# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Robin Hicks' _publ_contact_author_address ; Chemistry Department University of Victoria PO Box 3065 Victoria BC V8W 3V6 CANADA ; _publ_contact_author_email RHICKS@UVIC.CA _publ_section_title ; Formazans as beta-diketiminate analogues. Structural characterization of boratatetrazines and their reduction to borataverdazyl radical anions. ; loop_ _publ_author_name 'Robin Hicks' 'Michael A. J. Ferguson' 'Joe B. Gilroy' 'Robert McDonald' 'Brian O. Patrick' # Attachment 'Hicks.cif' data_rh003 _database_code_depnum_ccdc_archive 'CCDC 613050' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H20 N4' _chemical_formula_weight 328.41 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P bca' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 7.8300(10) _cell_length_b 21.154(2) _cell_length_c 22.289(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3691.9(8) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1626 _cell_measurement_theta_min 2.92 _cell_measurement_theta_max 21.55 _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.182 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1392 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.588 _exptl_absorpt_correction_T_max 0.993 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker X8 APEX' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9155 _diffrn_reflns_av_R_equivalents 0.0553 _diffrn_reflns_av_sigmaI/netI 0.0707 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 22.62 _reflns_number_total 2431 _reflns_number_gt 1194 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0751P)^2^+1.5572P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2431 _refine_ls_number_parameters 230 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1413 _refine_ls_R_factor_gt 0.0576 _refine_ls_wR_factor_ref 0.1788 _refine_ls_wR_factor_gt 0.1341 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.8815(5) 0.04089(18) 0.40803(17) 0.0491(10) Uani 1 1 d . . . C11 C 0.9254(5) 0.08951(18) 0.36393(17) 0.0518(11) Uani 1 1 d . . . C12 C 1.0244(6) 0.07615(19) 0.31442(19) 0.0659(13) Uani 1 1 d . . . H12 H 1.0627 0.0350 0.3083 0.079 Uiso 1 1 calc R . . C13 C 1.0678(6) 0.1229(2) 0.2736(2) 0.0787(14) Uani 1 1 d . . . H13 H 1.1363 0.1129 0.2409 0.094 Uiso 1 1 calc R . . C14 C 1.0107(7) 0.1837(2) 0.2810(2) 0.0855(16) Uani 1 1 d . . . H14 H 1.0388 0.2149 0.2533 0.103 Uiso 1 1 calc R . . C15 C 0.9110(7) 0.1980(2) 0.3302(2) 0.0853(16) Uani 1 1 d . . . H15 H 0.8718 0.2391 0.3355 0.102 Uiso 1 1 calc R . . C16 C 0.8684(6) 0.15186(19) 0.37178(19) 0.0686(13) Uani 1 1 d . . . H16 H 0.8020 0.1623 0.4049 0.082 Uiso 1 1 calc R . . C21 C 0.9635(5) -0.12500(18) 0.42322(19) 0.0547(11) Uani 1 1 d . . . C22 C 1.0527(6) -0.14134(19) 0.37216(19) 0.0668(13) Uani 1 1 d . . . H22 H 1.0804 -0.1107 0.3439 0.080 Uiso 1 1 calc R . . C23 C 1.1008(6) -0.2038(2) 0.3632(2) 0.0745(14) Uani 1 1 d . . . H23 H 1.1590 -0.2145 0.3283 0.089 Uiso 1 1 calc R . . C24 C 1.0650(6) -0.25036(19) 0.4045(2) 0.0647(12) Uani 1 1 d . . . C25 C 0.9811(7) -0.23269(19) 0.4557(2) 0.0837(16) Uani 1 1 d . . . H25 H 0.9577 -0.2630 0.4847 0.100 Uiso 1 1 calc R . . C26 C 0.9299(6) -0.1706(2) 0.4654(2) 0.0794(15) Uani 1 1 d . . . H26 H 0.8728 -0.1600 0.5006 0.095 Uiso 1 1 calc R . . C27 C 1.1172(7) -0.31854(19) 0.3934(2) 0.0926(17) Uani 1 1 d . . . H27A H 1.1748 -0.3216 0.3555 0.139 Uiso 0.50 1 calc PR . . H27B H 1.0173 -0.3449 0.3929 0.139 Uiso 0.50 1 calc PR . . H27C H 1.1925 -0.3322 0.4248 0.139 Uiso 0.50 1 calc PR . . H27D H 1.0816 -0.3442 0.4266 0.139 Uiso 0.50 1 calc PR . . H27E H 1.2391 -0.3209 0.3892 0.139 Uiso 0.50 1 calc PR . . H27F H 1.0639 -0.3335 0.3573 0.139 Uiso 0.50 1 calc PR . . C31 C 0.6520(5) 0.04009(19) 0.54726(18) 0.0525(11) Uani 1 1 d . . . C32 C 0.6268(6) -0.00180(19) 0.5937(2) 0.0686(13) Uani 1 1 d . . . H32 H 0.6728 -0.0423 0.5914 0.082 Uiso 1 1 calc R . . C33 C 0.5339(6) 0.0157(2) 0.6437(2) 0.0777(14) Uani 1 1 d . . . H33 H 0.5173 -0.0135 0.6743 0.093 Uiso 1 1 calc R . . C34 C 0.4654(6) 0.0752(3) 0.6492(2) 0.0719(13) Uani 1 1 d . . . C35 C 0.4909(6) 0.1167(2) 0.6026(2) 0.0781(14) Uani 1 1 d . . . H35 H 0.4443 0.1570 0.6050 0.094 Uiso 1 1 calc R . . C36 C 0.5831(6) 0.1004(2) 0.5523(2) 0.0692(13) Uani 1 1 d . . . H36 H 0.5992 0.1298 0.5217 0.083 Uiso 1 1 calc R . . C37 C 0.3632(7) 0.0935(3) 0.7035(2) 0.118(2) Uani 1 1 d . . . H37A H 0.3588 0.0585 0.7309 0.177 Uiso 0.50 1 calc PR . . H37B H 0.2494 0.1047 0.6916 0.177 Uiso 0.50 1 calc PR . . H37C H 0.4162 0.1289 0.7229 0.177 Uiso 0.50 1 calc PR . . H37D H 0.3241 0.1363 0.6994 0.177 Uiso 0.50 1 calc PR . . H37E H 0.4335 0.0900 0.7387 0.177 Uiso 0.50 1 calc PR . . H37F H 0.2667 0.0658 0.7073 0.177 Uiso 0.50 1 calc PR . . N1 N 0.9387(4) -0.01808(16) 0.39662(14) 0.0571(9) Uani 1 1 d . . . N2 N 0.9061(4) -0.06292(15) 0.43601(14) 0.0584(10) Uani 1 1 d . . . N3 N 0.7878(5) 0.06005(14) 0.45631(16) 0.0619(10) Uani 1 1 d . . . N4 N 0.7491(4) 0.01892(15) 0.49817(15) 0.0573(9) Uani 1 1 d . . . H1 H 0.814(3) -0.0440(11) 0.4863(10) 0.017(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.056(3) 0.046(3) 0.045(3) -0.007(2) -0.001(2) -0.004(2) C11 0.063(3) 0.046(2) 0.047(3) -0.001(2) -0.006(2) -0.006(2) C12 0.083(3) 0.056(3) 0.059(3) 0.003(2) -0.001(3) -0.005(3) C13 0.091(4) 0.079(3) 0.066(3) 0.009(3) 0.005(3) -0.011(3) C14 0.108(4) 0.077(4) 0.072(4) 0.021(3) -0.009(3) -0.018(3) C15 0.116(5) 0.056(3) 0.084(4) 0.007(3) -0.005(4) -0.006(3) C16 0.089(3) 0.052(3) 0.065(3) 0.003(2) 0.004(3) -0.005(3) C21 0.060(3) 0.050(3) 0.053(3) -0.001(2) 0.001(2) -0.002(2) C22 0.086(3) 0.053(3) 0.062(3) 0.008(2) 0.008(3) -0.004(3) C23 0.089(4) 0.065(3) 0.070(3) -0.002(3) 0.011(3) 0.006(3) C24 0.076(3) 0.049(3) 0.070(3) 0.000(2) -0.004(3) 0.009(3) C25 0.129(5) 0.044(3) 0.078(3) 0.007(3) 0.026(3) 0.008(3) C26 0.114(4) 0.060(3) 0.064(3) 0.007(2) 0.029(3) 0.005(3) C27 0.117(4) 0.066(3) 0.094(4) -0.001(3) 0.000(3) 0.015(3) C31 0.056(3) 0.055(3) 0.047(3) 0.000(2) -0.004(2) -0.008(3) C32 0.080(3) 0.056(3) 0.071(3) -0.002(3) 0.008(3) 0.000(3) C33 0.084(4) 0.083(3) 0.067(3) 0.008(3) 0.008(3) -0.005(3) C34 0.067(3) 0.099(4) 0.050(3) -0.013(3) 0.001(3) 0.003(3) C35 0.084(4) 0.080(3) 0.070(3) -0.009(3) 0.004(3) 0.022(3) C36 0.083(3) 0.063(3) 0.062(3) 0.009(2) 0.001(3) 0.009(3) C37 0.113(5) 0.169(5) 0.071(4) -0.019(4) 0.004(4) 0.026(5) N1 0.062(2) 0.052(2) 0.058(2) 0.0005(18) -0.0027(18) -0.008(2) N2 0.071(3) 0.044(2) 0.060(2) 0.0023(18) 0.005(2) -0.006(2) N3 0.068(3) 0.054(2) 0.064(2) 0.000(2) -0.009(2) -0.008(2) N4 0.064(2) 0.055(2) 0.053(2) 0.0033(19) 0.000(2) -0.005(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.350(4) . ? C1 N3 1.364(5) . ? C1 C11 1.464(5) . ? C11 C12 1.378(5) . ? C11 C16 1.403(5) . ? C12 C13 1.385(5) . ? C12 H12 0.9300 . ? C13 C14 1.374(6) . ? C13 H13 0.9300 . ? C14 C15 1.379(6) . ? C14 H14 0.9300 . ? C15 C16 1.387(6) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C21 C26 1.374(5) . ? C21 C22 1.379(5) . ? C21 N2 1.417(5) . ? C22 C23 1.388(5) . ? C22 H22 0.9300 . ? C23 C24 1.377(5) . ? C23 H23 0.9300 . ? C24 C25 1.368(5) . ? C24 C27 1.519(5) . ? C25 C26 1.390(5) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C27 H27D 0.9600 . ? C27 H27E 0.9600 . ? C27 H27F 0.9600 . ? C31 C32 1.377(5) . ? C31 C36 1.390(5) . ? C31 N4 1.406(5) . ? C32 C33 1.381(6) . ? C32 H32 0.9300 . ? C33 C34 1.375(6) . ? C33 H33 0.9300 . ? C34 C35 1.374(6) . ? C34 C37 1.503(6) . ? C35 C36 1.376(6) . ? C35 H35 0.9300 . ? C36 H36 0.9300 . ? C37 H37A 0.9600 . ? C37 H37B 0.9600 . ? C37 H37C 0.9600 . ? C37 H37D 0.9600 . ? C37 H37E 0.9600 . ? C37 H37F 0.9600 . ? N1 N2 1.318(4) . ? N2 H1 1.39(2) . ? N3 N4 1.311(4) . ? N4 H1 1.45(2) . ? 