# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2010 data_global _journal_coden_Cambridge 440 _publ_requested_journal 'New Journal of Chemistry' loop_ _publ_author_name 'Aramaki, Yoshitaka' 'Yamashita, Makoto' 'Nozaki, Kyoko' _publ_contact_author_name 'Makoto Yamashita' _publ_contact_author_address ; 7-3-1 Hongo Tokyo Bunkyo-ku Japan 113-8656 ; _publ_contact_author_email makotoy@chembio.t.u-tokyo.ac.jp # Attachment '- CIFs.cif' #----------2-----------# data_2 _database_code_depnum_ccdc_archive 'CCDC 777065' #TrackingRef '- CIFs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H29 B F2 N2 O' _chemical_formula_weight 398.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.866(5) _cell_length_b 12.250(5) _cell_length_c 15.775(7) _cell_angle_alpha 100.107(4) _cell_angle_beta 100.940(4) _cell_angle_gamma 104.311(5) _cell_volume 2121.0(15) _cell_formula_units_Z 4 _cell_measurement_temperature 103.1500 _cell_measurement_reflns_used 5466 _cell_measurement_theta_min 3.3178 _cell_measurement_theta_max 27.4835 _exptl_crystal_description Block _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.247 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9658 _exptl_absorpt_correction_T_max 0.9887 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 103(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'RIGAKU/MSC Meacury CCD' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 7.31 _diffrn_reflns_number 13859 _diffrn_reflns_av_R_equivalents 0.0325 _diffrn_reflns_av_sigmaI/netI 0.0555 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.32 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7298 _reflns_number_gt 5606 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RIGAKU CrystalClear' _computing_cell_refinement 'RIGAKU CrystalClear' _computing_data_reduction 'RIGAKU CrystalClear' _computing_structure_solution SIR-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP-III _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^)+(0.1204P)^2^+0.8589P] 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 7298 _refine_ls_number_parameters 535 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1021 _refine_ls_R_factor_gt 0.0797 _refine_ls_wR_factor_ref 0.2153 _refine_ls_wR_factor_gt 0.1969 _refine_ls_goodness_of_fit_ref 1.104 _refine_ls_restrained_S_all 1.104 _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 0.7175(3) 0.7816(3) 1.0991(2) 0.0210(7) Uani 1 1 d . . . F1 F 0.61407(16) 0.70992(18) 1.11208(12) 0.0316(5) Uani 1 1 d . . . F2 F 0.73423(18) 0.89377(16) 1.14607(11) 0.0324(5) Uani 1 1 d . . . N1 N 0.7124(2) 0.7753(2) 1.00077(16) 0.0192(6) Uani 1 1 d . . . C1 C 0.6370(3) 0.8360(3) 0.95761(18) 0.0171(6) Uani 1 1 d . . . C2 C 0.5145(3) 0.7770(3) 0.91869(19) 0.0199(7) Uani 1 1 d . . . C3 C 0.4425(3) 0.8400(3) 0.8823(2) 0.0223(7) Uani 1 1 d . . . H1 H 0.3603 0.8020 0.8543 0.027 Uiso 1 1 calc R . . C4 C 0.4885(3) 0.9569(3) 0.8863(2) 0.0219(7) Uani 1 1 d . . . H2 H 0.4372 0.9990 0.8636 0.026 Uiso 1 1 calc R . . C5 C 0.6084(3) 1.0121(3) 0.92333(19) 0.0202(7) Uani 1 1 d . . . H3 H 0.6395 1.0917 0.9242 0.024 Uiso 1 1 calc R . . C6 C 0.6857(3) 0.9530(3) 0.9598(2) 0.0203(7) Uani 1 1 d . . . C7 C 0.4607(3) 0.6492(3) 0.9129(2) 0.0243(7) Uani 1 1 d . . . H4 H 0.5258 0.6198 0.9421 0.029 Uiso 1 1 calc R . . C8 C 0.4151(3) 0.5808(3) 0.8163(2) 0.0377(9) Uani 1 1 d . . . H5 H 0.3486 0.6054 0.7867 0.057 Uiso 1 1 calc R . . H6 H 0.3873 0.4979 0.8144 0.057 Uiso 1 1 calc R . . H7 H 0.4803 0.5952 0.7860 0.057 Uiso 1 1 calc R . . C9 C 0.3608(3) 0.6287(3) 0.9621(2) 0.0353(8) Uani 1 1 d . . . H8 H 0.3921 0.6724 1.0241 0.053 Uiso 1 1 calc R . . H9 H 0.3319 0.5459 0.9601 0.053 Uiso 1 1 calc R . . H10 H 0.2945 0.6546 0.9337 0.053 Uiso 1 1 calc R . . C10 C 0.8182(3) 1.0144(3) 0.9961(2) 0.0253(7) Uani 1 1 d . . . H11 H 0.8561 0.9598 1.0225 0.030 Uiso 1 1 calc R . . C11 C 0.8763(3) 1.0432(3) 0.9206(2) 0.0338(8) Uani 1 1 d . . . H12 H 0.8628 0.9717 0.8759 0.051 Uiso 1 1 calc R . . H13 H 0.9627 1.0795 0.9446 0.051 Uiso 1 1 calc R . . H14 H 0.8407 1.0966 0.8932 0.051 Uiso 1 1 calc R . . C12 C 0.8440(3) 1.1233(3) 1.0687(3) 0.0399(9) Uani 1 1 d . . . H15 H 0.8094 1.1793 1.0443 0.060 Uiso 1 1 calc R . . H16 H 0.9309 1.1572 1.0914 0.060 Uiso 1 1 calc R . . H17 H 0.8082 1.1033 1.1171 0.060 Uiso 1 1 calc R . . C13 C 0.7725(3) 0.7174(2) 0.95185(19) 0.0170(6) Uani 1 1 d . . . C14 C 0.8555(3) 0.6648(3) 0.9937(2) 0.0213(7) Uani 1 1 d . . . C15 C 0.8782(3) 0.6814(2) 1.0874(2) 0.0198(7) Uani 1 1 d . . . N2 N 0.8256(2) 0.7387(2) 1.13706(16) 0.0184(5) Uani 1 1 d . . . C16 C 0.7582(3) 0.7078(3) 0.8599(2) 0.0225(7) Uani 1 1 d . . . H18 H 0.7052 0.7433 0.8298 0.027 Uiso 1 1 calc R . . C17 C 0.8191(3) 0.6484(3) 0.8132(2) 0.0267(7) Uani 1 1 d . . . H19 H 0.8063 0.6425 0.7510 0.032 Uiso 1 1 calc R . . C18 C 0.9003(3) 0.5957(3) 0.8542(2) 0.0301(8) Uani 1 1 d . . . H20 H 0.9422 0.5550 0.8208 0.036 Uiso 1 1 calc R . . C19 C 0.9169(3) 0.6052(3) 0.9437(2) 0.0269(7) Uani 1 1 d . . . H21 H 0.9714 0.5704 0.9728 0.032 Uiso 1 1 calc R . . O1 O 0.96097(19) 0.64191(19) 1.13218(14) 0.0275(5) Uani 1 1 d . . . C20 C 0.9468(3) 0.6596(3) 1.2238(2) 0.0279(7) Uani 1 1 d . . . H22 H 1.0256 0.6819 1.2671 0.033 Uiso 1 1 calc R . . H23 H 0.8949 0.5884 1.2334 0.033 Uiso 1 1 calc R . . C21 C 0.8886(3) 0.7574(3) 1.2328(2) 0.0220(7) Uani 1 1 d . . . C22 C 0.9819(3) 0.8762(3) 1.2615(2) 0.0274(7) Uani 1 1 d . . . H24 H 1.0371 0.8805 1.2224 0.041 Uiso 1 1 calc R . . H25 H 1.0270 0.8879 1.3229 0.041 Uiso 1 1 calc R . . H26 H 0.9414 0.9366 1.2577 0.041 Uiso 1 1 calc R . . C23 C 0.8023(3) 0.7457(3) 1.2923(2) 0.0249(7) Uani 1 1 d . . . H27 H 0.7609 0.8055 1.2901 0.037 Uiso 1 1 calc R . . H28 H 0.8468 0.7550 1.3534 0.037 Uiso 1 1 calc R . . H29 H 0.7433 0.6690 1.2717 0.037 Uiso 1 1 calc R . . B2 B 0.7224(3) 0.2946(3) 0.6022(2) 0.0193(7) Uani 1 1 d . . . F3 F 0.80402(16) 0.22985(17) 0.61503(11) 0.0285(5) Uani 1 1 d . . . F4 F 0.77972(16) 0.40798(16) 0.65018(11) 0.0285(5) Uani 1 1 d . . . N3 N 0.6730(2) 0.2867(2) 0.50422(16) 0.0186(5) Uani 1 1 d . . . C24 C 0.7571(2) 0.3454(3) 0.45958(18) 0.0178(6) Uani 1 1 d . . . C25 C 0.8256(3) 0.2829(3) 0.41874(19) 0.0195(6) Uani 1 1 d . . . C26 C 0.9097(3) 0.3426(3) 0.3796(2) 0.0225(7) Uani 1 1 d . . . H30 H 0.9561 0.3024 0.3507 0.027 Uiso 1 1 calc R . . C27 C 0.9269(3) 0.4588(3) 0.3819(2) 0.0234(7) Uani 1 1 d . . . H31 H 0.9860 0.4982 0.3559 0.028 Uiso 1 1 calc R . . C28 C 0.8584(3) 0.5179(3) 0.4217(2) 0.0226(7) Uani 1 1 d . . . H32 H 0.8708 0.5978 0.4228 0.027 Uiso 1 1 calc R . . C29 C 0.7714(3) 0.4625(3) 0.46030(19) 0.0198(7) Uani 1 1 d . . . C30 C 0.8102(3) 0.1554(3) 0.4146(2) 0.0226(7) Uani 1 1 d . . . H33 H 0.7453 0.1275 0.4446 0.027 Uiso 1 1 calc R . . C31 C 0.9242(3) 0.1349(3) 0.4634(2) 0.0319(8) Uani 1 1 d . . . H34 H 0.9880 0.1567 0.4328 0.048 Uiso 1 1 calc R . . H35 H 0.9086 0.0527 0.4643 0.048 Uiso 1 1 calc R . . H36 H 0.9493 0.1820 0.5245 0.048 Uiso 1 1 calc R . . C32 C 0.7708(3) 0.0853(3) 0.3183(2) 0.0291(8) Uani 1 1 d . . . H37 H 0.6955 0.0967 0.2889 0.044 Uiso 1 1 calc R . . H38 H 0.7589 0.0030 0.3172 0.044 Uiso 1 1 calc R . . H39 H 0.8329 0.1115 0.2873 0.044 Uiso 1 1 calc R . . C33 C 0.6920(3) 0.5280(3) 0.4988(2) 0.0233(7) Uani 1 1 d . . . H40 H 0.6503 0.4811 0.5357 0.028 Uiso 1 1 calc R . . C34 C 0.5957(3) 0.5403(3) 0.4242(2) 0.0321(8) Uani 1 1 d . . . H41 H 0.6343 0.5823 0.3850 0.048 Uiso 1 1 calc R . . H42 H 0.5459 0.5832 0.4499 0.048 Uiso 1 1 calc R . . H43 H 0.5453 0.4632 0.3900 0.048 Uiso 1 1 calc R . . C35 C 0.7613(3) 0.6471(3) 0.5580(2) 0.0352(8) Uani 1 1 d . . . H44 H 0.8277 0.6402 0.6024 0.053 Uiso 1 1 calc R . . H45 H 0.7076 0.6792 0.5882 0.053 Uiso 1 1 calc R . . H46 H 0.7933 0.6985 0.5217 0.053 Uiso 1 1 calc R . . C36 C 0.5617(3) 0.2182(2) 0.45500(19) 0.0174(6) Uani 1 1 d . . . C37 C 0.4779(3) 0.1561(3) 0.4955(2) 0.0197(6) Uani 1 1 d . . . C38 C 0.5112(3) 0.1755(3) 0.5903(2) 0.0204(7) Uani 1 1 d . . . N4 N 0.6146(2) 0.2421(2) 0.64034(15) 0.0181(5) Uani 1 1 d . . . C39 C 0.5241(3) 0.2049(3) 0.3623(2) 0.0216(7) Uani 1 1 d . . . H47 H 0.5763 0.2461 0.3323 0.026 Uiso 1 1 calc R . . C40 C 0.4130(3) 0.1333(3) 0.3151(2) 0.0242(7) Uani 1 1 d . . . H48 H 0.3901 0.1261 0.2528 0.029 Uiso 1 1 calc R . . C41 C 0.3328(3) 0.0709(3) 0.3559(2) 0.0295(8) Uani 1 1 d . . . H49 H 0.2568 0.0211 0.3220 0.035 Uiso 1 1 calc R . . C42 C 0.3664(3) 0.0830(3) 0.4462(2) 0.0267(7) Uani 1 1 d . . . H50 H 0.3130 0.0412 0.4751 0.032 Uiso 1 1 calc R . . O2 O 0.43345(18) 0.12943(19) 0.63471(14) 0.0257(5) Uani 1 1 d . . . C43 C 0.5022(3) 0.1523(3) 0.72721(19) 0.0221(7) Uani 1 1 d . . . H51 H 0.5296 0.0849 0.7384 0.027 Uiso 1 1 calc R . . H52 H 0.4534 0.1701 0.7693 0.027 Uiso 1 1 calc R . . C44 C 0.6091(3) 0.2576(3) 0.73614(19) 0.0198(6) Uani 1 1 d . . . C45 C 0.7235(3) 0.2534(3) 0.7950(2) 0.0257(7) Uani 1 1 d . . . H53 H 0.7412 0.1813 0.7724 0.039 Uiso 1 1 calc R . . H54 H 0.7138 0.2564 0.8556 0.039 Uiso 1 1 calc R . . H55 H 0.7897 0.3198 0.7952 0.039 Uiso 1 1 calc R . . C46 C 0.5812(3) 0.3714(3) 0.7647(2) 0.0246(7) Uani 1 1 d . . . H56 H 0.6452 0.4357 0.7590 0.037 Uiso 1 1 calc R . . H57 H 0.5757 0.3822 0.8266 0.037 Uiso 1 1 calc R . . H58 H 0.5047 0.3694 0.7268 0.037 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 B1 0.0207(18) 0.0265(19) 0.0173(18) 0.0066(15) 0.0040(14) 0.0089(15) F1 0.0226(10) 0.0516(13) 0.0240(10) 0.0159(9) 0.0080(8) 0.0100(9) F2 0.0518(13) 0.0338(11) 0.0181(10) 0.0049(8) 0.0068(9) 0.0261(10) N1 0.0231(14) 0.0230(13) 0.0167(13) 0.0072(11) 0.0066(10) 0.0128(11) C1 0.0201(15) 0.0233(16) 0.0109(14) 0.0052(12) 0.0028(12) 0.0117(12) C2 0.0243(16) 0.0202(16) 0.0148(15) 0.0030(12) 0.0059(12) 0.0061(13) C3 0.0201(16) 0.0270(17) 0.0202(16) 0.0051(13) 0.0026(13) 0.0094(13) C4 0.0245(17) 0.0282(17) 0.0188(16) 0.0082(13) 0.0064(13) 0.0154(14) C5 0.0261(17) 0.0206(15) 0.0190(16) 0.0088(12) 0.0097(13) 0.0095(13) C6 0.0224(16) 0.0210(16) 0.0192(16) 0.0086(13) 0.0031(13) 0.0077(13) C7 0.0213(16) 0.0227(17) 0.0260(17) 0.0059(13) 0.0016(13) 0.0042(13) C8 0.040(2) 0.0250(18) 0.038(2) -0.0043(15) 0.0014(17) 0.0055(16) C9 0.0310(19) 0.0305(19) 0.041(2) 0.0147(16) 0.0054(16) 0.0011(15) C10 0.0220(16) 0.0228(16) 0.0328(19) 0.0142(14) 0.0047(14) 0.0056(13) C11 0.0237(18) 0.041(2) 0.046(2) 0.0240(18) 0.0143(16) 0.0120(16) C12 0.030(2) 0.034(2) 0.045(2) -0.0032(17) 0.0044(17) 0.0022(16) C13 0.0187(15) 0.0129(14) 0.0182(15) 0.0036(11) 0.0039(12) 0.0027(11) C14 0.0217(16) 0.0176(15) 0.0252(17) 0.0066(13) 0.0073(13) 0.0047(12) C15 0.0190(15) 0.0175(15) 0.0248(17) 0.0084(13) 0.0050(13) 0.0068(12) N2 0.0206(13) 0.0191(13) 0.0155(13) 0.0062(10) 0.0027(10) 0.0053(10) C16 0.0263(17) 0.0211(16) 0.0205(17) 0.0056(13) 0.0043(13) 0.0082(13) C17 0.0328(18) 0.0273(17) 0.0204(17) 0.0031(13) 0.0106(14) 0.0081(14) C18 0.0328(19) 0.0260(18) 0.034(2) 0.0045(15) 0.0099(15) 0.0127(15) C19 0.0327(18) 0.0232(16) 0.0265(18) 0.0069(14) 0.0057(14) 0.0115(14) O1 0.0285(12) 0.0352(13) 0.0253(12) 0.0115(10) 0.0044(10) 0.0192(10) C20 0.0291(18) 0.0376(19) 0.0202(17) 0.0119(14) 0.0000(14) 0.0165(15) C21 0.0172(15) 0.0247(16) 0.0223(17) 0.0085(13) 0.0009(12) 0.0040(13) C22 0.0267(17) 0.0301(18) 0.0195(17) 0.0049(14) 0.0035(13) -0.0004(14) C23 0.0284(18) 0.0277(17) 0.0182(16) 0.0093(13) 0.0041(13) 0.0058(14) B2 0.0176(17) 0.0212(17) 0.0172(18) 0.0058(14) 0.0038(14) 0.0020(14) F3 0.0260(10) 0.0462(12) 0.0196(9) 0.0126(8) 0.0078(8) 0.0169(9) F4 0.0287(10) 0.0305(10) 0.0183(9) 0.0053(8) 0.0041(8) -0.0040(8) N3 0.0160(13) 0.0205(13) 0.0166(13) 0.0048(10) 0.0040(10) 0.0002(10) C24 0.0160(15) 0.0228(16) 0.0115(14) 0.0031(12) 0.0027(11) 0.0011(12) C25 0.0186(15) 0.0207(15) 0.0165(15) 0.0054(12) 0.0015(12) 0.0022(12) C26 0.0193(16) 0.0316(18) 0.0198(16) 0.0076(13) 0.0078(13) 0.0096(13) C27 0.0219(16) 0.0298(17) 0.0212(16) 0.0113(13) 0.0076(13) 0.0070(13) C28 0.0253(17) 0.0211(16) 0.0242(17) 0.0129(13) 0.0051(13) 0.0070(13) C29 0.0186(16) 0.0230(16) 0.0171(16) 0.0062(12) 0.0015(12) 0.0057(12) C30 0.0254(17) 0.0196(16) 0.0224(17) 0.0038(13) 0.0079(13) 0.0048(13) C31 0.041(2) 0.0299(19) 0.033(2) 0.0133(15) 0.0135(16) 0.0176(16) C32 0.0339(19) 0.0234(17) 0.0280(19) 0.0017(14) 