# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Xianhui Bu' _publ_contact_author_email XBU@CSULB.EDU _publ_section_title ; Hydrogen-Bonded Boron Imidazolate Frameworks ; loop_ _publ_author_name 'Xianhui Bu' 'Pingyun Feng' 'Tao Wu' 'Jian Zhang' # Attachment 'compounds.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 738772' #TrackingRef 'compounds.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H24 B Li N8 O4' _chemical_formula_weight 458.22 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 0.0000 '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' Li Li -0.0003 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M I-4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'y, -x, -z' '-y, x, -z' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' 'y+1/2, -x+1/2, -z+1/2' '-y+1/2, x+1/2, -z+1/2' _cell_length_a 10.1374(9) _cell_length_b 10.1374(9) _cell_length_c 24.286(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2495.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1443 _cell_measurement_theta_min 2.84 _cell_measurement_theta_max 24.42 _exptl_crystal_description diamond _exptl_crystal_colour colorless _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.219 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5590 _diffrn_reflns_av_R_equivalents 0.0419 _diffrn_reflns_av_sigmaI/netI 0.0331 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 25.11 _reflns_number_total 1146 _reflns_number_gt 939 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1004P)^2^+0.5888P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 10(10) _refine_ls_number_reflns 1146 _refine_ls_number_parameters 161 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0663 _refine_ls_R_factor_gt 0.0510 _refine_ls_wR_factor_ref 0.1528 _refine_ls_wR_factor_gt 0.1397 _refine_ls_goodness_of_fit_ref 1.143 _refine_ls_restrained_S_all 1.143 _refine_ls_shift/su_max 0.012 _refine_ls_shift/su_mean 0.002 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 0.5886(4) -0.3626(4) -0.24013(16) 0.0490(10) Uani 1 1 d . . . H1O H 0.568(7) -0.328(7) -0.210(3) 0.073 Uiso 1 1 d . . . O2 O 0.3288(3) -0.4771(3) -0.31778(13) 0.0364(8) Uani 1 1 d . . . H2O H 0.315(6) -0.445(6) -0.353(3) 0.055 Uiso 1 1 d . . . B1 B 0.5000 0.0000 -0.0330(2) 0.0230(14) Uani 1 2 d S . . Li1 Li 0.5000 -0.5000 -0.2800(4) 0.037(3) Uani 1 2 d S . . N1 N 0.5020(3) -0.1247(3) -0.07026(13) 0.0239(8) Uani 1 1 d . . . N2 N 0.5427(4) -0.2598(4) -0.14038(16) 0.0337(9) Uani 1 1 d . . . N3 N 0.7556(4) 0.0411(4) 0.07603(14) 0.0291(9) Uani 1 1 d . . . N4 N 0.6233(3) 0.0023(3) 0.00458(14) 0.0230(8) Uani 1 1 d . . . C1 C 0.7279(5) -0.3835(7) -0.2440(3) 0.070(2) Uani 1 1 d . . . C2 C 0.2421(6) -0.5815(6) -0.3017(2) 0.0565(16) Uani 1 1 d . . . C3 C 0.4466(5) -0.3140(5) -0.1079(2) 0.0350(11) Uani 1 1 d . . . H3A H 0.4056 -0.3947 -0.1142 0.042 Uiso 1 1 calc R . . C4 C 0.6731(5) -0.0536(5) -0.14103(19) 0.0342(11) Uani 1 1 d . . . H4A H 0.7101 -0.0914 -0.1738 0.051 Uiso 1 1 calc R . . H4B H 0.7421 -0.0380 -0.1147 0.051 Uiso 1 1 calc R . . H4C H 0.6307 0.0284 -0.1499 0.051 Uiso 1 1 calc R . . C5 C 0.4204(4) -0.2322(4) -0.06527(17) 0.0291(10) Uani 1 1 d . . . H5A H 0.3585 -0.2462 -0.0376 0.035 Uiso 1 1 calc R . . C6 C 0.5529(5) 0.1764(5) 0.07398(18) 0.0328(11) Uani 1 1 d . . . H6A