# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_939164 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H21 B F2 N2 O2' _chemical_formula_weight 382.21 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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 C2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 32.799(2) _cell_length_b 7.9896(4) _cell_length_c 7.2920(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.511(2) _cell_angle_gamma 90.00 _cell_volume 1910.79(19) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needlike _exptl_crystal_colour orange-yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.329 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9807 _exptl_absorpt_correction_T_max 0.9903 _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12361 _diffrn_reflns_av_R_equivalents 0.0488 _diffrn_reflns_av_sigmaI/netI 0.0434 _diffrn_reflns_limit_h_min -38 _diffrn_reflns_limit_h_max 38 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 24.99 _reflns_number_total 3363 _reflns_number_gt 2483 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RAPID-AUTO (Rigaku Corporation, 1998)' _computing_cell_refinement RAPID-AUTO _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0929P)^2^+0.3345P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0086(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.7(11) _refine_ls_number_reflns 3363 _refine_ls_number_parameters 254 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0728 _refine_ls_R_factor_gt 0.0467 _refine_ls_wR_factor_ref 0.1547 _refine_ls_wR_factor_gt 0.1169 _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_restrained_S_all 1.094 _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 0.19185(12) 0.6099(5) 0.3447(5) 0.0336(9) Uani 1 1 d . . . F1 F 0.18950(6) 0.4378(2) 0.3767(3) 0.0492(6) Uani 1 1 d . . . F2 F 0.22619(6) 0.6422(2) 0.2389(3) 0.0428(5) Uani 1 1 d . . . N1 N 0.15335(8) 0.6708(3) 0.2438(4) 0.0365(7) Uani 1 1 d . . . N2 N 0.19475(8) 0.7054(3) 0.5276(4) 0.0331(6) Uani 1 1 d . . . O1 O 0.03992(9) 1.5668(3) 0.6798(4) 0.0561(8) Uani 1 1 d . . . O2 O -0.00523(8) 1.3667(4) 0.7477(4) 0.0545(7) Uani 1 1 d . . . C1 C 0.03085(12) 1.4217(5) 0.6902(5) 0.0435(9) Uani 1 1 d . . . C2 C -0.03458(12) 1.4942(6) 0.7966(6) 0.0606(12) Uani 1 1 d . . . H2A H -0.0599 1.4407 0.8364 0.091 Uiso 1 1 calc R . . H2B H -0.0402 1.5653 0.6899 0.091 Uiso 1 1 calc R . . H2C H -0.0235 1.5627 0.8967 0.091 Uiso 1 1 calc R . . C3 C 0.05810(10) 1.2792(4) 0.6368(5) 0.0361(8) Uani 1 1 d . . . C4 C 0.04628(10) 1.1142(4) 0.6614(4) 0.0386(8) Uani 1 1 d . . . H4A H 0.0207 1.0894 0.7149 0.046 Uiso 1 1 calc R . . C5 C 0.07196(10) 0.9852(4) 0.6077(4) 0.0352(8) Uani 1 1 d . . . H5A H 0.0640 0.8720 0.6247 0.042 Uiso 1 1 calc R . . C6 C 0.10922(9) 