data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 #TrackingRef 'ccdc.cif' #====================================================================== _audit_creation_method SHELXL-97 # SUBMISSION DETAILS _publ_contact_author_name K.M.Muraleedharan _publ_contact_author_address ; Department of Chemistry Indian Institute of Technology Madras Chennai - 600 036 ; _publ_contact_author_email mkm@iitm.ac.in _publ_contact_author_fax ' ' _publ_contact_author_phone ' ' #======================================================================= _publ_section_title ; Pseudo alkaloid from Ala-Ala dipeptide. A novel synthetic approach towards complex molecular framework. ; loop_ _publ_author_name _publ_author_address 'V.Kasi Pandi' ; Department of chemistry, Indian Institute of Technology-Madras Chennai-600 036 India ; 'N.John Victor' ; Department of chemistry, Indian Institute of Technology-Madras Chennai-600 036 India ; V.Ramkumar ; Department of chemistry, Indian Institute of Technology-Madras Chennai-600 036 India ; K.M.Muraleedharan ; Department of Chemistry Indian Institute of Technology-Madras Chennai-600 036 India ; data_new _database_code_depnum_ccdc_archive 'CCDC 766965' #TrackingRef 'ccdc.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H33 B3 N4 O3' _chemical_formula_sum 'C14 H33 B3 N4 O3' _chemical_formula_weight 337.87 _chemical_absolute_configuration unk loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) _symmetry_space_group_name_Hall 'P 2ac 2ab ' 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 10.7127(15) _cell_length_b 11.6890(16) _cell_length_c 15.5054(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1941.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2604 _cell_measurement_theta_min 2.18 _cell_measurement_theta_max 23.37 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.156 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9681 _exptl_absorpt_correction_T_max 0.9923 _exptl_absorpt_process_details 'SADABS (Bruker, 1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 ApexII 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 8309 _diffrn_reflns_av_R_equivalents 0.0301 _diffrn_reflns_av_sigmaI/netI 0.0470 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 28.15 _reflns_number_total 4201 _reflns_number_gt 2903 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEXII (Bruker, 2004)' _computing_cell_refinement 'APEXII/SAINT (Bruker, 2004)' _computing_data_reduction 'SAINT/XPREP (Bruker, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0670P)^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 -0.2(14) _refine_ls_number_reflns 4201 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0798 _refine_ls_R_factor_gt 0.0501 _refine_ls_wR_factor_ref 0.1284 _refine_ls_wR_factor_gt 0.1147 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 B1 B 