H 0.5888 0.2117 0.1074 0.049 Uiso 1 1 calc R . . H6B H 0.4682 0.1378 0.0814 0.049 Uiso 1 1 calc R . . H6C H 0.5431 0.2459 0.0475 0.049 Uiso 1 1 calc R . . C7 C 0.7312(4) -0.0810(4) 0.00052(17) 0.0269(9) Uani 1 1 d . . . H7A H 0.7464 -0.1427 -0.0271 0.032 Uiso 1 1 calc R . . C8 C 0.8099(5) -0.0561(5) 0.04378(18) 0.0319(11) Uani 1 1 d . . . H8A H 0.8895 -0.0985 0.0509 0.038 Uiso 1 1 calc R . . C9 C 0.6439(4) 0.0732(4) 0.05164(17) 0.0256(9) Uani 1 1 d . . . C10 C 0.5749(4) -0.1458(4) -0.11723(17) 0.0275(10) 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 0.0378(19) 0.068(3) 0.041(2) -0.0308(19) 0.0047(16) -0.0014(18) O2 0.0403(19) 0.044(2) 0.0253(16) 0.0109(16) -0.0089(14) -0.0122(16) B1 0.030(4) 0.022(4) 0.017(3) 0.000 0.000 0.006(3) Li1 0.040(6) 0.044(7) 0.026(6) 0.000 0.000 -0.001(5) N1 0.026(2) 0.026(2) 0.0197(17) -0.0005(14) 0.0025(14) -0.0015(16) N2 0.032(2) 0.038(2) 0.031(2) -0.0108(18) 0.0021(18) -0.0008(18) N3 0.031(2) 0.032(2) 0.0247(18) 0.0045(16) -0.0044(15) -0.0028(18) N4 0.027(2) 0.023(2) 0.0186(16) 0.0007(14) 0.0006(14) 0.0022(16) C1 0.035(3) 0.108(6) 0.068(4) -0.052(4) 0.013(3) -0.013(3) C2 0.051(3) 0.065(4) 0.053(3) 0.033(3) -0.009(3) -0.019(3) C3 0.038(3) 0.029(3) 0.038(3) -0.006(2) 0.000(2) -0.001(2) C4 0.033(3) 0.041(3) 0.029(2) -0.006(2) 0.006(2) -0.003(2) C5 0.031(2) 0.032(3) 0.025(2) 0.0005(18) 0.0065(19) -0.002(2) C6 0.036(3) 0.035(3) 0.027(2) -0.0067(19) 0.0003(19) 0.002(2) C7 0.029(2) 0.029(2) 0.023(2) 0.0009(18) 0.0036(18) 0.0023(19) C8 0.025(2) 0.037(3) 0.034(2) 0.009(2) -0.0040(19) 0.004(2) C9 0.028(2) 0.030(2) 0.019(2) 0.0051(18) -0.0025(17) -0.0036(19) C10 0.025(2) 0.035(3) 0.023(2) -0.0032(18) -0.0008(17) 0.0044(19) _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 C1 1.432(7) . ? O1 Li1 1.920(6) . ? O1 H1O 0.83(7) . ? O2 C2 1.430(6) . ? O2 Li1 1.976(5) . ? O2 H2O 0.92(7) . ? B1 N4 1.548(5) . ? B1 N4 1.548(5) 2_655 ? B1 N1 1.555(5) . ? B1 N1 1.555(5) 2_655 ? Li1 O1 1.920(6) 2_645 ? Li1 O2 1.976(5) 2_645 ? Li1 C1 2.738(6) . ? Li1 C1 2.738(6) 2_645 ? N1 C5 1.373(6) . ? N1 C10 1.376(5) . ? N2 C10 1.325(6) . ? N2 C3 1.370(6) . ? N3 C9 1.319(6) . ? N3 C8 1.374(6) . ? N4 C9 1.366(5) . ? N4 C7 1.386(5) . ? C1 C2 1.477(8) 2_645 ? C2 C1 1.477(8) 2_645 ? C3 C5 1.352(7) . ? C3 H3A 0.9300 . ? C4 C10 1.483(6) . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 H5A 0.9300 . ? C6 C9 1.497(6) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 C8 1.343(6) . ? C7 H7A 0.9300 . ? C8 H8A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 Li1 108.7(3) . . ? C1 O1 H1O 111(5) . . ? Li1 O1 H1O 129(5) . . ? C2 O2 Li1 109.1(3) . . ? C2 O2 H2O 115(4) . . ? Li1 O2 H2O 127(4) . . ? N4 B1 N4 107.7(4) . 2_655 ? N4 B1 N1 110.18(18) . . ? N4 B1 N1 109.96(18) 2_655 . ? N4 B1 N1 109.96(18) . 2_655 ? N4 B1 N1 110.18(18) 2_655 2_655 ? N1 B1 N1 108.9(4) . 2_655 ? O1 Li1 O1 119.3(5) . 2_645 ? O1 Li1 O2 84.75(14) . 2_645 ? O1 Li1 O2 124.04(15) 2_645 2_645 ? O1 Li1 O2 124.04(15) . . ? O1 Li1 O2 84.75(14) 2_645 . ? O2 Li1 O2 124.7(5) 2_645 . ? O1 Li1 C1 29.68(17) . . ? O1 Li1 C1 123.1(4) 2_645 . ? O2 Li1 C1 57.17(15) 2_645 . ? O2 Li1 C1 147.0(2) . . ? O1 Li1 C1 123.1(4) . 2_645 ? O1 Li1 C1 29.68(17) 2_645 2_645 ? O2 Li1 C1 147.0(2) 2_645 2_645 ? O2 Li1 C1 57.17(15) . 2_645 ? C1 Li1 C1 142.7(5) . 