1.0224(4) 0.5292(4) 0.0324(7) Uani 1 1 d . . . C7 C 0.12077(11) 1.1883(4) 0.5025(5) 0.0374(8) Uani 1 1 d . . . H7A H 0.1461 1.2133 0.4467 0.045 Uiso 1 1 calc R . . C8 C 0.09531(10) 1.3167(4) 0.5574(5) 0.0398(8) Uani 1 1 d . . . H8A H 0.1033 1.4300 0.5408 0.048 Uiso 1 1 calc R . . C9 C 0.13658(9) 0.8837(4) 0.4705(4) 0.0323(7) Uani 1 1 d . . . C10 C 0.16894(10) 0.8356(4) 0.5805(4) 0.0316(7) Uani 1 1 d . . . C11 C 0.18351(10) 0.8952(4) 0.7551(4) 0.0357(8) Uani 1 1 d . . . C12 C 0.21688(11) 0.8007(5) 0.7987(5) 0.0396(8) Uani 1 1 d . . . H12A H 0.2330 0.8119 0.9069 0.048 Uiso 1 1 calc R . . C13 C 0.22350(10) 0.6853(4) 0.6589(5) 0.0390(8) Uani 1 1 d . . . C14 C 0.13942(11) 0.6164(5) 0.0798(5) 0.0406(8) Uani 1 1 d . . . C15 C 0.10572(11) 0.7137(5) 0.0281(5) 0.0438(9) Uani 1 1 d . . . H15A H 0.0904 0.7011 -0.0820 0.053 Uiso 1 1 calc R . . C16 C 0.09844(10) 0.8307(5) 0.1631(5) 0.0394(8) Uani 1 1 d . . . C17 C 0.12862(9) 0.8042(4) 0.3011(4) 0.0343(7) Uani 1 1 d . . . C18 C 0.16830(12) 1.0388(5) 0.8662(5) 0.0446(9) Uani 1 1 d . . . H18A H 0.1844 1.0478 0.9795 0.067 Uiso 1 1 calc R . . H18B H 0.1396 1.0204 0.8965 0.067 Uiso 1 1 calc R . . H18C H 0.1709 1.1425 0.7955 0.067 Uiso 1 1 calc R . . C19 C 0.25619(12) 0.5575(5) 0.6485(6) 0.0518(10) Uani 1 1 d . . . H19A H 0.2530 0.4930 0.5350 0.078 Uiso 1 1 calc R . . H19B H 0.2544 0.4822 0.7541 0.078 Uiso 1 1 calc R . . H19C H 0.2828 0.6131 0.6494 0.078 Uiso 1 1 calc R . . C20 C 0.15768(13) 0.4725(5) -0.0186(5) 0.0521(10) Uani 1 1 d . . . H20A H 0.1810 0.4295 0.0521 0.078 Uiso 1 1 calc R . . H20B H 0.1669 0.5090 -0.1396 0.078 Uiso 1 1 calc R . . H20C H 0.1372 0.3839 -0.0332 0.078 Uiso 1 1 calc R . . C21 C 0.06455(13) 0.9562(6) 0.1579(6) 0.0561(11) Uani 1 1 d . . . H21A H 0.0489 0.9429 0.0439 0.084 Uiso 1 1 calc R . . H21B H 0.0760 1.0694 0.1634 0.084 Uiso 1 1 calc R . . H21C H 0.0466 0.9385 0.2630 0.084 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 0.037(2) 0.0214(19) 0.042(2) -0.0044(17) 0.0052(17) 0.0003(16) F1 0.0539(13) 0.0279(11) 0.0660(13) -0.0027(10) 0.0045(11) -0.0029(9) F2 0.0365(11) 0.0461(12) 0.0460(11) -0.0048(9) 0.0095(9) 0.0009(9) N1 0.0331(15) 0.0338(16) 0.0426(15) -0.0052(13) 0.0055(12) -0.0034(13) N2 0.0284(14) 0.0307(14) 0.0403(15) 0.0005(13) 0.0048(12) 0.0015(12) O1 0.0619(19) 0.0367(15) 0.0696(18) -0.0106(13) -0.0086(14) 0.0091(13) O2 0.0402(15) 0.0587(17) 0.0647(17) -0.0175(14) 0.0037(13) 0.0129(13) C1 0.042(2) 0.045(2) 0.044(2) -0.0085(18) -0.0084(16) 0.0107(18) C2 0.046(2) 0.076(3) 0.061(2) -0.027(2) -0.0046(19) 0.028(2) C3 0.0342(18) 0.0335(17) 0.0407(18) -0.0033(15) 0.0007(14) 0.0032(14) C4 0.0296(18) 0.044(2) 0.0418(18) 0.0024(18) 0.0030(15) 0.0049(16) C5 0.0332(17) 0.0331(18) 0.0394(19) 0.0010(15) 0.0059(14) 0.0007(15) C6 0.0304(17) 0.0275(16) 