0.0106(15) 0.0056(14) C33 0.0238(17) 0.0265(17) 0.0256(17) 0.0120(14) 0.0107(13) 0.0103(13) C34 0.0306(19) 0.037(2) 0.034(2) 0.0113(16) 0.0083(15) 0.0174(16) C35 0.036(2) 0.033(2) 0.032(2) -0.0062(15) 0.0110(16) 0.0073(16) C36 0.0189(15) 0.0172(15) 0.0170(15) 0.0044(12) 0.0048(12) 0.0065(12) C37 0.0210(16) 0.0193(15) 0.0230(16) 0.0086(12) 0.0091(13) 0.0082(12) C38 0.0228(16) 0.0192(15) 0.0221(16) 0.0081(13) 0.0093(13) 0.0063(12) N4 0.0233(14) 0.0201(13) 0.0124(12) 0.0066(10) 0.0043(10) 0.0070(11) C39 0.0228(16) 0.0235(16) 0.0205(16) 0.0070(13) 0.0060(13) 0.0086(13) C40 0.0251(17) 0.0278(17) 0.0167(16) -0.0001(13) 0.0013(13) 0.0089(14) C41 0.0235(17) 0.0266(18) 0.0301(19) -0.0020(14) 0.0040(14) 0.0005(14) C42 0.0221(17) 0.0289(17) 0.0285(19) 0.0066(14) 0.0096(14) 0.0040(14) O2 0.0235(12) 0.0281(12) 0.0251(12) 0.0097(10) 0.0105(9) 0.0008(9) C43 0.0290(17) 0.0245(16) 0.0145(15) 0.0080(13) 0.0097(13) 0.0049(13) C44 0.0184(15) 0.0261(16) 0.0184(16) 0.0070(13) 0.0076(12) 0.0088(13) C45 0.0290(18) 0.0363(19) 0.0180(16) 0.0129(14) 0.0064(14) 0.0153(15) C46 0.0293(18) 0.0280(17) 0.0203(17) 0.0042(13) 0.0069(14) 0.0153(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 B1 F2 1.389(4) . ? B1 F1 1.395(4) . ? B1 N1 1.528(4) . ? B1 N2 1.560(4) . ? N1 C13 1.369(4) . ? N1 C1 1.446(4) . ? C1 C6 1.398(4) . ? C1 C2 1.414(4) . ? C2 C3 1.396(4) . ? C2 C7 1.516(4) . ? C3 C4 1.386(4) . ? C3 H1 0.9500 . ? C4 C5 1.376(4) . ? C4 H2 0.9500 . ? C5 C6 1.403(4) . ? C5 H3 0.9500 . ? C6 C10 1.513(4) . ? C7 C8 1.526(5) . ? C7 C9 1.530(5) . ? C7 H4 1.0000 . ? C8 H5 0.9800 . ? C8 H6 0.9800 . ? C8 H7 0.9800 . ? C9 H8 0.9800 . ? C9 H9 0.9800 . ? C9 H10 0.9800 . ? C10 C12 1.521(5) . ? C10 C11 1.535(5) . ? C10 H11 1.0000 . ? C11 H12 0.9800 . ? C11 H13 0.9800 . ? C11 H14 0.9800 . ? C12 H15 0.9800 . ? C12 H16 0.9800 . ? C12 H17 0.9800 . ? C13 C16 1.409(4) . ? C13 C14 1.427(4) . ? C14 C19 1.401(4) . ? C14 C15 1.420(4) . ? C15 N2 1.306(4) . ? C15 O1 1.338(4) . ? N2 C21 1.503(4) . ? C16 C17 1.368(4) . ? C16 H18 0.9500 . ? C17 C18 1.408(5) . ? C17 H19 0.9500 . ? C18 C19 1.369(5) . ? C18 H20 0.9500 . ? C19 H21 0.9500 . ? O1 C20 1.472(4) . ? C20 C21 1.523(4) . ? C20 H22 0.9900 . ? C20 H23 0.9900 . ? C21 C23 1.512(4) . ? C21 C22 1.526(4) . ? C22 H24 0.9800 . ? C22 H25 0.9800 . ? C22 H26 0.9800 . ? C23 H27 0.9800 . ? C23 H28 0.9800 . ? C23 H29 0.9800 . ? B2 F4 1.391(4) . ? B2 F3 1.404(4) . ? B2 N3 1.522(4) . ? B2 N4 1.560(4) . ? N3 C36 1.373(4) . ? N3 C24 1.448(4) . ? C24 C29 1.400(4) . ? C24 C25 1.413(4) . ? C25 C26 1.394(4) . ? C25 C30 1.515(4) . ? C26 C27 1.380(4) . ? C26 H30 0.9500 . ? C27 C28 1.381(4) . ? C27 H31 0.9500 . ? C28 C29 1.390(4) . ? C28 H32 0.9500 . ? C29 C33 1.523(4) . ? C30 C31 1.526(4) . ? C30 C32 1.528(4) . ? C30 H33 1.0000 . ? C31 H34 0.9800 . ? C31 H35 0.9800 . ? C31 H36 0.9800 . ? C32 H37 0.9800 . ? C32 H38 0.9800 . ? C32 H39 0.9800 . ? C33 C35 1.521(5) . ? C33 C34 1.533(4) . ? C33 H40 1.0000 . ? C34 H41 0.9800 . ? C34 H42 0.9800 . ? C34 H43 0.9800 . ? C35 H44 0.9800 . ? C35 H45 0.9800 . ? C35 H46 0.9800 . ? C36 C39 1.413(4) . ? C36 C37 1.420(4) . ? C37 C42 1.392(4) . ? C37 C38 1.432(4) . ? C38 N4 1.306(4) . ? C38 O2 1.337(4) . ? N4 C44 1.505(4) . ? C39 C40 1.374(4) . ? C39 H47 0.9500 . ? C40 C41 1.396(5) . ? C40 H48 0.9500 . ? C41 C42 1.376(5) . ? C41 H49 0.9500 . ? C42 H50 0.9500 . ? O2 C43 1.472(4) . ? C43 C44 1.533(4) . ? C43 H51 0.9900 . ? C43 H52 0.9900 . ? C44 C45 1.509(4) . ? C44 C46 1.524(4) . ? C45 H53 0.9800 . ? C45 H54 0.9800 . ? C45 H55 0.9800 . ? C46 H56 0.9800 . ? C46 H57 0.9800 . ? C46 H58 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag F2 B1 F1 108.3(3) . . ? F2 B1 N1 111.9(3) . . ? F1 B1 N1 112.2(3) . . ? F2 B1 N2 109.2(3) . . ? F1 B1 N2 108.0(2) . . ? N1 B1 N2 107.1(2) . . ? C13 N1 C1 118.7(2) . . ? C13 N1 B1 125.3(2) . . ? C1 N1 B1 116.0(2) . . ? C6 C1 C2 121.8(3) . . ? C6 C1 N1 119.1(3) . . ? C2 C1 N1 119.0(3) . . ? C3 C2 C1 117.6(3) . . ? C3 C2 C7 119.7(3) . . ? C1 C2 C7 122.7(3) . . ? C4 C3 C2 121.3(3) . . ? C4 C3 H1 119.3 . . ? C2 C3 H1 119.3 . . ? C5 C4 C3 120.0(3) . . ? C5 C4 H2 120.0 . . ? C3 C4 H2 120.0 . . ? C4 C5 C6 121.3(3) . . ? C4 C5 H3 119.4 . . ? C6 C5 H3 119.4 . . ? C1 C6 C5 118.0(3) . . ? C1 C6 C10 122.0(3) . . ? C5 C6 C10 120.0(3) . . ? C2 C7 C8 111.0(3) . . ? C2 C7 C9 111.9(3) . . ? C8 C7 C9 110.7(3) . . ? C2 C7 H4 107.7 . . ? C8 C7 H4 107.7 . . ? C9 C7 H4 107.7 . . ? C7 C8 H5 109.5 . . ? C7 C8 H6 109.5 . . ? H5 C8 H6 109.5 . . ? C7 C8 H7 109.5 . . ? H5 C8 H7 109.5 . . ? H6 C8 H7 109.5 . . ? C7 C9 H8 109.5 . . ? C7 C9 H9 109.5 . . ? H8 C9 H9 109.5 . . ? C7 C9 H10 109.5 . . ? H8 C9 H10 109.5 . . ? H9 C9 H10 109.5 . . ? C6 C10 C12 113.2(3) . . ? C6 C10 C11 110.3(3) . . ? C12 C10 C11 110.3(3) . . ? C6 C10 H11 107.6 . . ? C12 C10 H11 107.6 . . ? C11 C10 H11 107.6 . . ? C10 C11 H12 109.5 . . ? C10 C11 H13 109.5 . . ? H12 C11 H13 109.5 . . ? C10 C11 H14 109.5 . . ? H12 C11 H14 109.5 . . ? H13 C11 H14 109.5 . . ? C10 C12 H15 109.5 . . ? C10 C12 H16 109.5 . . ? H15 C12 H16 109.5 . . ? C10 C12 H17 109.5 . . ? H15 C12 H17 109.5 . . ? H16 C12 H17 109.5 . . ? N1 C13 C16 122.9(3) . . ? N1 C13 C14 120.3(3) . . ? C16 C13 C14 116.8(3) . . ? C19 C14 C15 121.9(3) . . ? C19 C14 C13 120.5(3) . . ? C15 C14 C13 117.5(3) . . ? N2 C15 O1 114.6(3) . . ? N2 C15 C14 124.3(3) . . ? O1 C15 C14 121.1(3) . . ? C15 N2 C21 108.8(2) . . ? C15 N2 B1 123.5(3) . . ? C21 N2 B1 127.6(2) . . ? C17 C16 C13 121.1(3) . . ? C17 C16 H18 119.4 . . ? C13 C16 H18 119.4 . . ? C16 C17 C18 122.1(3) . . ? C16 C17 H19 118.9 . . ? C18 C17 H19 118.9 . . ? C19 C18 C17 117.7(3) . . ? C19 C18 H20 121.1 . . ? C17 C18 H20 121.1 . . ? C18 C19 C14 121.7(3) . . ? C18 C19 H21 119.1 . . ? C14 C19 H21 119.1 . . ? C15 O1 C20 105.6(2) . . ? O1 C20 C21 104.2(2) . . ? O1 C20 H22 110.9 . . ? C21 C20 H22 110.9 . . ? O1 C20 H23 110.9 . . ? C21 C20 H23 110.9 . . ? H22 C20 H23 108.9 . . ? N2 C21 C23 112.3(2) . . ? N2 C21 C20 98.9(2) . . ? C23 C21 C20 113.1(3) . . ? N2 C21 C22 108.5(2) . . ? C23 C21 C22 111.5(3) . . ? C20 C21 C22 111.8(3) . . ? C21 C22 H24 109.5 . . ? C21 C22 H25 109.5 . . ? H24 C22 H25 109.5 . . ? C21 C22 H26 109.5 . . ? H24 C22 H26 109.5 . . ? H25 C22 H26 109.5 . . ? C21 C23 H27 109.5 . . ? C21 C23 H28 109.5 . . ? H27 C23 H28 109.5 . . ? C21 C23 H29 109.5 . . ? H27 C23 H29 109.5 . . ? H28 C23 H29 109.5 . . ? F4 B2 F3 107.8(2) . . ? F4 B2 N3 112.6(2) . . ? F3 B2 N3 112.0(3) . . ? F4 B2 N4 109.3(3) . . ? F3 B2 N4 107.5(2) . . ? N3 B2 N4 107.5(2) . . ? C36 N3 C24 119.1(2) . . ? C36 N3 B2 124.6(2) . . ? C24 N3 B2 115.8(2) . . ? C29 C24 C25 121.7(3) . . ? C29 C24 N3 119.7(3) . . ? C25 C24 N3 118.5(3) . . ? C26 C25 C24 117.5(3) . . ? C26 C25 C30 119.3(3) . . ? C24 C25 C30 123.1(3) . . ? C27 C26 C25 121.3(3) . . ? C27 C26 H30 119.3 . . ? C25 C26 H30 119.3 . . ? C26 C27 C28 120.1(3) . . ? C26 C27 H31 119.9 . . ? C28 C27 H31 119.9 . . ? C27 C28 C29 121.1(3) . . ? C27 C28 H32 119.4 . . ? C29 C28 H32 119.4 . . ? C28 C29 C24 118.1(3) . . ? C28 C29 C33 120.0(3) . . ? C24 C29 C33 121.9(3) . . ? C25 C30 C31 111.8(3) . . ? C25 C30 C32 110.8(3) . . ? C31 C30 C32 110.6(3) . . ? C25 C30 H33 107.8 . . ? C31 C30 H33 107.8 . . ? C32 C30 H33 107.8 . . ? C30 C31 H34 109.5 . . ? C30 C31 H35 109.5 . . ? H34 C31 H35 109.5 . . ? C30 C31 H36 109.5 . . ? H34 C31 H36 109.5 . . ? H35 C31 H36 109.5 . . ? C30 C32 H37 109.5 . . ? C30 C32 H38 109.5 . . ? H37 C32 H38 109.5 . . ? C30 C32 H39 109.5 . . ? H37 C32 H39 109.5 . . ? H38 C32 H39 109.5 . . ? C35 C33 C29 113.5(3) . . ? C35 C33 C34 109.4(3) . . ? C29 C33 C34 110.4(3) . . ? C35 C33 H40 107.7 . . ? C29 C33 H40 107.7 . . ? C34 C33 H40 107.7 . . ? C33 C34 H41 109.5 . . ? C33 C34 H42 109.5 . . ? H41 C34 H42 109.5 . . ? C33 C34 H43 109.5 . . ? H41 C34 H43 109.5 . . ? H42 C34 H43 109.5 . . ? C33 C35 H44 109.5 . . ? C33 C35 H45 109.5 . . ? H44 C35 H45 109.5 . . ? C33 C35 H46 109.5 . . ? H44 C35 H46 109.5 . . ? H45 C35 H46 109.5 . . ? N3 C36 C39 122.6(3) . . ? N3 C36 C37 121.0(3) . . ? C39 C36 C37 116.3(3) . . ? C42 C37 C36 121.8(3) . . ? C42 C37 C38 121.2(3) . . ? C36 C37 C38 117.0(3) . . ? N4 C38 O2 114.7(3) . . ? N4 C38 C37 124.2(3) . . ? O2 C38 C37 121.0(3) . . ? C38 N4 C44 109.0(2) . . ? C38 N4 B2 123.1(2) . . ? C44 N4 B2 128.0(2) . . ? C40 C39 C36 120.9(3) . . ? C40 C39 H47 119.6 . . ? C36 C39 H47 119.6 . . ? C39 C40 C41 122.0(3) . . ? C39 C40 H48 119.0 . . ? C41 C40 H48 119.0 . . ? C42 C41 C40 118.5(3) . . ? C42 C41 H49 120.7 . . ? C40 C41 H49 120.7 . . ? C41 C42 C37 120.5(3) . . ? C41 C42 H50 119.8 . . ? C37 C42 H50 119.8 . . ? C38 O2 C43 106.1(2) . . ? O2 C43 C44 104.0(2) . . ? O2 C43 H51 111.0 . . ? C44 C43 H51 111.0 . . ? O2 C43 H52 111.0 . . ? C44 C43 H52 111.0 . . ? H51 C43 H52 109.0 . . ? N4 C44 C45 111.9(2) . . ? N4 C44 C46 108.3(2) . . ? C45 C44 C46 111.8(3) . . ? N4 C44 C43 99.3(2) . . ? C45 C44 C43 112.9(3) . . ? C46 C44 C43 111.9(3) . . ? C44 C45 H53 109.5 . . ? C44 C45 H54 109.5 . . ? H53 C45 H54 109.5 . . ? C44 C45 H55 109.5 . . ? H53 C45 H55 109.5 . . ? H54 C45 H55 109.5 . . ? C44 C46 H56 109.5 . . ? C44 C46 H57 109.5 . . ? H56 C46 H57 109.5 . . ? C44 C46 H58 109.5 . . ? H56 C46 H58 109.5 . . ? H57 C46 H58 109.5 . . ? 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 F2 B1 N1 C13 133.7(3) . . . . ? F1 B1 N1 C13 -104.2(3) . . . . ? N2 B1 N1 C13 14.1(4) . . . . ? F2 B1 N1 C1 -46.4(4) . . . . ? F1 B1 N1 C1 75.6(3) . . . . ? N2 B1 N1 C1 -166.1(2) . . . . ? C13 N1 C1 C6 -92.2(3) . . . . ? B1 N1 C1 C6 87.9(3) . . . . ? C13 N1 C1 C2 91.3(3) . . . . ? B1 N1 C1 C2 -88.6(3) . . . . ? C6 C1 C2 C3 -0.2(4) . . . . ? N1 C1 C2 C3 176.2(3) . . . . ? C6 C1 C2 C7 177.9(3) . . . . ? N1 C1 C2 C7 -5.7(4) . . . . ? C1 C2 C3 C4 -1.8(4) . . . . ? C7 C2 C3 C4 -180.0(3) . . . . ? C2 C3 C4 C5 2.8(5) . . . . ? C3 C4 C5 C6 -1.8(5) . . . . ? C2 C1 C6 C5 1.2(4) . . . . ? N1 C1 C6 C5 -175.2(2) . . . . ? C2 C1 C6 C10 -176.1(3) . . . . ? N1 C1 C6 C10 7.6(4) . . . . ? C4 C5 C6 C1 -0.2(4) . . . . ? C4 C5 C6 C10 177.1(3) . . . . ? C3 C2 C7 C8 62.1(4) . . . . ? C1 C2 C7 C8 -116.0(3) . . . . ? C3 C2 C7 C9 -62.1(4) . . . . ? C1 C2 C7 C9 119.8(3) . . . . ? C1 C6 C10 C12 -125.4(3) . . . . ? C5 C6 C10 C12 57.4(4) . . . . ? C1 C6 C10 C11 110.5(3) . . . . ? C5 C6 C10 C11 -66.7(4) . . . . ? C1 N1 C13 C16 -4.3(4) . . . . ? B1 N1 C13 C16 175.5(3) . . . . ? C1 N1 C13 C14 174.7(3) . . . . ? B1 N1 C13 C14 -5.4(4) . . . . ? N1 C13 C14 C19 179.8(3) . . . . ? C16 C13 C14 C19 -1.1(4) . . . . ? N1 C13 C14 C15 -4.0(4) . . . . ? C16 C13 C14 C15 175.1(3) . . . . ? C19 C14 C15 N2 178.3(3) . . . . ? C13 C14 C15 N2 2.1(4) . . . . ? C19 C14 C15 O1 0.9(5) . . . . ? C13 C14 C15 O1 -175.2(3) . . . . ? O1 C15 N2 C21 8.2(3) . . . . ? C14 C15 N2 C21 -169.3(3) . . . . ? O1 C15 N2 B1 -173.4(3) . . . . ? C14 C15 N2 B1 9.1(5) . . . . ? F2 B1 N2 C15 -137.2(3) . . . . ? F1 B1 N2 C15 105.3(3) . . . . ? N1 B1 N2 C15 -15.8(4) . . . . ? F2 B1 N2 C21 40.9(4) . . . . ? F1 B1 N2 C21 -76.7(4) . . . . ? N1 B1 N2 C21 162.3(3) . . . . ? N1 C13 C16 C17 -179.4(3) . . . . ? C14 C13 C16 C17 1.5(4) . . . . ? C13 C16 C17 C18 -1.1(5) . . . . ? C16 C17 C18 C19 0.2(5) . . . . ? C17 C18 C19 C14 0.1(5) . . . . ? C15 C14 C19 C18 -175.7(3) . . . . ? C13 C14 C19 C18 0.3(5) . . . . ? N2 C15 O1 C20 10.5(3) . . . . ? C14 C15 O1 C20 -171.9(3) . . . . ? C15 O1 C20 C21 -24.1(3) . . . . ? C15 N2 C21 C23 -141.5(3) . . . . ? B1 N2 C21 C23 40.2(4) . . . . ? C15 N2 C21 C20 -22.0(3) . . . . ? B1 N2 C21 C20 159.8(3) . . . . ? C15 N2 C21 C22 94.7(3) . . . . ? B1 N2 C21 C22 -83.6(3) . . . . ? O1 C20 C21 N2 26.8(3) . . . . ? O1 C20 C21 C23 145.8(3) . . . . ? O1 C20 C21 C22 -87.3(3) . . . . ? F4 B2 N3 C36 -136.4(3) . . . . ? F3 B2 N3 C36 101.9(3) . . . . ? N4 B2 N3 C36 -16.0(4) . . . . ? F4 B2 N3 C24 51.6(4) . . . . ? F3 B2 N3 C24 -70.1(3) . . . . ? N4 B2 N3 C24 172.0(2) . . . . ? C36 N3 C24 C29 99.7(3) . . . . ? B2 N3 C24 C29 -87.8(3) . . . . ? C36 N3 C24 C25 -82.4(3) . . . . ? B2 N3 C24 C25 90.1(3) . . . . ? C29 C24 C25 C26 0.6(4) . . . . ? N3 C24 C25 C26 -177.2(2) . . . . ? C29 C24 C25 C30 -178.3(3) . . . . ? N3 C24 C25 C30 3.8(4) . . . . ? C24 C25 C26 C27 1.1(4) . . . . ? C30 C25 C26 C27 -179.9(3) . . . . ? C25 