2_645 ? C5 N1 C10 105.8(4) . . ? C5 N1 B1 125.9(3) . . ? C10 N1 B1 128.0(3) . . ? C10 N2 C3 106.3(4) . . ? C9 N3 C8 105.4(4) . . ? C9 N4 C7 105.0(3) . . ? C9 N4 B1 128.7(3) . . ? C7 N4 B1 125.9(3) . . ? O1 C1 C2 107.5(5) . 2_645 ? O1 C1 Li1 41.6(2) . . ? C2 C1 Li1 76.5(4) 2_645 . ? O2 C2 C1 108.1(5) . 2_645 ? C5 C3 N2 109.5(4) . . ? C5 C3 H3A 125.2 . . ? N2 C3 H3A 125.2 . . ? C10 C4 H4A 109.5 . . ? C10 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C10 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C3 C5 N1 107.5(4) . . ? C3 C5 H5A 126.2 . . ? N1 C5 H5A 126.2 . . ? C9 C6 H6A 109.5 . . ? C9 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C9 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C8 C7 N4 107.4(4) . . ? C8 C7 H7A 126.3 . . ? N4 C7 H7A 126.3 . . ? C7 C8 N3 110.0(4) . . ? C7 C8 H8A 125.0 . . ? N3 C8 H8A 125.0 . . ? N3 C9 N4 112.2(4) . . ? N3 C9 C6 122.6(4) . . ? N4 C9 C6 125.2(4) . . ? N2 C10 N1 110.8(4) . . ? N2 C10 C4 123.3(4) . . ? N1 C10 C4 125.8(4) . . ? 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 O1 H1O N2 0.83(7) 1.85(7) 2.678(5) 173(7) . O2 H2O N3 0.92(7) 1.84(7) 2.690(5) 153(5) 5_444 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.11 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.372 _refine_diff_density_min -0.247 _refine_diff_density_rms 0.067 #end data_2 _database_code_depnum_ccdc_archive 'CCDC 738773' #TrackingRef 'compounds.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H27 B Li N9 O3' _chemical_formula_weight 435.24 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 0.0000 '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' Li Li -0.0003 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 7.44740(10) _cell_length_b 10.1434(2) _cell_length_c 30.0269(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2268.29(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3173 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 18.64 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.274 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 920 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16895 _diffrn_reflns_av_R_equivalents 0.0491 _diffrn_reflns_av_sigmaI/netI 0.0385 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2295 _reflns_number_gt 1629 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0536P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0054(10) _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 -10(10) _refine_ls_number_reflns 2295 _refine_ls_number_parameters 290 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0699 _refine_ls_R_factor_gt 0.0379 _refine_ls_wR_factor_ref 0.0961 _refine_ls_wR_factor_gt 0.0827 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _refine_ls_shift/su_max 0.008 _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 Li1 Li 0.3099(7) 0.1154(5) 0.08767(17) 0.0461(13) Uani 1 1 d . . . B1 B 0.7687(5) 0.4741(3) 0.17788(11) 0.0407(9) Uani 1 1 d . . . N1 N 0.1706(4) -0.0067(2) 0.03214(8) 0.0477(7) Uani 1 1 d . . . N2 N 0.9396(4) 0.5045(3) 0.29480(9) 0.0619(8) Uani 1 1 d . . . N3 N 0.4617(4) 0.2118(2) 0.13766(8) 0.0528(7) Uani 1 1 d . . . N4 N 1.0983(4) 0.4414(3) 0.08537(9) 0.0619(8) Uani 1 1 d . . . N5 N 0.6442(4) 0.5956(2) 0.17354(8) 0.0425(6) Uani 1 1 d . . . N6 N 0.8648(4) 0.4708(2) 0.22369(8) 