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 N1 C1 N3 127.0(3) . . ? N1 C1 C11 116.4(4) . . ? N3 C1 C11 116.6(4) . . ? C12 C11 C16 118.1(4) . . ? C12 C11 C1 121.7(4) . . ? C16 C11 C1 120.2(4) . . ? C11 C12 C13 121.2(4) . . ? C11 C12 H12 119.4 . . ? C13 C12 H12 119.4 . . ? C14 C13 C12 120.7(5) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C13 C14 C15 119.0(4) . . ? C13 C14 H14 120.5 . . ? C15 C14 H14 120.5 . . ? C14 C15 C16 120.9(4) . . ? C14 C15 H15 119.5 . . ? C16 C15 H15 119.5 . . ? C15 C16 C11 120.1(4) . . ? C15 C16 H16 119.9 . . ? C11 C16 H16 119.9 . . ? C26 C21 C22 119.1(4) . . ? C26 C21 N2 116.9(4) . . ? C22 C21 N2 124.0(4) . . ? C21 C22 C23 119.6(4) . . ? C21 C22 H22 120.2 . . ? C23 C22 H22 120.2 . . ? C24 C23 C22 122.0(4) . . ? C24 C23 H23 119.0 . . ? C22 C23 H23 119.0 . . ? C25 C24 C23 117.3(4) . . ? C25 C24 C27 121.6(4) . . ? C23 C24 C27 121.0(4) . . ? C24 C25 C26 121.8(4) . . ? C24 C25 H25 119.1 . . ? C26 C25 H25 119.1 . . ? C21 C26 C25 120.1(4) . . ? C21 C26 H26 120.0 . . ? C25 C26 H26 120.0 . . ? C24 C27 H27A 109.5 . . ? C24 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C24 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C24 C27 H27D 109.5 . . ? H27A C27 H27D 141.1 . . ? H27B C27 H27D 56.3 . . ? H27C C27 H27D 56.3 . . ? C24 C27 H27E 109.5 . . ? H27A C27 H27E 56.3 . . ? H27B C27 H27E 141.1 . . ? H27C C27 H27E 56.3 . . ? H27D C27 H27E 109.5 . . ? C24 C27 H27F 109.5 . . ? H27A C27 H27F 56.3 . . ? H27B C27 H27F 56.3 . . ? H27C C27 H27F 141.1 . . ? H27D C27 H27F 109.5 . . ? H27E C27 H27F 109.5 . . ? C32 C31 C36 118.3(4) . . ? C32 C31 N4 117.2(4) . . ? C36 C31 N4 124.4(4) . . ? C31 C32 C33 120.7(4) . . ? C31 C32 H32 119.7 . . ? C33 C32 H32 119.7 . . ? C34 C33 C32 121.5(4) . . ? C34 C33 H33 119.3 . . ? C32 C33 H33 119.3 . . ? C35 C34 C33 117.5(4) . . ? C35 C34 C37 121.6(5) . . ? C33 C34 C37 121.0(5) . . ? C34 C35 C36 122.2(4) . . ? C34 C35 H35 118.9 . . ? C36 C35 H35 118.9 . . ? C35 C36 C31 119.9(4) . . ? C35 C36 H36 120.0 . . ? C31 C36 H36 120.0 . . ? C34 C37 H37A 109.5 . . ? C34 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C34 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C34 C37 H37D 109.5 . . ? H37A C37 H37D 141.1 . . ? H37B C37 H37D 56.3 . . ? H37C C37 H37D 56.3 . . ? C34 C37 H37E 109.5 . . ? H37A C37 H37E 56.3 . . ? H37B C37 H37E 141.1 . . ? H37C C37 H37E 56.3 . . ? H37D C37 H37E 109.5 . . ? C34 C37 H37F 109.5 . . ? H37A C37 H37F 56.3 . . ? H37B C37 H37F 56.3 . . ? H37C C37 H37F 141.1 . . ? H37D C37 H37F 109.5 . . ? H37E C37 H37F 109.5 . . ? N2 N1 C1 118.4(3) . . ? N1 N2 C21 118.1(3) . . ? N1 N2 H1 115.5(10) . . ? C21 N2 H1 126.3(10) . . ? N4 N3 C1 119.2(3) . . ? N3 N4 C31 117.9(3) . . ? N3 N4 H1 113.5(10) . . ? C31 N4 H1 128.6(10) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C11 C12 -2.0(6) . . . . ? N3 C1 C11 C12 177.8(4) . . . . ? N1 C1 C11 C16 178.9(4) . . . . ? N3 C1 C11 C16 -1.3(6) . . . . ? C16 C11 C12 C13 0.4(6) . . . . ? C1 C11 C12 C13 -178.7(4) . . . . ? C11 C12 C13 C14 -1.1(7) . . . . ? C12 C13 C14 C15 0.8(7) . . . . ? C13 C14 C15 C16 0.0(7) . . . . ? C14 C15 C16 C11 -0.6(7) . . . . ? C12 C11 C16 C15 0.4(6) . . . . ? C1 C11 C16 C15 179.6(4) . . . . ? C26 C21 C22 C23 2.5(7) . . . . ? N2 C21 C22 C23 -178.9(4) . . . . ? C21 C22 C23 C24 -1.2(7) . . . . ? C22 C23 C24 C25 -0.8(7) . . . . ? C22 C23 C24 C27 179.3(4) . . . . ? C23 C24 C25 C26 1.5(7) . . . . ? C27 C24 C25 C26 -178.6(5) . . . . ? C22 C21 C26 C25 -1.9(7) . . . . ? N2 C21 C26 C25 179.4(4) . . . . ? C24 C25 C26 C21 -0.2(8) . . . . ? C36 C31 C32 C33 0.6(6) . . . . ? N4 C31 C32 C33 179.5(4) . . . . ? C31 C32 C33 C34 -0.7(7) . . . . ? C32 C33 C34 C35 0.9(7) . . . . ? C32 C33 C34 C37 179.4(4) . . . . ? C33 C34 C35 C36 -0.9(7) . . . . ? C37 C34 C35 C36 -179.5(4) . . . . ? C34 C35 C36 C31 0.8(7) . . . . ? C32 C31 C36 C35 -0.6(6) . . . . ? N4 C31 C36 C35 -179.5(4) . . . . ? N3 C1 N1 N2 -1.6(6) . . . . ? C11 C1 N1 N2 178.2(3) . . . . ? C1 N1 N2 C21 178.7(4) . . . . ? C26 C21 N2 N1 179.1(4) . . . . ? C22 C21 N2 N1 0.5(6) . . . . ? N1 C1 N3 N4 1.8(6) . . . . ? C11 C1 N3 N4 -178.0(3) . . . . ? C1 N3 N4 C31 -179.8(3) . . . . ? C32 C31 N4 N3 -173.7(4) . . . . ? C36 C31 N4 N3 5.2(6) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 22.62 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.248 _refine_diff_density_min -0.182 _refine_diff_density_rms 0.039 #===END data_vic0416 _database_code_depnum_ccdc_archive 'CCDC 613051' _audit_creation_method SHELXL-97 _chemical_name_systematic (E)-1-[(Z)-(4-methylphenyl)(phenylhydrazono)methyl]-2-phenyldiazene _chemical_formula_moiety 'C20 H18 N4' _chemical_formula_sum 'C20 H18 N4' _chemical_formula_weight 314.38 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.7762(8) _cell_length_b 13.4272(9) _cell_length_c 12.0220(8) _cell_angle_alpha 90.00 _cell_angle_beta 118.5943(12) _cell_angle_gamma 90.00 _cell_volume 1669.08(19) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 3778 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 26.13 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.251 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8248 _exptl_absorpt_correction_T_max 0.9789 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker PLATFORM diffractometer/SMART 1000 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 11781 _diffrn_reflns_av_R_equivalents 0.0310 _diffrn_reflns_av_sigmaI/netI 0.0303 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 26.40 _reflns_number_total 3429 _reflns_number_gt 2495 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART (Bruker, 1997)' _computing_cell_refinement 'Bruker SAINT (Bruker, 1997)' _computing_data_reduction 'Bruker SAINT (Bruker, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL (Bruker, 1997)' _computing_publication_material 'Bruker SHELXTL (Bruker, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0566P)^2^+0.5757P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3429 _refine_ls_number_parameters 222 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0742 _refine_ls_R_factor_gt 0.0503 _refine_ls_wR_factor_ref 0.1364 _refine_ls_wR_factor_gt 0.1224 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.27826(13) -0.01555(10) 0.19221(13) 0.0375(3) Uani 1 1 d . . . N2 N 0.36074(14) -0.07519(11) 0.18141(15) 0.0418(4) Uani 1 1 d . . . H2N H 0.343(2) -0.0660(18) 0.079(2) 0.080(7) Uiso 1 1 d . . . N3 N 0.18741(13) 0.04064(10) -0.02697(14) 0.0385(4) Uani 1 1 d . . . N4 N 0.26558(14) -0.01324(11) -0.04777(14) 0.0424(4) Uani 1 1 d . . . C1 C 0.19487(15) 0.03602(12) 0.09046(16) 0.0351(4) Uani 1 1 d . . . C11 C 0.10172(15) 0.09940(12) 0.10681(15) 0.0351(4) Uani 1 1 d . . . C12 C 0.09793(17) 0.10350(14) 0.22067(17) 0.0430(4) Uani 1 1 d . . . H12 H 0.1572 0.0644 0.2902 0.052 Uiso 1 1 calc R . . C13 C 0.01043(18) 0.16274(14) 0.23504(17) 0.0453(4) Uani 1 1 d . . . H13 H 0.0111 0.1640 0.3144 