . . . ? C18 C19 C20 C15 -1.4(6) . . . . ? C16 C15 C20 C19 0.0(5) . . . . ? B1 C15 C20 C19 -177.1(4) . . . . ? C26 C21 C22 C23 -0.3(6) . . . . ? B2 C21 C22 C23 172.1(4) . . . . ? C21 C22 C23 C24 -1.3(7) . . . . ? C22 C23 C24 C25 1.6(7) . . . . ? C23 C24 C25 C26 -0.4(8) . . . . ? C24 C25 C26 C21 -1.3(7) . . . . ? C22 C21 C26 C25 1.6(6) . . . . ? B2 C21 C26 C25 -170.5(4) . . . . ? C30 O1 C27 C28 22.0(7) . . . . ? Na1 O1 C27 C28 -168.0(5) . . . . ? O1 C27 C28 C29 -0.9(9) . . . . ? C27 C28 C29 C30 -19.4(8) . . . . ? C27 O1 C30 C29 -34.6(5) . . . . ? Na1 O1 C30 C29 155.7(3) . . . . ? C28 C29 C30 O1 33.4(6) . . . . ? C34 O2 C31 C32 -24.4(7) . . . . ? Na1 O2 C31 C32 137.1(5) . . . . ? O2 C31 C32 C33 9.9(8) . . . . ? C31 C32 C33 C34 7.9(8) . . . . ? C31 O2 C34 C33 30.1(6) . . . . ? Na1 O2 C34 C33 -129.6(4) . . . . ? C32 C33 C34 O2 -23.3(7) . . . . ? C38 O3 C35 C36 3.5(7) . . . . ? Na1 O3 C35 C36 180.0(4) . . . . ? O3 C35 C36 C37 -15.8(7) . . . . ? C35 C36 C37 C38 23.2(10) . . . . ? C36 C37 C38 O3 -23.0(12) . . . . ? C35 O3 C38 C37 12.7(11) . . . . ? Na1 O3 C38 C37 -163.6(6) . . . . ? C3 N1 B1 C1 -158.5(3) . . . . ? N2 N1 B1 C1 -8.0(4) . . . . ? C3 N1 B1 C15 17.2(6) . . . . ? N2 N1 B1 C15 167.7(3) . . . . ? B2 C1 B1 N1 5.0(4) . . . . ? C2 C1 B1 N1 177.0(3) . . . . ? Na1 C1 B1 N1 -80.7(3) . . . . ? B2 C1 B1 C15 -170.3(4) . . . . ? C2 C1 B1 C15 1.8(6) . . . . ? Na1 C1 B1 C15 104.0(4) . . . . ? C16 C15 B1 N1 129.0(4) . . . . ? C20 C15 B1 N1 -54.0(5) . . . . ? C16 C15 B1 C1 -56.3(6) . . . . ? C20 C15 B1 C1 120.7(5) . . . . ? C9 N2 B2 C1 -145.2(3) . . . . ? N1 N2 B2 C1 -4.6(4) . . . . ? C9 N2 B2 C21 29.3(5) . . . . ? N1 N2 B2 C21 169.9(3) . . . . ? C9 N2 B2 Na1 -77.9(3) . . . . ? N1 N2 B2 Na1 62.7(3) . . . . ? B1 C1 B2 N2 -0.3(4) . . . . ? C2 C1 B2 N2 -172.1(4) . . . . ? Na1 C1 B2 N2 94.0(3) . . . . ? B1 C1 B2 C21 -174.4(4) . . . . ? C2 C1 B2 C21 13.8(6) . . . . ? Na1 C1 B2 C21 -80.1(4) . . . . ? B1 C1 B2 Na1 -94.3(3) . . . . ? C2 C1 B2 Na1 93.9(4) . . . . ? C22 C21 B2 N2 139.5(4) . . . . ? C26 C21 B2 N2 -48.7(6) . . . . ? C22 C21 B2 C1 -47.2(6) . . . . ? C26 C21 B2 C1 124.7(4) . . . . ? C22 C21 B2 Na1 -111.6(3) . . . . ? C26 C21 B2 Na1 60.2(4) . . . . ? O2 Na1 B2 N2 164.1(2) . . . . ? O1 Na1 B2 N2 -49.9(3) . . . . ? O3 Na1 B2 N2 67.4(2) . . . . ? C1 Na1 B2 N2 -105.2(3) . . . . ? O2 Na1 B2 C1 -90.7(2) . . . . ? O1 Na1 B2 C1 55.2(3) . . . . ? O3 Na1 B2 C1 172.6(2) . . . . ? O2 Na1 B2 C21 37.9(3) . . . . ? O1 Na1 B2 C21 -176.2(2) . . . . ? O3 Na1 B2 C21 -58.9(2) . . . . ? C1 Na1 B2 C21 128.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.269 _refine_diff_density_min -0.283 _refine_diff_density_rms 0.043 # Attachment '3c.cif' data_3c _database_code_depnum_ccdc_archive 'CCDC 678564' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H31 B2 K N2 O' _chemical_formula_sum 'C30 H31 B2 K N2 O' _chemical_formula_weight 496.29 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' K K 0.2009 0.2494 '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' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.393(2) _cell_length_b 9.782(2) _cell_length_c 24.168(5) _cell_angle_alpha 90.00 _cell_angle_beta 99.73(3) _cell_angle_gamma 90.00 _cell_volume 2654.8(9) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 8217 _cell_measurement_theta_min 3.30 _cell_measurement_theta_max 