C26 C27 C28 -1.5(5) . . . . ? C26 C27 C28 C29 0.1(5) . . . . ? C27 C28 C29 C24 1.5(4) . . . . ? C27 C28 C29 C33 -176.3(3) . . . . ? C25 C24 C29 C28 -1.9(4) . . . . ? N3 C24 C29 C28 175.9(3) . . . . ? C25 C24 C29 C33 175.9(3) . . . . ? N3 C24 C29 C33 -6.3(4) . . . . ? C26 C25 C30 C31 63.0(4) . . . . ? C24 C25 C30 C31 -118.0(3) . . . . ? C26 C25 C30 C32 -60.8(4) . . . . ? C24 C25 C30 C32 118.1(3) . . . . ? C28 C29 C33 C35 -47.3(4) . . . . ? C24 C29 C33 C35 134.9(3) . . . . ? C28 C29 C33 C34 76.0(4) . . . . ? C24 C29 C33 C34 -101.7(3) . . . . ? C24 N3 C36 C39 -1.8(4) . . . . ? B2 N3 C36 C39 -173.7(3) . . . . ? C24 N3 C36 C37 177.9(3) . . . . ? B2 N3 C36 C37 6.1(4) . . . . ? N3 C36 C37 C42 -177.6(3) . . . . ? C39 C36 C37 C42 2.2(4) . . . . ? N3 C36 C37 C38 4.8(4) . . . . ? C39 C36 C37 C38 -175.4(3) . . . . ? C42 C37 C38 N4 179.4(3) . . . . ? C36 C37 C38 N4 -3.1(4) . . . . ? C42 C37 C38 O2 -4.0(4) . . . . ? C36 C37 C38 O2 173.6(3) . . . . ? O2 C38 N4 C44 -6.5(3) . . . . ? C37 C38 N4 C44 170.3(3) . . . . ? O2 C38 N4 B2 173.7(2) . . . . ? C37 C38 N4 B2 -9.4(4) . . . . ? F4 B2 N4 C38 140.0(3) . . . . ? F3 B2 N4 C38 -103.2(3) . . . . ? N3 B2 N4 C38 17.6(4) . . . . ? F4 B2 N4 C44 -39.7(4) . . . . ? F3 B2 N4 C44 77.1(3) . . . . ? N3 B2 N4 C44 -162.1(2) . . . . ? N3 C36 C39 C40 178.4(3) . . . . ? C37 C36 C39 C40 -1.4(4) . . . . ? C36 C39 C40 C41 0.0(5) . . . . ? C39 C40 C41 C42 0.8(5) . . . . ? C40 C41 C42 C37 0.0(5) . . . . ? C36 C37 C42 C41 -1.5(5) . . . . ? C38 C37 C42 C41 175.9(3) . . . . ? N4 C38 O2 C43 -11.2(3) . . . . ? C37 C38 O2 C43 171.8(3) . . . . ? C38 O2 C43 C44 23.4(3) . . . . ? C38 N4 C44 C45 139.4(3) . . . . ? B2 N4 C44 C45 -40.8(4) . . . . ? C38 N4 C44 C46 -96.9(3) . . . . ? B2 N4 C44 C46 82.9(3) . . . . ? C38 N4 C44 C43 20.1(3) . . . . ? B2 N4 C44 C43 -160.2(3) . . . . ? O2 C43 C44 N4 -25.3(3) . . . . ? O2 C43 C44 C45 -143.9(2) . . . . ? O2 C43 C44 C46 88.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.932 _refine_diff_density_min -0.263 _refine_diff_density_rms 0.078 #----------4-pyr-----------# data_4-pyr _database_code_depnum_ccdc_archive 'CCDC 777066' #TrackingRef '- CIFs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H31 B F2 N2' _chemical_formula_weight 384.31 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 13.975(6) _cell_length_b 11.390(5) _cell_length_c 14.556(7) _cell_angle_alpha 90 _cell_angle_beta 114.7635(19) _cell_angle_gamma 90 _cell_volume 2104.0(16) _cell_formula_units_Z 4 _cell_measurement_temperature 103.1500 _cell_measurement_reflns_used 5699 _cell_measurement_theta_min 3.0817 _cell_measurement_theta_max 27.4835 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.213 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 0.082 _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 103(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'RIGAKU/MSC Meacury CCD' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 7.31 _diffrn_reflns_number 13221 _diffrn_reflns_av_R_equivalents 0.0378 _diffrn_reflns_av_sigmaI/netI 0.0336 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3570 _reflns_number_gt 3069 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RIGAKU CrystalClear' _computing_cell_refinement 'RIGAKU CrystalClear' _computing_data_reduction 'RIGAKU CrystalClear' _computing_structure_solution SIR-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP-III _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^)+(0.0669P)^2^+1.1954P] 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 3570 _refine_ls_number_parameters 257 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0697 _refine_ls_R_factor_gt 0.0585 _refine_ls_wR_factor_ref 0.1493 _refine_ls_wR_factor_gt 0.1406 _refine_ls_goodness_of_fit_ref 1.124 _refine_ls_restrained_S_all 1.124 _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 0.2460(2) 0.3840(2) 0.89150(18) 0.0206(5) Uani 1 1 d . . . F1 F 0.35619(10) 0.39009(12) 0.93246(10) 0.0316(4) Uani 1 1 d . . . F2 F 0.20862(11) 0.47826(11) 0.92762(9) 0.0292(3) Uani 1 1 d . . . N1 N 0.19445(14) 0.37684(14) 0.77806(13) 0.0180(4) Uani 1 1 d . . . N2 N 0.21917(14) 0.26584(15) 0.93693(13) 0.0188(4) Uani 1 1 d . . . C1 C 0.17955(17) 0.48550(17) 0.72232(15) 0.0189(5) Uani 1 1 d . . . C2 C 0.08477(17) 0.54752(19) 0.69431(16) 0.0219(5) Uani 1 1 d . . . C3 C 0.07474(19) 0.6557(2) 0.64622(17) 0.0276(5) Uani 1 1 d . . . H1 H 0.0121 0.7002 0.6291 0.033 Uiso 1 1 calc R . . C4 C 0.15422(19) 0.6993(2) 0.62299(17) 0.0290(5) Uani 1 1 d . . . H2 H 0.1461 0.7730 0.5901 0.035 Uiso 1 1 calc R . . C5 C 0.24562(19) 0.63514(19) 0.64775(17) 0.0252(5) Uani 1 1 d . . . H3 H 0.2991 0.6646 0.6299 0.030 Uiso 1 1 calc R . . C6 C 0.26097(17) 0.52811(18) 0.69845(15) 0.0201(5) Uani 1 1 d . . . C7 C -0.00866(18) 0.4971(2) 0.70961(17) 0.0266(5) Uani 1 1 d . . . H4 H 0.0117 0.4170 0.7395 0.032 Uiso 1 1 calc R . . C8 C -0.0378(2) 0.5693(3) 0.7821(2) 0.0416(7) Uani 1 1 d . . . H5 H 0.0230 0.5742 0.8479 0.062 Uiso 1 1 calc R . . H6 H -0.0967 0.5318 0.7905 0.062 Uiso 1 1 calc R . . H7 H -0.0584 0.6485 0.7547 0.062 Uiso 1 1 calc R . . C9 C -0.1044(2) 0.4833(3) 0.6076(2) 0.0475(7) Uani 1 1 d . . . H8 H -0.1324 0.5610 0.5808 0.071 Uiso 1 1 calc R . . H9 H -0.1590 0.4375 0.6171 0.071 Uiso 1 1 calc R . . H10 H -0.0831 0.4425 0.5599 0.071 Uiso 1 1 calc R . . C10 C 0.36313(17) 0.46110(19) 0.72453(17) 0.0239(5) Uani 1 1 d . . . H11 H 0.3628 0.3920 0.7668 0.029 Uiso 1 1 calc R . . C11 C 0.45923(19) 0.5362(2) 0.78696(19) 0.0329(6) Uani 1 1 d . . . H12 H 0.4627 0.6036 0.7466 0.049 Uiso 1 1 calc R . . H13 H 0.5233 0.4889 0.8062 0.049 Uiso 1 1 calc R . . H14 H 0.4533 0.5641 0.8480 0.049 Uiso 1 1 calc R . . C12 C 0.3705(2) 0.4142(2) 0.62877(19) 0.0327(6) Uani 1 1 d . . . H15 H 0.3090 0.3648 0.5910 0.049 Uiso 1 1 calc R . . H16 H 0.4349 0.3676 0.6479 0.049 Uiso 1 1 calc R . . H17 H 0.3721 0.4802 0.5863 0.049 Uiso 1 1 calc R . . C13 C 0.17519(16) 0.27090(17) 0.72541(16) 0.0175(4) Uani 1 1 d . . . C14 C 0.20144(16) 0.16379(18) 0.77966(16) 0.0188(5) Uani 1 1 d . . . C15 C 0.17898(17) 0.05763(18) 0.72718(16) 0.0217(5) Uani 1 1 d . . . H18 H 0.1959 -0.0139 0.7642 0.026 Uiso 1 1 calc R . . C16 C 0.13277(17) 0.05378(19) 0.62270(17) 0.0231(5) Uani 1 1 d . . . H19 H 0.1189 -0.0192 0.5879 0.028 Uiso 1 1 calc R . . C17 C 0.10709(17) 0.15886(19) 0.56977(17) 0.0228(5) Uani 1 1 d . . . H20 H 0.0752 0.1573 0.4979 0.027 Uiso 1 1 calc R . . C18 C 0.12682(17) 0.26594(18) 0.61913(16) 0.0203(5) Uani 1 1 d . . . H21 H 0.1076 0.3366 0.5810 0.024 Uiso 1 1 calc R . . C19 C 0.25481(18) 0.16390(18) 0.89295(16) 0.0219(5) Uani 1 1 d . . . H22 H 0.3320 0.1684 0.9151 0.026 Uiso 1 1 calc R . . H23 H 0.2389 0.0895 0.9189 0.026 Uiso 1 1 calc R . . C20 C 0.10316(17) 0.25549(19) 0.91364(17) 0.0235(5) Uani 1 1 d . . . H24 H 0.0692 0.3337 0.8996 0.028 Uiso 1 1 calc R . . H25 H 0.0667 0.2044 0.8541 0.028 Uiso 1 1 calc R . . C21 C 0.0991(2) 0.2028(3) 1.0060(2) 0.0452(7) Uani 1 1 d . . . H26 H 0.1066 0.1163 1.0064 0.054 Uiso 1 1 calc R . . H27 H 0.0322 0.2226 1.0105 0.054 Uiso 1 1 calc R . . C22 C 0.1917(2) 0.2582(3) 1.09106(18) 0.0374(6) Uani 1 1 d . . . H28 H 0.2148 0.2096 1.1530 0.045 Uiso 1 1 calc R . . H29 H 0.1736 0.3376 1.1063 0.045 Uiso 1 1 calc R . . C23 C 0.27660(18) 0.26419(19) 1.05259(16) 0.0241(5) Uani 1 1 d . . . H30 H 0.3236 0.1950 1.0757 0.029 Uiso 1 1 calc R . . H31 H 0.3195 0.3361 1.0775 0.029 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 B1 0.0230(13) 0.0182(12) 0.0188(12) 0.0008(9) 0.0070(11) -0.0020(9) F1 0.0238(7) 0.0408(8) 0.0243(7) 0.0072(6) 0.0043(6) -0.0089(6) F2 0.0465(9) 0.0200(7) 0.0202(7) -0.0024(5) 0.0131(6) 0.0007(6) N1 0.0225(10) 0.0144(9) 0.0168(9) 0.0016(7) 0.0078(8) 0.0006(7) N2 0.0203(10) 0.0200(9) 0.0155(9) -0.0010(7) 0.0070(8) -0.0007(7) C1 0.0249(12) 0.0166(10) 0.0130(10) -0.0007(8) 0.0059(9) 0.0002(8) C2 0.0246(12) 0.0235(11) 0.0154(10) -0.0026(8) 0.0063(9) 0.0018(9) C3 0.0303(13) 0.0259(12) 0.0235(12) 0.0025(9) 0.0082(10) 0.0100(10) C4 0.0423(15) 0.0199(11) 0.0237(12) 0.0050(9) 0.0128(11) 0.0047(10) C5 0.0345(13) 0.0222(11) 0.0210(12) 0.0009(9) 0.0136(10) -0.0012(9) C6 0.0252(12) 0.0193(10) 0.0163(10) -0.0009(8) 0.0092(9) -0.0004(9) C7 0.0222(12) 0.0301(12) 0.0257(12) 0.0006(9) 0.0083(10) 0.0036(9) C8 0.0365(15) 0.0544(17) 0.0400(16) -0.0101(13) 0.0218(13) -0.0044(12) C9 0.0304(15) 0.074(2) 0.0349(15) -0.0132(14) 0.0105(13) -0.0061(13) C10 0.0277(12) 0.0230(11) 0.0261(12) 0.0020(9) 0.0163(10) 0.0027(9) C11 0.0280(13) 0.0351(14) 0.0353(14) -0.0043(11) 0.0128(11) 0.0018(10) C12 0.0360(14) 0.0324(13) 0.0379(14) -0.0032(11) 0.0235(12) 0.0015(11) C13 0.0158(11) 0.0180(10) 0.0207(11) -0.0012(8) 0.0096(9) -0.0007(8) C14 0.0199(11) 0.0197(11) 0.0185(11) 0.0020(8) 0.0096(9) 0.0024(8) C15 0.0248(12) 0.0177(11) 0.0258(12) 0.0028(9) 0.0137(10) 0.0032(8) C16 0.0281(12) 0.0185(11) 0.0272(12) -0.0052(9) 0.0159(10) 0.0001(9) C17 0.0236(12) 0.0254(11) 0.0191(11) -0.0017(9) 0.0087(10) 0.0013(9) C18 0.0240(12) 0.0189(10) 0.0185(11) 0.0021(8) 0.0093(9) 0.0023(8) C19 0.0266(12) 0.0174(11) 0.0230(12) 0.0016(8) 0.0117(10) 0.0035(9) C20 0.0205(12) 0.0267(12) 0.0229(12) -0.0018(9) 0.0089(10) -0.0031(9) C21 0.0384(16) 0.0649(19) 0.0363(15) 0.0082(14) 0.0195(13) -0.0052(13) C22 0.0375(15) 0.0568(17) 0.0196(12) -0.0002(11) 0.0137(12) -0.0028(12) C23 0.0279(13) 0.0249(12) 0.0163(11) 0.0021(9) 0.0061(10) -0.0015(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 B1 F2 1.390(3) . ? B1 F1 1.401(3) . ? B1 N1 1.502(3) . ? B1 N2 1.612(3) . ? N1 C13 1.394(3) . ? N1 C1 1.446(3) . ? N2 C19 1.508(3) . ? N2 C20 1.516(3) . ? N2 C23 1.532(3) . ? C1 C2 1.403(3) . ? C1 C6 1.408(3) . ? C2 C3 1.395(3) . ? C2 C7 1.526(3) . ? C3 C4 1.382(3) . ? C3 H1 0.9500 . ? C4 C5 1.382(3) . ? C4 H2 0.9500 . ? C5 C6 1.394(3) . ? C5 H3 0.9500 . ? C6 C10 1.520(3) . ? C7 C8 1.522(3) . ? C7 C9 1.535(4) . ? C7 H4 1.0000 . ? C8 H5 0.9800 . ? C8 H6 0.9800 . ? C8 H7 0.9800 . ? C9 H8 0.9800 . ? C9 H9 0.9800 . ? C9 H10 0.9800 . ? C10 C11 1.529(3) . ? C10 C12 1.536(3) . ? C10 H11 1.0000 . ? C11 H12 0.9800 . ? C11 H13 0.9800 . ? C11 H14 0.9800 . ? C12 H15 0.9800 . ? C12 H16 0.9800 . ? C12 H17 0.9800 . ? C13 C18 1.406(3) . ? C13 C14 1.416(3) . ? C14 C15 1.394(3) . ? C14 C19 1.498(3) . ? C15 C16 1.382(3) . ? C15 H18 0.9500 . ? C16 C17 1.387(3) . ? C16 H19 0.9500 . ? C17 C18 1.383(3) . ? C17 H20 0.9500 . ? C18 H21 0.9500 . ? C19 H22 0.9900 . ? C19 H23 0.9900 . ? C20 C21 1.495(3) . ? C20 H24 0.9900 . ? C20 H25 0.9900 . ? C21 C22 1.504(4) . ? C21 H26 0.9900 . ? C21 H27 0.9900 . ? C22 C23 1.511(3) . ? C22 H28 0.9900 . ? C22 H29 0.9900 . ? C23 H30 0.9900 . ? C23 H31 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag F2 B1 F1 108.75(18) . . ? F2 B1 N1 112.02(18) . . ? F1 B1 N1 113.96(18) . . ? F2 B1 N2 107.52(18) . . ? F1 B1 N2 105.64(17) . . ? N1 B1 N2 108.58(17) . . ? C13 N1 C1 118.88(17) . . ? C13 N1 B1 123.02(17) . . ? C1 N1 B1 117.39(16) . . ? C19 N2 C20 110.96(16) . . ? C19 N2 C23 110.06(16) . . ? C20 N2 C23 105.30(15) . . ? C19 N2 B1 107.10(16) . . ? C20 N2 B1 112.58(16) . . ? C23 N2 B1 110.87(16) . . ? C2 C1 C6 121.14(19) . . ? C2 C1 N1 119.38(18) . . ? C6 C1 N1 119.48(18) . . ? C3 C2 C1 118.4(2) . . ? C3 C2 C7 119.6(2) . . ? C1 C2 C7 121.98(19) . . ? C4 C3 C2 121.2(2) . . ? C4 C3 H1 119.4 . . ? C2 C3 H1 119.4 . . ? C3 C4 C5 119.8(2) . . ? C3 C4 H2 120.1 . . ? C5 C4 H2 120.1 . . ? C4 C5 C6 121.4(2) . . ? C4 C5 H3 119.3 . . ? C6 C5 H3 119.3 . . ? C5 C6 C1 118.1(2) . . ? C5 C6 C10 119.43(19) . . ? C1 C6 C10 122.47(19) . . ? C8 C7 C2 113.0(2) . . ? C8 C7 C9 110.4(2) . . ? C2 C7 C9 110.5(2) . . ? C8 C7 H4 107.6 . . ? C2 C7 H4 107.6 . . ? C9 C7 H4 107.6 . . ? C7 C8 H5 109.5 . . ? C7 C8 H6 109.5 . . ? H5 C8 H6 109.5 . . ? C7 C8 H7 109.5 . . ? H5 C8 H7 109.5 . . ? H6 C8 H7 109.5 . . ? C7 C9 H8 109.5 . . ? C7 C9 H9 109.5 . . ? H8 C9 H9 109.5 . . ? C7 C9 H10 109.5 . . ? H8 C9 H10 109.5 . . ? H9 C9 H10 109.5 . . ? C6 C10 C11 111.52(18) . . ? C6 C10 C12 111.15(19) . . ? C11 C10 C12 110.98(19) . . ? C6 C10 H11 107.7 . . ? C11 C10 H11 107.7 . . ? C12 C10 H11 107.7 . . ? C10 C11 H12 109.5 . . ? C10 C11 H13 109.5 . . ? H12 C11 H13 109.5 . . ? C10 C11 H14 109.5 . . ? H12 C11 H14 109.5 . . ? H13 C11 H14 109.5 . . ? C10 C12 H15 109.5 . . ? C10 C12 H16 109.5 . . ? H15 C12 H16 109.5 . . ? C10 C12 H17 109.5 . . ? H15 C12 H17 109.5 . . ? H16 C12 H17 109.5 . . ? N1 C13 C18 122.19(18) . . ? N1 C13 C14 119.61(19) . . ? C18 C13 C14 118.16(18) . . ? C15 C14 C13 119.71(19) . . ? C15 C14 C19 119.86(18) . . ? C13 C14 C19 120.43(18) . . ? C16 C15 C14 121.66(19) . . ? C16 C15 H18 119.2 . . ? C14 C15 H18 119.2 . . ? C15 C16 C17 118.5(2) . . ? C15 C16 H19 120.8 . . ? C17 C16 H19 120.8 . . ? C18 C17 C16 121.6(2) . . ? C18 C17 H20 119.2 . . ? C16 C17 H20 119.2 . . ? C17 C18 C13 120.40(19) . . ? C17 C18 H21 119.8 . . ? C13 C18 H21 119.8 . . ? C14 C19 N2 111.54(17) . . ? C14 C19 H22 109.3 . . ? N2 C19 H22 109.3 . . ? C14 C19 H23 109.3 . . ? N2 C19 H23 109.3 . . ? H22 C19 H23 108.0 . . ? C21 C20 N2 105.66(19) . . ? C21 C20 H24 110.6 . . ? N2 C20 H24 110.6 . . ? C21 C20 H25 110.6 . . ? N2 C20 H25 110.6 . . ? H24 C20 H25 108.7 . . ? C20 C21 C22 103.2(2) . . ? C20 C21 H26 111.1 . . ? C22 C21 H26 111.1 . . ? C20 C21 H27 111.1 . . ? C22 C21 H27 111.1 . . ? H26 C21 H27 109.1 . . ? C21 C22 C23 104.6(2) . . ? C21 C22 H28 110.8 . . ? C23 C22 H28 110.8 . . ? C21 C22 H29 110.8 . . ? C23 C22 H29 110.8 . . ? H28 C22 H29 108.9 . . ? C22 C23 N2 106.05(18) . . ? C22 C23 H30 110.5 . . ? N2 C23 H30 110.5 . . ? C22 C23 H31 110.5 . . ? N2 C23 H31 110.5 . . ? H30 C23 H31 108.7 . . ? 