0.054 Uiso 1 1 calc R . . C14 C -0.07911(16) 0.22095(13) 0.13588(17) 0.0409(4) Uani 1 1 d . . . C15 C -0.07538(18) 0.21676(14) 0.02222(17) 0.0454(5) Uani 1 1 d . . . H15 H -0.1350 0.2556 -0.0474 0.054 Uiso 1 1 calc R . . C16 C 0.01219(18) 0.15808(13) 0.00766(17) 0.0427(4) Uani 1 1 d . . . H16 H 0.0118 0.1574 -0.0715 0.051 Uiso 1 1 calc R . . C17 C -0.17637(19) 0.28366(16) 0.1497(2) 0.0546(5) Uani 1 1 d . . . H17A H -0.1428 0.3515 0.1736 0.065 Uiso 1 1 calc R . . H17B H -0.1931 0.2553 0.2156 0.065 Uiso 1 1 calc R . . H17C H -0.2570 0.2852 0.0691 0.065 Uiso 1 1 calc R . . C21 C 0.45114(16) -0.12633(12) 0.28868(17) 0.0381(4) Uani 1 1 d . . . C22 C 0.46751(16) -0.11101(13) 0.40955(17) 0.0409(4) Uani 1 1 d . . . H22 H 0.4138 -0.0651 0.4229 0.049 Uiso 1 1 calc R . . C23 C 0.56221(18) -0.16276(15) 0.51021(19) 0.0506(5) Uani 1 1 d . . . H23 H 0.5743 -0.1514 0.5932 0.061 Uiso 1 1 calc R . . C24 C 0.6396(2) -0.23072(15) 0.4922(2) 0.0582(6) Uani 1 1 d . . . H24 H 0.7035 -0.2670 0.5619 0.070 Uiso 1 1 calc R . . C25 C 0.6234(2) -0.24544(16) 0.3721(2) 0.0640(6) Uani 1 1 d . . . H25 H 0.6771 -0.2916 0.3592 0.077 Uiso 1 1 calc R . . C26 C 0.5301(2) -0.19395(15) 0.2705(2) 0.0539(5) Uani 1 1 d . . . H26 H 0.5197 -0.2046 0.1880 0.065 Uiso 1 1 calc R . . C31 C 0.25425(17) -0.00541(13) -0.16984(17) 0.0402(4) Uani 1 1 d . . . C32 C 0.16283(19) 0.05353(15) -0.26606(18) 0.0480(5) Uani 1 1 d . . . H32 H 0.1044 0.0930 -0.2513 0.058 Uiso 1 1 calc R . . C33 C 0.1576(2) 0.05436(17) -0.3828(2) 0.0576(5) Uani 1 1 d . . . H33 H 0.0953 0.0947 -0.4487 0.069 Uiso 1 1 calc R . . C34 C 0.2422(2) -0.00294(16) -0.4053(2) 0.0585(6) Uani 1 1 d . . . H34 H 0.2373 -0.0025 -0.4865 0.070 Uiso 1 1 calc R . . C35 C 0.3331(2) -0.06042(16) -0.3100(2) 0.0573(6) Uani 1 1 d . . . H35 H 0.3916 -0.0994 -0.3253 0.069 Uiso 1 1 calc R . . C36 C 0.34010(19) -0.06204(15) -0.1925(2) 0.0494(5) Uani 1 1 d . . . H36 H 0.4035 -0.1018 -0.1267 0.059 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0357(7) 0.0347(7) 0.0380(8) -0.0020(6) 0.0142(6) -0.0023(6) N2 0.0382(8) 0.0392(8) 0.0426(9) -0.0020(7) 0.0152(7) 0.0041(6) N3 0.0370(8) 0.0373(8) 0.0396(9) -0.0027(6) 0.0171(7) -0.0037(6) N4 0.0409(8) 0.0433(8) 0.0427(9) -0.0046(7) 0.0197(7) 0.0013(7) C1 0.0328(8) 0.0326(8) 0.0357(9) -0.0030(7) 0.0130(7) -0.0061(7) C11 0.0340(8) 0.0324(9) 0.0330(9) -0.0002(7) 0.0114(7) -0.0083(7) C12 0.0407(10) 0.0477(10) 0.0345(10) 0.0048(8) 0.0129(8) 0.0047(8) C13 0.0465(10) 0.0534(11) 0.0338(10) 0.0008(8) 0.0174(8) 0.0004(9) C14 0.0364(9) 0.0385(10) 0.0436(10) -0.0021(8) 0.0158(8) -0.0021(7) C15 0.0454(10) 0.0473(11) 0.0378(10) 0.0094(8) 0.0154(9) 0.0071(8) C16 0.0479(10) 0.0449(10) 0.0347(9) 0.0053(8) 0.0192(8) 0.0056(8) C17 0.0529(12) 0.0591(13) 0.0547(13) 0.0015(10) 0.0282(10) 0.0092(10) C21 0.0340(9) 0.0320(9) 0.0413(10) -0.0005(7) 0.0123(8) -0.0024(7) C22 0.0366(9) 0.0404(10) 0.0459(11) 0.0007(8) 0.0199(8) -0.0027(8) C23 0.0472(11) 0.0521(11) 0.0448(11) 0.0084(9) 0.0158(9) -0.0050(9) C24 0.0503(12) 0.0442(11) 0.0591(14) 0.0107(10) 0.0092(10) 0.0043(9) C25 0.0592(13) 0.0461(12) 0.0711(16) -0.0023(11) 0.0185(12) 0.0187(10) C26 0.0587(12) 0.0449(11) 0.0518(12) -0.0071(9) 0.0213(10) 0.0110(9) C31 0.0429(10) 0.0395(9) 0.0382(10) -0.0015(8) 0.0194(8) -0.0045(8) C32 0.0482(11) 0.0500(11) 0.0456(11) 0.0029(9) 0.0222(9) 0.0039(9) C33 0.0652(13) 0.0612(13) 0.0441(12) 0.0095(10) 0.0243(11) 0.0029(11) C34 0.0766(15) 0.0590(13) 0.0497(12) -0.0012(10) 0.0380(12) -0.0072(12) C35 0.0674(14) 0.0555(12) 0.0639(14) -0.0041(11) 0.0435(12) -0.0006(11) C36 0.0506(11) 0.0485(11) 0.0523(12) 0.0010(9) 0.0272(10) 0.0039(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 N2 1.3123(19) . ? N1 C1 1.338(2) . ? N2 C21 1.398(2) . ? N2 H2N 1.16(2) . ? N3 N4 1.2859(19) . ? N3 C1 1.373(2) . ? N4 C31 1.412(2) . ? N4 H2N 1.52(2) . ? C1 C11 1.474(2) . ? C11 C12 1.392(2) . ? C11 C16 1.397(2) . ? C12 C13 1.377(3) . ? C13 C14 1.393(2) . ? C14 C15 1.389(2) . ? C14 C17 1.494(2) . ? C15 C16 1.374(3) . ? C21 C22 1.387(2) . ? C21 C26 1.390(2) . ? C22 C23 1.378(2) . ? C23 C24 1.378(3) . ? C24 C25 1.377(3) . ? C25 C26 1.375(3) . ? C31 C32 1.390(3) . ? C31 C36 1.392(3) . ? C32 C33 1.376(3) . ? C33 C34 1.383(3) . ? C34 C35 1.371(3) . ? C35 C36 1.376(3) . ? 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 N2 N1 C1 118.65(15) . . ? N1 N2 C21 118.78(15) . . ? N1 N2 H2N 106.2(12) . . ? C21 N2 H2N 134.8(12) . . ? N4 N3 C1 118.36(14) . . ? N3 N4 C31 116.09(15) . . ? N3 N4 H2N 102.2(9) . . ? C31 N4 H2N 141.7(9) . . ? N1 C1 N3 128.39(15) . . ? N1 C1 C11 116.38(15) . . ? N3 C1 C11 115.19(15) . . ? C12 C11 C16 116.79(16) . . ? C12 C11 C1 122.02(16) . . ? C16 C11 C1 121.20(15) . . ? C13 C12 C11 121.64(17) . . ? C12 C13 C14 121.50(17) . . ? C15 C14 C13 116.85(16) . . ? C15 C14 C17 121.30(17) . . ? C13 C14 C17 121.85(17) . . ? C16 C15 C14 121.84(17) . . ? C15 C16 C11 121.39(17) . . ? C22 C21 C26 119.59(17) . . ? C22 C21 N2 123.80(16) . . ? C26 C21 N2 116.58(17) . . ? C23 C22 C21 119.57(17) . . ? C22 C23 C24 120.9(2) . . ? C25 C24 C23 119.31(19) . . ? C26 C25 C24 120.7(2) . . ? C25 C26 C21 119.9(2) . . ? C32 C31 C36 119.62(17) . . ? C32 C31 N4 123.88(16) . . ? C36 C31 N4 116.50(16) . . ? C33 C32 C31 119.50(18) . . ? C32 C33 C34 120.7(2) . . ? C35 C34 C33 119.8(2) . . ? C34 C35 C36 120.4(2) . . ? C35 C36 C31 120.00(19) . . ? 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 N1 N2 C21 177.64(14) . . . . ? C1 N3 N4 C31 -179.74(14) . . . . ? C1 N3 N4 H2N -0.1(9) . . . . ? N2 N1 C1 N3 -4.5(2) . . . . ? N2 N1 C1 C11 178.12(13) . . . . ? N4 N3 C1 N1 2.9(2) . . . . ? N4 N3 C1 C11 -179.66(14) . . . . ? N1 C1 C11 C12 -1.7(2) . . . . ? N3 C1 C11 C12 -179.47(15) . . . . ? N1 C1 C11 C16 178.60(15) . . . . ? N3 C1 C11 C16 0.9(2) . . . . ? C16 C11 C12 C13 -0.2(3) . . . . ? C1 C11 C12 C13 -179.86(16) . . . . ? C11 C12 C13 C14 0.4(3) . . . . ? C12 C13 C14 C15 -0.3(3) . . . . ? C12 C13 C14 C17 178.58(18) . . . . ? C13 C14 C15 C16 0.0(3) . . . . ? C17 C14 C15 C16 -178.89(18) . . . . ? C14 C15 C16 C11 0.2(3) . . . . ? C12 C11 C16 C15 -0.1(3) . . . . ? C1 C11 C16 C15 179.56(16) . . . . ? N1 N2 C21 C22 -6.3(2) . . . . ? N1 N2 C21 C26 175.48(16) . . . . ? C26 C21 C22 C23 0.2(3) . . . . ? N2 C21 C22 C23 -177.88(16) . . . . ? C21 C22 C23 C24 -1.0(3) . . . . ? C22 C23 C24 C25 1.3(3) . . . . ? C23 C24 C25 C26 -0.7(3) . . . . ? C24 C25 C26 C21 0.0(3) . . . . ? C22 C21 C26 C25 0.3(3) . . . . ? N2 C21 C26 C25 178.52(19) . . . . ? N3 N4 C31 C32 -2.0(2) . . . . ? N3 N4 C31 C36 178.83(15) . . . . ? C36 C31 C32 C33 0.6(3) . . . . ? N4 C31 C32 C33 -178.49(18) . . . . ? C31 C32 C33 C34 0.1(3) . . . . ? C32 C33 C34 C35 -0.7(3) . . . . ? C33 C34 C35 C36 0.5(3) . . . . ? C34 C35 C36 C31 0.3(3) . . . . ? C32 C31 C36 C35 -0.8(3) . . . . ? N4 C31 C36 C35 178.37(17) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2N N4 1.16(2) 1.52(2) 2.566(2) 146(2) . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.40 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.271 _refine_diff_density_min -0.156 _refine_diff_density_rms 0.037 _chemical_name_common ;(E)-1-((Z)-(4-methylphenyl)(phenylhydrazono)methyl)-2- phenyldiazene ; #===END data_vic0504 _database_code_depnum_ccdc_archive 'CCDC 613052' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H23 B N4 O4' _chemical_formula_sum 'C24 H23 B N4 O4' _chemical_formula_weight 442.