0.0439(6) Uani 1 1 d . . . N7 N 0.6573(3) 0.3484(2) 0.17079(7) 0.0390(6) Uani 1 1 d . . . N8 N 0.9180(3) 0.4846(2) 0.14266(8) 0.0409(6) Uani 1 1 d . . . N9 N 0.5246(4) 0.7798(3) 0.14542(11) 0.0665(8) Uani 1 1 d . . . C1 C 0.4690(6) -0.1053(4) 0.03871(12) 0.0755(12) Uani 1 1 d . . . H1A H 0.5300 -0.1895 0.0410 0.091 Uiso 1 1 calc R . . H1B H 0.5235 -0.0563 0.0145 0.091 Uiso 1 1 calc R . . C2 C 0.1615(5) 0.2196(3) 0.00413(12) 0.0598(10) Uani 1 1 d . . . H2A H 0.1875 0.2736 -0.0217 0.072 Uiso 1 1 calc R . . H2B H 0.0382 0.2358 0.0130 0.072 Uiso 1 1 calc R . . C3 C -0.0195(5) -0.0389(4) 0.09750(11) 0.0680(11) Uani 1 1 d . . . H3A H -0.1433 -0.0375 0.1076 0.082 Uiso 1 1 calc R . . H3B H 0.0341 -0.1218 0.1065 0.082 Uiso 1 1 calc R . . C4 C -0.0121(5) -0.0252(4) 0.04792(11) 0.0649(10) Uani 1 1 d . . . H4A H -0.0624 -0.1037 0.0343 0.078 Uiso 1 1 calc R . . H4B H -0.0848 0.0495 0.0389 0.078 Uiso 1 1 calc R . . C5 C 0.1849(5) 0.0774(3) -0.00737(10) 0.0625(10) Uani 1 1 d . . . H5A H 0.0939 0.0518 -0.0288 0.075 Uiso 1 1 calc R . . H5B H 0.3015 0.0647 -0.0211 0.075 Uiso 1 1 calc R . . C6 C 0.2729(5) -0.1283(3) 0.02843(13) 0.0693(11) Uani 1 1 d . . . H6A H 0.2612 -0.1631 -0.0015 0.083 Uiso 1 1 calc R . . H6B H 0.2247 -0.1931 0.0490 0.083 Uiso 1 1 calc R . . C8 C 1.0163(5) 0.3985(3) 0.23279(10) 0.0600(10) Uani 1 1 d . . . H8A H 1.0778 0.3447 0.2129 0.072 Uiso 1 1 calc R . . C9 C 0.9575(5) 0.4031(3) 0.10874(10) 0.0507(9) Uani 1 1 d . . . H9A H 0.8922 0.3272 0.1024 0.061 Uiso 1 1 calc R . . C10 C 0.4990(5) 0.6299(3) 0.19933(11) 0.0595(9) Uani 1 1 d . . . H10A H 0.4561 0.5839 0.2239 0.071 Uiso 1 1 calc R . . C11 C 1.0494(5) 0.5802(3) 0.14092(12) 0.0572(9) Uani 1 1 d . . . H11A H 1.0626 0.6505 0.1605 0.069 Uiso 1 1 calc R . . C12 C 1.1546(5) 0.5536(3) 0.10599(12) 0.0586(9) Uani 1 1 d . . . H12A H 1.2521 0.6044 0.0971 0.070 Uiso 1 1 calc R . . C13 C 1.0601(5) 0.4198(3) 0.27594(11) 0.0627(10) Uani 1 1 d . . . H13A H 1.1576 0.3822 0.2906 0.075 Uiso 1 1 calc R . . C14 C 0.4300(5) 0.7422(3) 0.18259(13) 0.0670(11) Uani 1 1 d . . . H14A H 0.3326 0.7876 0.1944 0.080 Uiso 1 1 calc R . . C15 C 0.6888(5) 0.2231(3) 0.18613(10) 0.0500(9) Uani 1 1 d . . . H15A H 0.7760 0.1985 0.2067 0.060 Uiso 1 1 calc R . . C16 C 0.6500(5) 0.6889(3) 0.14164(11) 0.0526(9) Uani 1 1 d . . . H16A H 0.7350 0.6891 0.1190 0.063 Uiso 1 1 calc R . . C17 C 0.5710(5) 0.1424(3) 0.16607(10) 0.0533(9) Uani 1 1 d . . . H17A H 0.5643 0.0519 0.1708 0.064 Uiso 1 1 calc R . . C18 C 0.8266(5) 0.5326(3) 0.26240(10) 0.0520(9) Uani 1 1 d . . . H18A H 0.7297 0.5896 0.2659 0.062 Uiso 1 1 calc R . . C19 C 0.5188(4) 0.3336(3) 0.14190(10) 0.0503(9) Uani 1 1 d . . . H19A H 0.4685 0.4038 0.1264 0.060 Uiso 1 1 calc R . . O1 O 0.4909(3) -0.0348(2) 0.07883(8) 0.0679(7) Uani 1 1 d . . . H1O H 0.4953 -0.0867 0.0997 0.081 Uiso 1 1 calc R . . O2 O 0.2785(3) 0.2538(2) 0.03934(6) 0.0503(6) Uani 1 1 d . . . H2O H 0.2457 0.3236 0.0505 0.060 Uiso 1 1 calc R . . O3 O 0.0767(3) 0.0683(2) 0.11651(7) 0.0604(7) Uani 1 1 d . . . H3O H 0.0658 0.0665 0.1437 0.072 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Li1 0.042(3) 0.046(3) 0.051(3) -0.004(2) -0.001(3) -0.007(2) B1 0.044(2) 0.0355(18) 0.042(2) -0.0065(16) -0.0064(18) 0.0000(17) N1 0.0463(18) 0.0508(16) 0.0458(16) -0.0049(13) -0.0007(13) -0.0016(14) N2 