25.02 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.242 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1048 _exptl_absorpt_coefficient_mu 0.226 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.8764 _exptl_absorpt_correction_T_max 0.9394 _exptl_absorpt_process_details 'SADABS (SHELXTL-NT v5.1, Bruker)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enraf Nonius FR590D, fine-focus sealed tube' _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_device_type 'KappaCCD (Nonius, FR540C)' _diffrn_measurement_method 'phi\omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8217 _diffrn_reflns_av_R_equivalents 0.0356 _diffrn_reflns_av_sigmaI/netI 0.0450 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 3.30 _diffrn_reflns_theta_max 25.02 _reflns_number_total 4623 _reflns_number_gt 3556 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND (Brandenburg & Berndt, 1999)' _computing_publication_material 'WinGX v1.70-01 (L. J. Farrugia)' _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^)+(0.0576P)^2^+1.9284P] 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 4623 _refine_ls_number_parameters 325 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0672 _refine_ls_R_factor_gt 0.0479 _refine_ls_wR_factor_ref 0.1323 _refine_ls_wR_factor_gt 0.1205 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _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 K1 K 0.55460(5) 0.44226(6) 0.80316(2) 0.03746(18) Uani 1 1 d . . . O1 O 0.37358(16) 0.5219(2) 0.85086(8) 0.0520(5) Uani 1 1 d . . . N1 N 0.76961(15) 0.15684(19) 0.86521(7) 0.0270(4) Uani 1 1 d . . . N2 N 0.81797(15) 0.18405(19) 0.81486(7) 0.0263(4) Uani 1 1 d . . . B1 B 0.6407(2) 0.1416(3) 0.85087(11) 0.0272(6) Uani 1 1 d . . . B2 B 0.7179(2) 0.1676(3) 0.76668(11) 0.0268(5) Uani 1 1 d . . . C1 C 0.60580(18) 0.1427(2) 0.78822(9) 0.0280(5) Uani 1 1 d . . . C2 C 0.4811(2) 0.1224(3) 0.75480(10) 0.0373(6) Uani 1 1 d . . . H2A H 0.4247 0.1078 0.7807 0.056 Uiso 1 1 calc R . . H2B H 0.4807 0.0425 0.7303 0.056 Uiso 1 1 calc R . . H2C H 0.4577 0.2037 0.7319 0.056 Uiso 1 1 calc R . . C3 C 0.55508(18) 0.1446(2) 0.89603(9) 0.0285(5) Uani 1 1 d . . . C4 C 0.45974(19) 0.0530(3) 0.89182(10) 0.0344(5) Uani 1 1 d . . . H4 H 0.4504 -0.0135 0.8628 0.041 Uiso 1 1 calc R . . C5 C 0.3785(2) 0.0560(3) 0.92842(11) 0.0430(6) Uani 1 1 d . . . H5 H 0.3165 -0.0100 0.9252 0.052 Uiso 1 1 calc R . . C6 C 0.3878(2) 0.1548(3) 0.96964(11) 0.0471(7) Uani 1 1 d . . . H6 H 0.3316 0.1581 0.9945 0.056 Uiso 1 1 calc R . . C7 C 0.4789(2) 0.2486(3) 0.97452(11) 0.0454(7) Uani 1 1 d . . . H7 H 0.4850 0.3173 1.0026 0.054 Uiso 1 1 calc R . . C8 C 0.5621(2) 0.2435(3) 0.93867(10) 0.0361(6) Uani 1 1 d . . . H8 H 0.6251 0.3083 0.9430 0.043 Uiso 1 1 calc R . . C9 C 0.84430(18) 0.1737(2) 0.91721(9) 0.0261(5) Uani 1 1 d . . . C10 C 0.8233(2) 0.0961(2) 0.96292(10) 0.0317(5) Uani 1 1 d . . . H10 H 0.7604 0.0312 0.9580 0.038 Uiso 1 1 calc R . . C11 C 0.8925(2) 0.1119(3) 1.01523(10) 0.0368(6) Uani 1 1 d . . . H11 H 0.8760 0.0588 1.0459 0.044 Uiso 1 1 calc R . . C12 C 0.9855(2) 0.2041(3) 1.02330(10) 0.0372(6) Uani 1 1 d . . . H12 H 1.0322 0.2160 1.0594 0.045 Uiso 1 1 calc R . . C13 C 1.0097(2) 0.2790(3) 0.97791(10) 0.0362(6) Uani 1 1 d . . . H13 H 1.0741 0.3420 0.9829 0.043 Uiso 1 1 calc R . . C14 C 0.94114(19) 0.2631(2) 0.92539(9) 