0.8845(3) 0.4051(3) 1.14019(18) 0.0740(9) Uani 1 1 d . . . H1A H 0.8354 0.3383 1.1554 0.089 Uiso 1 1 calc R . . H1B H 0.9285 0.4311 1.1912 0.089 Uiso 1 1 calc R . . B2 B 0.9183(2) 0.36896(18) 0.97157(16) 0.0433(5) Uani 1 1 d . . . B3 B 0.9718(3) 0.5638(2) 0.87835(18) 0.0579(7) Uani 1 1 d . . . H3A H 0.8955 0.5580 0.8462 0.087 Uiso 1 1 calc R . . H3B H 1.0360 0.5952 0.8422 0.087 Uiso 1 1 calc R . . H3C H 0.9592 0.6129 0.9272 0.087 Uiso 1 1 calc R . . C1 C 0.7221(2) 0.5777(2) 1.15765(15) 0.0683(7) Uani 1 1 d . . . H1 H 0.6782 0.5330 1.2017 0.082 Uiso 1 1 calc R . . C2 C 0.6263(3) 0.6236(3) 1.09307(17) 0.0885(9) Uani 1 1 d . . . H2A H 0.5418 0.6116 1.1136 0.106 Uiso 1 1 calc R . . H2B H 0.6389 0.7046 1.0824 0.106 Uiso 1 1 calc R . . C3 C 0.75143(19) 0.49128(15) 1.02875(14) 0.0428(5) Uani 1 1 d . . . C4 C 1.0040(2) 0.2408(2) 0.87466(18) 0.0722(8) Uani 1 1 d . . . H4A H 0.9771 0.1870 0.8308 0.087 Uiso 1 1 calc R . . H4B H 1.0791 0.2115 0.9017 0.087 Uiso 1 1 calc R . . C5 C 1.0276(2) 0.3572(2) 0.83559(16) 0.0681(7) Uani 1 1 d . . . H5 H 0.9584 0.3728 0.7960 0.082 Uiso 1 1 calc R . . C6 C 1.12808(19) 0.4488(2) 0.96549(14) 0.0539(6) Uani 1 1 d . . . H6A H 1.1788 0.3802 0.9613 0.065 Uiso 1 1 calc R . . H6B H 1.1777 0.5140 0.9476 0.065 Uiso 1 1 calc R . . C7 C 1.0811(2) 0.46474(18) 1.05509(13) 0.0501(6) Uani 1 1 d . . . H7 H 1.0402 0.5397 1.0578 0.060 Uiso 1 1 calc R . . C8 C 0.7970(4) 0.6676(3) 1.2012(3) 0.1199(13) Uani 1 1 d . . . H8A H 0.8422 0.7107 1.1588 0.180 Uiso 1 1 calc R . . H8B H 0.8547 0.6324 1.2404 0.180 Uiso 1 1 calc R . . H8C H 0.7424 0.7177 1.2325 0.180 Uiso 1 1 calc R . . C9 C 0.5981(2) 0.5833(2) 0.93136(16) 0.0585(6) Uani 1 1 d . . . H9 H 0.6383 0.5341 0.8884 0.070 Uiso 1 1 calc R . . C10 C 0.6235(3) 0.7076(2) 0.90670(19) 0.0743(7) Uani 1 1 d . . . H10A H 0.6075 0.7170 0.8455 0.089 Uiso 1 1 calc R . . H10B H 0.5656 0.7564 0.9376 0.089 Uiso 1 1 calc R . . C11 C 0.4578(2) 0.5596(3) 0.9292(2) 0.0971(11) Uani 1 1 d . . . H11A H 0.4168 0.6056 0.9719 0.146 Uiso 1 1 calc R . . H11B H 0.4430 0.4802 0.9410 0.146 Uiso 1 1 calc R . . H11C H 0.4255 0.5783 0.8731 0.146 Uiso 1 1 calc R . . C12 C 1.1464(3) 0.3704(3) 0.78480(19) 0.1068(12) Uani 1 1 d . . . H12A H 1.2166 0.3543 0.8213 0.160 Uiso 1 1 calc R . . H12B H 1.1525 0.4473 0.7635 0.160 Uiso 1 1 calc R . . H12C H 1.1459 0.3180 0.7371 0.160 Uiso 1 1 calc R . . C13 C 1.1846(2) 0.4638(3) 1.12270(18) 0.0819(8) Uani 1 1 d . . . H13A H 1.2364 0.5301 1.1155 0.123 Uiso 1 1 calc R . . H13B H 1.2343 0.3960 1.1159 0.123 Uiso 1 1 calc R . . H13C H 1.1483 0.4645 1.1793 0.123 Uiso 1 1 calc R . . C14 C 1.0390(3) 0.2615(2) 1.09051(19) 0.0792(8) Uani 1 1 d . . . H14A H 1.0667 0.2648 1.1493 0.119 Uiso 1 1 calc R . . H14B H 1.1089 0.2462 1.0536 0.119 Uiso 1 1 calc R . . H14C H 0.9783 0.2016 1.0843 0.119 Uiso 1 1 calc R . . N1 N 0.65088(17) 0.55617(16) 