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 F2 B1 N1 C13 -147.52(19) . . . . ? F1 B1 N1 C13 88.5(2) . . . . ? N2 B1 N1 C13 -28.9(3) . . . . ? F2 B1 N1 C1 42.2(3) . . . . ? F1 B1 N1 C1 -81.8(2) . . . . ? N2 B1 N1 C1 160.79(17) . . . . ? F2 B1 N2 C19 177.06(16) . . . . ? F1 B1 N2 C19 -66.9(2) . . . . ? N1 B1 N2 C19 55.7(2) . . . . ? F2 B1 N2 C20 54.8(2) . . . . ? F1 B1 N2 C20 170.82(16) . . . . ? N1 B1 N2 C20 -66.6(2) . . . . ? F2 B1 N2 C23 -62.9(2) . . . . ? F1 B1 N2 C23 53.1(2) . . . . ? N1 B1 N2 C23 175.76(16) . . . . ? C13 N1 C1 C2 97.4(2) . . . . ? B1 N1 C1 C2 -91.9(2) . . . . ? C13 N1 C1 C6 -83.6(2) . . . . ? B1 N1 C1 C6 87.1(2) . . . . ? C6 C1 C2 C3 -3.0(3) . . . . ? N1 C1 C2 C3 176.04(18) . . . . ? C6 C1 C2 C7 173.55(19) . . . . ? N1 C1 C2 C7 -7.4(3) . . . . ? C1 C2 C3 C4 2.4(3) . . . . ? C7 C2 C3 C4 -174.2(2) . . . . ? C2 C3 C4 C5 -0.1(3) . . . . ? C3 C4 C5 C6 -1.8(3) . . . . ? C4 C5 C6 C1 1.2(3) . . . . ? C4 C5 C6 C10 -179.7(2) . . . . ? C2 C1 C6 C5 1.2(3) . . . . ? N1 C1 C6 C5 -177.80(18) . . . . ? C2 C1 C6 C10 -177.88(19) . . . . ? N1 C1 C6 C10 3.1(3) . . . . ? C3 C2 C7 C8 -66.2(3) . . . . ? C1 C2 C7 C8 117.3(2) . . . . ? C3 C2 C7 C9 58.0(3) . . . . ? C1 C2 C7 C9 -118.5(2) . . . . ? C5 C6 C10 C11 56.1(3) . . . . ? C1 C6 C10 C11 -124.9(2) . . . . ? C5 C6 C10 C12 -68.4(3) . . . . ? C1 C6 C10 C12 110.7(2) . . . . ? C1 N1 C13 C18 -9.9(3) . . . . ? B1 N1 C13 C18 180.00(19) . . . . ? C1 N1 C13 C14 172.38(18) . . . . ? B1 N1 C13 C14 2.2(3) . . . . ? N1 C13 C14 C15 177.83(18) . . . . ? C18 C13 C14 C15 0.0(3) . . . . ? N1 C13 C14 C19 -3.2(3) . . . . ? C18 C13 C14 C19 178.92(19) . . . . ? C13 C14 C15 C16 0.9(3) . . . . ? C19 C14 C15 C16 -178.0(2) . . . . ? C14 C15 C16 C17 -1.0(3) . . . . ? C15 C16 C17 C18 0.1(3) . . . . ? C16 C17 C18 C13 0.8(3) . . . . ? N1 C13 C18 C17 -178.63(19) . . . . ? C14 C13 C18 C17 -0.8(3) . . . . ? C15 C14 C19 N2 -147.36(19) . . . . ? C13 C14 C19 N2 33.7(3) . . . . ? C20 N2 C19 C14 64.8(2) . . . . ? C23 N2 C19 C14 -179.10(17) . . . . ? B1 N2 C19 C14 -58.5(2) . . . . ? C19 N2 C20 C21 97.7(2) . . . . ? C23 N2 C20 C21 -21.4(2) . . . . ? B1 N2 C20 C21 -142.3(2) . . . . ? N2 C20 C21 C22 37.0(3) . . . . ? C20 C21 C22 C23 -38.2(3) . . . . ? C21 C22 C23 N2 24.9(3) . . . . ? C19 N2 C23 C22 -122.0(2) . . . . ? C20 N2 C23 C22 -2.3(2) . . . . ? B1 N2 C23 C22 119.7(2) . . . . ? _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.960 _refine_diff_density_max 0.884 _refine_diff_density_min -0.325 _refine_diff_density_rms 0.047 #----------4-iPr-----------# data_4-iPr _database_code_depnum_ccdc_archive 'CCDC 777067' #TrackingRef '- CIFs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H37 B F2 N2' _chemical_formula_weight 414.38 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' 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.9370(13) _cell_length_b 11.0234(10) _cell_length_c 20.180(2) _cell_angle_alpha 90 _cell_angle_beta 101.4026(18) _cell_angle_gamma 90 _cell_volume 2384.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 163.1500 _cell_measurement_reflns_used 7368 _cell_measurement_theta_min 3.0677 _cell_measurement_theta_max 27.4835 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.55 _exptl_crystal_size_min 0.55 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.154 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 0.077 _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 163(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'RIGAKU/MSC Meacury CCD' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 7.31 _diffrn_reflns_number 14829 _diffrn_reflns_av_R_equivalents 0.0263 _diffrn_reflns_av_sigmaI/netI 0.0225 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.12 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4067 _reflns_number_gt 3751 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RIGAKU CrystalClear' _computing_cell_refinement 'RIGAKU CrystalClear' _computing_data_reduction 'RIGAKU CrystalClear' _computing_structure_solution SIR-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP-III _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^)+(0.0457P)^2^+0.6285P] 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 4067 _refine_ls_number_parameters 279 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0495 _refine_ls_R_factor_gt 0.0449 _refine_ls_wR_factor_ref 0.1053 _refine_ls_wR_factor_gt 0.1024 _refine_ls_goodness_of_fit_ref 1.117 _refine_ls_restrained_S_all 1.117 _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 0.74255(14) 0.16847(14) 0.18735(8) 0.0241(3) Uani 1 1 d . . . F1 F 0.79763(8) 0.14995(8) 0.25487(4) 0.0335(2) Uani 1 1 d . . . F2 F 0.71892(8) 0.29052(7) 0.17696(4) 0.0331(2) Uani 1 1 d . . . N1 N 0.82074(10) 0.12291(10) 0.13828(6) 0.0219(3) Uani 1 1 d . . . N2 N 0.61119(10) 0.08964(10) 0.17542(6) 0.0253(3) Uani 1 1 d . . . C1 C 0.92201(13) 0.19933(12) 0.12781(7) 0.0245(3) Uani 1 1 d . . . C2 C 1.04039(13) 0.18470(13) 0.16924(7) 0.0287(3) Uani 1 1 d . . . C3 C 1.13606(15) 0.26207(14) 0.15962(8) 0.0358(4) Uani 1 1 d . . . H1 H 1.2164 0.2536 0.1875 0.043 Uiso 1 1 calc R . . C4 C 1.11651(16) 0.35028(14) 0.11060(9) 0.0400(4) Uani 1 1 d . . . H2 H 1.1825 0.4031 0.1052 0.048 Uiso 1 1 calc R . . C5 C 1.00086(17) 0.36176(14) 0.06932(8) 0.0384(4) Uani 1 1 d . . . H3 H 0.9884 0.4223 0.0351 0.046 Uiso 1 1 calc R . . C6 C 0.90135(15) 0.28677(13) 0.07638(7) 0.0299(3) Uani 1 1 d . . . C7 C 1.06789(14) 0.08688(15) 0.22281(8) 0.0342(4) Uani 1 1 d . . . H4 H 0.9895 0.0394 0.2215 0.041 Uiso 1 1 calc R . . C8 C 1.10608(19) 0.1413(2) 0.29358(9) 0.0563(5) Uani 1 1 d . . . H5 H 1.1827 0.1888 0.2962 0.084 Uiso 1 1 calc R . . H6 H 1.1207 0.0759 0.3271 0.084 Uiso 1 1 calc R . . H7 H 1.0393 0.1942 0.3027 0.084 Uiso 1 1 calc R . . C9 C 1.16781(16) -0.00069(17) 0.20828(11) 0.0516(5) Uani 1 1 d . . . H8 H 1.1400 -0.0374 0.1636 0.077 Uiso 1 1 calc R . . H9 H 1.1818 -0.0645 0.2428 0.077 Uiso 1 1 calc R . . H10 H 1.2457 0.0437 0.2091 0.077 Uiso 1 1 calc R . . C10 C 0.77762(16) 0.29824(14) 0.02765(8) 0.0374(4) Uani 1 1 d . . . H11 H 0.7171 0.2431 0.0439 0.045 Uiso 1 1 calc R . . C11 C 0.7247(2) 0.42623(17) 0.02523(11) 0.0565(5) Uani 1 1 d . . . H12 H 0.7173 0.4514 0.0709 0.085 Uiso 1 1 calc R . . H13 H 0.6422 0.4277 -0.0045 0.085 Uiso 1 1 calc R . . H14 H 0.7805 0.4820 0.0078 0.085 Uiso 1 1 calc R . . C12 C 0.7887(2) 0.25611(18) -0.04330(9) 0.0550(5) Uani 1 1 d . . . H15 H 0.8466 0.3093 -0.0609 0.082 Uiso 1 1 calc R . . H16 H 0.7065 0.2595 -0.0733 0.082 Uiso 1 1 calc R . . H17 H 0.8199 0.1726 -0.0411 0.082 Uiso 1 1 calc R . . C13 C 0.81331(12) 0.00733(12) 0.11041(7) 0.0225(3) Uani 1 1 d . . . C14 C 0.72673(13) -0.07491(12) 0.12808(7) 0.0248(3) Uani 1 1 d . . . C15 C 0.71466(14) -0.19002(13) 0.09956(8) 0.0311(3) Uani 1 1 d . . . H18 H 0.6555 -0.2449 0.1114 0.037 Uiso 1 1 calc R . . C16 C 0.78722(15) -0.22613(13) 0.05425(8) 0.0342(4) Uani 1 1 d . . . H19 H 0.7788 -0.3054 0.0354 0.041 Uiso 1 1 calc R . . C17 C 0.87199(14) -0.14553(13) 0.03669(8) 0.0331(4) Uani 1 1 d . . . H20 H 0.9218 -0.1695 0.0054 0.040 Uiso 1 1 calc R . . C18 C 0.88522(13) -0.03011(13) 0.06423(7) 0.0290(3) Uani 1 1 d . . . H21 H 0.9440 0.0243 0.0515 0.035 Uiso 1 1 calc R . . C19 C 0.65638(14) -0.04049(12) 0.18156(7) 0.0285(3) Uani 1 1 d . . . H22 H 0.7109 -0.0522 0.2265 0.034 Uiso 1 1 calc R . . H23 H 0.5837 -0.0951 0.1787 0.034 Uiso 1 1 calc R . . C20 C 0.53330(13) 0.10785(14) 0.10344(7) 0.0303(3) Uani 1 1 d . . . H24 H 0.5930 0.1011 0.0719 0.036 Uiso 1 1 calc R . . C21 C 0.43472(15) 0.00980(17) 0.08192(9) 0.0430(4) Uani 1 1 d . . . H25 H 0.3799 0.0055 0.1148 0.064 Uiso 1 1 calc R . . H26 H 0.4758 -0.0687 0.0799 0.064 Uiso 1 1 calc R . . H27 H 0.3852 0.0297 0.0373 0.064 Uiso 1 1 calc R . . C22 C 0.47275(16) 0.23228(16) 0.09103(9) 0.0432(4) Uani 1 1 d . . . H28 H 0.4404 0.2431 0.0425 0.065 Uiso 1 1 calc R . . H29 H 0.5348 0.2952 0.1071 0.065 Uiso 1 1 calc R . . H30 H 0.4040 0.2386 0.1155 0.065 Uiso 1 1 calc R . . C23 C 0.53084(14) 0.11440(14) 0.22913(8) 0.0341(4) Uani 1 1 d . . . H31 H 0.4429 0.0943 0.2074 0.041 Uiso 1 1 calc R . . C24 C 0.56304(19) 0.03599(17) 0.29243(9) 0.0492(5) Uani 1 1 d . . . H32 H 0.6503 0.0494 0.3142 0.074 Uiso 1 1 calc R . . H33 H 0.5507 -0.0497 0.2799 0.074 Uiso 1 1 calc R . . H34 H 0.5088 0.0578 0.3238 0.074 Uiso 1 1 calc R . . C25 C 0.53069(15) 0.24604(15) 0.25175(9) 0.0390(4) Uani 1 1 d . . . H35 H 0.4661 0.2576 0.2786 0.059 Uiso 1 1 calc R . . H36 H 0.5135 0.2990 0.2120 0.059 Uiso 1 1 calc R . . H37 H 0.6124 0.2664 0.2792 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 B1 0.0224(8) 0.0253(8) 0.0239(8) -0.0021(6) 0.0030(6) -0.0025(6) F1 0.0282(4) 0.0487(5) 0.0227(4) -0.0047(4) 0.0029(3) -0.0023(4) F2 0.0358(5) 0.0239(4) 0.0417(5) -0.0051(4) 0.0130(4) -0.0010(3) N1 0.0224(6) 0.0203(6) 0.0232(6) -0.0008(4) 0.0049(5) -0.0037(4) N2 0.0238(6) 0.0284(6) 0.0238(6) -0.0002(5) 0.0049(5) -0.0019(5) C1 0.0289(8) 0.0220(7) 0.0249(7) -0.0056(5) 0.0108(6) -0.0060(6) C2 0.0276(8) 0.0312(8) 0.0287(8) -0.0080(6) 0.0094(6) -0.0057(6) C3 0.0302(8) 0.0400(9) 0.0393(9) -0.0119(7) 0.0119(7) -0.0117(7) C4 0.0447(10) 0.0360(9) 0.0445(10) -0.0132(7) 0.0215(8) -0.0201(7) C5 0.0578(11) 0.0282(8) 0.0342(9) -0.0013(6) 0.0208(8) -0.0105(7) C6 0.0415(9) 0.0237(7) 0.0263(8) -0.0033(6) 0.0115(7) -0.0055(6) C7 0.0242(8) 0.0422(9) 0.0346(8) 0.0015(7) 0.0018(6) -0.0044(6) C8 0.0533(12) 0.0748(14) 0.0349(10) 0.0005(9) -0.0058(9) -0.0070(10) C9 0.0316(9) 0.0475(11) 0.0757(14) 0.0107(9) 0.0102(9) 0.0035(8) C10 0.0476(10) 0.0301(8) 0.0334(9) 0.0086(6) 0.0051(7) -0.0031(7) C11 0.0705(13) 0.0406(10) 0.0562(12) 0.0101(9) 0.0072(10) 0.0080(9) C12 0.0693(13) 0.0566(12) 0.0335(10) 0.0015(8) -0.0033(9) -0.0025(10) C13 0.0225(7) 0.0220(7) 0.0210(7) 0.0002(5) -0.0007(5) -0.0001(5) C14 0.0250(7) 0.0227(7) 0.0247(7) 0.0033(5) 0.0002(6) -0.0006(6) C15 0.0337(8) 0.0238(7) 0.0335(8) 0.0017(6) 0.0011(6) -0.0052(6) C16 0.0393(9) 0.0229(7) 0.0374(9) -0.0076(6) 0.0003(7) 0.0003(6) C17 0.0340(8) 0.0316(8) 0.0338(8) -0.0079(6) 0.0064(7) 0.0008(7) C18 0.0279(7) 0.0283(8) 0.0311(8) -0.0031(6) 0.0068(6) -0.0035(6) C19 0.0303(8) 0.0252(7) 0.0304(8) 0.0027(6) 0.0067(6) -0.0051(6) C20 0.0247(7) 0.0396(8) 0.0246(7) -0.0027(6) -0.0004(6) -0.0002(6) C21 0.0281(8) 0.0576(11) 0.0407(10) -0.0134(8) 0.0006(7) -0.0068(7) C22 0.0376(9) 0.0519(10) 0.0361(9) 0.0009(8) -0.0027(7) 0.0129(8) C23 0.0262(8) 0.0450(9) 0.0338(8) -0.0059(7) 0.0119(7) -0.0051(7) C24 0.0626(12) 0.0527(11) 0.0403(10) 0.0040(8) 0.0298(9) -0.0036(9) C25 0.0342(9) 0.0471(10) 0.0376(9) -0.0088(7) 0.0116(7) 0.0034(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B1 F2 1.3783(18) . ? B1 F1 1.3917(18) . ? B1 N1 1.5162(19) . ? B1 N2 1.6554(19) . ? N1 