0.0394(18) -0.0015(14) 0.0012(14) 0.0004(14) C7 0.0339(18) 0.0307(19) 0.048(2) -0.0006(16) 0.0033(15) -0.0017(15) C8 0.0394(19) 0.0281(17) 0.052(2) -0.0031(16) -0.0008(16) 0.0008(16) C9 0.0270(16) 0.0327(17) 0.0372(17) -0.0013(15) 0.0045(14) -0.0054(14) C10 0.0335(17) 0.0229(17) 0.0384(17) -0.0026(14) 0.0064(14) 0.0005(14) C11 0.0341(18) 0.0345(18) 0.0385(18) -0.0022(15) 0.0029(14) -0.0053(15) C12 0.0392(19) 0.043(2) 0.0366(18) 0.0006(17) -0.0016(15) -0.0003(17) C13 0.0339(19) 0.040(2) 0.0434(19) 0.0027(16) 0.0055(15) -0.0002(16) C14 0.044(2) 0.0365(19) 0.0418(18) -0.0061(17) 0.0081(16) -0.0093(16) C15 0.038(2) 0.054(2) 0.0394(19) -0.0040(18) 0.0023(16) -0.0092(18) C16 0.0293(17) 0.046(2) 0.0429(19) 0.0029(17) 0.0010(15) -0.0046(16) C17 0.0292(16) 0.0364(18) 0.0374(17) -0.0023(15) 0.0035(14) 0.0020(15) C18 0.047(2) 0.045(2) 0.0421(19) -0.0086(17) 0.0045(16) -0.0017(18) C19 0.049(2) 0.053(3) 0.054(2) 0.000(2) 0.0040(18) 0.0148(19) C20 0.060(2) 0.048(2) 0.049(2) -0.0166(19) 0.0031(18) -0.006(2) C21 0.051(2) 0.064(3) 0.054(2) 0.003(2) -0.0061(18) 0.012(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B1 F2 1.395(4) . ? B1 F1 1.397(4) . ? B1 N1 1.535(5) . ? B1 N2 1.538(4) . ? N1 C14 1.348(4) . ? N1 C17 1.405(4) . ? N2 C13 1.347(4) . ? N2 C10 1.398(4) . ? O1 C1 1.199(5) . ? O2 C1 1.333(5) . ? O2 C2 1.448(4) . ? C1 C3 1.501(5) . ? C3 C4 1.386(5) . ? C3 C8 1.388(5) . ? C4 C5 1.389(5) . ? C5 C6 1.386(4) . ? C6 C7 1.393(5) . ? C6 C9 1.491(5) . ? C7 C8 1.384(5) . ? C9 C10 1.379(5) . ? C9 C17 1.411(5) . ? C10 C11 1.437(4) . ? C11 C12 1.365(5) . ? C11 C18 1.493(5) . ? C12 C13 1.393(5) . ? C13 C19 1.483(5) . ? C14 C15 1.400(6) . ? C14 C20 1.485(5) . ? C15 C16 1.380(5) . ? C16 C17 1.421(5) . ? C16 C21 1.497(5) . ? 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 108.6(3) . . ? F2 B1 N1 109.9(3) . . ? F1 B1 N1 110.2(3) . . ? F2 B1 N2 110.1(3) . . ? F1 B1 N2 110.3(3) . . ? N1 B1 N2 107.6(3) . . ? C14 N1 C17 108.4(3) . . ? C14 N1 B1 126.5(3) . . ? C17 N1 B1 124.9(3) . . ? C13 N2 C10 108.3(3) . . ? C13 N2 B1 126.5(3) . . ? C10 N2 B1 125.1(3) . . ? C1 O2 C2 116.1(3) . . ? O1 C1 O2 124.0(4) . . ? O1 C1 C3 124.6(4) . . ? O2 C1 C3 111.3(3) . . ? C4 C3 C8 120.5(3) . . ? C4 C3 C1 121.3(3) . . ? C8 C3 C1 118.2(3) . . ? C3 C4 C5 119.9(3) . . ? C6 C5 C4 119.8(3) . . ? C5 C6 C7 120.2(3) . . ? C5 C6 C9 119.7(3) . . ? C7 C6 C9 120.1(3) . . ? C8 C7 C6 120.0(3) . . ? C7 C8 C3 119.7(3) . . ? C10 C9 C17 121.3(3) . . ? C10 C9 C6 120.1(3) . . ? C17 C9 C6 118.6(3) . . ? C9 C10 N2 120.8(3) . . ? C9 C10 C11 132.1(3) . . ? N2 C10 C11 107.1(3) . . ? C12 C11 C10 106.4(3) . . ? C12 C11 C18 124.7(3) . . ? C10 C11 C18 128.7(3) . . ? C11 C12 C13 109.0(3) . . ? N2 C13 C12 109.2(3) . . ? N2 C13 C19 123.2(3) . . ? C12 C13 C19 127.6(3) . . ? N1 