0.0306(5) Uani 1 1 d . . . H14 H 0.9602 0.3136 0.8945 0.037 Uiso 1 1 calc R . . C15 C 0.92966(18) 0.1194(2) 0.81335(9) 0.0261(5) Uani 1 1 d . . . C16 C 0.9561(2) -0.0107(3) 0.83579(9) 0.0336(5) Uani 1 1 d . . . H16 H 0.8994 -0.0578 0.8533 0.040 Uiso 1 1 calc R . . C17 C 1.0646(2) -0.0715(3) 0.83265(10) 0.0427(6) Uani 1 1 d . . . H17 H 1.0817 -0.1600 0.8482 0.051 Uiso 1 1 calc R . . C18 C 1.1479(2) -0.0051(3) 0.80724(11) 0.0463(7) Uani 1 1 d . . . H18 H 1.2219 -0.0476 0.8050 0.056 Uiso 1 1 calc R . . C19 C 1.1231(2) 0.1240(3) 0.78510(11) 0.0441(7) Uani 1 1 d . . . H19 H 1.1800 0.1699 0.7673 0.053 Uiso 1 1 calc R . . C20 C 1.0151(2) 0.1870(3) 0.78877(10) 0.0346(6) Uani 1 1 d . . . H20 H 0.9997 0.2768 0.7744 0.042 Uiso 1 1 calc R . . C21 C 0.74223(18) 0.1690(2) 0.70403(9) 0.0268(5) Uani 1 1 d . . . C22 C 0.80770(19) 0.2700(2) 0.68139(10) 0.0310(5) Uani 1 1 d . . . H22 H 0.8385 0.3450 0.7043 0.037 Uiso 1 1 calc R . . C23 C 0.8289(2) 0.2637(3) 0.62658(10) 0.0371(6) Uani 1 1 d . . . H23 H 0.8738 0.3336 0.6126 0.045 Uiso 1 1 calc R . . C24 C 0.7849(2) 0.1561(3) 0.59225(10) 0.0381(6) Uani 1 1 d . . . H24 H 0.8011 0.1505 0.5550 0.046 Uiso 1 1 calc R . . C25 C 0.7174(2) 0.0568(3) 0.61233(10) 0.0378(6) Uani 1 1 d . . . H25 H 0.6855 -0.0164 0.5887 0.045 Uiso 1 1 calc R . . C26 C 0.6960(2) 0.0637(2) 0.66730(10) 0.0321(5) Uani 1 1 d . . . H26 H 0.6484 -0.0050 0.6803 0.039 Uiso 1 1 calc R . . C27 C 0.2846(3) 0.4207(3) 0.84897(14) 0.0604(8) Uani 1 1 d . . . H27A H 0.3216 0.3303 0.8585 0.072 Uiso 1 1 calc R . . H27B H 0.2370 0.4155 0.8108 0.072 Uiso 1 1 calc R . . C28 C 0.2074(3) 0.4586(4) 0.89009(17) 0.0788(11) Uani 1 1 d . . . H28A H 0.1999 0.3817 0.9159 0.095 Uiso 1 1 calc R . . H28B H 0.1269 0.4851 0.8708 0.095 Uiso 1 1 calc R . . C29 C 0.2692(4) 0.5765(5) 0.92105(18) 0.0944(14) Uani 1 1 d . . . H29A H 0.3240 0.5460 0.9550 0.113 Uiso 1 1 calc R . . H29B H 0.2114 0.6425 0.9321 0.113 Uiso 1 1 calc R . . C30 C 0.3368(3) 0.6380(3) 0.87840(17) 0.0730(10) Uani 1 1 d . . . H30A H 0.2847 0.6979 0.8517 0.088 Uiso 1 1 calc R . . H30B H 0.4061 0.6916 0.8970 0.088 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 K1 0.0379(3) 0.0362(3) 0.0385(3) 0.0019(2) 0.0071(2) 0.0020(2) O1 0.0478(11) 0.0534(12) 0.0598(12) -0.0016(10) 0.0237(9) -0.0032(9) N1 0.0236(9) 0.0344(11) 0.0244(9) 0.0015(8) 0.0085(7) -0.0013(8) N2 0.0243(9) 0.0319(10) 0.0248(9) 0.0012(8) 0.0098(7) -0.0014(8) B1 0.0258(13) 0.0249(13) 0.0320(14) 0.0023(11) 0.0078(11) 0.0005(10) B2 0.0286(13) 0.0230(13) 0.0288(13) 0.0014(11) 0.0049(10) 0.0016(11) C1 0.0234(11) 0.0293(12) 0.0309(12) 0.0011(10) 0.0032(9) 0.0020(9) C2 0.0278(12) 0.0470(15) 0.0359(13) 0.0006(12) 0.0020(10) -0.0010(11) C3 0.0223(11) 0.0336(13) 0.0297(12) 0.0055(10) 0.0049(9) 0.0044(10) C4 0.0277(12) 0.0397(14) 0.0364(13) -0.0001(11) 0.0071(10) -0.0018(11) C5 0.0324(13) 0.0526(17) 0.0475(16) 0.0021(13) 0.0165(12) -0.0084(12) C6 0.0366(14) 0.0674(19) 0.0427(15) 0.0020(14) 0.0224(12) 0.0012(14) C7 0.0425(14) 0.0583(18) 0.0382(14) -0.0104(13) 0.0150(12) 0.0017(13) C8 0.0296(12) 0.0420(15) 0.0378(14) -0.0026(11) 0.0088(10) -0.0018(11) C9 0.0229(11) 0.0302(12) 0.0260(11) -0.0001(10) 0.0068(9) 0.0040(10) C10 0.0269(11) 0.0379(14) 0.0305(12) 0.0035(10) 0.0059(10) -0.0014(10) C11 0.0338(13) 0.0496(15) 0.0277(12) 0.0067(11) 0.0071(10) 0.0027(12) C12 