1.01532(12) 0.0530(5) Uani 1 1 d . . . N2 N 1.01328(13) 0.43819(14) 0.91116(10) 0.0426(4) Uani 1 1 d . . . N3 N 0.98100(16) 0.37431(14) 1.06587(11) 0.0471(4) Uani 1 1 d . . . N4 N 0.79993(17) 0.49972(17) 1.10592(12) 0.0579(5) Uani 1 1 d . . . O2 O 0.90864(13) 0.25755(12) 0.93686(11) 0.0623(5) Uani 1 1 d . . . O3 O 0.7460(2) 0.74395(17) 0.92446(15) 0.0912(7) Uani 1 1 d . . . H1X H 0.793(3) 0.688(3) 0.9136(18) 0.086(10) Uiso 1 1 d . . . O1 O 0.79222(12) 0.42133(11) 0.97048(9) 0.0445(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 B1 0.073(2) 0.092(2) 0.0576(18) 0.0235(17) 0.0057(16) 0.0013(18) B2 0.0333(11) 0.0372(10) 0.0595(16) -0.0021(11) -0.0038(12) 0.0008(9) B3 0.0538(15) 0.0585(14) 0.0614(17) 0.0148(12) -0.0012(13) -0.0029(13) C1 0.0705(16) 0.0807(16) 0.0536(13) -0.0099(13) 0.0239(13) -0.0042(15) C2 0.087(2) 0.107(2) 0.0718(18) -0.0271(17) 0.0068(17) 0.0382(19) C3 0.0359(10) 0.0394(9) 0.0532(13) -0.0026(9) 0.0104(11) -0.0066(9) C4 0.0634(15) 0.0662(15) 0.0871(19) -0.0330(14) -0.0142(14) 0.0215(13) C5 0.0663(16) 0.0866(17) 0.0513(14) -0.0159(12) -0.0049(13) 0.0285(14) C6 0.0338(10) 0.0635(13) 0.0644(14) 0.0091(12) -0.0042(10) -0.0042(10) C7 0.0450(11) 0.0494(11) 0.0560(14) 0.0008(9) -0.0158(11) -0.0041(10) C8 0.101(3) 0.111(3) 0.148(3) -0.058(2) 0.003(2) -0.006(2) C9 0.0477(12) 0.0547(12) 0.0732(16) -0.0153(12) -0.0060(12) 0.0116(11) C10 0.0691(17) 0.0663(15) 0.0874(19) -0.0019(14) -0.0011(16) 0.0191(14) C11 0.0514(15) 0.0790(18) 0.161(3) -0.0294(19) -0.0269(18) 0.0178(15) C12 0.111(3) 0.141(3) 0.0684(18) 0.0000(19) 0.0321(19) 0.047(2) C13 0.0754(18) 0.0918(19) 0.0786(17) -0.0010(15) -0.0398(15) -0.0050(16) C14 0.0846(18) 0.0524(13) 0.101(2) 0.0234(13) -0.0237(17) 0.0108(13) N1 0.0434(9) 0.0541(10) 0.0616(12) -0.0120(9) 0.0069(9) 0.0102(9) N2 0.0333(8) 0.0507(9) 0.0438(9) -0.0031(7) -0.0041(7) 0.0052(7) N3 0.0465(10) 0.0420(8) 0.0529(11) 0.0100(7) -0.0043(9) 0.0010(8) N4 0.0592(11) 0.0736(12) 0.0410(11) 0.0020(9) 0.0073(10) 0.0095(11) O2 0.0453(8) 0.0433(7) 0.0985(13) -0.0225(8) -0.0020(9) 0.0019(7) O3 0.0814(14) 0.0609(12) 0.1312(18) 0.0047(11) 0.0033(13) 0.0024(12) O1 0.0341(7) 0.0412(6) 0.0583(8) -0.0129(6) -0.0020(6) 0.0032(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B1 N4 1.525(4) . ? B1 N3 1.589(3) . ? B1 H1A 0.9700 . ? B1 H1B 0.9700 . ? B2 O2 1.413(3) . ? B2 O1 1.483(3) . ? B2 N2 1.602(3) . ? B2 N3 1.610(3) . ? B3 N2 1.617(3) . ? B3 H3A 0.9600 . ? B3 H3B 0.9600 . ? B3 H3C 0.9600 . ? C1 N4 1.473(3) . ? C1 C8 1.484(4) . ? C1 C2 1.531(4) . ? C1 H1 0.9800 . ? C2 N1 1.464(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 O1 1.295(2) . ? C3 N4 1.308(3) . ? C3 N1 1.334(3) . ? C4 O2 1.418(3) . ? C4 C5 1.511(4) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C12 1.505(4) . ? C5 N2 1.514(3) . ? C5 H5 0.9800 . ? C6 C7 1.489(3) . ? C6 N2 