0.063(2) 0.078(2) 0.0451(15) -0.0048(15) -0.0114(17) -0.0057(18) N3 0.0516(17) 0.0427(15) 0.0640(17) -0.0011(14) -0.0170(16) -0.0043(14) N4 0.067(2) 0.063(2) 0.0562(18) -0.0026(15) 0.0106(17) 0.0049(17) N5 0.0446(16) 0.0370(14) 0.0460(15) -0.0017(13) -0.0035(13) 0.0045(13) N6 0.0481(17) 0.0413(13) 0.0422(14) -0.0067(12) -0.0080(13) 0.0015(14) N7 0.0424(16) 0.0345(13) 0.0400(14) -0.0008(11) -0.0081(13) 0.0026(12) N8 0.0430(15) 0.0379(13) 0.0420(14) -0.0060(12) -0.0046(13) 0.0005(12) N9 0.062(2) 0.0459(16) 0.091(2) 0.0007(17) -0.012(2) 0.0098(16) C1 0.074(3) 0.072(2) 0.081(3) -0.021(2) -0.008(2) 0.026(2) C2 0.056(2) 0.067(2) 0.057(2) 0.0062(18) -0.006(2) -0.004(2) C3 0.064(2) 0.077(2) 0.063(2) 0.002(2) 0.004(2) -0.026(2) C4 0.055(2) 0.081(2) 0.059(2) -0.0128(19) -0.003(2) -0.019(2) C5 0.068(2) 0.077(3) 0.0421(19) -0.0002(18) -0.0069(18) -0.005(2) C6 0.083(3) 0.053(2) 0.072(2) -0.0218(19) -0.014(2) 0.004(2) C8 0.058(2) 0.063(2) 0.059(2) -0.0116(18) -0.0150(19) 0.017(2) C9 0.059(2) 0.0452(18) 0.0476(19) -0.0040(17) -0.0037(19) 0.0004(18) C10 0.056(2) 0.063(2) 0.060(2) -0.0040(18) 0.001(2) 0.014(2) C11 0.050(2) 0.0455(19) 0.076(2) -0.0087(19) 0.002(2) -0.0048(18) C12 0.047(2) 0.054(2) 0.075(2) 0.0090(19) 0.007(2) 0.0040(19) C13 0.063(2) 0.066(2) 0.060(2) 0.0017(19) -0.029(2) -0.002(2) C14 0.054(2) 0.057(2) 0.090(3) -0.026(2) -0.010(2) 0.012(2) C15 0.057(2) 0.0429(18) 0.0503(19) 0.0067(15) -0.0143(18) -0.0005(17) C16 0.052(2) 0.0424(18) 0.064(2) 0.0035(17) 0.0005(19) 0.0020(17) C17 0.066(2) 0.0397(17) 0.054(2) -0.0004(16) -0.0082(19) -0.0083(18) C18 0.052(2) 0.0550(19) 0.049(2) -0.0102(17) -0.0003(18) -0.0028(19) C19 0.051(2) 0.0380(18) 0.062(2) 0.0044(16) -0.0236(19) 0.0009(16) O1 0.0716(16) 0.0569(13) 0.0751(15) -0.0102(13) -0.0223(14) 0.0158(14) O2 0.0462(14) 0.0524(13) 0.0523(13) -0.0058(11) 0.0003(12) 0.0032(11) O3 0.0659(16) 0.0726(15) 0.0426(12) -0.0037(11) 0.0037(12) -0.0199(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 Li1 O3 1.999(5) . ? Li1 O2 2.033(5) . ? Li1 O1 2.051(6) . ? Li1 N3 2.118(5) . ? Li1 N1 2.321(5) . ? B1 N7 1.536(4) . ? B1 N8 1.538(4) . ? B1 N5 1.548(4) . ? B1 N6 1.551(4) . ? N1 C6 1.455(4) . ? N1 C4 1.453(4) . ? N1 C5 1.465(4) . ? N2 C18 1.318(4) . ? N2 C13 1.366(4) . ? N3 C19 1.313(4) . ? N3 C17 1.373(4) . ? N4 C9 1.320(4) . ? N4 C12 1.361(4) . ? N5 C16 1.347(4) . ? N5 C10 1.375(4) . ? N6 C18 1.351(4) . ? N6 C8 1.373(4) . ? N7 C19 1.356(4) . ? N7 C15 1.372(4) . ? N8 C9 1.345(4) . ? N8 C11 1.378(4) . ? N9 C16 1.317(4) . ? N9 C14 1.374(5) . ? C1 O1 1.411(4) . ? C1 C6 1.510(6) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 O2 1.413(4) . ? C2 C5 1.493(5) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 O3 1.421(4) . ? C3 C4 1.496(5) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C8 C13 1.354(4) . ? C8 H8A 0.9300 . ? C9 H9A 0.9300 . ? C10 C14 1.347(4) . ? C10 H10A 0.9300 . ? C11 C12 1.336(5) . ? C11 H11A 0.9300 . ? C12 H12A 0.9300 . ? C13 H13A 0.9300 . ? C14 H14A 0.9300 . ? C15 C17 1.343(4) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C17 H17A 0.9300 . ? C18 H18A 0.9300 . ? C19 H19A 0.9300 . ? O1 H1O 0.8200 . ? O2 H2O 0.8200 . ? O3 H3O 0.8200 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Li1 O2 112.0(3) . . ? O3 Li1 O1 116.7(3) . . ? O2 Li1 O1 119.7(3) . . ? O3 