0.0329(13) 0.0513(16) 0.0261(12) -0.0021(11) 0.0012(10) 0.0021(12) C13 0.0308(12) 0.0458(15) 0.0319(13) -0.0055(11) 0.0050(10) -0.0077(11) C14 0.0295(12) 0.0345(13) 0.0290(12) 0.0011(10) 0.0083(10) -0.0014(10) C15 0.0219(11) 0.0320(13) 0.0242(11) -0.0038(10) 0.0029(9) -0.0033(9) C16 0.0337(12) 0.0405(14) 0.0264(12) -0.0020(10) 0.0044(10) 0.0022(11) C17 0.0425(14) 0.0517(17) 0.0314(13) -0.0033(12) -0.0010(11) 0.0164(13) C18 0.0282(13) 0.071(2) 0.0379(14) -0.0156(14) 0.0001(11) 0.0128(13) C19 0.0249(12) 0.0666(19) 0.0427(15) -0.0168(14) 0.0113(11) -0.0123(13) C20 0.0304(12) 0.0412(14) 0.0332(13) -0.0067(11) 0.0083(10) -0.0071(11) C21 0.0228(11) 0.0282(12) 0.0293(12) 0.0030(10) 0.0045(9) 0.0045(9) C22 0.0306(12) 0.0285(13) 0.0335(13) 0.0002(10) 0.0046(10) -0.0010(10) C23 0.0354(13) 0.0420(15) 0.0360(13) 0.0076(11) 0.0116(11) -0.0043(11) C24 0.0376(13) 0.0510(16) 0.0272(12) 0.0030(12) 0.0099(10) -0.0002(12) C25 0.0421(14) 0.0400(14) 0.0307(13) -0.0059(11) 0.0041(11) -0.0073(12) C26 0.0311(12) 0.0353(13) 0.0302(12) 0.0031(10) 0.0062(10) -0.0041(10) C27 0.0544(18) 0.059(2) 0.066(2) 0.0006(16) 0.0065(16) -0.0117(16) C28 0.0528(19) 0.102(3) 0.085(3) 0.024(2) 0.0235(19) -0.001(2) C29 0.075(2) 0.136(4) 0.082(3) -0.041(3) 0.041(2) 0.000(3) C30 0.076(2) 0.051(2) 0.095(3) -0.0098(19) 0.021(2) -0.0006(18) _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 K1 O1 2.6443(19) . ? K1 C1 3.021(2) . ? K1 C26 3.052(2) 2_656 ? K1 C19 3.217(3) 2_656 ? K1 C25 3.222(3) 2_656 ? K1 C21 3.232(2) 2_656 ? K1 B1 3.249(3) . ? K1 C18 3.260(3) 2_656 ? K1 C20 3.272(2) 2_656 ? K1 C17 3.336(3) 2_656 ? K1 C15 3.337(2) 2_656 ? K1 C16 3.371(2) 2_656 ? O1 C27 1.411(3) . ? O1 C30 1.416(4) . ? N1 C9 1.404(3) . ? N1 N2 1.443(2) . ? N1 B1 1.458(3) . ? N2 C15 1.427(3) . ? N2 B2 1.494(3) . ? B1 C1 1.499(3) . ? B1 C3 1.583(3) . ? B2 C1 1.479(3) . ? B2 C21 1.585(3) . ? C1 C2 1.524(3) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 C4 1.398(3) . ? C3 C8 1.406(3) . ? C4 C5 1.385(3) . ? C4 H4 0.9500 . ? C5 C6 1.380(4) . ? C5 H5 0.9500 . ? C6 C7 1.375(4) . ? C6 H6 0.9500 . ? C7 C8 1.389(3) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 C10 1.394(3) . ? C9 C14 1.395(3) . ? C10 C11 1.381(3) . ? C10 H10 0.9500 . ? C11 C12 1.380(3) . ? C11 H11 0.9500 . ? C12 C13 1.385(3) . ? C12 H12 0.9500 . ? C13 C14 1.382(3) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C20 1.391(3) . ? C15 C16 1.397(3) . ? C15 K1 3.337(2) 2_646 ? C16 C17 1.385(3) . ? C16 K1 3.371(2) 2_646 ? C16 H16 0.9500 . ? C17 C18 1.378(4) . ? C17 K1 3.336(3) 2_646 ? C17 H17 0.9500 . ? C18 C19 1.381(4) . ? C18 K1 3.260(3) 2_646 ? C18 H18 0.9500 . ? C19 C20 1.392(3) . ? C19 K1 3.217(3) 2_646 ? C19 H19 0.9500 . ? C20 K1 3.272(2) 2_646 ? C20 H20 0.9500 . ? C21 C26 1.403(3) . ? C21 C22 1.404(3) . ? C21 K1 3.232(2) 2_646 ? C22 C23 1.387(3) . ? C22 H22 0.9500 . ? C23 C24 1.381(4) . ? C23 H23 0.9500 . ? C24 C25 1.377(3) . ? C24 H24 0.9500 . ? C25 C26 1.392(3) . ? C25 K1 3.222(3) 2_646 ? C25 H25 0.9500 . ? C26 K1 3.052(2) 2_646 ? C26 H26 0.9500 . ? C27 C28 1.482(5) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 C29 1.486(6) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 C30 1.512(5) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 K1 C1 121.21(6) . . ? O1 K1 C26 123.19(7) . 2_656 ? C1 K1 C26 102.40(6) . 2_656 ? O1 K1 C19 71.13(6) . 