C13 1.3885(17) . ? N1 C1 1.4399(17) . ? N2 C19 1.5143(18) . ? N2 C20 1.5450(18) . ? N2 C23 1.5485(18) . ? C1 C6 1.402(2) . ? C1 C2 1.405(2) . ? C2 C3 1.393(2) . ? C2 C7 1.514(2) . ? C3 C4 1.373(2) . ? C3 H1 0.9500 . ? C4 C5 1.376(3) . ? C4 H2 0.9500 . ? C5 C6 1.396(2) . ? C5 H3 0.9500 . ? C6 C10 1.513(2) . ? C7 C8 1.529(2) . ? C7 C9 1.529(2) . ? C7 H4 1.0000 . ? C8 H5 0.9800 . ? C8 H6 0.9800 . ? C8 H7 0.9800 . ? C9 H8 0.9800 . ? C9 H9 0.9800 . ? C9 H10 0.9800 . ? C10 C11 1.522(2) . ? C10 C12 1.532(2) . ? C10 H11 1.0000 . ? C11 H12 0.9800 . ? C11 H13 0.9800 . ? C11 H14 0.9800 . ? C12 H15 0.9800 . ? C12 H16 0.9800 . ? C12 H17 0.9800 . ? C13 C18 1.395(2) . ? C13 C14 1.4069(19) . ? C14 C15 1.389(2) . ? C14 C19 1.493(2) . ? C15 C16 1.382(2) . ? C15 H18 0.9500 . ? C16 C17 1.380(2) . ? C16 H19 0.9500 . ? C17 C18 1.385(2) . ? C17 H20 0.9500 . ? C18 H21 0.9500 . ? C19 H22 0.9900 . ? C19 H23 0.9900 . ? C20 C22 1.522(2) . ? C20 C21 1.528(2) . ? C20 H24 1.0000 . ? C21 H25 0.9800 . ? C21 H26 0.9800 . ? C21 H27 0.9800 . ? C22 H28 0.9800 . ? C22 H29 0.9800 . ? C22 H30 0.9800 . ? C23 C25 1.521(2) . ? C23 C24 1.525(2) . ? C23 H31 1.0000 . ? C24 H32 0.9800 . ? C24 H33 0.9800 . ? C24 H34 0.9800 . ? C25 H35 0.9800 . ? C25 H36 0.9800 . ? C25 H37 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag F2 B1 F1 108.90(11) . . ? F2 B1 N1 109.69(12) . . ? F1 B1 N1 113.58(12) . . ? F2 B1 N2 111.04(11) . . ? F1 B1 N2 105.10(11) . . ? N1 B1 N2 108.46(11) . . ? C13 N1 C1 117.55(11) . . ? C13 N1 B1 124.96(11) . . ? C1 N1 B1 116.84(11) . . ? C19 N2 C20 108.07(10) . . ? C19 N2 C23 109.33(11) . . ? C20 N2 C23 110.58(11) . . ? C19 N2 B1 103.03(10) . . ? C20 N2 B1 111.70(10) . . ? C23 N2 B1 113.71(10) . . ? C6 C1 C2 120.95(13) . . ? C6 C1 N1 119.66(13) . . ? C2 C1 N1 119.39(12) . . ? C3 C2 C1 118.43(14) . . ? C3 C2 C7 119.13(14) . . ? C1 C2 C7 122.42(12) . . ? C4 C3 C2 121.31(16) . . ? C4 C3 H1 119.3 . . ? C2 C3 H1 119.3 . . ? C3 C4 C5 119.65(14) . . ? C3 C4 H2 120.2 . . ? C5 C4 H2 120.2 . . ? C4 C5 C6 121.71(15) . . ? C4 C5 H3 119.1 . . ? C6 C5 H3 119.1 . . ? C5 C6 C1 117.90(15) . . ? C5 C6 C10 119.95(14) . . ? C1 C6 C10 122.11(13) . . ? C2 C7 C8 111.48(14) . . ? C2 C7 C9 111.18(13) . . ? C8 C7 C9 110.68(15) . . ? C2 C7 H4 107.8 . . ? C8 C7 H4 107.8 . . ? C9 C7 H4 107.8 . . ? C7 C8 H5 109.5 . . ? C7 C8 H6 109.5 . . ? H5 C8 H6 109.5 . . ? C7 C8 H7 109.5 . . ? H5 C8 H7 109.5 . . ? H6 C8 H7 109.5 . . ? C7 C9 H8 109.5 . . ? C7 C9 H9 109.5 . . ? H8 C9 H9 109.5 . . ? C7 C9 H10 109.5 . . ? H8 C9 H10 109.5 . . ? H9 C9 H10 109.5 . . ? C6 C10 C11 112.58(14) . . ? C6 C10 C12 110.88(15) . . ? C11 C10 C12 110.54(14) . . ? C6 C10 H11 107.5 . . ? C11 C10 H11 107.5 . . ? C12 C10 H11 107.5 . . ? C10 C11 H12 109.5 . . ? C10 C11 H13 109.5 . . ? H12 C11 H13 109.5 . . ? C10 C11 H14 109.5 . . ? H12 C11 H14 109.5 . . ? H13 C11 H14 109.5 . . ? C10 C12 H15 109.5 . . ? C10 C12 H16 109.5 . . ? H15 C12 H16 109.5 . . ? C10 C12 H17 109.5 . . ? H15 C12 H17 109.5 . . ? H16 C12 H17 109.5 . . ? N1 C13 C18 123.11(12) . . ? N1 C13 C14 118.49(12) . . ? C18 C13 C14 118.38(12) . . ? C15 C14 C13 119.82(13) . . ? C15 C14 C19 120.76(13) . . ? C13 C14 C19 119.24(12) . . ? C16 C15 C14 121.14(14) . . ? C16 C15 H18 119.4 . . ? C14 C15 H18 119.4 . . ? C17 C16 C15 119.15(13) . . ? C17 C16 H19 120.4 . . ? C15 C16 H19 120.4 . . ? C16 C17 C18 120.72(14) . . ? C16 C17 H20 119.6 . . ? C18 C17 H20 119.6 . . ? C17 C18 C13 120.79(13) . . ? C17 C18 H21 119.6 . . ? C13 C18 H21 119.6 . . ? C14 C19 N2 112.84(11) . . ? C14 C19 H22 109.0 . . ? N2 C19 H22 109.0 . . ? C14 C19 H23 109.0 . . ? N2 C19 H23 109.0 . . ? H22 C19 H23 107.8 . . ? C22 C20 C21 109.34(13) . . ? C22 C20 N2 114.38(12) . . ? C21 C20 N2 113.72(13) . . ? C22 C20 H24 106.3 . . ? C21 C20 H24 106.3 . . ? N2 C20 H24 106.3 . . ? C20 C21 H25 109.5 . . ? C20 C21 H26 109.5 . . ? H25 C21 H26 109.5 . . ? C20 C21 H27 109.5 . . ? H25 C21 H27 109.5 . . ? H26 C21 H27 109.5 . . ? C20 C22 H28 109.5 . . ? C20 C22 H29 109.5 . . ? H28 C22 H29 109.5 . . ? C20 C22 H30 109.5 . . ? H28 C22 H30 109.5 . . ? H29 C22 H30 109.5 . . ? C25 C23 C24 107.64(13) . . ? C25 C23 N2 114.36(12) . . ? C24 C23 N2 114.67(13) . . ? C25 C23 H31 106.5 . . ? C24 C23 H31 106.5 . . ? N2 C23 H31 106.5 . . ? C23 C24 H32 109.5 . . ? C23 C24 H33 109.5 . . ? H32 C24 H33 109.5 . . ? C23 C24 H34 109.5 . . ? H32 C24 H34 109.5 . . ? H33 C24 H34 109.5 . . ? C23 C25 H35 109.5 . . ? C23 C25 H36 109.5 . . ? H35 C25 H36 109.5 . . ? C23 C25 H37 109.5 . . ? H35 C25 H37 109.5 . . ? H36 C25 H37 109.5 . . ? 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 F2 B1 N1 C13 -146.95(12) . . . . ? F1 B1 N1 C13 90.93(15) . . . . ? N2 B1 N1 C13 -25.52(17) . . . . ? F2 B1 N1 C1 42.54(16) . . . . ? F1 B1 N1 C1 -79.59(15) . . . . ? N2 B1 N1 C1 163.97(11) . . . . ? F2 B1 N2 C19 174.16(11) . . . . ? F1 B1 N2 C19 -68.23(12) . . . . ? N1 B1 N2 C19 53.56(13) . . . . ? F2 B1 N2 C20 58.39(14) . . . . ? F1 B1 N2 C20 175.99(10) . . . . ? N1 B1 N2 C20 -62.21(14) . . . . ? F2 B1 N2 C23 -67.63(15) . . . . ? F1 B1 N2 C23 49.97(15) . . . . ? N1 B1 N2 C23 171.77(11) . . . . ? C13 N1 C1 C6 98.52(15) . . . . ? B1 N1 C1 C6 -90.24(15) . . . . ? C13 N1 C1 C2 -81.22(16) . . . . ? B1 N1 C1 C2 90.02(15) . . . . ? C6 C1 C2 C3 2.2(2) . . . . ? N1 C1 C2 C3 -178.05(12) . . . . ? C6 C1 C2 C7 -176.68(13) . . . . ? N1 C1 C2 C7 3.1(2) . . . . ? C1 C2 C3 C4 -0.5(2) . . . . ? C7 C2 C3 C4 178.42(14) . . . . ? C2 C3 C4 C5 -1.0(2) . . . . ? C3 C4 C5 C6 0.8(2) . . . . ? C4 C5 C6 C1 0.8(2) . . . . ? C4 C5 C6 C10 -176.88(14) . . . . ? C2 C1 C6 C5 -2.4(2) . . . . ? N1 C1 C6 C5 177.91(12) . . . . ? C2 C1 C6 C10 175.29(13) . . . . ? N1 C1 C6 C10 -4.4(2) . . . . ? C3 C2 C7 C8 63.52(18) . . . . ? C1 C2 C7 C8 -117.60(16) . . . . ? C3 C2 C7 C9 -60.50(19) . . . . ? C1 C2 C7 C9 118.38(16) . . . . ? C5 C6 C10 C11 -56.2(2) . . . . ? C1 C6 C10 C11 126.17(16) . . . . ? C5 C6 C10 C12 68.19(18) . . . . ? C1 C6 C10 C12 -109.41(16) . . . . ? C1 N1 C13 C18 -10.99(19) . . . . ? B1 N1 C13 C18 178.56(13) . . . . ? C1 N1 C13 C14 170.84(12) . . . . ? B1 N1 C13 C14 0.39(19) . . . . ? N1 C13 C14 C15 178.19(12) . . . . ? C18 C13 C14 C15 -0.1(2) . . . . ? N1 C13 C14 C19 -6.72(19) . . . . ? C18 C13 C14 C19 175.02(13) . . . . ? C13 C14 C15 C16 0.6(2) . . . . ? C19 C14 C15 C16 -174.46(13) . . . . ? C14 C15 C16 C17 -0.7(2) . . . . ? C15 C16 C17 C18 0.4(2) . . . . ? C16 C17 C18 C13 0.1(2) . . . . ? N1 C13 C18 C17 -178.41(13) . . . . ? C14 C13 C18 C17 -0.2(2) . . . . ? C15 C14 C19 N2 -142.75(13) . . . . ? C13 C14 C19 N2 42.22(17) . . . . ? C20 N2 C19 C14 55.20(14) . . . . ? C23 N2 C19 C14 175.63(11) . . . . ? B1 N2 C19 C14 -63.14(14) . . . . ? C19 N2 C20 C22 175.58(13) . . . . ? C23 N2 C20 C22 55.95(16) . . . . ? B1 N2 C20 C22 -71.76(15) . . . . ? C19 N2 C20 C21 48.99(15) . . . . ? C23 N2 C20 C21 -70.64(15) . . . . ? B1 N2 C20 C21 161.64(12) . . . . ? C19 N2 C23 C25 152.46(13) . . . . ? C20 N2 C23 C25 -88.66(15) . . . . ? B1 N2 C23 C25 37.95(17) . . . . ? C19 N2 C23 C24 27.42(17) . . . . ? C20 N2 C23 C24 146.30(13) . . . . ? B1 N2 C23 C24 -87.10(16) . . . . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.155 _refine_diff_density_min -0.176 _refine_diff_density_rms 0.036 #----------6-----------# data_6 _database_code_depnum_ccdc_archive 'CCDC 777068' #TrackingRef '- CIFs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C46 H58 B2 F2 N4 O2' _chemical_formula_weight 758.58 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.393(8) _cell_length_b 17.539(13) _cell_length_c 11.564(9) _cell_angle_alpha 90 _cell_angle_beta 99.422(5) _cell_angle_gamma 90 _cell_volume 2080(3) _cell_formula_units_Z 2 _cell_measurement_temperature 103.1500 _cell_measurement_reflns_used 4876 _cell_measurement_theta_min 3.0585 _cell_measurement_theta_max 27.4835 _exptl_crystal_description Platelet _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.211 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 812 _exptl_absorpt_coefficient_mu 0.079 _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 103(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'RIGAKU/MSC Meacury CCD' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 7.31 _diffrn_reflns_number 13022 _diffrn_reflns_av_R_equivalents 0.0627 _diffrn_reflns_av_sigmaI/netI 0.0691 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3592 _reflns_number_gt 2757 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RIGAKU CrystalClear' _computing_cell_refinement 'RIGAKU CrystalClear' _computing_data_reduction 'RIGAKU CrystalClear' _computing_structure_solution SIR-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP-III _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^)+(0.1268P)^2^+2.4576P] 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 3592 _refine_ls_number_parameters 259 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1656 _refine_ls_R_factor_gt 0.1355 _refine_ls_wR_factor_ref 0.3278 _refine_ls_wR_factor_gt 0.3076 _refine_ls_goodness_of_fit_ref 1.268 _refine_ls_restrained_S_all 1.268 _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 0.3224(5) -0.1109(3) 0.3868(5) 0.0354(13) Uani 1 1 d . . . N1 N 0.3070(4) -0.0679(2) 0.2819(3) 0.0358(10) Uani 1 1 d . . . C1 C 0.3061(4) 0.0124(3) 0.2888(4) 0.0369(12) Uani 1 1 d . . . C2 C 0.3557(4) 0.0476(3) 0.3978(4) 0.0359(12) Uani 1 1 d . . . C3 C 0.4237(5) 0.0010(3) 0.4982(4) 0.0404(13) Uani 1 1 d . . . N2 N 0.3691(4) -0.0761(3) 0.4950(3) 0.0435(11) Uani 1 1 d . . . F1 F 0.2862(3) -0.18418(19) 0.3834(3) 0.0573(10) Uani 1 1 d . . . C4 C 0.2553(5) 0.0573(3) 0.1945(5) 0.0482(14) Uani 1 1 d . . . H1 H 0.2247 0.0341 0.1209 0.058 Uiso 1 1 calc R . . C5 C 0.2483(6) 0.1361(3) 0.2056(5) 0.0561(16) Uani 1 1 d . . . H2 H 0.2160 0.1662 0.1388 0.067 Uiso 1 1 calc R . . C6 C 0.2883(5) 0.1719(3) 0.3142(5) 0.0568(17) Uani 1 1 d . . . H3 H 0.2796 0.2254 0.3232 0.068 Uiso 1 1 calc R . . C7 C 0.3413(5) 0.1260(3) 0.4080(5) 0.0469(14) Uani 1 1 d . . . H4 H 0.3687 0.1491 0.4822 0.056 Uiso 1 1 calc R . . C8 C 0.2513(5) -0.1041(3) 0.1728(4) 0.0344(12) Uani 1 1 d . . . C9 C 0.3344(5) -0.1298(3) 0.0979(4) 0.0364(12) Uani 1 1 d . . . C10 C 0.2799(5) -0.1666(3) -0.0053(4) 0.0410(13) Uani 1 1 d . . . H5 H 0.3353 -0.1848 -0.0569 0.049 Uiso 1 1 calc R . . C11 C 0.1474(6) -0.1769(3) -0.0340(4) 0.0471(15) Uani 1 1 d . . . H6 H 0.1116 -0.2026 -0.1042 0.057 Uiso 1 1 calc R . . C12 C 0.0678(5) -0.1498(3) 0.0398(5) 0.0521(15) Uani 1 1 d . . . H7 H -0.0238 -0.1564 0.0192 0.062 Uiso 1 1 calc R . . C13 C 0.1172(5) -0.1126(3) 0.1447(5) 0.0487(14) Uani 1 1 d . . . C14 C 0.4811(5) -0.1219(3) 0.1316(4) 0.0402(13) Uani 1 1 d . . . H8 H 0.4988 -0.0753 0.1815 0.048 Uiso 1 1 calc R . . C15 C 0.5524(7) -0.1125(4) 0.0260(5) 0.0693(19) Uani 1 1 d . . . H9 H 0.6448 -0.1019 0.0538 0.104 Uiso 1 1 calc R . . H10 H 0.5136 -0.0701 -0.0229 0.104 Uiso 1 1 calc R . . H11 H 0.5441 -0.1595 -0.0204 0.104 Uiso 1 1 calc R . . C16 C 0.5378(5) -0.1891(4) 0.2033(5) 0.0570(16) Uani 1 1 d . . . H12 H 0.4964 -0.1936 0.2732 0.086 Uiso 1 1 calc R . . H13 H 0.6319 -0.1817 0.2269 0.086 Uiso 1 1 calc R . . H14 H 0.5221 -0.2357 0.1563 0.086 Uiso 1 1 calc R . . C17 C 0.0244(5) -0.0827(4) 0.2208(5) 0.066(2) Uani 1 1 d . . . H15 H 0.0775 -0.0552 0.2879 0.079 Uiso 1 1 calc R . . C18 C -0.0698(6) -0.0238(4) 0.1525(6) 0.084(3) Uani 1 1 d . . . H16 H -0.0194 0.0182 0.1264 0.126 Uiso 1 1 calc R . . H17 H -0.1283 -0.0038 0.2037 0.126 Uiso 1 1 calc R . . H18 H -0.1214 -0.0485 0.0842 0.126 Uiso 1 1 calc R . . C19 C -0.0465(6) -0.1459(5) 0.2716(6) 0.087(3) Uani 1 1 d . . . H19 H -0.0956 -0.1761 0.2079 0.131 Uiso 1 1 calc R . . H20 H -0.1068 -0.1241 0.3195 0.131 Uiso 1 1 calc R . . H21 H 0.0167 -0.1787 0.3205 0.131 Uiso 1 1 calc R . . O1 O 0.4008(4) 0.0328(2) 0.6067(3) 0.0528(11) Uani 1 1 d . . . C20 C 0.3685(7) -0.0315(5) 0.6821(6) 0.093(3) Uani 1 1 d . . . H22 H 0.4485 -0.0518 0.7307 0.111 Uiso 1 1 calc R . . H23 H 0.3077 -0.0144 0.7344 0.111 Uiso 1 1 calc R . . C21 C 0.3076(5) -0.0893(4) 0.6000(5) 0.0534(16) Uani 1 1 d . . . C22 C 0.1598(6) -0.0830(5) 0.5709(6) 0.076(2) Uani 1 1 d . . . H24 H 0.1222 -0.0888 0.6428 0.115 Uiso 1 1 calc R . . H25 H 0.1260 -0.1232 0.5152 0.115 Uiso 1 1 calc R . . H26 H 0.1360 -0.0330 0.5361 0.115 Uiso 1 1 calc R . . C23 C 0.3350(8) -0.1714(5) 0.6518(7) 0.091(3) Uani 1 1 d . . . H27 H 0.4294 -0.1797 0.6704 0.137 Uiso 1 1 calc R . . H28 H 0.2963 -0.2093 0.5941 0.137 Uiso 1 1 calc R . . H29 H 0.2965 -0.1766 0.7233 0.137 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 B1 0.021(3) 0.049(4) 0.033(3) -0.009(2) -0.002(2) -0.003(2) N1 0.032(2) 0.051(3) 0.019(2) -0.0077(17) -0.0104(16) 0.0030(18) C1 0.027(2) 0.050(3) 0.030(3) -0.016(2) -0.007(2) 0.002(2) C2 0.024(2) 0.051(3) 0.031(3) -0.010(2) -0.0032(19) 0.002(2) C3 0.034(3) 0.063(3) 0.021(3) -0.016(2) -0.0080(19) 0.005(2) N2 0.032(2) 0.071(3) 0.025(2) -0.010(2) -0.0029(17) -0.001(2) F1 0.063(2) 0.068(2) 0.0386(19) -0.0024(15) 0.0006(15) -0.0090(17) C4 0.047(3) 0.056(4) 0.034(3) -0.010(2) -0.016(2) 0.003(3) C5 0.051(3) 0.055(4) 0.052(4) -0.006(3) -0.020(3) 0.007(3) C6 0.052(3) 0.051(3) 0.055(4) -0.022(3) -0.029(3) 0.012(3) C7 0.036(3) 0.059(4) 0.042(3) -0.022(3) -0.006(2) 0.004(3) C8 0.034(3) 0.044(3) 0.022(2) -0.007(2) -0.005(2) 0.002(2) C9 0.046(3) 0.034(3) 0.025(3) -0.001(2) -0.008(2) 0.001(2) C10 0.051(3) 0.039(3) 0.029(3) -0.002(2) -0.004(2) 0.003(2) C11 0.062(4) 0.039(3) 0.032(3) -0.012(2) -0.017(3) 0.010(3) C12 0.040(3) 0.056(4) 0.051(3) -0.014(3) -0.019(3) 0.001(3) C13 0.042(3) 0.063(4) 0.035(3) -0.015(3) -0.012(2) 0.007(3) C14 0.043(3) 0.050(3) 0.027(3) -0.006(2) 0.004(2) -0.008(2) C15 0.073(4) 0.100(5) 0.036(3) 0.000(3) 0.011(3) -0.023(4) C16 0.041(3) 0.075(4) 0.054(4) 0.007(3) 0.005(3) 0.011(3) C17 0.027(3) 0.114(6) 0.054(4) -0.035(4) -0.005(3) 0.000(3) C18 0.041(4) 0.116(6) 0.087(5) -0.045(5) -0.010(3) 0.021(4) C19 0.044(4) 0.147(7) 0.072(5) -0.035(5) 0.014(3) -0.021(4) O1 0.047(2) 0.084(3) 0.024(2) -0.0187(18) -0.0011(16) 0.004(2) C20 0.074(5) 0.153(8) 0.054(4) -0.042(5) 0.020(4) -0.052(5) C21 0.039(3) 0.093(5) 0.028(3) -0.004(3) 0.006(2) -0.008(3) C22 0.040(3) 0.133(7) 0.056(4) -0.031(4) 0.008(3) -0.022(4) C23 0.088(6) 0.128(7) 0.061(5) 0.002(5) 0.022(4) -0.016(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 B1 F1 1.337(7) . ? B1 N2 1.405(7) . ? B1 N1 1.416(7) . ? N1 C1 1.411(6) . ? N1 C8 1.446(6) . ? C1 C4 1.378(7) . ? C1 C2 1.421(6) . ? C2 C7 1.391(7) . ? C2 C3 1.499(7) . ? C3 O1 1.427(6) . ? C3 N2 1.465(7) . ? C3 C3 1.580(10) 3_656 ? N2 C21 1.480(7) . ? C4 C5 1.392(8) . ? C4 H1 0.9500 . ? C5 C6 1.404(8) . ? C5 H2 0.9500 . ? C6 C7 1.391(8) . ? C6 H3 0.9500 . ? C7 H4 0.9500 . ? C8 C13 1.386(7) . ? C8 C9 1.394(7) . ? C9 C10 1.393(7) . ? C9 C14 1.517(7) . ? C10 C11 1.374(8) . ? C10 H5 0.9500 . ? C11 C12 1.368(8) . ? C11 H6 0.9500 . ? C12 C13 1.399(7) . ? C12 H7 0.9500 . ? C13 C17 1.503(8) . ? C14 C16 1.504(8) . ? C14 C15 1.538(7) . ? C14 H8 1.0000 . ? C15 H9 0.9800 . ? C15 H10 0.9800 . ? C15 H11 0.9800 . ? C16 H12 0.9800 . ? C16 H13 0.9800 . ? C16 H14 0.9800 . ? C17 C19 1.503(10) . ? C17 C18 1.548(9) . ? C17 H15 1.0000 . ? C18 H16 0.9800 . ? C18 H17 0.9800 . ? C18 H18 0.9800 . ? C19 H19 0.9800 . ? C19 H20 0.9800 . ? C19 H21 0.9800 . ? O1 C20 1.497(9) . ? C20 C21 1.461(8) . ? C20 H22 0.9900 . ? C20 H23 0.9900 . ? C21 C22 1.522(8) . ? C21 C23 1.568(10) . ? C22 H24 0.9800 . ? C22 H25 0.9800 . ? C22 H26 0.9800 . ? C23 H27 0.9800 . ? C23 H28 0.9800 . ? C23 H29 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag F1 B1 N2 119.9(5) . . ? F1 B1 N1 119.7(4) . . ? N2 B1 N1 120.3(5) . . ? C1 N1 B1 119.0(4) . . ? C1 N1 C8 118.9(4) . . ? B1 N1 C8 119.1(4) . . ? C4 C1 N1 122.0(4) . . ? C4 C1 C2 119.4(5) . . ? N1 C1 C2 118.6(4) . . ? C7 C2 C1 118.4(5) . . ? C7 C2 C3 121.1(4) . . ? C1 C2 C3 120.5(5) . . ? O1 C3 N2 105.2(4) . . ? O1 C3 C2 110.1(4) . . ? N2 C3 C2 110.6(4) . . ? O1 C3 C3 107.3(4) . 3_656 ? N2 C3 C3 111.3(5) . 3_656 ? C2 C3 C3 112.1(5) . 3_656 ? B1 N2 C3 120.0(4) . . ? B1 N2 C21 122.0(4) . . ? C3 N2 C21 110.0(4) . . ? C1 C4 C5 120.8(5) . . ? C1 C4 H1 119.6 . . ? C5 C4 H1 119.6 . . ? C4 C5 C6 121.0(5) . . ? C4 C5 H2 119.5 . . ? C6 C5 H2 119.5 . . ? C7 C6 C5 117.3(5) . . ? C7 C6 H3 121.3 . . ? C5 C6 H3 121.3 . . ? C2 C7 C6 122.8(5) . . ? C2 C7 H4 118.6 . . ? C6 C7 H4 118.6 . . ? C13 C8 C9 121.4(4) . . ? C13 C8 N1 119.7(4) . . ? C9 C8 N1 118.9(4) . . ? C10 C9 C8 118.3(5) . . ? C10 C9 C14 120.9(5) . . ? C8 C9 C14 120.7(4) . . ? C11 C10 C9 121.3(5) . . ? C11 C10 H5 119.4 . . ? C9 C10 H5 119.4 . . ? C12 C11 C10 119.2(5) . . ? C12 C11 H6 120.4 . . ? C10 C11 H6 120.4 . . ? C11 C12 C13 122.0(5) . . ? C11 C12 H7 119.0 . . ? C13 C12 H7 119.0 . . ? C8 C13 C12 117.7(5) . . ? C8 C13 C17 122.9(5) . . ? C12 C13 C17 119.4(5) . . ? C16 C14 C9 110.9(4) . . ? C16 C14 C15 109.0(5) . . ? C9 C14 C15 113.6(4) . . ? C16 C14 H8 107.7 . . ? C9 C14 H8 107.7 . . ? C15 C14 H8 107.7 . . ? C14 C15 H9 109.5 . . ? C14 C15 H10 109.5 . . ? H9 C15 H10 109.5 . . ? C14 C15 H11 109.5 . . ? H9 C15 H11 109.5 . . ? H10 C15 H11 109.5 . . ? C14 C16 H12 109.5 . . ? C14 C16 H13 109.5 . . ? H12 C16 H13 109.5 . . ? C14 C16 H14 109.5 . . ? H12 C16 H14 109.5 . . ? H13 C16 H14 109.5 . . ? C13 C17 C19 112.0(6) . . ? C13 C17 C18 110.3(6) . . ? C19 C17 C18 112.5(5) . . ? C13 C17 H15 107.3 . . ? C19 C17 H15 107.3 . . ? C18 C17 H15 107.3 . . ? C17 C18 H16 109.5 . . ? C17 C18 H17 109.5 . . ? H16 C18 H17 109.5 . . ? C17 C18 H18 109.5 . . ? H16 C18 H18 109.5 . . ? H17 C18 H18 109.5 . . ? C17 C19 H19 109.5 . . ? C17 C19 H20 109.5 . . ? H19 C19 H20 109.5 . . ? C17 C19 H21 109.5 . . ? H19 C19 H21 109.5 . . ? H20 C19 H21 109.5 . . ? C3 O1 C20 107.7(4) . . ? C21 C20 O1 105.0(5) . . ? C21 C20 H22 110.8 . . ? O1 C20 H22 110.8 . . ? C21 C20 H23 110.8 . . ? O1 C20 H23 110.8 . . ? H22 C20 H23 108.8 . . ? C20 C21 N2 103.0(5) . . ? C20 C21 C22 114.1(6) . . ? N2 C21 C22 111.3(5) . . ? C20 C21 C23 110.9(6) . . ? N2 C21 C23 112.4(5) . . ? C22 C21 C23 105.4(6) . . ? C21 C22 H24 109.5 . . ? C21 C22 H25 109.5 . . ? H24 C22 H25 109.5 . . ? C21 C22 H26 109.5 . . ? H24 C22 H26 109.5 . . ? H25 C22 H26 109.5 . . ? C21 C23 H27 109.5 . . ? C21 C23 H28 109.5 . . ? H27 C23 H28 109.5 . . ? C21 C23 H29 109.5 . . ? H27 C23 H29 109.5 . . ? H28 C23 H29 109.5 . . ? 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 F1 B1 N1 C1 160.5(4) . . . . ? N2 B1 N1 C1 -16.2(7) . . . . ? F1 B1 N1 C8 0.5(7) . . . . ? N2 B1 N1 C8 -176.2(4) . . . . ? B1 N1 C1 C4 -160.9(5) . . . . ? C8 N1 C1 C4 -0.8(7) . . . . ? B1 N1 C1 C2 17.1(6) . . . . ? C8 N1 C1 C2 177.2(4) . . . . ? C4 C1 C2 C7 5.3(7) . . . . ? N1 C1 C2 C7 -172.8(4) . . . . ? C4 C1 C2 C3 -173.8(5) . . . . ? N1 C1 C2 C3 8.1(7) . . . . ? C7 C2 C3 O1 33.1(6) . . . . ? C1 C2 C3 O1 -147.9(4) . . . . ? C7 C2 C3 N2 148.9(5) . . . . ? C1 C2 C3 N2 -32.0(6) . . . . ? C7 C2 C3 C3 -86.2(6) . . . 3_656 ? C1 C2 C3 C3 92.8(6) . . . 3_656 ? F1 B1 N2 C3 172.5(4) . . . . ? N1 B1 N2 C3 -10.8(7) . . . . ? F1 B1 N2 C21 -41.9(7) . . . . ? N1 B1 N2 C21 134.8(5) . . . . ? O1 C3 N2 B1 152.0(4) . . . . ? C2 C3 N2 B1 33.1(6) . . . . ? C3 C3 N2 B1 -92.2(6) 3_656 . . . ? O1 C3 N2 C21 2.6(5) . . . . ? C2 C3 N2 C21 -116.2(4) . . . . ? C3 C3 N2 C21 118.5(5) 3_656 . . . ? N1 C1 C4 C5 176.0(5) . . . . ? C2 C1 C4 C5 -2.0(8) . . . . ? C1 C4 C5 C6 -2.3(9) . . . . ? C4 C5 C6 C7 3.3(9) . . . . ? C1 C2 C7 C6 -4.4(8) . . . . ? C3 C2 C7 C6 174.6(5) . . . . ? C5 C6 C7 C2 0.2(9) . . . . ? C1 N1 C8 C13 -79.9(6) . . . . ? B1 N1 C8 C13 80.2(6) . . . . ? C1 N1 C8 C9 100.2(5) . . . . ? B1 N1 C8 C9 -99.8(6) . . . . ? C13 C8 C9 C10 -1.8(8) . . . . ? N1 C8 C9 C10 178.2(4) . . . . ? C13 C8 C9 C14 -178.3(5) . . . . ? N1 C8 C9 C14 1.6(7) . . . . ? C8 C9 C10 C11 0.6(7) . . . . ? C14 C9 C10 C11 177.1(5) . . . . ? C9 C10 C11 C12 0.7(8) . . . . ? C10 C11 C12 C13 -0.8(9) . . . . ? C9 C8 C13 C12 1.7(8) . . . . ? N1 C8 C13 C12 -178.3(5) . . . . ? C9 C8 C13 C17 -177.4(5) . . . . ? N1 C8 C13 C17 2.6(9) . . . . ? C11 C12 C13 C8 -0.3(9) . . . . ? C11 C12 C13 C17 178.8(6) . . . . ? C10 C9 C14 C16 -89.6(6) . . . . ? C8 C9 C14 C16 86.9(6) . . . . ? C10 C9 C14 C15 33.6(7) . . . . ? C8 C9 C14 C15 -150.0(5) . . . . ? C8 C13 C17 C19 -114.5(6) . . . . ? C12 C13 C17 C19 66.4(7) . . . . ? C8 C13 C17 C18 119.4(6) . . . . ? C12 C13 C17 C18 -59.6(8) . . . . ? N2 C3 O1 C20 16.1(5) . . . . ? C2 C3 O1 C20 135.3(5) . . . . ? C3 C3 O1 C20 -102.5(6) 3_656 . . . ? C3 O1 C20 C21 -29.2(6) . . . . ? O1 C20 C21 N2 29.1(7) . . . . ? O1 C20 C21 C22 -91.7(6) . . . . ? O1 C20 C21 C23 149.6(5) . . . . ? B1 N2 C21 C20 -168.9(6) . . . . ? C3 N2 C21 C20 -20.3(6) . . . . ? B1 N2 C21 C22 -46.3(8) . . . . ? C3 N2 C21 C22 102.4(6) . . . . ? B1 N2 C21 C23 71.7(6) . . . . ? C3 N2 C21 C23 -139.7(5) . . . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.694 _refine_diff_density_min -0.336 _refine_diff_density_rms 0.064 #----------13-pyr-----------# data_13-pyr _database_code_depnum_ccdc_archive 'CCDC 777069' #TrackingRef '- CIFs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H31 B N2' _chemical_formula_weight 346.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.440(5) _cell_length_b 10.504(5) _cell_length_c 10.892(5) _cell_angle_alpha 89.733(3) _cell_angle_beta 107.726(6) _cell_angle_gamma 103.128(7) _cell_volume 999.4(8) _cell_formula_units_Z 2 _cell_measurement_temperature 103.1500 _cell_measurement_reflns_used 3077 _cell_measurement_theta_min 3.4124 _cell_measurement_theta_max 27.4835 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.151 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 0.066 _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 103(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'RIGAKU/MSC Meacury CCD' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 7.31 _diffrn_reflns_number 6464 _diffrn_reflns_av_R_equivalents 0.0147 _diffrn_reflns_av_sigmaI/netI 0.0232 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.41 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3415 _reflns_number_gt 2980 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RIGAKU CrystalClear' _computing_cell_refinement 'RIGAKU CrystalClear' _computing_data_reduction 'RIGAKU CrystalClear' _computing_structure_solution SIR-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP-III _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^)+(0.0397P)^2^+0.3266P] 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 3415 _refine_ls_number_parameters 239 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0471 _refine_ls_R_factor_gt 0.0401 _refine_ls_wR_factor_ref 0.0968 _refine_ls_wR_factor_gt 0.0923 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group B1 B 0.69397(17) 0.33429(14) 0.71131(14) 0.0193(3) Uani 1 1 d . . . N1 N 0.77421(12) 0.23519(10) 0.76335(10) 0.0181(2) Uani 1 1 d . . . N2 N 0.58320(13) 0.37434(11) 0.75174(10) 0.0226(3) Uani 1 1 d . . . C1 C 0.87354(14) 0.22130(13) 0.69128(12) 0.0197(3) Uani 1 1 d . . . C2 C 0.96400(15) 0.13168(13) 0.70563(13) 0.0236(3) Uani 1 1 d . . . H1 H 0.9669 0.0712 0.7710 0.028 Uiso 1 1 calc R . . C3 C 1.05047(16) 0.13215(15) 0.62227(14) 0.0291(3) Uani 1 1 d . . . H2 H 1.1123 0.0708 0.6304 0.035 Uiso 1 1 calc R . . C4 C 1.04742(16) 0.22121(15) 0.52755(14) 0.0298(3) Uani 1 1 d . . . H3 H 1.1072 0.2209 0.4714 0.036 Uiso 1 1 calc R . . C5 C 0.95661(16) 0.31110(14) 0.51494(13) 0.0254(3) Uani 1 1 d . . . H4 H 0.9556 0.3728 0.4508 0.031 Uiso 1 1 calc R . . C6 C 0.86793(15) 0.31098(13) 0.59524(12) 0.0209(3) Uani 1 1 d . . . C7 C 0.75346(15) 0.39077(13) 0.59564(12) 0.0206(3) Uani 1 1 d . . . H5 H 0.6691 0.3764 0.5128 0.025 Uiso 1 1 calc R . . H6 H 0.8030 0.4855 0.6125 0.025 Uiso 1 1 calc R . . C8 C 0.75650(14) 0.14506(12) 0.86059(12) 0.0166(3) Uani 1 1 d . . . C9 C 0.83612(14) 0.18474(12) 0.99142(12) 0.0183(3) Uani 1 1 d . . . C10 C 0.81916(15) 0.09436(13) 1.08296(13) 0.0233(3) Uani 1 1 d . . . H7 H 0.8724 0.1188 1.1718 0.028 Uiso 1 1 calc R . . C11 C 0.72634(16) -0.03017(14) 1.04683(13) 0.0263(3) Uani 1 1 d . . . H8 H 0.7170 -0.0907 1.1107 0.032 Uiso 1 1 calc R . . C12 C 0.64708(16) -0.06702(13) 0.91819(13) 0.0244(3) Uani 1 1 d . . . H9 H 0.5822 -0.1524 0.8945 0.029 Uiso 1 1 calc R . . C13 C 0.66087(14) 0.01937(13) 0.82250(12) 0.0196(3) Uani 1 1 d . . . C14 C 0.94022(15) 0.32054(13) 1.03348(12) 0.0210(3) Uani 1 1 d . . . H10 H 0.9090 0.3790 