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.3612(15) _cell_length_b 14.925(2) _cell_length_c 15.608(2) _cell_angle_alpha 103.098(2) _cell_angle_beta 97.538(3) _cell_angle_gamma 95.549(3) _cell_volume 2310.5(6) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 3947 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 25.82 _exptl_crystal_description prism _exptl_crystal_colour purple _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.271 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 928 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.7572 _exptl_absorpt_correction_T_max 0.9887 _exptl_absorpt_process_details 'Bruker SHELXTL (Bruker, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker PLATFORM diffractometer/SMART 1000 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 17953 _diffrn_reflns_av_R_equivalents 0.0505 _diffrn_reflns_av_sigmaI/netI 0.0800 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.36 _diffrn_reflns_theta_max 26.50 _reflns_number_total 9430 _reflns_number_gt 5492 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART (Bruker, 1997)' _computing_cell_refinement 'Bruker SAINT (Bruker, 1997)' _computing_data_reduction 'Bruker SAINT (Bruker, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL (Bruker, 1997)' _computing_publication_material 'Bruker SHELXTL (Bruker, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0669P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9430 _refine_ls_number_parameters 601 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1064 _refine_ls_R_factor_gt 0.0514 _refine_ls_wR_factor_ref 0.1460 _refine_ls_wR_factor_gt 0.1178 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _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 O1A O 0.07906(15) 0.62005(10) 0.39157(10) 0.0307(4) Uani 1 1 d . . . O2A O 0.06777(18) 0.67949(12) 0.27142(12) 0.0461(5) Uani 1 1 d . . . O3A O 0.13094(15) 0.47518(10) 0.40402(10) 0.0327(4) Uani 1 1 d . . . O4A O 0.20441(19) 0.36431(12) 0.30679(12) 0.0501(5) Uani 1 1 d . . . N1A N 0.26700(18) 0.52429(13) 0.22411(12) 0.0310(5) Uani 1 1 d . . . N2A N 0.24746(17) 0.55651(12) 0.30554(12) 0.0289(4) Uani 1 1 d . . . N3A N 0.04316(18) 0.45583(13) 0.17857(12) 0.0300(4) Uani 1 1 d . . . N4A N 0.01474(17) 0.48787(12) 0.25790(12) 0.0279(4) Uani 1 1 d . . . C1A C 0.1673(2) 0.47044(15) 0.16570(14) 0.0291(5) Uani 1 1 d . . . C2A C 0.0604(2) 0.68798(16) 0.34924(17) 0.0360(6) Uani 1 1 d . . . C3A C 0.0302(3) 0.77364(18) 0.4081(2) 0.0633(9) Uani 1 1 d . . . H3AA H 0.0241 0.8220 0.3750 0.076 Uiso 1 1 calc R . . H3BA H 0.1002 0.7949 0.4596 0.076 Uiso 1 1 calc R . . H3CA H -0.0535 0.7607 0.4285 0.076 Uiso 1 1 calc R . . C4A C 0.1691(2) 0.39045(16) 0.37761(17) 0.0357(6) Uani 1 1 d . . . C5A C 0.1626(3) 0.33565(18) 0.44576(18) 0.0512(7) Uani 1 1 d . . . H5AA H 0.1756 0.2715 0.4201 0.061 Uiso 1 1 calc R . . H5BA H 0.0764 0.3363 0.4652 0.061 Uiso 1 1 calc R . . H5CA H 0.2314 0.3630 0.4970 0.061 Uiso 1 1 calc R . . C11A C 0.1958(2) 0.42709(16) 0.07600(15) 0.0313(5) Uani 1 1 d . . . C12A C 0.3218(3) 0.43584(19) 0.05753(16) 0.0464(7) Uani 1 1 d . . . H12A H 0.3905 0.4721 0.1017 0.056 Uiso 1 1 calc R . . C13A C 0.3494(3) 0.3923(2) -0.02502(17) 0.0504(7) Uani 1 1 d . . . H13A H 0.4376 0.3987 -0.0358 0.060 Uiso 1 1 calc R . . C14A C 0.2535(3) 0.33994(16) -0.09209(16) 0.0382(6) Uani 1 1 d . . . C15A C 0.1269(3) 0.33419(19) -0.07353(17) 0.0491(7) Uani 1 1 d . . . H15A H 0.0576 0.3004 -0.1186 0.059 Uiso 1 1 calc R . . C16A C 0.0984(3) 0.37616(19) 0.00877(16) 0.0469(7) Uani 1 1 d . . . H16A H 0.0102 0.3700 0.0195 0.056 Uiso 1 1 calc R . . C17A C 0.2840(3) 0.29258(19) -0.18152(17) 0.0535(8) Uani 1 1 d . . . H17A H 0.2215 0.2362 -0.2068 0.064 Uiso 1 1 calc R . . H17B H 0.3734 0.2762 -0.1746 0.064 Uiso 1 1 calc R . . H17C H 0.2768 0.3345 -0.2215 0.064 Uiso 1 1 calc R . . C21A C 0.3522(2) 0.62361(15) 0.36036(15) 0.0303(5) Uani 1 1 d . . . C22A C 0.4349(2) 0.67579(17) 0.32283(17) 0.0395(6) Uani 1 1 d . . . H22A H 0.4253 0.6666 0.2600 0.047 Uiso 1 1 calc R . . C23A C 0.5319(3) 0.74152(18) 0.37726(18) 0.0457(7) Uani 1 1 d . . . H23A H 0.5885 0.7779 0.3514 0.055 Uiso 1 1 calc R . . C24A C 0.5479(3) 0.75525(18) 0.46798(18) 0.0457(7) Uani 1 1 d . . . H24A H 0.6152 0.8009 0.5045 0.055 Uiso 1 1 calc R . . C25A C 0.4661(3) 0.70261(19) 0.50622(17) 0.0488(7) Uani 1 1 d . . . H25A H 0.4776 0.7114 0.5691 0.059 Uiso 1 1 calc R . . C26A C 0.3668(2) 0.63671(18) 0.45230(16) 0.0425(6) Uani 1 1 d . . . H26A H 0.3094 0.6009 0.4782 0.051 Uiso 1 1 calc R . . C31A C -0.1231(2) 0.48137(15) 0.26105(15) 0.0291(5) Uani 1 1 d . . . C32A C -0.2113(2) 0.46980(17) 0.18338(17) 0.0385(6) Uani 1 1 d . . . H32A H -0.1803 0.4674 0.1283 0.046 Uiso 1 1 calc R . . C33A C -0.3439(2) 0.46179(18) 0.18640(18) 0.0439(7) Uani 1 1 d . . . H33A H -0.4045 0.4522 0.1329 0.053 Uiso 1 1 calc R . . C34A C -0.3901(2) 0.46751(17) 0.26637(19) 0.0430(6) Uani 1 1 d . . . H34A H -0.4818 0.4625 0.2681 0.052 Uiso 1 1 calc R . . C35A C -0.3017(3) 0.48051(17) 0.34368(18) 0.0430(6) Uani 1 1 d . . . H35A H -0.3330 0.4852 0.3989 0.052 Uiso 1 1 calc R . . C36A C -0.1681(2) 0.48682(16) 0.34194(16) 0.0357(6) Uani 1 1 d . . . H36A H -0.1078 0.4948 0.3953 0.043 Uiso 1 1 calc R . . B1A B 0.1179(3) 0.53473(18) 0.34155(17) 0.0292(6) Uani 1 1 d . . . O1B O 0.05342(15) -0.00443(10) 0.12276(10) 0.0321(4) Uani 1 1 d . . . O2B O -0.05501(17) -0.09420(11) 0.19431(11) 0.0425(4) Uani 1 1 d . . . O3B O 0.23796(15) 0.10332(10) 0.17179(10) 0.0330(4) Uani 1 1 d . . . O4B O 0.36987(17) 0.15138(12) 0.30364(12) 0.0463(5) Uani 1 1 d . . . N1B N 0.25008(18) -0.05083(12) 0.31092(12) 0.0296(4) Uani 1 1 d . . . N2B N 0.22692(18) -0.04067(12) 0.22978(12) 0.0293(4) Uani 1 1 d . . . N3B N 0.12120(18) 0.06924(12) 0.36194(12) 0.0299(4) Uani 1 1 d . . . N4B N 0.09176(18) 0.08187(12) 0.28210(12) 0.0291(4) Uani 1 1 d . . . C1B C 0.2041(2) 0.00817(15) 0.37487(14) 0.0285(5) Uani 1 1 d . . . C2B C -0.0459(2) -0.06627(16) 0.12878(16) 0.0358(6) Uani 1 1 d . . . C3B C -0.1425(3) -0.0951(2) 0.0454(2) 0.0724(10) Uani 1 1 d . . . H3AB H -0.1032 -0.1335 -0.0014 0.087 Uiso 1 1 calc R . . H3BB H -0.1673 -0.0399 0.0267 0.087 Uiso 1 1 calc R . . H3CB H -0.2207 -0.1310 0.0559 0.087 Uiso 1 1 calc R . . C4B C 0.3371(2) 0.15880(16) 0.22882(17) 0.0360(6) Uani 1 1 d . . . C5B C 0.4009(3) 0.22922(19) 0.18793(19) 0.0554(8) Uani 1 1 d . . . H5AB H 0.4784 0.2641 0.2291 0.066 Uiso 1 1 calc R . . H5BB H 0.3386 0.2719 0.1758 0.066 Uiso 1 1 calc R . . H5CB H 0.4276 0.1978 0.1320 0.066 Uiso 1 1 calc R . . C11B C 0.2430(2) 0.00360(15) 0.46788(14) 0.0280(5) Uani 1 1 d . . . C12B C 0.3425(2) -0.04606(17) 0.49186(16) 0.0366(6) Uani 1 1 d . . . H12B H 0.3821 -0.0826 0.4469 0.044 Uiso 1 1 calc R . . C13B C 0.3850(2) -0.04308(17) 0.58054(16) 0.0381(6) Uani 1 1 d . . . H13B H 0.4533 -0.0778 0.5952 0.046 Uiso 1 1 calc R . . C14B C 0.3306(2) 0.00918(16) 0.64837(15) 0.0346(6) Uani 1 1 d . . . C15B C 0.2269(2) 0.05531(16) 0.62400(15) 0.0355(6) Uani 1 1 d . . . H15B H 0.1844 0.0891 0.6689 0.043 Uiso 1 1 calc R . . C16B C 0.1842(2) 0.05308(16) 0.53593(15) 0.0337(6) Uani 1 1 d . . . H16B H 0.1136 0.0859 0.5214 0.040 Uiso 1 1 calc R . . C17B C 0.3809(3) 0.0154(2) 0.74504(16) 0.0491(7) Uani 1 1 d . . . H17D