2_656 ? C1 K1 C19 124.69(7) . 2_656 ? C26 K1 C19 113.38(7) 2_656 2_656 ? O1 K1 C25 103.05(7) . 2_656 ? O1 K1 C21 116.10(6) . 2_656 ? O1 K1 B1 108.84(6) . . ? C1 K1 B1 27.35(6) . . ? C26 K1 B1 93.21(7) 2_656 . ? C19 K1 B1 148.63(8) 2_656 . ? C25 K1 B1 85.81(7) 2_656 . ? C21 K1 B1 117.65(6) 2_656 . ? O1 K1 C18 79.27(7) . 2_656 ? C1 K1 C18 100.35(7) . 2_656 ? B1 K1 C18 124.26(8) . 2_656 ? O1 K1 C20 87.87(6) . 2_656 ? C1 K1 C20 131.16(7) . 2_656 ? B1 K1 C20 158.03(7) . 2_656 ? O1 K1 C17 102.89(7) . 2_656 ? C1 K1 C17 84.14(7) . 2_656 ? B1 K1 C17 111.15(7) . 2_656 ? O1 K1 C15 111.84(6) . 2_656 ? C1 K1 C15 111.34(6) . 2_656 ? B1 K1 C15 135.51(6) . 2_656 ? B1 K1 C16 115.78(7) . 2_656 ? C27 O1 C30 108.1(2) . . ? C27 O1 K1 112.83(17) . . ? C30 O1 K1 139.11(18) . . ? C9 N1 N2 118.25(16) . . ? C9 N1 B1 131.20(18) . . ? N2 N1 B1 109.33(17) . . ? C15 N2 N1 114.15(17) . . ? C15 N2 B2 119.92(17) . . ? N1 N2 B2 106.72(16) . . ? N1 B1 C1 108.92(19) . . ? N1 B1 C3 123.2(2) . . ? C1 B1 C3 127.4(2) . . ? N1 B1 K1 102.92(14) . . ? C1 B1 K1 67.83(13) . . ? C3 B1 K1 92.52(13) . . ? C1 B2 N2 109.51(19) . . ? C1 B2 C21 129.7(2) . . ? N2 B2 C21 120.68(19) . . ? C1 B2 K1 60.35(12) . . ? N2 B2 K1 95.16(13) . . ? C21 B2 K1 115.13(14) . . ? B2 C1 B1 105.01(19) . . ? B2 C1 C2 128.2(2) . . ? B1 C1 C2 126.8(2) . . ? B2 C1 K1 94.47(14) . . ? B1 C1 K1 84.82(14) . . ? C2 C1 K1 90.48(14) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C4 C3 C8 116.2(2) . . ? C4 C3 B1 120.0(2) . . ? C8 C3 B1 123.5(2) . . ? C5 C4 C3 122.4(2) . . ? C5 C4 H4 118.8 . . ? C3 C4 H4 118.8 . . ? C6 C5 C4 119.9(2) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C7 C6 C5 119.6(2) . . ? C7 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? C6 C7 C8 120.5(2) . . ? C6 C7 H7 119.7 . . ? C8 C7 H7 119.7 . . ? C7 C8 C3 121.4(2) . . ? C7 C8 H8 119.3 . . ? C3 C8 H8 119.3 . . ? C10 C9 C14 117.8(2) . . ? C10 C9 N1 119.1(2) . . ? C14 C9 N1 123.09(19) . . ? C11 C10 C9 121.1(2) . . ? C11 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? C12 C11 C10 120.6(2) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C11 C12 C13 119.0(2) . . ? C11 C12 H12 120.5 . . ? C13 C12 H12 120.5 . . ? C14 C13 C12 120.7(2) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C13 C14 C9 120.7(2) . . ? C13 C14 H14 119.6 . . ? C9 C14 H14 119.6 . . ? C20 C15 C16 118.6(2) . . ? C20 C15 N2 119.5(2) . . ? C16 C15 N2 121.93(19) . . ? C17 C16 C15 120.4(2) . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? K1 C16 H16 117.7 2_646 . ? C18 C17 C16 120.7(3) . . ? C18 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? K1 C17 H17 116.6 2_646 . ? C17 C18 C19 119.5(2) . . ? C17 C18 H18 120.3 . . ? C19 C18 H18 120.3 . . ? K1 C18 H18 113.3 2_646 . ? C18 C19 C20 120.4(2) . . ? C18 C19 H19 119.8 . . ? C20 C19 H19 119.8 . . ? K1 C19 H19 111.2 2_646 . ? C15 C20 C19 120.4(3) . . ? C15 C20 H20 119.8 . . ? C19 C20 H20 119.8 . . ? K1 C20 H20 114.8 2_646 . ? C26 C21 C22 115.9(2) . . ? C26 C21 B2 119.4(2) . . ? C22 C21 B2 124.7(2) . . ? C23 C22 C21 122.0(2) . . ? C23 C22 H22 119.0 . . ? C21 C22 H22 119.0 . . ? C24 C23 C22 120.2(2) . . ? C24 C23 H23 119.9 . . ? C22 C23 H23 119.9 . . ? C25 C24 C23 119.6(2) . . ? C25 C24 H24 120.2 . . ? C23 C24 H24 120.2 . . ? C24 C25 C26 120.0(2) . . ? C24 C25 H25 120.0 . . ? C26 C25 H25 120.0 . . ? K1 C25 H25 107.8 