C14 C15 108.7(3) . . ? N1 C14 C20 122.9(3) . . ? C15 C14 C20 128.4(3) . . ? C16 C15 C14 109.0(3) . . ? C15 C16 C17 106.3(3) . . ? C15 C16 C21 124.7(3) . . ? C17 C16 C21 129.1(3) . . ? N1 C17 C9 119.9(3) . . ? N1 C17 C16 107.6(3) . . ? C9 C17 C16 132.5(3) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.232 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.059 _database_code_depnum_ccdc_archive 'CCDC 939164' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_939165 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H42 B2 F4 N4 O4' _chemical_formula_weight 764.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.9124(13) _cell_length_b 14.511(2) _cell_length_c 17.330(3) _cell_angle_alpha 86.939(3) _cell_angle_beta 77.665(3) _cell_angle_gamma 75.267(3) _cell_volume 1879.9(5) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour deep-red _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.350 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9707 _exptl_absorpt_correction_T_max 0.9803 _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9446 _diffrn_reflns_av_R_equivalents 0.0160 _diffrn_reflns_av_sigmaI/netI 0.0288 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.45 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6491 _reflns_number_gt 5991 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RAPID-AUTO (Rigaku Corporation, 1998)' _computing_cell_refinement RAPID-AUTO _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1147P)^2^+1.2045P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6491 _refine_ls_number_parameters 505 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0697 _refine_ls_R_factor_gt 0.0656 _refine_ls_wR_factor_ref 0.1934 _refine_ls_wR_factor_gt 0.1884 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.085 _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 0.0376(3) 0.87044(18) 0.27480(16) 0.0244(5) Uani 1 1 d . . . B2 B 0.5566(3) 0.69311(17) 0.22343(15) 0.0239(5) Uani 1 1 d . . . N1 N 0.1073(2) 0.89997(13) 0.18928(11) 0.0247(4) Uani 1 1 d . . . N2 N 0.1359(2) 0.91119(13) 0.32817(11) 0.0243(4) Uani 1 1 d . . . N3 N 0.4610(2) 0.65322(13) 0.16863(11) 0.0243(4) Uani 1 1 d . . . N4 N 0.4856(2) 0.66246(13) 0.30844(11) 0.0240(4) Uani 1 1 d . . . F1 F -0.14560(17) 0.91174(10) 0.29678(8) 0.0328(3) Uani 1 1 d . . . F2 F 0.06929(19) 0.77302(9) 0.28226(8) 0.0335(3) Uani 1 1 d . . . F3 F 0.73975(17) 0.65358(10) 0.20142(8) 0.0313(3) Uani 1 1 d . . . F4 F 0.52242(19) 0.79121(9) 0.21781(9) 0.0345(4) Uani 1 1 d . . . O1 O 0.9122(2) 1.22247(14) 0.13936(15) 0.0529(6) Uani 1 1 d . . . O2 O 0.6712(2) 1.34206(11) 0.13704(10) 0.0309(4) Uani 1 1 d . . . O3 O -0.3180(2) 0.33839(14) 0.34263(13) 0.0461(5) Uani 1 1 d . . . O4 O -0.0742(2) 0.22118(11) 0.34738(10) 0.0314(4) Uani 