1.496(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 N3 1.515(3) . ? C7 C13 1.526(3) . ? C7 H7 0.9800 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 N1 1.454(3) . ? C9 C10 1.527(4) . ? C9 C11 1.529(3) . ? C9 H9 0.9800 . ? C10 O3 1.407(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 N3 1.507(3) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? O3 H1X 0.84(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 N4 B1 N3 107.33(18) . . ? N4 B1 H1A 110.2 . . ? N3 B1 H1A 110.2 . . ? N4 B1 H1B 110.2 . . ? N3 B1 H1B 110.2 . . ? H1A B1 H1B 108.5 . . ? O2 B2 O1 108.01(16) . . ? O2 B2 N2 106.83(18) . . ? O1 B2 N2 111.30(16) . . ? O2 B2 N3 114.35(16) . . ? O1 B2 N3 111.96(17) . . ? N2 B2 N3 104.27(15) . . ? N2 B3 H3A 109.5 . . ? N2 B3 H3B 109.5 . . ? H3A B3 H3B 109.5 . . ? N2 B3 H3C 109.5 . . ? H3A B3 H3C 109.5 . . ? H3B B3 H3C 109.5 . . ? N4 C1 C8 112.3(2) . . ? N4 C1 C2 103.90(18) . . ? C8 C1 C2 114.3(3) . . ? N4 C1 H1 108.7 . . ? C8 C1 H1 108.7 . . ? C2 C1 H1 108.7 . . ? N1 C2 C1 103.2(2) . . ? N1 C2 H2A 111.1 . . ? C1 C2 H2A 111.1 . . ? N1 C2 H2B 111.1 . . ? C1 C2 H2B 111.1 . . ? H2A C2 H2B 109.1 . . ? O1 C3 N4 123.50(18) . . ? O1 C3 N1 121.52(19) . . ? N4 C3 N1 114.88(18) . . ? O2 C4 C5 105.58(18) . . ? O2 C4 H4A 110.6 . . ? C5 C4 H4A 110.6 . . ? O2 C4 H4B 110.6 . . ? C5 C4 H4B 110.6 . . ? H4A C4 H4B 108.8 . . ? C12 C5 C4 116.3(2) . . ? C12 C5 N2 115.3(2) . . ? C4 C5 N2 103.6(2) . . ? C12 C5 H5 107.0 . . ? C4 C5 H5 107.0 . . ? N2 C5 H5 107.0 . . ? C7 C6 N2 104.94(16) . . ? C7 C6 H6A 110.8 . . ? N2 C6 H6A 110.8 . . ? C7 C6 H6B 110.8 . . ? N2 C6 H6B 110.8 . . ? H6A C6 H6B 108.8 . . ? C6 C7 N3 104.76(16) . . ? C6 C7 C13 113.2(2) . . ? N3 C7 C13 115.68(19) . . ? C6 C7 H7 107.6 . . ? N3 C7 H7 107.6 . . ? C13 C7 H7 107.6 . . ? C1 C8 H8A 109.5 . . ? C1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N1 C9 C10 111.2(2) . . ? N1 C9 C11 111.3(2) . . ? C10 C9 C11 110.0(2) . . ? N1 C9 H9 108.1 . . ? C10 C9 H9 108.1 . . ? C11 C9 H9 108.1 . . ? O3 C10 C9 113.9(2) . . ? O3 C10 H10A 108.8 . . ? C9 C10 H10A 108.8 . . ? O3 C10 H10B 108.8 . . ? C9 C10 H10B 108.8 . . ? H10A C10 H10B 107.7 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C5 C12 H12A 109.5 . . ? C5 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C5 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C7 C13 H13A 109.5 . . ? C7 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C7 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N3 C14 H14A 109.5 . . ? N3 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N3 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C3 N1 C9 125.29(18) . . ? C3 N1 C2 108.84(19) . . ? C9 N1 C2 123.34(19) . . ? C6 N2 C5 113.85(16) . . ? C6 N2 B2 103.57(15) . . ? C5 N2 B2 101.59(17) . . ? C6 N2 B3 109.15(17) . . ? C5 N2 B3 110.62(17) . . ? B2 N2 B3 117.92(16) . . ? C14 N3 C7 110.29(16) . . ? C14 N3 B1 