2_646 . ? C25 C26 C21 122.1(2) . . ? C25 C26 H26 118.9 . . ? C21 C26 H26 118.9 . . ? O1 C27 C28 107.9(3) . . ? C28 C27 K1 149.7(2) . . ? O1 C27 H27A 110.1 . . ? C28 C27 H27A 110.1 . . ? K1 C27 H27A 76.3 . . ? O1 C27 H27B 110.1 . . ? C28 C27 H27B 110.1 . . ? K1 C27 H27B 94.7 . . ? H27A C27 H27B 108.4 . . ? C27 C28 C29 104.3(3) . . ? C27 C28 H28A 110.9 . . ? C29 C28 H28A 110.9 . . ? C27 C28 H28B 110.9 . . ? C29 C28 H28B 110.9 . . ? H28A C28 H28B 108.9 . . ? C28 C29 C30 102.6(3) . . ? C28 C29 H29A 111.2 . . ? C30 C29 H29A 111.2 . . ? C28 C29 H29B 111.2 . . ? C30 C29 H29B 111.2 . . ? H29A C29 H29B 109.2 . . ? O1 C30 C29 103.1(3) . . ? O1 C30 H30A 111.1 . . ? C29 C30 H30A 111.1 . . ? O1 C30 H30B 111.1 . . ? C29 C30 H30B 111.1 . . ? H30A C30 H30B 109.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 K1 O1 C27 -21.6(2) . . . . ? C26 K1 O1 C27 -155.75(18) 2_656 . . . ? C19 K1 O1 C27 98.1(2) 2_656 . . . ? C25 K1 O1 C27 -138.67(19) 2_656 . . . ? C21 K1 O1 C27 175.84(18) 2_656 . . . ? B1 K1 O1 C27 -48.7(2) . . . . ? C18 K1 O1 C27 74.07(19) 2_656 . . . ? C20 K1 O1 C27 116.77(19) 2_656 . . . ? C17 K1 O1 C27 69.31(19) 2_656 . . . ? C15 K1 O1 C27 112.91(19) 2_656 . . . ? C16 K1 O1 C27 87.61(19) 2_656 . . . ? C1 K1 O1 C30 158.6(3) . . . . ? C26 K1 O1 C30 24.5(3) 2_656 . . . ? C19 K1 O1 C30 -81.6(3) 2_656 . . . ? C25 K1 O1 C30 41.6(3) 2_656 . . . ? C21 K1 O1 C30 -3.9(3) 2_656 . . . ? B1 K1 O1 C30 131.6(3) . . . . ? C18 K1 O1 C30 -105.7(3) 2_656 . . . ? C20 K1 O1 C30 -63.0(3) 2_656 . . . ? C17 K1 O1 C30 -110.4(3) 2_656 . . . ? C15 K1 O1 C30 -66.8(3) 2_656 . . . ? C16 K1 O1 C30 -92.1(3) 2_656 . . . ? C9 N1 N2 C15 49.0(2) . . . . ? B1 N1 N2 C15 -142.15(19) . . . . ? C9 N1 N2 B2 -176.12(19) . . . . ? B1 N1 N2 B2 -7.3(2) . . . . ? C9 N1 B1 C1 173.7(2) . . . . ? N2 N1 B1 C1 6.8(2) . . . . ? C9 N1 B1 C3 1.2(4) . . . . ? N2 N1 B1 C3 -165.7(2) . . . . ? C9 N1 B1 K1 103.0(2) . . . . ? N2 N1 B1 K1 -63.89(16) . . . . ? O1 K1 B1 N1 -132.43(13) . . . . ? C1 K1 B1 N1 105.41(19) . . . . ? C26 K1 B1 N1 -5.67(14) 2_656 . . . ? C19 K1 B1 N1 143.13(13) 2_656 . . . ? C25 K1 B1 N1 -30.05(14) 2_656 . . . ? C21 K1 B1 N1 2.28(16) 2_656 . . . ? C18 K1 B1 N1 137.89(13) 2_656 . . . ? C20 K1 B1 N1 89.8(2) 2_656 . . . ? C17 K1 B1 N1 114.95(14) 2_656 . . . ? C15 K1 B1 N1 72.32(17) 2_656 . . . ? C16 K1 B1 N1 89.42(15) 2_656 . . . ? O1 K1 B1 C1 122.16(13) . . . . ? C26 K1 B1 C1 -111.08(13) 2_656 . . . ? C19 K1 B1 C1 37.72(19) 2_656 . . . ? C25 K1 B1 C1 -135.46(13) 2_656 . . . ? C21 K1 B1 C1 -103.13(13) 2_656 . . . ? C18 K1 B1 C1 32.48(15) 2_656 . . . ? C20 K1 B1 C1 -15.6(2) 2_656 . . . ? C17 K1 B1 C1 9.54(14) 2_656 . . . ? C15 K1 B1 C1 -33.09(16) 2_656 . . . ? C16 K1 B1 C1 -15.99(14) 2_656 . . . ? O1 K1 B1 C3 -7.50(15) . . . . ? C1 K1 B1 C3 -129.7(2) . . . . ? C26 K1 B1 C3 119.26(13) 2_656 . . . ? C19 K1 B1 C3 -91.94(17) 2_656 . . . ? C25 K1 B1 C3 94.88(14) 2_656 . . . ? C21 K1 B1 C3 127.21(13) 2_656 . . . ? C18 K1 B1 C3 -97.18(14) 2_656 . . . ? C20 K1 B1 C3 -145.29(16) 2_656 . . . ? C17 K1 B1 C3 -120.12(13) 2_656 . . . ? C15 K1 B1 C3 -162.75(11) 2_656 . . . ? C16 K1 B1 C3 -145.64(12) 2_656 . . . ? C15 N2 B2 C1 136.9(2) . . . . ? N1 N2 B2 C1 5.2(2) . . . . ? C15 N2 B2 C21 -39.4(3) . . . . ? N1 N2 B2 C21 -171.17(19) . . . . ? C15 N2 B2 K1 -162.76(16) . . . . ? N1 N2 B2 K1 65.51(14) . . . . ? O1 