0.9625 0.025 Uiso 1 1 calc R . . C15 C 1.10620(17) 0.31800(16) 1.05110(17) 0.0382(4) Uani 1 1 d . . . H11 H 1.1398 0.2605 1.1195 0.057 Uiso 1 1 calc R . . H12 H 1.1712 0.4069 1.0750 0.057 Uiso 1 1 calc R . . H13 H 1.1142 0.2850 0.9700 0.057 Uiso 1 1 calc R . . C16 C 0.92578(18) 0.37933(15) 1.15588(14) 0.0320(4) Uani 1 1 d . . . H14 H 0.8174 0.3715 1.1462 0.048 Uiso 1 1 calc R . . H15 H 0.9799 0.4720 1.1699 0.048 Uiso 1 1 calc R . . H16 H 0.9707 0.3322 1.2300 0.048 Uiso 1 1 calc R . . C17 C 0.56957(15) -0.02404(13) 0.68190(13) 0.0227(3) Uani 1 1 d . . . H17 H 0.5988 0.0484 0.6279 0.027 Uiso 1 1 calc R . . C18 C 0.6074(2) -0.14643(15) 0.63686(15) 0.0368(4) Uani 1 1 d . . . H18 H 0.7179 -0.1299 0.6512 0.055 Uiso 1 1 calc R . . H19 H 0.5525 -0.1677 0.5446 0.055 Uiso 1 1 calc R . . H20 H 0.5761 -0.2201 0.6859 0.055 Uiso 1 1 calc R . . C19 C 0.39853(17) -0.04550(19) 0.66144(15) 0.0416(4) Uani 1 1 d . . . H21 H 0.3670 -0.1151 0.7146 0.062 Uiso 1 1 calc R . . H22 H 0.3417 -0.0711 0.5702 0.062 Uiso 1 1 calc R . . H23 H 0.3769 0.0358 0.6864 0.062 Uiso 1 1 calc R . . C20 C 0.50181(17) 0.47049(14) 0.68170(14) 0.0283(3) Uani 1 1 d . . . H24 H 0.4261 0.4302 0.5987 0.034 Uiso 1 1 calc R . . H25 H 0.5746 0.5469 0.6642 0.034 Uiso 1 1 calc R . . C21 C 0.42274(18) 0.51109(15) 0.77204(15) 0.0313(3) Uani 1 1 d . . . H26 H 0.3278 0.5370 0.7232 0.038 Uiso 1 1 calc R . . H27 H 0.4911 0.5847 0.8338 0.038 Uiso 1 1 calc R . . C22 C 0.38746(17) 0.38753(14) 0.84126(14) 0.0281(3) Uani 1 1 d . . . H28 H 0.3738 0.4084 0.9249 0.034 Uiso 1 1 calc R . . H29 H 0.2939 0.3249 0.7875 0.034 Uiso 1 1 calc R . . C23 C 0.52778(16) 0.33230(14) 0.86152(13) 0.0247(3) Uani 1 1 d . . . H30 H 0.6066 0.3681 0.9446 0.030 Uiso 1 1 calc R . . H31 H 0.5003 0.2355 0.8610 0.030 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 B1 0.0195(7) 0.0173(8) 0.0178(7) -0.0002(6) 0.0040(6) 0.0003(6) N1 0.0217(6) 0.0183(6) 0.0154(5) 0.0034(4) 0.0078(4) 0.0042(5) N2 0.0262(6) 0.0231(6) 0.0216(6) 0.0062(5) 0.0106(5) 0.0078(5) C1 0.0189(6) 0.0202(7) 0.0183(6) -0.0027(5) 0.0057(5) 0.0016(5) C2 0.0234(7) 0.0239(7) 0.0241(7) 0.0025(6) 0.0072(6) 0.0072(6) C3 0.0275(8) 0.0320(8) 0.0302(8) -0.0025(6) 0.0101(6) 0.0102(6) C4 0.0274(8) 0.0380(9) 0.0280(8) -0.0008(6) 0.0156(6) 0.0062(7) C5 0.0283(7) 0.0267(8) 0.0217(7) 0.0007(6) 0.0120(6) 0.0015(6) C6 0.0213(7) 0.0218(7) 0.0173(6) -0.0018(5) 0.0063(5) -0.0001(5) C7 0.0238(7) 0.0193(7) 0.0170(6) 0.0031(5) 0.0057(5) 0.0023(5) C8 0.0178(6) 0.0175(7) 0.0180(6) 0.0050(5) 0.0086(5) 0.0070(5) C9 0.0178(6) 0.0189(7) 0.0199(7) 0.0022(5) 0.0076(5) 0.0056(5) C10 0.0250(7) 0.0268(8) 0.0169(6) 0.0045(5) 0.0056(5) 0.0052(6) C11 0.0311(8) 0.0251(8) 0.0236(7) 0.0104(6) 0.0109(6) 0.0051(6) C12 0.0264(7) 0.0180(7) 0.0268(7) 0.0038(6) 0.0090(6) 0.0002(6) C13 0.0189(6) 0.0207(7) 0.0204(7) 0.0026(5) 0.0069(5) 0.0057(5) C14 0.0239(7) 0.0208(7) 0.0173(6) 0.0026(5) 0.0068(5) 0.0029(6) C15 0.0263(8) 0.0324(9) 0.0540(10) -0.0062(7) 0.0164(7) -0.0021(7) C16 0.0381(9) 0.0294(8) 0.0270(8) -0.0055(6) 0.0138(7) -0.0001(7) C17 0.0248(7) 0.0210(7) 0.0202(7) 0.0010(5) 0.0070(6) 0.0013(6) C18 0.0516(10) 0.0275(8) 0.0282(8) -0.0042(6) 0.0082(7) 0.0093(7) C19 0.0258(8) 0.0658(12) 0.0260(8) -0.0057(8) 0.0040(6) 0.0022(8) C20 0.0352(8) 0.0302(8) 0.0287(8) 0.0110(6) 0.0154(6) 0.0186(7) C21 0.0352(8) 0.0340(9) 0.0326(8) 0.0082(6) 0.0155(7) 0.0171(7) C22 0.0281(8) 0.0317(8) 0.0283(8) 0.0024(6) 0.0139(6) 0.0075(6) C23 0.0284(7) 0.0264(8) 0.0236(7) 0.0066(6) 0.0146(6) 0.0066(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 N2 1.395(2) . ? B1 N1 1.4387(19) . ? B1 C7 1.5896(19) . ? N1 C1 1.4242(17) . ? N1 C8 1.4395(16) . ? N2 C23 1.4729(17) . ? N2 C20 1.4767(18) . ? C1 C2 1.386(2) . ? C1 C6 1.4014(19) . ? C2 C3 1.393(2) . ? C2 H1 0.9500 . ? C3 C4 1.388(2) . ? C3 H2 0.9500 . ? C4 C5 1.393(2) . ? C4 H3 0.9500 . ? C5 C6 1.3824(19) . ? C5 H4 0.9500 . ? C6 C7 1.511(2) . ? C7 H5 0.9900 . ? C7 H6 0.9900 . ? C8 C13 1.4020(19) . ? C8 C9 1.4072(18) . ? C9 C10 1.3929(18) . ? C9 C14 1.5183(19) . ? C10 C11 1.381(2) . ? C10 H7 0.9500 . ? C11 C12 1.381(2) . ? C11 H8 0.9500 . ? C12 C13 1.3952(19) . ? C12 H9 0.9500 . ? C13 C17 1.5233(19) . ? C14 C15 1.526(2) . ? C14 C16 1.5277(19) . ? C14 H10 1.0000 . ? C15 H11 0.9800 . ? C15 H12 0.9800 . ? C15 H13 0.9800 . ? C16 H14 0.9800 . ? C16 H15 0.9800 . ? C16 H16 0.9800 . ? C17 C19 1.524(2) . ? C17 C18 1.530(2) . ? C17 H17 1.0000 . ? C18 H18 0.9800 . ? C18 H19 0.9800 . ? C18 H20 0.9800 . ? C19 H21 0.9800 . ? C19 H22 0.9800 . ? C19 H23 0.9800 . ? C20 C21 1.517(2) . ? C20 H24 0.9900 . ? C20 H25 0.9900 . ? C21 C22 1.520(2) . ? C21 H26 0.9900 . ? C21 H27 0.9900 . ? C22 C23 1.520(2) . ? C22 H28 0.9900 . ? C22 H29 0.9900 . ? C23 H30 0.9900 . ? C23 H31 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 B1 N1 127.51(12) . . ? N2 B1 C7 125.34(12) . . ? N1 B1 C7 107.15(11) . . ? C1 N1 B1 109.58(11) . . ? C1 N1 C8 118.98(10) . . ? B1 N1 C8 131.03(11) . . ? B1 N2 C23 128.72(11) . . ? B1 N2 C20 121.17(11) . . ? C23 N2 C20 110.11(11) . . ? C2 C1 C6 121.31(12) . . ? C2 C1 N1 127.68(12) . . ? C6 C1 N1 110.99(11) . . ? C1 C2 C3 118.63(13) . . ? C1 C2 H1 120.7 . . ? C3 C2 H1 120.7 . . ? C4 C3 C2 120.77(14) . . ? C4 C3 H2 119.6 . . ? C2 C3 H2 119.6 . . ? C3 C4 C5 119.86(13) . . ? C3 C4 H3 120.1 . . ? C5 C4 H3 120.1 . . ? C6 C5 C4 120.34(13) . . ? C6 C5 H4 119.8 . . ? C4 C5 H4 119.8 . . ? C5 C6 C1 119.07(13) . . ? C5 C6 C7 130.56(13) . . ? C1 C6 C7 110.31(11) . . ? C6 C7 B1 101.93(11) . . ? C6 C7 H5 111.4 . . ? B1 C7 H5 111.4 . . ? C6 C7 H6 111.4 . . ? B1 C7 H6 111.4 . . ? H5 C7 H6 109.2 . . ? C13 C8 C9 121.54(11) . . ? C13 C8 N1 119.13(11) . . ? C9 C8 N1 119.33(11) . . ? C10 C9 C8 117.96(12) . . ? C10 C9 C14 120.15(12) . . ? C8 C9 C14 121.88(11) . . ? C11 C10 C9 121.17(13) . . ? C11 C10 H7 119.4 . . ? C9 C10 H7 119.4 . . ? C10 C11 C12 120.20(12) . . ? C10 C11 H8 119.9 . . ? C12 C11 H8 119.9 . . ? C11 C12 C13 120.96(13) . . ? C11 C12 H9 119.5 . . ? C13 C12 H9 119.5 . . ? C12 C13 C8 118.17(12) . . ? C12 C13 C17 119.42(12) . . ? C8 C13 C17 122.39(11) . . ? C9 C14 C15 110.55(11) . . ? C9 C14 C16 112.67(11) . . ? C15 C14 C16 110.66(12) . . ? C9 C14 H10 107.6 . . ? C15 C14 H10 107.6 . . ? C16 C14 H10 107.6 . . ? C14 C15 H11 109.5 . . ? C14 C15 H12 109.5 . . ? H11 C15 H12 109.5 . . ? C14 C15 H13 109.5 . . ? H11 C15 H13 109.5 . . ? H12 C15 H13 109.5 . . ? C14 C16 H14 109.5 . . ? C14 C16 H15 109.5 . . ? H14 C16 H15 109.5 . . ? C14 C16 H16 109.5 . . ? H14 C16 H16 109.5 . . ? H15 C16 H16 109.5 . . ? C13 C17 C19 110.55(11) . . ? C13 C17 C18 111.73(12) . . ? C19 C17 C18 111.27(13) . . ? C13 C17 H17 107.7 . . ? C19 C17 H17 107.7 . . ? C18 C17 H17 107.7 . . ? C17 C18 H18 109.5 . . ? C17 C18 H19 109.5 . . ? H18 C18 H19 109.5 . . ? C17 C18 H20 109.5 . . ? H18 C18 H20 109.5 . . ? H19 C18 H20 109.5 . . ? C17 C19 H21 109.5 . . ? C17 C19 H22 109.5 . . ? H21 C19 H22 109.5 . . ? C17 C19 H23 109.5 . . ? H21 C19 H23 109.5 . . ? H22 C19 H23 109.5 . . ? N2 C20 C21 104.45(11) . . ? N2 C20 H24 110.9 . . ? C21 C20 H24 110.9 . . ? N2 C20 H25 110.9 . . ? C21 C20 H25 110.9 . . ? H24 C20 H25 108.9 . . ? C20 C21 C22 102.92(12) . . ? C20 C21 H26 111.2 . . ? C22 C21 H26 111.2 . . ? C20 C21 H27 111.2 . . ? C22 C21 H27 111.2 . . ? H26 C21 H27 109.1 . . ? C23 C22 C21 103.51(11) . . ? C23 C22 H28 111.1 . . ? C21 C22 H28 111.1 . . ? C23 C22 H29 111.1 . . ? C21 C22 H29 111.1 . . ? H28 C22 H29 109.0 . . ? N2 C23 C22 104.48(11) . . ? N2 C23 H30 110.9 . . ? C22 C23 H30 110.9 . . ? N2 C23 H31 110.9 . . ? C22 C23 H31 110.9 . . ? H30 C23 H31 108.9 . . ? 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 N2 B1 N1 C1 177.87(13) . . . . ? C7 B1 N1 C1 -1.50(14) . . . . ? N2 B1 N1 C8 5.5(2) . . . . ? C7 B1 N1 C8 -173.90(12) . . . . ? N1 B1 N2 C23 4.3(2) . . . . ? C7 B1 N2 C23 -176.48(12) . . . . ? N1 B1 N2 C20 -175.06(13) . . . . ? C7 B1 N2 C20 4.2(2) . . . . ? B1 N1 C1 C2 -176.08(13) . . . . ? C8 N1 C1 C2 -2.63(19) . . . . ? B1 N1 C1 C6 2.26(14) . . . . ? C8 N1 C1 C6 175.71(11) . . . . ? C6 C1 C2 C3 0.1(2) . . . . ? N1 C1 C2 C3 178.26(12) . . . . ? C1 C2 C3 C4 0.6(2) . . . . ? C2 C3 C4 C5 -0.2(2) . . . . ? C3 C4 C5 C6 -0.8(2) . . . . ? C4 C5 C6 C1 1.5(2) . . . . ? C4 C5 C6 C7 -175.44(13) . . . . ? C2 C1 C6 C5 -1.12(19) . . . . ? N1 C1 C6 C5 -179.59(11) . . . . ? C2 C1 C6 C7 176.39(12) . . . . ? N1 C1 C6 C7 -2.07(15) . . . . ? C5 C6 C7 B1 178.19(13) . . . . ? C1 C6 C7 B1 1.05(14) . . . . ? N2 B1 C7 C6 -179.10(12) . . . . ? N1 B1 C7 C6 0.29(13) . . . . ? C1 N1 C8 C13 -78.59(15) . . . . ? B1 N1 C8 C13 93.21(17) . . . . ? C1 N1 C8 C9 101.04(14) . . . . ? B1 N1 C8 C9 -87.16(17) . . . . ? C13 C8 C9 C10 0.97(18) . . . . ? N1 C8 C9 C10 -178.65(11) . . . . ? C13 C8 C9 C14 179.84(11) . . . . ? N1 C8 C9 C14 0.22(18) . . . . ? C8 C9 C10 C11 -0.43(19) . . . . ? C14 C9 C10 C11 -179.32(12) . . . . ? C9 C10 C11 C12 -0.6(2) . . . . ? C10 C11 C12 C13 1.0(2) . . . . ? C11 C12 C13 C8 -0.5(2) . . . . ? C11 C12 C13 C17 -178.98(12) . . . . ? C9 C8 C13 C12 -0.52(18) . . . . ? N1 C8 C13 C12 179.10(11) . . . . ? C9 C8 C13 C17 177.92(12) . . . . ? N1 C8 C13 C17 -2.45(18) . . . . ? C10 C9 C14 C15 82.98(15) . . . . ? C8 C9 C14 C15 -95.87(15) . . . . ? C10 C9 C14 C16 -41.42(17) . . . . ? C8 C9 C14 C16 139.73(13) . . . . ? C12 C13 C17 C19 65.72(17) . . . . ? C8 C13 C17 C19 -112.70(15) . . . . ? C12 C13 C17 C18 -58.77(17) . . . . ? C8 C13 C17 C18 122.80(14) . . . . ? B1 N2 C20 C21 -166.91(12) . . . . ? C23 N2 C20 C21 13.66(15) . . . . ? N2 C20 C21 C22 -31.94(15) . . . . ? C20 C21 C22 C23 38.31(15) . . . . ? B1 N2 C23 C22 -169.08(13) . . . . ? C20 N2 C23 C22 10.30(15) . . . . ? C21 C22 C23 N2 -30.06(14) . . . . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.198 _refine_diff_density_min -0.187 _refine_diff_density_rms 0.035 #----------13-iPr-----------# data_13-iPr _database_code_depnum_ccdc_archive 'CCDC 777070' #TrackingRef '- CIFs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H37 B N2' _chemical_formula_weight 376.38 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' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.969(4) _cell_length_b 10.684(5) _cell_length_c 11.315(5) _cell_angle_alpha 85.714(13) _cell_angle_beta 77.331(12) _cell_angle_gamma 83.324(13) _cell_volume 1166.4(9) _cell_formula_units_Z 2 _cell_measurement_temperature 103.15 _cell_measurement_reflns_used 3697 _cell_measurement_theta_min 3.0817 _cell_measurement_theta_max 27.4835 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.072 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 412 _exptl_absorpt_coefficient_mu 0.061 _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 103(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'RIGAKU/MSC Meacury CCD' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 7.31 _diffrn_reflns_number 7627 _diffrn_reflns_av_R_equivalents 0.0218 _diffrn_reflns_av_sigmaI/netI 0.0347 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4007 _reflns_number_gt 3450 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RIGAKU CrystalClear' _computing_cell_refinement 'RIGAKU CrystalClear' _computing_data_reduction 'RIGAKU CrystalClear' _computing_structure_solution SIR-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP-III _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^)+(0.0462P)^2^+0.2251P] 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 4007 _refine_ls_number_parameters 261 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0520 _refine_ls_R_factor_gt 0.0430 _refine_ls_wR_factor_ref 0.1066 _refine_ls_wR_factor_gt 0.1006 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _refine_ls_shift/su_max 0.014 _refine_ls_shift/su_mean 0.003 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 0.21496(15) 0.15083(14) 0.67082(13) 0.0193(3) Uani 1 1 d . . . N1 N 0.26846(11) 0.13598(10) 0.78166(9) 0.0179(2) Uani 1 1 d . . . C1 C 0.32622(13) 0.01000(12) 0.79856(12) 0.0201(3) Uani 1 1 d . . . C2 C 0.38688(14) -0.03990(13) 0.89351(12) 0.0254(3) Uani 1 1 d . . . H1 H 0.3916 0.0108 0.9577 0.030 Uiso 1 1 calc R . . C3 C 0.44057(15) -0.16598(14) 0.89224(14) 0.0309(3) Uani 1 1 d . . . H2 H 0.4828 -0.2019 0.9562 