H 0.4388 0.0740 0.7706 0.059 Uiso 1 1 calc R . . H17E H 0.4300 -0.0367 0.7496 0.059 Uiso 1 1 calc R . . H17F H 0.3066 0.0130 0.7777 0.059 Uiso 1 1 calc R . . C21B C 0.2620(2) -0.11393(16) 0.16315(15) 0.0322(6) Uani 1 1 d . . . C22B C 0.2480(3) -0.20401(17) 0.17238(17) 0.0456(7) Uani 1 1 d . . . H22B H 0.2171 -0.2180 0.2232 0.055 Uiso 1 1 calc R . . C23B C 0.2795(3) -0.2736(2) 0.10654(19) 0.0605(9) Uani 1 1 d . . . H23B H 0.2693 -0.3358 0.1121 0.073 Uiso 1 1 calc R . . C24B C 0.3251(3) -0.2540(2) 0.03345(19) 0.0643(9) Uani 1 1 d . . . H24B H 0.3481 -0.3023 -0.0107 0.077 Uiso 1 1 calc R . . C25B C 0.3375(3) -0.1643(2) 0.02424(18) 0.0582(8) Uani 1 1 d . . . H25B H 0.3685 -0.1507 -0.0267 0.070 Uiso 1 1 calc R . . C26B C 0.3052(3) -0.09395(19) 0.08848(16) 0.0448(7) Uani 1 1 d . . . H26B H 0.3126 -0.0321 0.0816 0.054 Uiso 1 1 calc R . . C31B C -0.0098(2) 0.13947(15) 0.27269(15) 0.0311(5) Uani 1 1 d . . . C32B C -0.0962(2) 0.15197(17) 0.33338(17) 0.0400(6) Uani 1 1 d . . . H32B H -0.0892 0.1223 0.3813 0.048 Uiso 1 1 calc R . . C33B C -0.1933(3) 0.20823(18) 0.3237(2) 0.0506(7) Uani 1 1 d . . . H33B H -0.2528 0.2173 0.3653 0.061 Uiso 1 1 calc R . . C34B C -0.2040(3) 0.25089(17) 0.25451(19) 0.0474(7) Uani 1 1 d . . . H34B H -0.2708 0.2893 0.2482 0.057 Uiso 1 1 calc R . . C35B C -0.1182(3) 0.23800(17) 0.19432(18) 0.0452(7) Uani 1 1 d . . . H35B H -0.1261 0.2676 0.1464 0.054 Uiso 1 1 calc R . . C36B C -0.0204(3) 0.18255(16) 0.20262(16) 0.0404(6) Uani 1 1 d . . . H36B H 0.0390 0.1740 0.1608 0.048 Uiso 1 1 calc R . . B1B B 0.1530(3) 0.03543(18) 0.20066(17) 0.0287(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 O1A 0.0328(9) 0.0292(9) 0.0291(9) 0.0033(7) 0.0079(7) 0.0037(7) O2A 0.0603(13) 0.0436(11) 0.0385(11) 0.0141(8) 0.0122(9) 0.0104(9) O3A 0.0364(10) 0.0302(9) 0.0303(9) 0.0055(7) 0.0038(7) 0.0051(7) O4A 0.0628(13) 0.0434(11) 0.0445(12) 0.0038(9) 0.0136(10) 0.0188(9) N1A 0.0275(11) 0.0355(11) 0.0268(11) 0.0017(9) 0.0040(9) 0.0035(9) N2A 0.0258(11) 0.0329(11) 0.0246(11) 0.0007(8) 0.0023(8) 0.0035(8) N3A 0.0288(11) 0.0326(11) 0.0262(11) 0.0013(8) 0.0052(8) 0.0048(8) N4A 0.0256(11) 0.0299(10) 0.0269(11) 0.0022(8) 0.0073(8) 0.0043(8) C1A 0.0253(13) 0.0335(13) 0.0264(13) 0.0029(10) 0.0035(10) 0.0039(10) C2A 0.0328(14) 0.0332(14) 0.0412(16) 0.0069(12) 0.0097(12) 0.0009(11) C3A 0.094(3) 0.0354(16) 0.068(2) 0.0118(14) 0.0338(19) 0.0192(16) C4A 0.0327(14) 0.0326(14) 0.0370(15) 0.0038(11) -0.0027(11) 0.0033(11) C5A 0.0610(19) 0.0408(16) 0.0492(18) 0.0107(13) -0.0009(14) 0.0072(14) C11A 0.0294(13) 0.0375(13) 0.0254(13) 0.0034(10) 0.0054(10) 0.0050(10) C12A 0.0332(15) 0.0675(19) 0.0303(15) -0.0056(13) 0.0050(11) 0.0088(13) C13A 0.0319(15) 0.074(2) 0.0399(16) 0.0004(14) 0.0101(12) 0.0082(14) C14A 0.0482(17) 0.0345(14) 0.0322(14) 0.0048(11) 0.0134(12) 0.0057(12) C15A 0.0466(18) 0.0582(18) 0.0291(15) -0.0088(12) 0.0056(12) -0.0120(13) C16A 0.0323(15) 0.0614(18) 0.0359(15) -0.0067(13) 0.0076(12) -0.0076(13) C17A 0.068(2) 0.0505(17) 0.0370(16) -0.0031(13) 0.0200(14) 0.0012(15) C21A 0.0246(13) 0.0326(13) 0.0293(13) 0.0001(10) 0.0017(10) 0.0039(10) C22A 0.0370(15) 0.0432(15) 0.0334(14) 0.0011(11) 0.0066(12) -0.0012(12) C23A 0.0382(16) 0.0425(16) 0.0497(17) 0.0012(13) 0.0081(13) -0.0057(12) C24A 0.0352(15) 0.0418(15) 0.0480(17) -0.0075(13) -0.0013(13) 0.0007(12) C25A 0.0476(17) 0.0566(18) 0.0319(15) -0.0020(13) -0.0023(13) -0.0014(14) C26A 0.0397(16) 0.0503(16) 0.0322(15) 0.0043(12) 0.0020(12) -0.0018(12) C31A 0.0280(13) 0.0243(12) 0.0333(13) 0.0019(10) 0.0064(10) 0.0042(10) C32A 0.0293(14) 0.0471(15) 0.0391(15) 0.0093(12) 0.0040(11) 0.0093(11) C33A 0.0304(15) 0.0502(16) 0.0483(17) 0.0076(13) 0.0004(12) 0.0089(12) C34A 0.0262(14) 0.0419(15) 0.0589(18) 0.0054(13) 0.0104(13) 0.0066(11) C35A 0.0383(16) 0.0412(15) 0.0462(17) 0.0003(12) 0.0164(13) 0.0016(12) C36A 0.0291(14) 0.0394(14) 0.0342(14) 0.0016(11) 0.0038(11) 0.0026(11) B1A 0.0279(15) 0.0339(15) 0.0242(14) 0.0036(11) 0.0046(11) 0.0039(12) O1B 0.0350(9) 0.0344(9) 0.0250(9) 0.0072(7) 0.0018(7) -0.0008(7) O2B 0.0472(11) 0.0456(10) 0.0336(10) 0.0121(8) 0.0066(8) -0.0059(8) O3B 0.0348(9) 0.0325(9) 0.0296(9) 0.0076(7) 0.0021(7) -0.0023(7) O4B 0.0430(11) 0.0480(11) 0.0406(11) 0.0083(9) -0.0094(9) -0.0014(8) N1B 0.0334(11) 0.0298(10) 0.0238(11) 0.0051(8) 0.0012(8) 0.0032(8) N2B 0.0318(11) 0.0324(11) 0.0218(10) 0.0039(8) 0.0029(8) 0.0035(8) N3B 0.0322(11) 0.0307(10) 0.0253(11) 0.0063(8) 0.0001(8) 0.0042(9) N4B 0.0325(11) 0.0282(10) 0.0239(10) 0.0043(8) -0.0014(8) 0.0036(8) C1B 0.0288(13) 0.0287(12) 0.0268(13) 0.0050(10) 0.0036(10) 0.0030(10) C2B 0.0367(15) 0.0348(14) 0.0338(15) 0.0080(11) 0.0021(11) -0.0008(11) C3B 0.063(2) 0.089(2) 0.053(2) 0.0269(17) -0.0198(16) -0.0332(18) C4B 0.0305(14) 0.0337(14) 0.0408(16) 0.0047(12) 0.0033(12) 0.0029(11) C5B 0.0519(18) 0.0506(17) 0.061(2) 0.0146(14) 0.0092(15) -0.0112(14) C11B 0.0313(13) 0.0272(12) 0.0252(12) 0.0063(10) 0.0043(10) 0.0026(10) C12B 0.0373(15) 0.0432(15) 0.0303(14) 0.0066(11) 0.0081(11) 0.0118(12) C13B 0.0332(14) 0.0483(16) 0.0357(15) 0.0149(12) 0.0022(11) 0.0128(12) C14B 0.0334(14) 0.0409(14) 0.0279(13) 0.0088(11) 0.0022(11) -0.0003(11) C15B 0.0429(15) 0.0368(14) 0.0248(13) 0.0022(10) 0.0064(11) 0.0064(11) C16B 0.0368(14) 0.0327(13) 0.0323(14) 0.0080(11) 0.0048(11) 0.0089(11) C17B 0.0532(18) 0.0628(19) 0.0292(15) 0.0093(13) -0.0006(13) 0.0108(14) C21B 0.0315(14) 0.0370(14) 0.0253(13) 0.0022(10) 0.0008(10) 0.0083(11) C22B 0.0607(19) 0.0368(15) 0.0376(15) 0.0043(12) 0.0069(13) 0.0114(13) C23B 0.091(2) 0.0423(17) 0.0440(18) -0.0011(13) 0.0037(16) 0.0255(16) C24B 0.088(3) 0.067(2) 0.0334(17) -0.0067(15) 0.0071(16) 0.0391(19) C25B 0.076(2) 0.070(2) 0.0320(16) 0.0072(14) 0.0172(15) 0.0280(17) C26B 0.0572(18) 0.0499(16) 0.0303(15) 0.0095(12) 0.0116(13) 0.0158(13) C31B 0.0303(13) 0.0252(12) 0.0340(14) 0.0042(10) -0.0027(11) 0.0027(10) C32B 0.0381(15) 0.0379(14) 0.0473(16) 0.0137(12) 0.0095(12) 0.0093(12) C33B 0.0456(17) 0.0451(16) 0.066(2) 0.0157(14) 0.0163(15) 0.0125(13) C34B 0.0387(16) 0.0362(15) 0.067(2) 0.0136(14) -0.0009(14) 0.0111(12) C35B 0.0489(17) 0.0395(15) 0.0495(17) 0.0178(13) -0.0022(14) 0.0134(13) C36B 0.0495(17) 0.0359(14) 0.0350(15) 0.0079(11) 0.0017(12) 0.0101(12) B1B 0.0273(15) 0.0324(15) 0.0239(14) 0.0049(11) -0.0010(11) 0.0023(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 O1A C2A 1.345(3) . ? O1A B1A 1.457(3) . ? O2A C2A 1.206(3) . ? O3A C4A 1.352(3) . ? O3A B1A 1.463(3) . ? O4A C4A 1.203(3) . ? N1A N2A 1.303(2) . ? N1A C1A 1.344(3) . ? N2A C21A 1.439(3) . ? N2A B1A 1.555(3) . ? N3A N4A 1.305(2) . ? N3A C1A 1.332(3) . ? N4A C31A 1.430(3) . ? N4A B1A 1.553(3) . ? C1A C11A 1.484(3) . ? C2A C3A 1.482(3) . ? C4A C5A 1.486(3) . ? C11A C12A 1.374(3) . ? C11A C16A 1.382(3) . ? C12A C13A 1.385(3) . ? C13A C14A 1.378(4) . ? C14A C15A 1.379(4) . ? C14A C17A 1.503(3) . ? C15A C16A 1.378(3) . ? C21A C22A 1.376(3) . ? C21A C26A 1.390(3) . ? C22A C23A 1.379(3) . ? C23A C24A 1.369(4) . ? C24A C25A 1.382(4) . ? C25A C26A 1.391(3) . ? C31A C32A 1.385(3) . ? C31A C36A 1.390(3) . ? C32A C33A 1.376(3) . ? C33A C34A 1.382(4) . ? C34A C35A 1.379(4) . ? C35A C36A 1.383(3) . ? O1B C2B 1.342(3) . ? O1B B1B 1.456(3) . ? O2B C2B 1.200(3) . ? O3B C4B 1.339(3) . ? O3B B1B 1.464(3) . ? O4B C4B 1.206(3) . ? N1B N2B 1.303(2) . ? N1B C1B 1.344(3) . ? N2B C21B 1.439(3) . ? N2B B1B 1.547(3) . ? N3B N4B 1.304(2) . ? N3B C1B 1.341(3) . ? N4B C31B 1.435(3) . ? N4B B1B 1.548(3) . ? C1B C11B 1.473(3) . ? C2B C3B 1.483(3) . ? C4B C5B 1.493(3) . ? C11B C12B 1.388(3) . ? C11B C16B 1.394(3) . ? C12B C13B 1.386(3) . ? C13B C14B 1.384(3) . ? C14B C15B 1.388(3) . ? C14B C17B 1.509(3) . ? C15B C16B 1.380(3) . ? C21B C22B 1.380(3) . ? C21B C26B 1.384(3) . ? C22B C23B 1.382(4) . ? C23B C24B 1.370(4) . ? C24B C25B 1.374(4) . ? C25B C26B 1.378(3) . ? C31B C32B 1.382(3) . ? C31B C36B 1.387(3) . ? C32B C33B 1.385(3) . ? C33B C34B 1.370(4) . ? C34B C35B 1.371(4) . ? C35B C36B 1.380(3) . ? 