K1 B2 C1 8.9(2) . . . . ? C26 K1 B2 C1 148.22(15) 2_656 . . . ? C19 K1 B2 C1 -99.58(15) 2_656 . . . ? C25 K1 B2 C1 124.83(14) 2_656 . . . ? C21 K1 B2 C1 169.25(14) 2_656 . . . ? B1 K1 B2 C1 42.59(14) . . . . ? C18 K1 B2 C1 -83.45(14) 2_656 . . . ? C20 K1 B2 C1 -127.78(14) 2_656 . . . ? C17 K1 B2 C1 -92.72(14) 2_656 . . . ? C15 K1 B2 C1 -133.39(14) 2_656 . . . ? C16 K1 B2 C1 -116.44(14) 2_656 . . . ? O1 K1 B2 N2 -100.64(15) . . . . ? C1 K1 B2 N2 -109.53(19) . . . . ? C26 K1 B2 N2 38.69(12) 2_656 . . . ? C19 K1 B2 N2 150.88(12) 2_656 . . . ? C25 K1 B2 N2 15.30(13) 2_656 . . . ? C21 K1 B2 N2 59.72(13) 2_656 . . . ? B1 K1 B2 N2 -66.94(13) . . . . ? C18 K1 B2 N2 167.01(12) 2_656 . . . ? C20 K1 B2 N2 122.68(12) 2_656 . . . ? C17 K1 B2 N2 157.75(13) 2_656 . . . ? C15 K1 B2 N2 117.08(12) 2_656 . . . ? C16 K1 B2 N2 134.02(13) 2_656 . . . ? O1 K1 B2 C21 131.89(15) . . . . ? C1 K1 B2 C21 123.0(2) . . . . ? C26 K1 B2 C21 -88.78(16) 2_656 . . . ? C19 K1 B2 C21 23.42(18) 2_656 . . . ? C25 K1 B2 C21 -112.17(16) 2_656 . . . ? C21 K1 B2 C21 -67.75(17) 2_656 . . . ? B1 K1 B2 C21 165.6(2) . . . . ? C18 K1 B2 C21 39.55(16) 2_656 . . . ? C20 K1 B2 C21 -4.78(18) 2_656 . . . ? C17 K1 B2 C21 30.28(15) 2_656 . . . ? C15 K1 B2 C21 -10.39(16) 2_656 . . . ? C16 K1 B2 C21 6.56(15) 2_656 . . . ? N2 B2 C1 B1 -1.1(3) . . . . ? C21 B2 C1 B1 174.8(2) . . . . ? K1 B2 C1 B1 -85.83(16) . . . . ? N2 B2 C1 C2 178.9(2) . . . . ? C21 B2 C1 C2 -5.2(4) . . . . ? K1 B2 C1 C2 94.1(2) . . . . ? N2 B2 C1 K1 84.74(17) . . . . ? C21 B2 C1 K1 -99.4(2) . . . . ? N1 B1 C1 B2 -3.4(3) . . . . ? C3 B1 C1 B2 168.7(2) . . . . ? K1 B1 C1 B2 93.25(16) . . . . ? N1 B1 C1 C2 176.6(2) . . . . ? C3 B1 C1 C2 -11.3(4) . . . . ? K1 B1 C1 C2 -86.7(2) . . . . ? N1 B1 C1 K1 -96.64(17) . . . . ? C3 B1 C1 K1 75.4(2) . . . . ? O1 K1 C1 B2 -174.23(13) . . . . ? C26 K1 C1 B2 -32.17(15) 2_656 . . . ? C19 K1 C1 B2 98.09(15) 2_656 . . . ? C25 K1 C1 B2 -58.25(15) 2_656 . . . ? C21 K1 C1 B2 -12.41(16) 2_656 . . . ? B1 K1 C1 B2 -104.70(19) . . . . ? C18 K1 C1 B2 102.11(14) 2_656 . . . ? C20 K1 C1 B2 67.61(16) 2_656 . . . ? C17 K1 C1 B2 84.24(14) 2_656 . . . ? C15 K1 C1 B2 51.05(15) 2_656 . . . ? C16 K1 C1 B2 60.94(14) 2_656 . . . ? O1 K1 C1 B1 -69.53(14) . . . . ? C26 K1 C1 B1 72.53(14) 2_656 . . . ? C19 K1 C1 B1 -157.21(12) 2_656 . . . ? C25 K1 C1 B1 46.45(14) 2_656 . . . ? C21 K1 C1 B1 92.29(14) 2_656 . . . ? C18 K1 C1 B1 -153.18(13) 2_656 . . . ? C20 K1 C1 B1 172.31(12) 2_656 . . . ? C17 K1 C1 B1 -171.06(13) 2_656 . . . ? C15 K1 C1 B1 155.75(12) 2_656 . . . ? C16 K1 C1 B1 165.64(13) 2_656 . . . ? O1 K1 C1 C2 57.40(15) . . . . ? C26 K1 C1 C2 -160.54(13) 2_656 . . . ? C19 K1 C1 C2 -30.28(15) 2_656 . . . ? C25 K1 C1 C2 173.38(13) 2_656 . . . ? C21 K1 C1 C2 -140.78(12) 2_656 . . . ? B1 K1 C1 C2 126.9(2) . . . . ? N1 B1 C3 C4 -139.1(2) . . . . ? C1 B1 C3 C4 49.9(3) . . . . ? K1 B1 C3 C4 113.68(19) . . . . ? N1 B1 C3 C8 46.8(3) . . . . ? C1 B1 C3 C8 -124.2(3) . . . . ? K1 B1 C3 C8 -60.4(2) . . . . ? C8 C3 C4 C5 -2.0(3) . . . . ? B1 C3 C4 C5 -176.5(2) . . . . ? C3 C4 C5 C6 2.3(4) . . . . ? C4 C5 C6 C7 -1.0(4) . . . . ? C5 C6 C7 C8 -0.6(4) . . . . ? C6 C7 C8 C3 0.9(4) . . . . ? C4 C3 C8 C7 0.4(3) . . . . ? B1 C3 C8 C7 174.7(2) . . . . ? N2 N1 C9 C10 -152.01(19) . . . . ? B1 N1 C9 C10 42.1(3) . . . . ? N2 N1 C9 C14 26.6(3) . . . . ? B1 