Li1 N3 105.5(2) . . ? O2 Li1 N3 104.4(2) . . ? O1 Li1 N3 94.8(2) . . ? O3 Li1 N1 78.19(19) . . ? O2 Li1 N1 78.70(18) . . ? O1 Li1 N1 78.74(19) . . ? N3 Li1 N1 173.5(3) . . ? N7 B1 N8 110.7(2) . . ? N7 B1 N5 109.0(2) . . ? N8 B1 N5 108.6(2) . . ? N7 B1 N6 110.8(2) . . ? N8 B1 N6 106.1(2) . . ? N5 B1 N6 111.6(2) . . ? C6 N1 C4 113.9(3) . . ? C6 N1 C5 113.2(3) . . ? C4 N1 C5 114.0(3) . . ? C6 N1 Li1 105.9(2) . . ? C4 N1 Li1 104.7(2) . . ? C5 N1 Li1 103.8(2) . . ? C18 N2 C13 104.5(3) . . ? C19 N3 C17 103.3(3) . . ? C19 N3 Li1 132.5(3) . . ? C17 N3 Li1 121.3(2) . . ? C9 N4 C12 104.4(3) . . ? C16 N5 C10 104.3(3) . . ? C16 N5 B1 126.9(3) . . ? C10 N5 B1 128.7(3) . . ? C18 N6 C8 104.5(3) . . ? C18 N6 B1 131.0(3) . . ? C8 N6 B1 124.5(3) . . ? C19 N7 C15 104.0(2) . . ? C19 N7 B1 126.2(2) . . ? C15 N7 B1 129.0(2) . . ? C9 N8 C11 104.4(3) . . ? C9 N8 B1 129.5(3) . . ? C11 N8 B1 126.0(3) . . ? C16 N9 C14 103.8(3) . . ? O1 C1 C6 111.4(3) . . ? O1 C1 H1A 109.4 . . ? C6 C1 H1A 109.4 . . ? O1 C1 H1B 109.4 . . ? C6 C1 H1B 109.4 . . ? H1A C1 H1B 108.0 . . ? O2 C2 C5 109.8(3) . . ? O2 C2 H2A 109.7 . . ? C5 C2 H2A 109.7 . . ? O2 C2 H2B 109.7 . . ? C5 C2 H2B 109.7 . . ? H2A C2 H2B 108.2 . . ? O3 C3 C4 108.1(3) . . ? O3 C3 H3A 110.1 . . ? C4 C3 H3A 110.1 . . ? O3 C3 H3B 110.1 . . ? C4 C3 H3B 110.1 . . ? H3A C3 H3B 108.4 . . ? N1 C4 C3 111.8(3) . . ? N1 C4 H4A 109.3 . . ? C3 C4 H4A 109.3 . . ? N1 C4 H4B 109.3 . . ? C3 C4 H4B 109.3 . . ? H4A C4 H4B 107.9 . . ? N1 C5 C2 111.5(3) . . ? N1 C5 H5A 109.3 . . ? C2 C5 H5A 109.3 . . ? N1 C5 H5B 109.3 . . ? C2 C5 H5B 109.3 . . ? H5A C5 H5B 108.0 . . ? N1 C6 C1 111.1(3) . . ? N1 C6 H6A 109.4 . . ? C1 C6 H6A 109.4 . . ? N1 C6 H6B 109.4 . . ? C1 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? C13 C8 N6 107.7(3) . . ? C13 C8 H8A 126.2 . . ? N6 C8 H8A 126.2 . . ? N4 C9 N8 113.3(3) . . ? N4 C9 H9A 123.4 . . ? N8 C9 H9A 123.4 . . ? C14 C10 N5 107.7(3) . . ? C14 C10 H10A 126.2 . . ? N5 C10 H10A 126.2 . . ? C12 C11 N8 107.7(3) . . ? C12 C11 H11A 126.1 . . ? N8 C11 H11A 126.1 . . ? C11 C12 N4 110.2(3) . . ? C11 C12 H12A 124.9 . . ? N4 C12 H12A 124.9 . . ? C8 C13 N2 109.8(3) . . ? C8 C13 H13A 125.1 . . ? N2 C13 H13A 125.1 . . ? C10 C14 N9 110.0(3) . . ? C10 C14 H14A 125.0 . . ? N9 C14 H14A 125.0 . . ? C17 C15 N7 107.6(3) . . ? C17 C15 H15A 126.2 . . ? N7 C15 H15A 126.2 . . ? N9 C16 N5 114.1(3) . . ? N9 C16 H16A 123.0 . . ? N5 C16 H16A 123.0 . . ? C15 C17 N3 110.7(3) . . ? C15 C17 H17A 124.6 . . ? N3 C17 H17A 124.6 . . ? N2 C18 N6 113.6(3) . . ? N2 C18 H18A 123.2 . . ? N6 C18 H18A 123.2 . . ? N3 C19 N7 114.3(3) . . ? N3 C19 H19A 122.8 . . ? N7 C19 H19A 122.8 . . ? C1 O1 Li1 114.3(2) . . ? C1 O1 H1O 109.5 . . ? Li1 O1 H1O 113.8 . . ? C2 O2 Li1 115.8(2) . . ? C2 O2 H2O 109.5 . . ? Li1 O2 H2O 109.8 . . ? C3 O3 Li1 116.5(2) . . ? C3 O3 H3O 109.5 . . ? Li1 O3 H3O 121.5 . . ? 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 O1 H1O N9 0.82 1.94 2.756(4) 173.8 1_545 O2 H2O N4 0.82 1.93 2.708(3) 157.6 1_455 O3 H3O N2 0.82 1.95 2.743(3) 161.9 3_645 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.132 _refine_diff_density_min -0.126 _refine_diff_density_rms 0.032 #end data_3 _database_code_depnum_ccdc_archive 'CCDC 738774' #TrackingRef 'compounds.