1 1 d . . . C1 C 0.7536(3) 1.25030(17) 0.14426(14) 0.0287(5) Uani 1 1 d . . . C2 C 0.7845(4) 1.40788(19) 0.12511(16) 0.0383(6) Uani 1 1 d . . . H2A H 0.7118 1.4729 0.1208 0.057 Uiso 1 1 calc R . . H2B H 0.8753 1.3912 0.0765 0.057 Uiso 1 1 calc R . . H2C H 0.8431 1.4042 0.1700 0.057 Uiso 1 1 calc R . . C3 C 0.6269(3) 1.18820(16) 0.16047(12) 0.0232(5) Uani 1 1 d . . . C4 C 0.4433(3) 1.22480(15) 0.16995(13) 0.0242(5) Uani 1 1 d . . . H4A H 0.3963 1.2910 0.1628 0.029 Uiso 1 1 calc R . . C5 C 0.3282(3) 1.16561(15) 0.18968(13) 0.0244(5) Uani 1 1 d . . . H5A H 0.2030 1.1913 0.1961 0.029 Uiso 1 1 calc R . . C6 C 0.3958(3) 1.06855(15) 0.20014(12) 0.0223(5) Uani 1 1 d . . . C7 C 0.5803(3) 1.03111(15) 0.18904(13) 0.0247(5) Uani 1 1 d . . . H7A H 0.6271 0.9646 0.1950 0.030 Uiso 1 1 calc R . . C8 C 0.6949(3) 1.09014(16) 0.16942(13) 0.0249(5) Uani 1 1 d . . . H8A H 0.8202 1.0642 0.1620 0.030 Uiso 1 1 calc R . . C9 C 0.2748(3) 1.00413(15) 0.22493(13) 0.0234(5) Uani 1 1 d . . . C10 C 0.2443(3) 0.97395(15) 0.30367(13) 0.0235(5) Uani 1 1 d . . . C11 C 0.3008(3) 0.99806(16) 0.37114(14) 0.0261(5) Uani 1 1 d . . . C12 C 0.2230(3) 0.94929(17) 0.43381(14) 0.0303(5) Uani 1 1 d . . . H12A H 0.2357 0.9513 0.4869 0.036 Uiso 1 1 calc R . . C13 C 0.1221(3) 0.89649(17) 0.40620(14) 0.0290(5) Uani 1 1 d . . . C14 C 0.0707(3) 0.87168(16) 0.12352(14) 0.0272(5) Uani 1 1 d . . . C15 C 0.1374(3) 0.92447(17) 0.05925(14) 0.0289(5) Uani 1 1 d . . . H15A H 0.1291 0.9179 0.0060 0.035 Uiso 1 1 calc R . . C16 C 0.2167(3) 0.98737(16) 0.08576(13) 0.0262(5) Uani 1 1 d . . . C17 C 0.2019(3) 0.97012(15) 0.16873(13) 0.0229(5) Uani 1 1 d . . . C18 C 0.4227(3) 1.06016(18) 0.37762(15) 0.0320(5) Uani 1 1 d . . . H18A H 0.4344 1.0619 0.4327 0.048 Uiso 1 1 calc R . . H18B H 0.3728 1.1249 0.3602 0.048 Uiso 1 1 calc R . . H18C H 0.5406 1.0343 0.3442 0.048 Uiso 1 1 calc R . . C19 C 0.0137(4) 0.83360(19) 0.45199(15) 0.0357(6) Uani 1 1 d . . . H19A H -0.0413 0.8061 0.4163 0.054 Uiso 1 1 calc R . . H19B H -0.0798 0.8711 0.4930 0.054 Uiso 1 1 calc R . . H19C H 0.0912 0.7823 0.4767 0.054 Uiso 1 1 calc R . . C20 C -0.0272(3) 0.79708(17) 0.12294(16) 0.0341(6) Uani 1 1 d . . . H20A H -0.0570 0.7726 0.1766 0.051 Uiso 1 1 calc R . . H20B H 0.0479 0.7449 0.0880 0.051 Uiso 1 1 calc R . . H20C H -0.1374 0.8245 0.1038 0.051 Uiso 1 1 calc R . . C21 C 0.2866(3) 1.06271(17) 0.03651(14) 0.0304(5) Uani 1 1 d . . . H21A H 0.2795 1.0557 -0.0186 0.046 Uiso 1 1 calc R . . H21B H 0.4112 1.0561 0.0397 0.046 Uiso 1 1 calc R . . H21C H 0.2147 1.1257 0.0561 0.046 Uiso 1 1 calc R . . C22 C -0.1591(3) 0.31230(16) 0.33974(13) 0.0258(5) Uani 1 1 d . . . C23 C -0.1830(4) 0.15377(19) 0.35545(16) 0.0387(6) Uani 1 1 d . . . H23A H -0.1088 0.0893 0.3605 0.058 Uiso 1 1 calc R . . H23B H -0.2353 