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 C2A O1A B1A 117.73(18) . . ? C4A O3A B1A 119.66(18) . . ? N2A N1A C1A 118.11(19) . . ? N1A N2A C21A 114.55(18) . . ? N1A N2A B1A 124.82(18) . . ? C21A N2A B1A 120.34(18) . . ? N4A N3A C1A 118.61(18) . . ? N3A N4A C31A 113.83(18) . . ? N3A N4A B1A 124.42(18) . . ? C31A N4A B1A 121.64(18) . . ? N3A C1A N1A 126.5(2) . . ? N3A C1A C11A 116.39(19) . . ? N1A C1A C11A 117.0(2) . . ? O2A C2A O1A 123.1(2) . . ? O2A C2A C3A 123.9(2) . . ? O1A C2A C3A 113.1(2) . . ? O4A C4A O3A 122.7(2) . . ? O4A C4A C5A 125.1(2) . . ? O3A C4A C5A 112.3(2) . . ? C12A C11A C16A 117.7(2) . . ? C12A C11A C1A 120.5(2) . . ? C16A C11A C1A 121.8(2) . . ? C11A C12A C13A 120.5(2) . . ? C14A C13A C12A 122.3(2) . . ? C13A C14A C15A 116.5(2) . . ? C13A C14A C17A 122.2(2) . . ? C15A C14A C17A 121.3(2) . . ? C16A C15A C14A 121.7(2) . . ? C15A C16A C11A 121.2(2) . . ? C22A C21A C26A 120.2(2) . . ? C22A C21A N2A 120.8(2) . . ? C26A C21A N2A 119.0(2) . . ? C21A C22A C23A 119.4(2) . . ? C24A C23A C22A 121.1(3) . . ? C23A C24A C25A 119.8(2) . . ? C24A C25A C26A 119.8(2) . . ? C21A C26A C25A 119.6(2) . . ? C32A C31A C36A 120.3(2) . . ? C32A C31A N4A 119.8(2) . . ? C36A C31A N4A 120.0(2) . . ? C33A C32A C31A 119.6(2) . . ? C32A C33A C34A 120.8(2) . . ? C35A C34A C33A 119.3(2) . . ? C34A C35A C36A 120.9(2) . . ? C35A C36A C31A 119.1(2) . . ? O1A B1A O3A 105.29(18) . . ? O1A B1A N4A 111.61(19) . . ? O3A B1A N4A 111.34(19) . . ? O1A B1A N2A 110.14(19) . . ? O3A B1A N2A 113.07(19) . . ? N4A B1A N2A 105.51(18) . . ? C2B O1B B1B 119.16(18) . . ? C4B O3B B1B 120.97(18) . . ? N2B N1B C1B 117.85(18) . . ? N1B N2B C21B 114.69(18) . . ? N1B N2B B1B 125.44(18) . . ? C21B N2B B1B 119.49(18) . . ? N4B N3B C1B 118.92(18) . . ? N3B N4B C31B 114.70(18) . . ? N3B N4B B1B 124.37(18) . . ? C31B N4B B1B 120.84(18) . . ? N3B C1B N1B 126.0(2) . . ? N3B C1B C11B 116.14(19) . . ? N1B C1B C11B 117.82(19) . . ? O2B C2B O1B 123.5(2) . . ? O2B C2B C3B 124.4(2) . . ? O1B C2B C3B 112.0(2) . . ? O4B C4B O3B 123.3(2) . . ? O4B C4B C5B 125.0(2) . . ? O3B C4B C5B 111.7(2) . . ? C12B C11B C16B 117.5(2) . . ? C12B C11B C1B 121.8(2) . . ? C16B C11B C1B 120.6(2) . . ? C13B C12B C11B 120.8(2) . . ? C14B C13B C12B 121.7(2) . . ? C13B C14B C15B 117.3(2) . . ? C13B C14B C17B 121.5(2) . . ? C15B C14B C17B 121.2(2) . . ? C16B C15B C14B 121.3(2) . . ? C15B C16B C11B 121.2(2) . . ? C22B C21B C26B 120.4(2) . . ? C22B C21B N2B 120.0(2) . . ? C26B C21B N2B 119.6(2) . . ? C21B C22B C23B 118.9(3) . . ? C24B C23B C22B 121.0(3) . . ? C23B C24B C25B 119.8(3) . . ? C24B C25B C26B 120.3(3) . . ? C25B C26B C21B 119.6(3) . . ? C32B C31B C36B 120.3(2) . . ? C32B C31B N4B 120.0(2) . . ? C36B C31B N4B 119.7(2) . . ? C31B C32B C33B 119.3(2) . . ? C34B C33B C32B 120.5(3) . . ? C33B C34B C35B 119.9(2) . . ? C34B C35B C36B 120.8(2) . . ? C35B C36B C31B 119.2(2) . . ? O1B B1B O3B 103.94(18) . . ? O1B B1B N2B 110.92(19) . . ? O3B B1B N2B 113.06(19) . . ? O1B B1B N4B 111.80(19) . . ? O3B B1B N4B 111.52(18) . . ? N2B B1B N4B 105.76(18) . . ? 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 C1A N1A N2A C21A -171.74(19) . . . . ? C1A N1A N2A B1A 2.1(3) . . . . ? C1A N3A N4A C31A 170.60(19) . . . . ? C1A N3A N4A B1A -5.8(3) . . . . ? N4A N3A C1A N1A -7.8(3) . . . . ? N4A N3A C1A C11A 175.96(19) . . . . ? N2A N1A C1A N3A 9.7(3) . . . . ? N2A N1A C1A C11A -174.13(18) . . . . ? B1A O1A C2A O2A 3.9(3) . . . . ? B1A O1A C2A C3A -176.0(2) . . . . ? B1A O3A C4A O4A 6.8(3) . . . . ? B1A O3A C4A C5A -173.6(2) . . . . ? N3A C1A C11A C12A -177.8(2) . . . . ? N1A C1A C11A C12A 5.6(3) . . . . ? N3A C1A C11A C16A 1.5(3) . . . . ? N1A C1A C11A C16A -175.1(2) . . . . ? C16A C11A C12A C13A -2.0(4) . . . . ? C1A C11A C12A C13A 177.4(2) . . . . ? C11A C12A C13A C14A 0.9(4) . . . . ? C12A C13A C14A C15A 1.1(4) . . . . ? C12A C13A C14A C17A -179.9(3) . . . . ? C13A C14A C15A C16A -2.0(4) . . . . ? C17A C14A C15A C16A 178.9(3) . . . . ? C14A C15A C16A C11A 0.9(4) . . . . ? C12A C11A C16A C15A 1.1(4) . . . . ? C1A C11A C16A C15A -178.2(2) . . . . ? N1A N2A C21A C22A 25.1(3) . . . . ? B1A N2A C21A C22A -149.0(2) . . . . ? N1A N2A C21A C26A -156.4(2) . . . . ? B1A N2A C21A C26A 29.5(3) . . . . ? C26A C21A C22A C23A -0.4(4) . . . . ? N2A C21A C22A C23A 178.0(2) . . . . ? C21A C22A C23A C24A 0.5(4) . . . . ? C22A C23A C24A C25A 0.0(4) . . . . ? C23A C24A C25A C26A -0.8(4) . . . . ? C22A C21A C26A C25A -0.3(4) . . . . ? N2A C21A C26A C25A -178.8(2) . . . . ? C24A C25A C26A C21A 0.9(4) . . . . ? N3A N4A C31A C32A -18.8(3) . . . . ? B1A N4A C31A C32A 157.7(2) . . . . ? N3A N4A C31A C36A 161.3(2) . . . . ? B1A N4A C31A C36A -22.2(3) . . . . ? C36A C31A C32A C33A -1.3(4) . . . . ? N4A C31A C32A C33A 178.8(2) . . . . ? C31A C32A C33A C34A 1.7(4) . . . . ? C32A C33A C34A C35A -0.6(4) . . . . ? C33A C34A C35A C36A -0.7(4) . . . . ? C34A C35A C36A C31A 1.0(4) . . . . ? C32A C31A C36A C35A 0.0(3) . . . . ? N4A C31A C36A C35A 179.9(2) . . . . ? C2A O1A B1A O3A 179.82(18) . . . . ? C2A O1A B1A N4A -59.2(3) . . . . ? C2A O1A B1A N2A 57.6(2) . . . . ? C4A O3A B1A O1A -178.68(17) . . . . ? C4A O3A B1A N4A 60.2(3) . . . . ? C4A O3A B1A N2A -58.4(3) . . . . ? N3A N4A B1A O1A 133.6(2) . . . . ? C31A N4A B1A O1A -42.5(3) . . . . ? N3A N4A B1A O3A -109.0(2) . . . . ? C31A N4A B1A O3A 74.9(2) . . . . ? N3A N4A B1A N2A 14.0(3) . . . . ? C31A N4A B1A N2A -162.10(18) . . . . ? N1A N2A B1A O1A -132.7(2) . . . . ? C21A N2A B1A O1A 40.8(3) . . . . ? N1A N2A B1A O3A 109.8(2) . . . . ? C21A N2A B1A O3A -76.7(2) . . . . ? N1A N2A B1A N4A -12.1(3) . . . . ? C21A N2A B1A N4A 161.38(18) . . . . ? C1B N1B N2B C21B -171.38(19) . . . . ? C1B N1B N2B B1B 1.4(3) . . . . ? C1B N3B N4B C31B 172.54(19) . . . . ? C1B N3B N4B B1B -4.1(3) . . . . ? N4B N3B C1B N1B -8.3(3) . . . . ? N4B N3B C1B C11B 174.45(18) . . . . ? N2B N1B C1B N3B 9.6(3) . . . . ? N2B N1B C1B C11B -173.18(19) . . . . ? B1B O1B C2B O2B -3.3(3) . . . . ? B1B O1B C2B C3B 176.4(2) . . . . ? B1B O3B C4B O4B 6.7(3) . . . . ? B1B O3B C4B C5B -173.7(2) . . . . ? N3B C1B C11B C12B -170.2(2) . . . . ? N1B C1B C11B C12B 12.3(3) . . . . ? N3B C1B C11B C16B 6.8(3) . . . . ? N1B C1B C11B C16B -170.7(2) . . . . ? C16B C11B C12B C13B -2.6(3) . . . . ? C1B C11B C12B C13B 174.5(2) . . . . ? C11B C12B C13B C14B -0.1(4) . . . . ? C12B C13B C14B C15B 3.0(4) . . . . ? C12B C13B C14B C17B -177.4(2) . . . . ? C13B C14B C15B C16B -3.3(4) . . . . ? C17B C14B C15B C16B 177.2(2) . . . . ? C14B C15B C16B C11B 0.6(4) . . . . ? C12B C11B C16B C15B 2.3(3) . . . . ? C1B C11B C16B C15B -174.8(2) . . . . ? N1B N2B C21B C22B 34.6(3) . . . . ? B1B N2B C21B C22B -138.7(2) . . . . ? N1B N2B C21B C26B -147.7(2) . . . . ? B1B N2B C21B C26B 39.0(3) . . . . ? C26B C21B C22B C23B 0.9(4) . . . . ? N2B C21B C22B C23B 178.6(2) . . . . ? C21B C22B C23B C24B 0.6(4) . . . . ? C22B C23B C24B C25B -1.3(5) . . . . ? C23B C24B C25B C26B 0.5(5) . . . . ? C24B C25B C26B C21B 1.0(4) . . . . ? C22B C21B C26B C25B -1.6(4) . . . . ? N2B C21B C26B C25B -179.4(2) . . . . ? N3B N4B C31B C32B -20.9(3) . . . . ? B1B N4B C31B C32B 155.8(2) . . . . ? N3B N4B C31B C36B 158.9(2) . . . . ? B1B N4B C31B C36B -24.4(3) . . . . ? C36B C31B C32B C33B -0.2(4) . . . . ? N4B C31B C32B C33B 179.6(2) . . . . ? C31B C32B C33B C34B 0.2(4) . . . . ? C32B C33B C34B C35B 0.0(4) . . . . ? C33B C34B C35B C36B -0.2(4) . . . . ? C34B C35B C36B C31B 0.2(4) . . . . ? C32B C31B C36B C35B 0.0(4) . . . . ? N4B C31B C36B C35B -179.8(2) . . . . ? C2B O1B B1B O3B -176.01(18) . . . . ? C2B O1B B1B N2B 62.2(3) . . . . ? C2B O1B B1B N4B -55.6(3) . . . . ? C4B O3B B1B O1B 175.50(18) . . . . ? C4B O3B B1B N2B -64.1(3) . . . . ? C4B O3B B1B N4B 54.9(3) . . . . ? N1B N2B B1B O1B -132.0(2) . . . . ? C21B N2B B1B O1B 40.5(3) . . . . ? N1B N2B B1B O3B 111.7(2) . . . . ? C21B N2B B1B O3B -75.8(2) . . . . ? N1B N2B B1B N4B -10.6(3) . . . . ? C21B N2B B1B N4B 161.86(18) . . . . ? N3B N4B B1B O1B 132.7(2) . . . . ? C31B N4B B1B O1B -43.7(3) . . . . ? N3B N4B B1B O3B -111.4(2) . . . . ? C31B N4B B1B O3B 72.2(3) . . . . ? N3B N4B B1B N2B 11.9(3) . . . . ? C31B N4B B1B N2B -164.49(18) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 26.50 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.296 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.051 #===END data_vic0505 _database_code_depnum_ccdc_archive 'CCDC 613053' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H25 B N4 O4' _chemical_formula_sum 'C25 H25 B N4 O4' _chemical_formula_weight 456.30 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.8688(13) _cell_length_b 10.6690(14) _cell_length_c 12.4677(17) _cell_angle_alpha 87.363(2) _cell_angle_beta 80.634(2) _cell_angle_gamma 66.5696(18) _cell_volume 1188.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 6240 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 26.37 _exptl_crystal_description prism _exptl_crystal_colour purple _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.23 _exptl_crystal_density_diffrn 1.275 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.8662 _exptl_absorpt_correction_T_max 0.9802 _exptl_absorpt_process_details 'Bruker SHELXTL (Bruker, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker PLATFORM diffractometer/SMART 1000 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 9195 _diffrn_reflns_av_R_equivalents 0.0224 _diffrn_reflns_av_sigmaI/netI 0.0329 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 26.42 _reflns_number_total 4822 _reflns_number_gt 4069 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART (Bruker, 1997)' _computing_cell_refinement 'Bruker SAINT (Bruker, 1997)' _computing_data_reduction 'Bruker SAINT (Bruker, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL (Bruker, 1997)' _computing_publication_material 'Bruker SHELXTL (Bruker, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0546P)^2^+0.2623P] 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 4822 _refine_ls_number_parameters 311 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0468 _refine_ls_R_factor_gt 0.0394 _refine_ls_wR_factor_ref 0.1117 _refine_ls_wR_factor_gt 0.1059 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _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 0.29089(9) 0.08721(8) 0.41375(7) 0.0306(2) Uani 1 1 d . . . O2 O 0.04384(11) 0.18331(10) 0.47049(9) 0.0485(3) Uani 1 1 d . . . O3 O 0.44287(9) 0.14221(8) 0.27656(7) 0.0294(2) Uani 1 1 d . . . O4 O 0.39193(11) 0.30545(10) 0.15167(8) 0.0419(2) Uani 1 1 d . . . N1 N 0.11621(11) 0.43513(10) 0.32983(9) 0.0302(2) Uani 1 1 d . . . N2 N 0.21971(11) 0.33547(10) 0.37034(8) 0.0282(2) Uani 1 1 d . . . N3 N 0.07881(11) 0.28578(10) 0.21186(9) 0.0301(2) Uani 1 1 d . . . N4 N 0.18356(11) 0.17955(10) 0.24563(8) 0.0287(2) Uani 1 1 d . . . C1 C 0.05275(13) 0.40891(12) 0.25145(10) 0.0294(3) Uani 1 1 d . . . C2 C 0.16471(15) 0.09653(13) 0.47869(11) 0.0341(3) Uani 1 1 d . . . C3 C 0.19155(19) -0.01393(17) 0.56073(13) 0.0510(4) Uani 1 1 d . . . H3A H 0.1074 0.0135 0.6208 0.061 Uiso 1 1 calc R . . H3B H 0.2839 -0.0293 0.5888 0.061 Uiso 1 1 calc R . . H3C H 0.2009 -0.0984 0.5264 0.061 Uiso 1 1 calc R . . C4 C 0.48066(14) 0.20906(13) 0.19131(10) 0.0311(3) Uani 1 1 d . . . C5 C 0.64569(16) 0.15035(16) 0.15116(13) 0.0467(4) Uani 1 1 d . . . H5A H 0.6726 0.2178 0.1069 0.056 Uiso 1 1 calc R . . H5B H 0.6724 0.0679 0.1070 0.056 Uiso 1 1 calc R . . H5C H 0.6999 0.1270 0.2133 0.056 Uiso 1 1 calc R . . C11 C -0.06087(13) 0.52798(13) 0.20671(11) 0.0308(3) Uani 1 1 d . . . C12 C -0.11376(16) 0.65725(14) 0.25516(12) 0.0404(3) Uani 1 1 d . . . H12 H -0.0781 0.6694 0.3186 0.048 Uiso 1 1 calc R . . C13 C -0.21794(18) 0.76783(15) 0.21111(14) 0.0486(4) Uani 1 1 d . . . H13 H -0.2545 0.8554 0.2452 0.058 Uiso 1 1 calc R . . C14 C -0.26963(17) 0.75244(15) 0.11798(14) 0.0467(4) Uani 1 1 d . . . H14 H -0.3392 0.8294 0.0870 0.056 Uiso 1 1 calc R . . C15 C -0.21943(17) 0.62460(16) 0.07047(14) 0.0479(4) Uani 1 1 d . . . H15 H -0.2556 0.6128 0.0072 0.057 Uiso 1 1 calc R . . C16 C -0.11643(16) 0.51354(14) 0.11486(12) 0.0408(3) Uani 1 1 d . . . H16 H -0.0830 0.4257 0.0819 0.049 Uiso 1 1 calc R . . C21 C 0.27455(14) 0.37654(13) 0.45625(10) 0.0293(3) Uani 1 1 d . . . C22 C 0.20806(15) 0.51162(13) 0.49472(11) 0.0340(3) Uani 1 1 d . . . H22 H 0.1228 0.5749 0.4672 0.041 Uiso 1 1 calc R . . C23 C 0.26647(16) 0.55296(14) 0.57273(11) 0.0372(3) Uani 1 1 d . . . H23 H 0.2203 0.6452 0.5982 0.045 Uiso 1 1 calc R . . C24 C 0.39078(15) 0.46393(14) 0.61520(11) 0.0356(3) Uani 1 1 d . . . C25 C 0.45430(15) 0.32885(15) 0.57758(12) 0.0378(3) Uani 1 1 d . . . H25 H 0.5384 0.2655 0.6063 0.045 Uiso 1 1 calc R . . C26 C 0.39769(15) 0.28478(13) 0.49925(11) 0.0344(3) Uani 1 1 d . . . H26 H 0.4428 0.1921 0.4748 0.041 Uiso 1 1 calc R . . C27 C 0.45288(19) 0.51286(17) 0.69926(13) 0.0468(4) Uani 1 1 d . . . H27A H 0.5589 0.4538 0.6970 0.056 Uiso 1 1 calc R . . H27B H 0.3980 0.5096 0.7716 0.056 Uiso 1 1 calc R . . H27C H 0.4422 0.6070 0.6841 0.056 Uiso 1 1 calc R . . C31 C 0.19420(14) 0.05160(12) 0.20617(10) 0.0304(3) Uani 1 1 d . . . C32 C 0.07333(15) 0.04154(14) 0.16931(12) 0.0393(3) Uani 1 1 d . . . H32 H -0.0169 0.1202 0.1692 0.047 Uiso 1 1 calc R . . C33 C 0.08465(17) -0.08342(15) 0.13272(13) 0.0440(3) Uani 1 1 d . . . H33 H 0.0011 -0.0894 0.1082 0.053 Uiso 1 1 calc R . . C34 C 0.21480(17) -0.19996(14) 0.13104(12) 0.0392(3) Uani 1 1 d . . . C35 C 0.33508(17) -0.18723(14) 0.16647(13) 0.0435(3) Uani 1 1 d . . . H35 H 0.4262 -0.2654 0.1646 0.052 Uiso 1 1 calc R . . C36 C 0.32595(16) -0.06388(14) 0.20452(13) 0.0398(3) Uani 1 1 d . . . H36 H 0.4094 -0.0582 0.2294 0.048 Uiso 1 1 calc R . . C37 C 0.2267(2) -0.33617(16) 0.09244(15) 0.0542(4) Uani 1 1 d . . . H37A H 0.1383 -0.3236 0.0600 0.065 Uiso 1 1 calc R . . H37B H 0.2330 -0.3974 0.1542 0.065 Uiso 1 1 calc R . . H37C H 0.3167 -0.3763 0.0380 0.065 Uiso 1 1 calc R . . B1 B 0.28580(15) 0.18447(14) 0.32713(12) 