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H24 B N6 O' _chemical_formula_weight 315.21 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Trigonal _symmetry_space_group_name_H-M P31c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'y, x, z+1/2' '-x, -x+y, z+1/2' 'x-y, -y, z+1/2' _cell_length_a 10.828(2) _cell_length_b 10.828(2) _cell_length_c 18.738(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 1902.6(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 488 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 19.16 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.100 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 676 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4854 _diffrn_reflns_av_R_equivalents 0.0673 _diffrn_reflns_av_sigmaI/netI 0.0353 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 22.20 _reflns_number_total 812 _reflns_number_gt 586 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1000P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -10(10) _refine_ls_number_reflns 812 _refine_ls_number_parameters 145 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0824 _refine_ls_R_factor_gt 0.0541 _refine_ls_wR_factor_ref 0.1515 _refine_ls_wR_factor_gt 0.1312 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.030 _refine_ls_shift/su_mean 0.005 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 N3 N 0.1536(5) 0.1005(6) 0.2840(3) 0.0541(15) Uani 1 1 d . . . N4 N 0.3892(6) 0.2215(6) 0.2759(4) 0.0707(17) Uani 1 1 d . . . C6 C 0.3021(13) -0.0918(11) 0.3477(6) 0.125(4) Uani 1 1 d . . . H6A H 0.3103 -0.1405 0.3886 0.188 Uiso 1 1 calc R . . H6B H 0.3847 -0.0603 0.3180 0.188 Uiso 1 1 calc R . . H6C H 0.2182 -0.1555 0.3211 0.188 Uiso 1 1 calc R . . C7 C 0.2910(9) 0.0380(8) 0.3722(5) 0.077(2) Uani 1 1 d . . . H7A H 0.2089 0.0056 0.4033 0.092 Uiso 1 1 calc R . . H7B H 0.3753 0.1009 0.3998 0.092 Uiso 1 1 calc R . . C8 C 0.1906(8) 0.1924(7) 0.2275(4) 0.0661(19) Uani 1 1 d . . . H8A H 0.1279 0.2023 0.1973 0.079 Uiso 1 1 calc R . . C9 C 0.3344(8) 0.2661(8) 0.2233(5) 0.076(2) Uani 1 1 d . . . H9A H 0.3875 0.3363 0.1898 0.091 Uiso 1 1 calc R . . C10 C 0.2771(8) 0.1204(8) 0.3117(4) 0.061(2) Uani 1 1 d . . . B2 B 0.0000 0.0000 0.3122(9) 0.053(3) Uani 1 3 d S . . N1 N 0.4399(5) 0.6220(5) 0.0679(3) 0.0521(15) Uani 1 1 d . . . N2 N 0.5650(6) 0.5127(7) 0.0790(3) 0.076(2) Uani 1 1 d . . . C1 C 0.2806(13) 0.2804(11) 0.0033(6) 0.128(4) Uani 1 1 d . . . H1A H 0.2349 0.2243 -0.0383 0.192 Uiso 1 1 calc R . . H1B H 0.2109 0.2851 0.0330 0.192 Uiso 1 1 calc R . . H1C H 0.3255 0.2372 0.0295 0.192 Uiso 1 1 calc R . . C2 C 0.3893(9) 0.4257(8) -0.0185(4) 0.080(3) Uani 1 1 d . . . H2A H 0.4580 0.4194 -0.0493 0.096 Uiso 1 1 calc R . . H2B H 0.3433 0.4670 -0.0462 0.096 Uiso 1 1 calc R . . C3 C 0.6058(8) 0.6133(9) 0.1319(5) 0.079(2) Uani 1 1 d . . . H3A H 0.6746 0.6319 0.1664 0.094 Uiso 1 1 calc R . . C4 C 0.5308(7) 0.6806(8) 0.1260(4) 0.069(2) Uani 1 1 d . . . H4A H 0.5383 0.7532 0.1553 0.082 Uiso 1 1 calc R . . C5 C 0.4662(7) 0.5218(7) 0.0416(3) 0.057(2) Uani 1 1 d . . . B1 B 0.3333 0.6667 0.0389(8) 0.058(4) Uani 1 3 d S . . O1W O 0.6667 0.3333 0.3121(6) 0.077(3) Uani 1 3 d S . . H1WA H 0.569(8) 0.306(8) 0.298(4) 0.092 Uiso 1 1 d . . . O2W O 0.6667 0.3333 0.0489(9) 0.115(5) Uani 1 3 d S . . H2WA H 0.628(10) 0.393(11) 0.057(5) 0.137 