N1 C9 C14 -139.4(2) . . . . ? C14 C9 C10 C11 3.1(3) . . . . ? N1 C9 C10 C11 -178.3(2) . . . . ? C9 C10 C11 C12 -0.9(4) . . . . ? C10 C11 C12 C13 -1.1(4) . . . . ? C11 C12 C13 C14 0.7(4) . . . . ? C12 C13 C14 C9 1.6(4) . . . . ? C10 C9 C14 C13 -3.4(3) . . . . ? N1 C9 C14 C13 178.0(2) . . . . ? N1 N2 C15 C20 -143.9(2) . . . . ? B2 N2 C15 C20 87.7(3) . . . . ? N1 N2 C15 C16 36.3(3) . . . . ? B2 N2 C15 C16 -92.1(3) . . . . ? C20 C15 C16 C17 -1.1(3) . . . . ? N2 C15 C16 C17 178.7(2) . . . . ? K1 C15 C16 C17 65.5(2) 2_646 . . . ? C20 C15 C16 K1 -66.56(19) . . . 2_646 ? N2 C15 C16 K1 113.25(19) . . . 2_646 ? C15 C16 C17 C18 -0.2(4) . . . . ? K1 C16 C17 C18 65.3(2) 2_646 . . . ? C15 C16 C17 K1 -65.5(2) . . . 2_646 ? C16 C17 C18 C19 0.5(4) . . . . ? K1 C17 C18 C19 68.2(2) 2_646 . . . ? C16 C17 C18 K1 -67.7(2) . . . 2_646 ? C17 C18 C19 C20 0.5(4) . . . . ? K1 C18 C19 C20 71.5(2) 2_646 . . . ? C17 C18 C19 K1 -71.0(2) . . . 2_646 ? C16 C15 C20 C19 2.1(3) . . . . ? N2 C15 C20 C19 -177.8(2) . . . . ? K1 C15 C20 C19 -66.8(2) 2_646 . . . ? C16 C15 C20 K1 68.83(19) . . . 2_646 ? N2 C15 C20 K1 -110.98(18) . . . 2_646 ? C18 C19 C20 C15 -1.8(4) . . . . ? K1 C19 C20 C15 69.5(2) 2_646 . . . ? C18 C19 C20 K1 -71.3(2) . . . 2_646 ? C1 B2 C21 C26 -45.9(3) . . . . ? N2 B2 C21 C26 129.6(2) . . . . ? K1 B2 C21 C26 -117.23(19) . . . . ? C1 B2 C21 C22 133.8(3) . . . . ? N2 B2 C21 C22 -50.7(3) . . . . ? K1 B2 C21 C22 62.5(2) . . . . ? C1 B2 C21 K1 -122.0(2) . . . 2_646 ? N2 B2 C21 K1 53.5(2) . . . 2_646 ? K1 B2 C21 K1 166.66(7) . . . 2_646 ? C26 C21 C22 C23 -2.1(3) . . . . ? B2 C21 C22 C23 178.1(2) . . . . ? K1 C21 C22 C23 66.4(2) 2_646 . . . ? C21 C22 C23 C24 0.2(4) . . . . ? C22 C23 C24 C25 1.6(4) . . . . ? C23 C24 C25 C26 -1.4(4) . . . . ? C23 C24 C25 K1 -69.7(2) . . . 2_646 ? C24 C25 C26 C21 -0.7(4) . . . . ? K1 C25 C26 C21 79.6(2) 2_646 . . . ? C24 C25 C26 K1 -80.3(2) . . . 2_646 ? C22 C21 C26 C25 2.4(3) . . . . ? B2 C21 C26 C25 -177.9(2) . . . . ? K1 C21 C26 C25 -79.4(2) 2_646 . . . ? C22 C21 C26 K1 81.83(18) . . . 2_646 ? B2 C21 C26 K1 -98.45(18) . . . 2_646 ? C30 O1 C27 C28 -16.4(4) . . . . ? K1 O1 C27 C28 163.8(2) . . . . ? C1 K1 C27 O1 161.32(18) . . . . ? C26 K1 C27 O1 34.5(2) 2_656 . . . ? C19 K1 C27 O1 -75.28(19) 2_656 . . . ? C25 K1 C27 O1 47.4(2) 2_656 . . . ? C21 K1 C27 O1 -5.6(2) 2_656 . . . ? B1 K1 C27 O1 134.59(19) . . . . ? C18 K1 C27 O1 -100.8(2) 2_656 . . . ? C20 K1 C27 O1 -64.23(19) 2_656 . . . ? C17 K1 C27 O1 -113.85(19) 2_656 . . . ? C15 K1 C27 O1 -77.2(2) 2_656 . . . ? C16 K1 C27 O1 -104.23(19) 2_656 . . . ? O1 K1 C27 C28 -31.7(4) . . . . ? C1 K1 C27 C28 129.6(5) . . . . ? C26 K1 C27 C28 2.8(5) 2_656 . . . ? C19 K1 C27 C28 -107.0(5) 2_656 . . . ? C25 K1 C27 C28 15.6(5) 2_656 . . . ? C21 K1 C27 C28 -37.3(5) 2_656 . . . ? B1 K1 C27 C28 102.9(5) . . . . ? C18 K1 C27 C28 -132.5(5) 2_656 . . . ? C20 K1 C27 C28 -96.0(5) 2_656 . . . ? C17 K1 C27 C28 -145.6(5) 2_656 . . . ? C15 K1 C27 C28 -108.9(5) 2_656 . . . ? C16 K1 C27 C28 -136.0(5) 2_656 . . . ? O1 C27 C28 C29 -8.0(4) . . . . ? K1 C27 C28 C29 15.0(6) . . . . ? C27 C28 C29 C30 27.3(4) . . . . ? C27 O1 C30 C29 33.4(4) . . . . ? K1 O1 C30 C29 -146.8(3) . . . . ? C28 C29 C30 O1 -37.3(4) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.469 _refine_diff_density_min -0.493 _refine_diff_density_rms 0.047