0.0281(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0302(4) 0.0265(4) 0.0328(5) 0.0041(4) -0.0069(4) -0.0084(4) O2 0.0340(5) 0.0394(6) 0.0612(7) 0.0087(5) 0.0008(5) -0.0072(4) O3 0.0272(4) 0.0276(4) 0.0312(5) 0.0033(3) -0.0067(3) -0.0079(3) O4 0.0396(5) 0.0418(6) 0.0418(6) 0.0136(4) -0.0129(4) -0.0125(4) N1 0.0270(5) 0.0259(5) 0.0344(6) 0.0030(4) -0.0069(4) -0.0064(4) N2 0.0266(5) 0.0257(5) 0.0310(5) 0.0028(4) -0.0068(4) -0.0084(4) N3 0.0267(5) 0.0275(5) 0.0341(6) 0.0037(4) -0.0080(4) -0.0077(4) N4 0.0268(5) 0.0247(5) 0.0330(6) 0.0019(4) -0.0070(4) -0.0078(4) C1 0.0269(6) 0.0275(6) 0.0325(6) 0.0017(5) -0.0059(5) -0.0091(5) C2 0.0353(7) 0.0289(6) 0.0364(7) -0.0001(5) -0.0039(5) -0.0115(5) C3 0.0513(9) 0.0477(9) 0.0482(9) 0.0147(7) -0.0018(7) -0.0171(7) C4 0.0330(6) 0.0299(6) 0.0305(6) 0.0006(5) -0.0073(5) -0.0117(5) C5 0.0368(8) 0.0455(8) 0.0488(9) 0.0071(7) 0.0023(6) -0.0110(7) C11 0.0252(6) 0.0284(6) 0.0364(7) 0.0048(5) -0.0054(5) -0.0082(5) C12 0.0427(8) 0.0306(7) 0.0436(8) 0.0021(6) -0.0132(6) -0.0076(6) C13 0.0501(9) 0.0290(7) 0.0574(10) 0.0032(6) -0.0128(7) -0.0044(6) C14 0.0378(8) 0.0363(8) 0.0584(10) 0.0144(7) -0.0183(7) -0.0041(6) C15 0.0442(8) 0.0454(8) 0.0524(9) 0.0076(7) -0.0236(7) -0.0106(7) C16 0.0397(7) 0.0336(7) 0.0464(8) 0.0013(6) -0.0169(6) -0.0080(6) C21 0.0285(6) 0.0298(6) 0.0305(6) 0.0006(5) -0.0044(5) -0.0124(5) C22 0.0323(6) 0.0293(6) 0.0374(7) 0.0004(5) -0.0063(5) -0.0086(5) C23 0.0417(7) 0.0332(7) 0.0376(7) -0.0027(6) -0.0046(6) -0.0161(6) C24 0.0391(7) 0.0423(7) 0.0315(7) 0.0012(6) -0.0053(5) -0.0227(6) C25 0.0349(7) 0.0413(7) 0.0379(7) 0.0039(6) -0.0120(6) -0.0138(6) C26 0.0333(7) 0.0306(6) 0.0371(7) 0.0001(5) -0.0088(5) -0.0089(5) C27 0.0566(9) 0.0522(9) 0.0425(8) 0.0010(7) -0.0147(7) -0.0304(8) C31 0.0330(6) 0.0265(6) 0.0317(6) 0.0010(5) -0.0068(5) -0.0113(5) C32 0.0335(7) 0.0339(7) 0.0508(8) 0.0001(6) -0.0109(6) -0.0119(6) C33 0.0444(8) 0.0414(8) 0.0544(9) -0.0011(7) -0.0139(7) -0.0229(7) C34 0.0509(8) 0.0328(7) 0.0368(7) 0.0010(6) -0.0058(6) -0.0200(6) C35 0.0443(8) 0.0271(7) 0.0548(9) -0.0019(6) -0.0135(7) -0.0073(6) C36 0.0364(7) 0.0303(7) 0.0519(8) -0.0018(6) -0.0151(6) -0.0091(6) C37 0.0698(11) 0.0381(8) 0.0611(10) -0.0044(7) -0.0110(9) -0.0273(8) B1 0.0265(6) 0.0243(6) 0.0309(7) 0.0023(5) -0.0078(5) -0.0063(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.3405(16) . ? O1 B1 1.4556(16) . ? O2 C2 1.2013(16) . ? O3 C4 1.3380(15) . ? O3 B1 1.4683(16) . ? O4 C4 1.2027(15) . ? N1 N2 1.2976(14) . ? N1 C1 1.3376(16) . ? N2 C21 1.4327(16) . ? N2 B1 1.5623(16) . ? N3 N4 1.3025(14) . ? N3 C1 1.3361(16) . ? N4 C31 1.4310(16) . ? N4 B1 1.5601(17) . ? C1 C11 1.4791(17) . ? C2 C3 1.4947(19) . ? C4 C5 1.4992(19) . ? C11 C16 1.3869(19) . ? C11 C12 1.3932(18) . ? C12 C13 1.3821(19) . ? C13 C14 1.383(2) . ? C14 C15 1.378(2) . ? C15 C16 1.382(2) . ? C21 C26 1.3930(18) . ? C21 C22 1.3952(17) . ? C22 C23 1.3772(19) . ? C23 C24 1.388(2) . ? C24 C25 1.3921(19) . ? C24 C27 1.5035(19) . ? C25 C26 1.3841(19) . ? C31 C36 1.3887(18) . ? C31 C32 1.3893(18) . ? C32 C33 1.385(2) . ? C33 C34 1.386(2) . ? C34 C35 1.388(2) . ? C34 C37 1.5058(19) . ? C35 C36 1.3836(19) . ? 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 C2 O1 B1 120.10(10) . . ? C4 O3 B1 120.41(9) . . ? N2 N1 C1 119.60(10) . . ? N1 N2 C21 114.04(10) . . ? N1 N2 B1 123.87(10) . . ? C21 N2 B1 122.03(10) . . ? N4 N3 C1 118.33(10) . . ? N3 N4 C31 114.19(10) . . ? N3 N4 B1 125.03(10) . . ? C31 N4 B1 120.69(10) . . ? N3 C1 N1 126.47(11) . . ? N3 C1 C11 116.92(11) . . ? N1 C1 C11 116.59(11) . . ? O2 C2 O1 123.41(12) . . ? O2 C2 C3 124.19(13) . . ? O1 C2 C3 112.40(12) . . ? O4 C4 O3 123.63(12) . . ? O4 C4 C5 123.99(12) . . ? O3 C4 C5 112.38(11) . . ? C16 C11 C12 118.45(12) . . ? C16 C11 C1 120.63(12) . . ? C12 C11 C1 120.92(12) . . ? C13 C12 C11 120.14(14) . . ? C12 C13 C14 120.75(14) . . ? C15 C14 C13 119.44(13) . . ? C14 C15 C16 119.99(14) . . ? C15 C16 C11 121.21(13) . . ? C26 C21 C22 119.19(12) . . ? C26 C21 N2 120.92(11) . . ? C22 C21 N2 119.84(11) . . ? C23 C22 C21 119.78(12) . . ? C22 C23 C24 122.00(13) . . ? C23 C24 C25 117.61(12) . . ? C23 C24 C27 120.63(13) . . ? C25 C24 C27 121.75(13) . . ? C26 C25 C24 121.49(12) . . ? C25 C26 C21 119.91(12) . . ? C36 C31 C32 119.41(12) . . ? C36 C31 N4 120.08(11) . . ? C32 C31 N4 120.51(11) . . ? C33 C32 C31 119.84(13) . . ? C32 C33 C34 121.62(13) . . ? C33 C34 C35 117.63(13) . . ? C33 C34 C37 121.68(14) . . ? C35 C34 C37 120.69(13) . . ? C36 C35 C34 121.81(13) . . ? C35 C36 C31 119.67(13) . . ? O1 B1 O3 103.77(9) . . ? O1 B1 N4 111.12(10) . . ? O3 B1 N4 112.63(10) . . ? O1 B1 N2 112.69(10) . . ? O3 B1 N2 111.00(10) . . ? N4 B1 N2 105.80(9) . . ? 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 N1 N2 C21 -177.85(11) . . . . ? C1 N1 N2 B1 4.89(18) . . . . ? C1 N3 N4 C31 174.73(11) . . . . ? C1 N3 N4 B1 -1.89(17) . . . . ? N4 N3 C1 N1 -5.44(19) . . . . ? N4 N3 C1 C11 176.58(11) . . . . ? N2 N1 C1 N3 3.92(19) . . . . ? N2 N1 C1 C11 -178.09(11) . . . . ? B1 O1 C2 O2 -0.64(19) . . . . ? B1 O1 C2 C3 178.55(12) . . . . ? B1 O3 C4 O4 0.29(18) . . . . ? B1 O3 C4 C5 -179.79(12) . . . . ? N3 C1 C11 C16 -11.42(18) . . . . ? N1 C1 C11 C16 170.40(12) . . . . ? N3 C1 C11 C12 169.08(12) . . . . ? N1 C1 C11 C12 -9.11(19) . . . . ? C16 C11 C12 C13 -0.7(2) . . . . ? C1 C11 C12 C13 178.82(13) . . . . ? C11 C12 C13 C14 -0.9(2) . . . . ? C12 C13 C14 C15 1.7(3) . . . . ? C13 C14 C15 C16 -1.1(3) . . . . ? C14 C15 C16 C11 -0.5(2) . . . . ? C12 C11 C16 C15 1.4(2) . . . . ? C1 C11 C16 C15 -178.15(14) . . . . ? N1 N2 C21 C26 -172.28(11) . . . . ? B1 N2 C21 C26 5.04(18) . . . . ? N1 N2 C21 C22 5.06(16) . . . . ? B1 N2 C21 C22 -177.62(11) . . . . ? C26 C21 C22 C23 1.26(19) . . . . ? N2 C21 C22 C23 -176.13(12) . . . . ? C21 C22 C23 C24 0.0(2) . . . . ? C22 C23 C24 C25 -1.1(2) . . . . ? C22 C23 C24 C27 179.21(13) . . . . ? C23 C24 C25 C26 1.1(2) . . . . ? C27 C24 C25 C26 -179.24(14) . . . . ? C24 C25 C26 C21 0.1(2) . . . . ? C22 C21 C26 C25 -1.3(2) . . . . ? N2 C21 C26 C25 176.08(12) . . . . ? N3 N4 C31 C36 158.76(12) . . . . ? B1 N4 C31 C36 -24.46(18) . . . . ? N3 N4 C31 C32 -21.29(17) . . . . ? B1 N4 C31 C32 155.50(12) . . . . ? C36 C31 C32 C33 0.8(2) . . . . ? N4 C31 C32 C33 -179.13(13) . . . . ? C31 C32 C33 C34 -0.4(2) . . . . ? C32 C33 C34 C35 -0.6(2) . . . . ? C32 C33 C34 C37 179.32(15) . . . . ? C33 C34 C35 C36 1.4(2) . . . . ? C37 C34 C35 C36 -178.59(15) . . . . ? C34 C35 C36 C31 -1.0(2) . . . . ? C32 C31 C36 C35 -0.1(2) . . . . ? N4 C31 C36 C35 179.84(13) . . . . ? C2 O1 B1 O3 179.30(10) . . . . ? C2 O1 B1 N4 -59.41(14) . . . . ? C2 O1 B1 N2 59.13(14) . . . . ? C4 O3 B1 O1 179.06(10) . . . . ? C4 O3 B1 N4 58.80(14) . . . . ? C4 O3 B1 N2 -59.64(14) . . . . ? N3 N4 B1 O1 131.01(12) . . . . ? C31 N4 B1 O1 -45.41(15) . . . . ? N3 N4 B1 O3 -113.05(12) . . . . ? C31 N4 B1 O3 70.53(14) . . . . ? N3 N4 B1 N2 8.39(16) . . . . ? C31 N4 B1 N2 -168.03(10) . . . . ? N1 N2 B1 O1 -131.47(12) . . . . ? C21 N2 B1 O1 51.48(15) . . . . ? N1 N2 B1 O3 112.63(12) . . . . ? C21 N2 B1 O3 -64.42(14) . . . . ? N1 N2 B1 N4 -9.86(15) . . . . ? C21 N2 B1 N4 173.09(10) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 26.42 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.230 _refine_diff_density_min -0.196 _refine_diff_density_rms 0.040