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 N3 0.047(4) 0.045(3) 0.071(4) 0.004(3) 0.000(3) 0.023(3) N4 0.040(4) 0.052(4) 0.114(5) 0.003(4) 0.006(4) 0.019(3) C6 0.147(10) 0.088(7) 0.162(11) -0.001(7) -0.052(8) 0.074(7) C7 0.067(5) 0.069(5) 0.099(6) 0.001(4) -0.014(4) 0.038(4) C8 0.065(5) 0.059(5) 0.087(5) 0.007(4) 0.009(4) 0.041(4) C9 0.056(6) 0.052(5) 0.116(7) 0.009(5) 0.025(5) 0.025(4) C10 0.048(5) 0.051(4) 0.089(6) -0.011(4) -0.012(4) 0.029(4) B2 0.043(5) 0.043(5) 0.074(9) 0.000 0.000 0.021(3) N1 0.045(3) 0.042(3) 0.068(4) -0.006(3) -0.002(3) 0.021(3) N2 0.058(4) 0.056(4) 0.115(6) 0.006(4) -0.002(4) 0.028(3) C1 0.146(10) 0.081(7) 0.118(8) -0.026(6) -0.029(7) 0.026(7) C2 0.089(6) 0.057(5) 0.089(6) -0.013(4) 0.003(5) 0.033(5) C3 0.050(5) 0.063(5) 0.115(7) -0.009(5) -0.038(5) 0.023(5) C4 0.058(5) 0.069(5) 0.082(5) -0.029(4) -0.027(4) 0.034(4) C5 0.047(4) 0.045(4) 0.082(6) -0.001(4) 0.000(4) 0.026(4) B1 0.038(5) 0.038(5) 0.096(12) 0.000 0.000 0.019(2) O1W 0.050(3) 0.050(3) 0.131(8) 0.000 0.000 0.0250(15) O2W 0.052(4) 0.052(4) 0.239(16) 0.000 0.000 0.026(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 N3 C10 1.348(8) . ? N3 C8 1.370(9) . ? N3 B2 1.555(8) . ? N4 C10 1.339(9) . ? N4 C9 1.357(10) . ? C6 C7 1.540(12) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 C10 1.497(11) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.351(10) . ? C8 H8A 0.9300 . ? C9 H9A 0.9300 . ? B2 N3 1.555(8) 3 ? B2 N3 1.555(8) 2 ? N1 C5 1.345(8) . ? N1 C4 1.389(9) . ? N1 B1 1.556(8) . ? N2 C5 1.324(8) . ? N2 C3 1.371(10) . ? C1 C2 1.475(13) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C5 1.476(10) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.338(9) . ? C3 H3A 0.9300 . ? C4 H4A 0.9300 . ? B1 N1 1.556(8) 2_665 ? B1 N1 1.556(8) 3_565 ? O1W H1WA 0.99(7) . ? O2W H2WA 0.94(9) . ? 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 C10 N3 C8 106.0(6) . . ? C10 N3 B2 127.6(7) . . ? C8 N3 B2 126.3(7) . . ? C10 N4 C9 106.1(6) . . ? C7 C6 H6A 109.5 . . ? C7 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C7 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C10 C7 C6 113.2(7) . . ? C10 C7 H7A 108.9 . . ? C6 C7 H7A 108.9 . . ? C10 C7 H7B 108.9 . . ? C6 C7 H7B 108.9 . . ? H7A C7 H7B 107.7 . . ? C9 C8 N3 107.8(7) . . ? C9 C8 H8A 126.1 . . ? N3 C8 H8A 126.1 . . ? C8 C9 N4 109.1(7) . . ? C8 C9 H9A 125.4 . . ? N4 C9 H9A 125.4 . . ? N4 C10 N3 111.1(6) . . ? N4 C10 C7 123.2(6) . . ? N3 C10 C7 125.7(7) . . ? N3 B2 N3 109.1(7) 3 . ? N3 B2 N3 109.1(7) 3 2 ? N3 B2 N3 109.1(7) . 2 ? C5 N1 C4 105.6(6) . . ? C5 N1 B1 127.7(7) . . ? C4 N1 B1 126.7(6) . . ? C5 N2 C3 105.9(6) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C5 C2 C1 114.1(7) . . ? C5 C2 H2A 108.7 . . ? C1 C2 H2A 108.7 . . ? C5 C2 H2B 108.7 . . ? C1 C2 H2B 108.7 . . ? H2A C2 H2B 107.6 . . ? C4 C3 N2 109.3(7) . . ? C4 C3 H3A 125.3 . . ? N2 C3 H3A 125.3 . . ? C3 C4 N1 107.5(7) . . ? C3 C4 H4A 126.3 . . ? N1 C4 H4A 126.3 . . ? N2 C5 N1 111.7(6) . . ? N2 C5 C2 123.0(6) . . ? N1 C5 C2 125.2(7) . . ? N1 B1 N1 108.5(6) 2_665 3_565 ? N1 B1 N1 108.5(6) 2_665 . ? N1 B1 N1 108.5(6) 3_565 . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 22.20 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.335 _refine_diff_density_min -0.142 _refine_diff_density_rms 0.034 #end