106.40(19) . . ? C7 N3 B1 112.49(19) . . ? C14 N3 B2 111.60(17) . . ? C7 N3 B2 102.83(14) . . ? B1 N3 B2 113.33(17) . . ? C3 N4 C1 108.66(18) . . ? C3 N4 B1 120.0(2) . . ? C1 N4 B1 126.54(19) . . ? B2 O2 C4 109.48(18) . . ? C10 O3 H1X 107(2) . . ? C3 O1 B2 124.07(16) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N4 C1 C2 N1 6.7(3) . . . . ? C8 C1 C2 N1 129.5(3) . . . . ? O2 C4 C5 C12 164.5(2) . . . . ? O2 C4 C5 N2 36.9(2) . . . . ? N2 C6 C7 N3 46.5(2) . . . . ? N2 C6 C7 C13 173.40(19) . . . . ? N1 C9 C10 O3 43.4(3) . . . . ? C11 C9 C10 O3 167.2(2) . . . . ? O1 C3 N1 C9 -19.0(3) . . . . ? N4 C3 N1 C9 164.5(2) . . . . ? O1 C3 N1 C2 178.6(2) . . . . ? N4 C3 N1 C2 2.2(3) . . . . ? C10 C9 N1 C3 -107.3(2) . . . . ? C11 C9 N1 C3 129.6(2) . . . . ? C10 C9 N1 C2 52.6(3) . . . . ? C11 C9 N1 C2 -70.5(3) . . . . ? C1 C2 N1 C3 -5.6(3) . . . . ? C1 C2 N1 C9 -168.4(2) . . . . ? C7 C6 N2 C5 -145.72(19) . . . . ? C7 C6 N2 B2 -36.3(2) . . . . ? C7 C6 N2 B3 90.1(2) . . . . ? C12 C5 N2 C6 -45.3(3) . . . . ? C4 C5 N2 C6 83.0(2) . . . . ? C12 C5 N2 B2 -155.9(2) . . . . ? C4 C5 N2 B2 -27.7(2) . . . . ? C12 C5 N2 B3 78.0(3) . . . . ? C4 C5 N2 B3 -153.70(19) . . . . ? O2 B2 N2 C6 -107.72(18) . . . . ? O1 B2 N2 C6 134.59(17) . . . . ? N3 B2 N2 C6 13.70(19) . . . . ? O2 B2 N2 C5 10.6(2) . . . . ? O1 B2 N2 C5 -107.11(18) . . . . ? N3 B2 N2 C5 132.00(16) . . . . ? O2 B2 N2 B3 131.62(18) . . . . ? O1 B2 N2 B3 13.9(2) . . . . ? N3 B2 N2 B3 -106.96(18) . . . . ? C6 C7 N3 C14 83.6(2) . . . . ? C13 C7 N3 C14 -41.8(3) . . . . ? C6 C7 N3 B1 -157.76(18) . . . . ? C13 C7 N3 B1 76.8(2) . . . . ? C6 C7 N3 B2 -35.50(19) . . . . ? C13 C7 N3 B2 -160.9(2) . . . . ? N4 B1 N3 C14 -164.8(2) . . . . ? N4 B1 N3 C7 74.4(2) . . . . ? N4 B1 N3 B2 -41.8(3) . . . . ? O2 B2 N3 C14 11.0(3) . . . . ? O1 B2 N3 C14 134.26(18) . . . . ? N2 B2 N3 C14 -105.30(19) . . . . ? O2 B2 N3 C7 129.20(18) . . . . ? O1 B2 N3 C7 -107.54(18) . . . . ? N2 B2 N3 C7 12.91(18) . . . . ? O2 B2 N3 B1 -109.1(2) . . . . ? O1 B2 N3 B1 14.2(2) . . . . ? N2 B2 N3 B1 134.60(18) . . . . ? O1 C3 N4 C1 -173.82(19) . . . . ? N1 C3 N4 C1 2.6(2) . . . . ? O1 C3 N4 B1 -16.8(3) . . . . ? N1 C3 N4 B1 159.5(2) . . . . ? C8 C1 N4 C3 -129.9(3) . . . . ? C2 C1 N4 C3 -5.9(3) . . . . ? C8 C1 N4 B1 75.0(4) . . . . ? C2 C1 N4 B1 -160.9(3) . . . . ? N3 B1 N4 C3 46.3(3) . . . . ? N3 B1 N4 C1 -161.1(2) . . . . ? O1 B2 O2 C4 132.19(19) . . . . ? N2 B2 O2 C4 12.4(2) . . . . ? N3 B2 O2 C4 -102.4(2) . . . . ? C5 C4 O2 B2 -30.9(2) . . . . ? N4 C3 O1 B2 -19.7(3) . . . . ? N1 C3 O1 B2 164.10(18) . . . . ? O2 B2 O1 C3 145.60(18) . . . . ? N2 B2 O1 C3 -97.4(2) . . . . ? N3 B2 O1 C3 18.8(2) . . . . ? _diffrn_measured_fraction_theta_max 0.894 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.947 _refine_diff_density_max 0.159 _refine_diff_density_min -0.175 _refine_diff_density_rms 0.039