0.037 Uiso 1 1 calc R . . C4 C 0.43327(16) -0.23973(14) 0.79899(14) 0.0342(4) Uani 1 1 d . . . H3 H 0.4701 -0.3258 0.7995 0.041 Uiso 1 1 calc R . . C5 C 0.37213(15) -0.18840(13) 0.70436(13) 0.0309(3) Uani 1 1 d . . . H4 H 0.3673 -0.2394 0.6404 0.037 Uiso 1 1 calc R . . C6 C 0.31838(14) -0.06305(13) 0.70350(12) 0.0225(3) Uani 1 1 d . . . C7 C 0.24971(15) 0.01551(13) 0.61266(12) 0.0256(3) Uani 1 1 d . . . H5 H 0.1645 -0.0192 0.6045 0.031 Uiso 1 1 calc R . . H6 H 0.3130 0.0204 0.5321 0.031 Uiso 1 1 calc R . . C8 C 0.28622(13) 0.22845(12) 0.86121(11) 0.0183(3) Uani 1 1 d . . . C9 C 0.39255(13) 0.30778(12) 0.82154(12) 0.0214(3) Uani 1 1 d . . . C10 C 0.40203(14) 0.40191(13) 0.89709(13) 0.0260(3) Uani 1 1 d . . . H7 H 0.4718 0.4575 0.8717 0.031 Uiso 1 1 calc R . . C11 C 0.31230(15) 0.41624(13) 1.00815(13) 0.0287(3) Uani 1 1 d . . . H8 H 0.3193 0.4824 1.0574 0.034 Uiso 1 1 calc R . . C12 C 0.21256(15) 0.33432(13) 1.04750(13) 0.0270(3) Uani 1 1 d . . . H9 H 0.1529 0.3434 1.1250 0.032 Uiso 1 1 calc R . . C13 C 0.19775(14) 0.23844(13) 0.97571(12) 0.0220(3) Uani 1 1 d . . . C14 C 0.49536(14) 0.28973(14) 0.70141(13) 0.0289(3) Uani 1 1 d . . . H10 H 0.4443 0.2628 0.6423 0.035 Uiso 1 1 calc R . . C15 C 0.60935(16) 0.18408(15) 0.71549(16) 0.0425(4) Uani 1 1 d . . . H11 H 0.6595 0.2067 0.7749 0.064 Uiso 1 1 calc R . . H12 H 0.6736 0.1725 0.6371 0.064 Uiso 1 1 calc R . . H13 H 0.5679 0.1054 0.7434 0.064 Uiso 1 1 calc R . . C16 C 0.56051(16) 0.40946(16) 0.64710(15) 0.0373(4) Uani 1 1 d . . . H14 H 0.4875 0.4783 0.6423 0.056 Uiso 1 1 calc R . . H15 H 0.6158 0.3942 0.5656 0.056 Uiso 1 1 calc R . . H16 H 0.6200 0.4327 0.6986 0.056 Uiso 1 1 calc R . . C17 C 0.08388(15) 0.15269(14) 1.02111(12) 0.0281(3) Uani 1 1 d . . . H17 H 0.0909 0.0896 0.9585 0.034 Uiso 1 1 calc R . . C18 C 0.10055(19) 0.07987(17) 1.13967(14) 0.0433(4) Uani 1 1 d . . . H18 H 0.0934 0.1395 1.2030 0.065 Uiso 1 1 calc R . . H19 H 0.1912 0.0304 1.1275 0.065 Uiso 1 1 calc R . . H20 H 0.0278 0.0231 1.1644 0.065 Uiso 1 1 calc R . . C19 C -0.05911(16) 0.22673(17) 1.03652(16) 0.0438(4) Uani 1 1 d . . . H21 H -0.0702 0.2872 1.0998 0.066 Uiso 1 1 calc R . . H22 H -0.1303 0.1682 1.0598 0.066 Uiso 1 1 calc R . . H23 H -0.0684 0.2722 0.9598 0.066 Uiso 1 1 calc R . . N2 N 0.14441(11) 0.26073(10) 0.62766(9) 0.0201(3) Uani 1 1 d . . . C20 C 0.08579(14) 0.36904(12) 0.70348(12) 0.0229(3) Uani 1 1 d . . . H24 H 0.1049 0.3459 0.7859 0.028 Uiso 1 1 calc R . . C21 C 0.15387(15) 0.48941(13) 0.65827(14) 0.0306(3) Uani 1 1 d . . . H25 H 0.2537 0.4732 0.6530 0.046 Uiso 1 1 calc R . . H26 H 0.1154 0.5560 0.7148 0.046 Uiso 1 1 calc R . . H27 H 0.1362 0.5163 0.5779 0.046 Uiso 1 1 calc R . . C22 C -0.07148(14) 0.39168(15) 0.71927(14) 0.0323(4) Uani 1 1 d . . . H28 H -0.0947 0.4203 0.6412 0.048 Uiso 1 1 calc R . . H29 H -0.1081 0.4563 0.7784 0.048 Uiso 1 1 calc R . . H30 H -0.1122 0.3130 0.7484 0.048 Uiso 1 1 calc R . . C23 C 0.11731(14) 0.27676(13) 0.50331(12) 0.0250(3) Uani 1 1 d . . . H31 H 0.0693 0.3637 0.4961 0.030 Uiso 1 1 calc R . . C24 C 0.25054(16) 0.27246(15) 0.40704(13) 0.0337(4) Uani 1 1 d . . . H32 H 0.3097 0.3327 0.4246 0.051 Uiso 1 1 calc R . . H33 H 0.2289 0.2946 0.3272 0.051 Uiso 1 1 calc R . . H34 H 0.2990 0.1872 0.4072 0.051 Uiso 1 1 calc R . . C25 C 0.01941(16) 0.18605(15) 0.48011(14) 0.0344(4) Uani 1 1 d . . . H35 H 0.0691 0.1017 0.4682 0.052 Uiso 1 1 calc R . . H36 H -0.0154 0.2158 0.4073 0.052 Uiso 1 1 calc R . . H37 H -0.0584 0.1823 0.5499 0.052 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 B1 0.0169(7) 0.0218(8) 0.0191(7) -0.0016(6) -0.0009(6) -0.0062(6) N1 0.0193(6) 0.0163(5) 0.0185(5) -0.0012(4) -0.0047(4) -0.0020(4) C1 0.0177(6) 0.0184(7) 0.0228(7) 0.0008(5) -0.0010(5) -0.0034(5) C2 0.0245(7) 0.0260(7) 0.0260(7) 0.0024(6) -0.0066(6) -0.0037(6) C3 0.0277(8) 0.0289(8) 0.0338(8) 0.0089(6) -0.0068(6) 0.0009(6) C4 0.0360(9) 0.0199(7) 0.0410(9) 0.0028(6) -0.0010(7) 0.0047(6) C5 0.0361(8) 0.0220(7) 0.0315(8) -0.0057(6) -0.0002(7) -0.0006(6) C6 0.0211(7) 0.0214(7) 0.0233(7) -0.0020(6) -0.0003(6) -0.0031(6) C7 0.0307(8) 0.0239(7) 0.0226(7) -0.0045(6) -0.0060(6) -0.0025(6) C8 0.0199(7) 0.0160(6) 0.0211(7) -0.0002(5) -0.0089(5) -0.0019(5) C9 0.0201(7) 0.0208(7) 0.0251(7) 0.0016(6) -0.0094(6) -0.0027(6) C10 0.0262(8) 0.0206(7) 0.0348(8) 0.0016(6) -0.0129(6) -0.0073(6) C11 0.0340(8) 0.0249(8) 0.0321(8) -0.0084(6) -0.0145(7) -0.0048(6) C12 0.0288(8) 0.0310(8) 0.0226(7) -0.0081(6) -0.0063(6) -0.0033(6) C13 0.0232(7) 0.0238(7) 0.0203(7) -0.0012(5) -0.0072(6) -0.0032(6) C14 0.0241(8) 0.0356(8) 0.0279(8) 0.0000(6) -0.0030(6) -0.0125(7) C15 0.0280(8) 0.0349(9) 0.0564(11) -0.0039(8) 0.0103(8) -0.0054(7) C16 0.0290(8) 0.0446(10) 0.0377(9) 0.0106(7) -0.0054(7) -0.0129(7) C17 0.0311(8) 0.0327(8) 0.0211(7) -0.0057(6) -0.0004(6) -0.0133(7) C18 0.0520(11) 0.0493(11) 0.0289(8) 0.0047(8) -0.0032(8) -0.0209(9) C19 0.0308(9) 0.0540(11) 0.0442(10) -0.0001(8) 0.0014(7) -0.0137(8) N2 0.0218(6) 0.0208(6) 0.0186(6) -0.0026(4) -0.0061(5) -0.0015(5) C20 0.0240(7) 0.0221(7) 0.0236(7) -0.0051(6) -0.0075(6) 0.0016(6) C21 0.0323(8) 0.0241(8) 0.0385(8) -0.0023(6) -0.0147(7) -0.0015(6) C22 0.0261(8) 0.0351(9) 0.0341(8) -0.0076(7) -0.0046(6) 0.0036(7) C23 0.0279(8) 0.0276(8) 0.0212(7) -0.0004(6) -0.0100(6) -0.0007(6) C24 0.0400(9) 0.0392(9) 0.0208(7) 0.0024(6) -0.0050(6) -0.0045(7) C25 0.0351(9) 0.0422(9) 0.0309(8) -0.0052(7) -0.0152(7) -0.0065(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B1 N2 1.4088(19) . ? B1 N1 1.4583(19) . ? B1 C7 1.603(2) . ? N1 C1 1.4176(17) . ? N1 C8 1.4357(17) . ? C1 C2 1.3888(19) . ? C1 C6 1.3960(19) . ? C2 C3 1.390(2) . ? C2 H1 0.9500 . ? C3 C4 1.382(2) . ? C3 H2 0.9500 . ? C4 C5 1.393(2) . ? C4 H3 0.9500 . ? C5 C6 1.384(2) . ? C5 H4 0.9500 . ? C6 C7 1.5085(19) . ? C7 H5 0.9900 . ? C7 H6 0.9900 . ? C8 C13 1.4020(19) . ? C8 C9 1.4095(19) . ? C9 C10 1.3918(19) . ? C9 C14 1.522(2) . ? C10 C11 1.381(2) . ? C10 H7 0.9500 . ? C11 C12 1.379(2) . ? C11 H8 0.9500 . ? C12 C13 1.3940(19) . ? C12 H9 0.9500 . ? C13 C17 1.519(2) . ? C14 C16 1.529(2) . ? C14 C15 1.531(2) . ? C14 H10 1.0000 . ? C15 H11 0.9800 . ? C15 H12 0.9800 . ? C15 H13 0.9800 . ? C16 H14 0.9800 . ? C16 H15 0.9800 . ? C16 H16 0.9800 . ? C17 C19 1.529(2) . ? C17 C18 1.531(2) . ? C17 H17 1.0000 . ? C18 H18 0.9800 . ? C18 H19 0.9800 . ? C18 H20 0.9800 . ? C19 H21 0.9800 . ? C19 H22 0.9800 . ? C19 H23 0.9800 . ? N2 C20 1.4792(17) . ? N2 C23 1.4841(17) . ? C20 C21 1.526(2) . ? C20 C22 1.531(2) . ? C20 H24 1.0000 . ? C21 H25 0.9800 . ? C21 H26 0.9800 . ? C21 H27 0.9800 . ? C22 H28 0.9800 . ? C22 H29 0.9800 . ? C22 H30 0.9800 . ? C23 C24 1.520(2) . ? C23 C25 1.527(2) . ? C23 H31 1.0000 . ? C24 H32 0.9800 . ? C24 H33 0.9800 . ? C24 H34 0.9800 . ? C25 H35 0.9800 . ? C25 H36 0.9800 . ? C25 H37 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 B1 N1 126.52(12) . . ? N2 B1 C7 128.15(12) . . ? N1 B1 C7 105.30(11) . . ? C1 N1 C8 118.55(11) . . ? C1 N1 B1 110.34(11) . . ? C8 N1 B1 130.53(11) . . ? C2 C1 C6 121.67(13) . . ? C2 C1 N1 127.05(12) . . ? C6 C1 N1 111.26(12) . . ? C1 C2 C3 118.29(13) . . ? C1 C2 H1 120.9 . . ? C3 C2 H1 120.9 . . ? C4 C3 C2 120.78(14) . . ? C4 C3 H2 119.6 . . ? C2 C3 H2 119.6 . . ? C3 C4 C5 120.29(14) . . ? C3 C4 H3 119.9 . . ? C5 C4 H3 119.9 . . ? C6 C5 C4 119.96(14) . . ? C6 C5 H4 120.0 . . ? C4 C5 H4 120.0 . . ? C5 C6 C1 119.01(13) . . ? C5 C6 C7 130.69(13) . . ? C1 C6 C7 110.29(12) . . ? C6 C7 B1 102.78(11) . . ? C6 C7 H5 111.2 . . ? B1 C7 H5 111.2 . . ? C6 C7 H6 111.2 . . ? B1 C7 H6 111.2 . . ? H5 C7 H6 109.1 . . ? C13 C8 C9 121.52(12) . . ? C13 C8 N1 119.65(11) . . ? C9 C8 N1 118.83(11) . . ? C10 C9 C8 117.70(12) . . ? C10 C9 C14 121.02(12) . . ? C8 C9 C14 121.27(12) . . ? C11 C10 C9 121.47(13) . . ? C11 C10 H7 119.3 . . ? C9 C10 H7 119.3 . . ? C12 C11 C10 119.91(13) . . ? C12 C11 H8 120.0 . . ? C10 C11 H8 120.0 . . ? C11 C12 C13 121.23(13) . . ? C11 C12 H9 119.4 . . ? C13 C12 H9 119.4 . . ? C12 C13 C8 118.05(12) . . ? C12 C13 C17 119.47(12) . . ? C8 C13 C17 122.43(12) . . ? C9 C14 C16 113.81(13) . . ? C9 C14 C15 110.46(12) . . ? C16 C14 C15 109.55(12) . . ? C9 C14 H10 107.6 . . ? C16 C14 H10 107.6 . . ? C15 C14 H10 107.6 . . ? C14 C15 H11 109.5 . . ? C14 C15 H12 109.5 . . ? H11 C15 H12 109.5 . . ? C14 C15 H13 109.5 . . ? H11 C15 H13 109.5 . . ? H12 C15 H13 109.5 . . ? C14 C16 H14 109.5 . . ? C14 C16 H15 109.5 . . ? H14 C16 H15 109.5 . . ? C14 C16 H16 109.5 . . ? H14 C16 H16 109.5 . . ? H15 C16 H16 109.5 . . ? C13 C17 C19 111.33(13) . . ? C13 C17 C18 111.73(12) . . ? C19 C17 C18 110.46(13) . . ? C13 C17 H17 107.7 . . ? C19 C17 H17 107.7 . . ? C18 C17 H17 107.7 . . ? C17 C18 H18 109.5 . . ? C17 C18 H19 109.5 . . ? H18 C18 H19 109.5 . . ? C17 C18 H20 109.5 . . ? H18 C18 H20 109.5 . . ? H19 C18 H20 109.5 . . ? C17 C19 H21 109.5 . . ? C17 C19 H22 109.5 . . ? H21 C19 H22 109.5 . . ? C17 C19 H23 109.5 . . ? H21 C19 H23 109.5 . . ? H22 C19 H23 109.5 . . ? B1 N2 C20 123.16(11) . . ? B1 N2 C23 123.16(11) . . ? C20 N2 C23 113.64(11) . . ? N2 C20 C21 113.17(11) . . ? N2 C20 C22 111.64(11) . . ? C21 C20 C22 111.32(12) . . ? N2 C20 H24 106.8 . . ? C21 C20 H24 106.8 . . ? C22 C20 H24 106.8 . . ? C20 C21 H25 109.5 . . ? C20 C21 H26 109.5 . . ? H25 C21 H26 109.5 . . ? C20 C21 H27 109.5 . . ? H25 C21 H27 109.5 . . ? H26 C21 H27 109.5 . . ? C20 C22 H28 109.5 . . ? C20 C22 H29 109.5 . . ? H28 C22 H29 109.5 . . ? C20 C22 H30 109.5 . . ? H28 C22 H30 109.5 . . ? H29 C22 H30 109.5 . . ? N2 C23 C24 111.84(11) . . ? N2 C23 C25 113.22(11) . . ? C24 C23 C25 112.11(12) . . ? N2 C23 H31 106.4 . . ? C24 C23 H31 106.4 . . ? C25 C23 H31 106.4 . . ? C23 C24 H32 109.5 . . ? C23 C24 H33 109.5 . . ? H32 C24 H33 109.5 . . ? C23 C24 H34 109.5 . . ? H32 C24 H34 109.5 . . ? H33 C24 H34 109.5 . . ? C23 C25 H35 109.5 . . ? C23 C25 H36 109.5 . . ? H35 C25 H36 109.5 . . ? C23 C25 H37 109.5 . . ? H35 C25 H37 109.5 . . ? H36 C25 H37 109.5 . . ? 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 N2 B1 N1 C1 176.67(12) . . . . ? C7 B1 N1 C1 -1.67(14) . . . . ? N2 B1 N1 C8 -12.3(2) . . . . ? C7 B1 N1 C8 169.32(12) . . . . ? C8 N1 C1 C2 7.81(19) . . . . ? B1 N1 C1 C2 -179.97(12) . . . . ? C8 N1 C1 C6 -170.88(11) . . . . ? B1 N1 C1 C6 1.33(15) . . . . ? C6 C1 C2 C3 0.0(2) . . . . ? N1 C1 C2 C3 -178.58(12) . . . . ? C1 C2 C3 C4 -0.2(2) . . . . ? C2 C3 C4 C5 0.2(2) . . . . ? C3 C4 C5 C6 0.0(2) . . . . ? C4 C5 C6 C1 -0.2(2) . . . . ? C4 C5 C6 C7 178.97(14) . . . . ? C2 C1 C6 C5 0.2(2) . . . . ? N1 C1 C6 C5 178.98(12) . . . . ? C2 C1 C6 C7 -179.12(12) . . . . ? N1 C1 C6 C7 -0.34(15) . . . . ? C5 C6 C7 B1 -179.88(14) . . . . ? C1 C6 C7 B1 -0.67(14) . . . . ? N2 B1 C7 C6 -176.92(13) . . . . ? N1 B1 C7 C6 1.39(13) . . . . ? C1 N1 C8 C13 -82.07(15) . . . . ? B1 N1 C8 C13 107.54(15) . . . . ? C1 N1 C8 C9 98.22(14) . . . . ? B1 N1 C8 C9 -72.16(17) . . . . ? C13 C8 C9 C10 -3.73(19) . . . . ? N1 C8 C9 C10 175.97(11) . . . . ? C13 C8 C9 C14 175.11(12) . . . . ? N1 C8 C9 C14 -5.19(18) . . . . ? C8 C9 C10 C11 1.1(2) . . . . ? C14 C9 C10 C11 -177.69(13) . . . . ? C9 C10 C11 C12 1.5(2) . . . . ? C10 C11 C12 C13 -1.7(2) . . . . ? C11 C12 C13 C8 -0.8(2) . . . . ? C11 C12 C13 C17 -178.27(13) . . . . ? C9 C8 C13 C12 3.57(19) . . . . ? N1 C8 C13 C12 -176.13(12) . . . . ? C9 C8 C13 C17 -179.05(12) . . . . ? N1 C8 C13 C17 1.25(19) . . . . ? C10 C9 C14 C16 -25.96(19) . . . . ? C8 C9 C14 C16 155.25(13) . . . . ? C10 C9 C14 C15 97.76(16) . . . . ? C8 C9 C14 C15 -81.04(16) . . . . ? C12 C13 C17 C19 63.18(17) . . . . ? C8 C13 C17 C19 -114.16(15) . . . . ? C12 C13 C17 C18 -60.84(18) . . . . ? C8 C13 C17 C18 121.82(15) . . . . ? N1 B1 N2 C20 -14.7(2) . . . . ? C7 B1 N2 C20 163.22(12) . . . . ? N1 B1 N2 C23 167.64(12) . . . . ? C7 B1 N2 C23 -14.4(2) . . . . ? B1 N2 C20 C21 115.87(14) . . . . ? C23 N2 C20 C21 -66.31(14) . . . . ? B1 N2 C20 C22 -117.60(14) . . . . ? C23 N2 C20 C22 60.22(14) . . . . ? B1 N2 C23 C24 -62.24(17) . . . . ? C20 N2 C23 C24 119.93(13) . . . . ? B1 N2 C23 C25 65.58(17) . . . . ? C20 N2 C23 C25 -112.24(14) . . . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.181 _refine_diff_density_min -0.169 _refine_diff_density_rms 0.034