0.1569 0.3087 0.058 Uiso 1 1 calc R . . H23C H -0.2786 0.1693 0.4026 0.058 Uiso 1 1 calc R . . C24 C -0.0367(3) 0.37658(15) 0.32748(12) 0.0230(5) Uani 1 1 d . . . C25 C 0.1447(3) 0.34292(15) 0.32719(13) 0.0243(5) Uani 1 1 d . . . H25A H 0.1913 0.2779 0.3389 0.029 Uiso 1 1 calc R . . C26 C 0.2579(3) 0.40344(15) 0.31002(13) 0.0238(5) Uani 1 1 d . . . H26A H 0.3816 0.3799 0.3095 0.029 Uiso 1 1 calc R . . C27 C 0.1890(3) 0.49907(15) 0.29344(12) 0.0214(5) Uani 1 1 d . . . C28 C 0.0073(3) 0.53352(15) 0.29611(13) 0.0243(5) Uani 1 1 d . . . H28A H -0.0399 0.5990 0.2862 0.029 Uiso 1 1 calc R . . C29 C -0.1056(3) 0.47288(16) 0.31319(13) 0.0247(5) Uani 1 1 d . . . H29A H -0.2299 0.4969 0.3152 0.030 Uiso 1 1 calc R . . C30 C 0.3100(3) 0.56419(15) 0.27054(13) 0.0223(5) Uani 1 1 d . . . C31 C 0.3738(3) 0.59993(15) 0.32851(13) 0.0231(5) Uani 1 1 d . . . C32 C 0.3414(3) 0.58869(17) 0.41248(14) 0.0291(5) Uani 1 1 d . . . C33 C 0.4350(3) 0.64378(19) 0.43945(15) 0.0346(6) Uani 1 1 d . . . H33A H 0.4400 0.6503 0.4931 0.042 Uiso 1 1 calc R . . C34 C 0.5213(3) 0.68859(17) 0.37534(14) 0.0298(5) Uani 1 1 d . . . C35 C 0.4831(3) 0.66597(17) 0.09029(14) 0.0294(5) Uani 1 1 d . . . C36 C 0.3908(3) 0.61070(18) 0.06009(14) 0.0313(5) Uani 1 1 d . . . H36A H 0.3859 0.6067 0.0061 0.038 Uiso 1 1 calc R . . C37 C 0.3079(3) 0.56287(16) 0.12191(13) 0.0257(5) Uani 1 1 d . . . C38 C 0.3526(3) 0.59007(15) 0.19128(13) 0.0225(5) Uani 1 1 d . . . C39 C 0.2274(4) 0.5321(2) 0.46357(15) 0.0415(6) Uani 1 1 d . . . H39A H 0.2329 0.5385 0.5189 0.062 Uiso 1 1 calc R . . H39B H 0.2709 0.4648 0.4481 0.062 Uiso 1 1 calc R . . H39C H 0.1036 0.5557 0.4572 0.062 Uiso 1 1 calc R . . C40 C 0.6357(4) 0.75564(19) 0.37707(16) 0.0381(6) Uani 1 1 d . . . H40A H 0.6787 0.7757 0.3231 0.057 Uiso 1 1 calc R . . H40B H 0.7379 0.7236 0.4003 0.057 Uiso 1 1 calc R . . H40C H 0.5656 0.8116 0.4089 0.057 Uiso 1 1 calc R . . C41 C 0.5909(4) 0.7300(2) 0.04604(16) 0.0427(7) Uani 1 1 d . . . H41A H 0.6397 0.7595 0.0830 0.064 Uiso 1 1 calc R . . H41B H 0.5146 0.7798 0.0194 0.064 Uiso 1 1 calc R . . H41C H 0.6891 0.6928 0.0067 0.064 Uiso 1 1 calc R . . C42 C 0.1906(3) 0.49939(18) 0.11263(14) 0.0321(5) Uani 1 1 d . . . H42A H 0.1872 0.4957 0.0567 0.048 Uiso 1 1 calc R . . H42B H 0.0695 0.5255 0.1430 0.048 Uiso 1 1 calc R . . H42C H 0.2385 0.4355 0.1321 0.048 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 0.0216(12) 0.0217(12) 0.0325(14) 0.0021(10) -0.0071(10) -0.0094(10) B2 0.0221(12) 0.0209(12) 0.0317(14) 0.0039(10) -0.0081(10) -0.0091(10) N1 0.0225(9) 0.0222(9) 0.0312(10) 0.0026(8) -0.0093(8) -0.0061(7) N2 0.0216(9) 0.0222(9) 0.0292(10) 0.0039(8) -0.0059(7) -0.0059(7) N3 0.0240(9) 0.0214(9) 0.0299(10) 0.0046(8) -0.0090(8) -0.0080(7) N4 0.0213(9) 0.0232(9) 0.0292(10) -0.0012(7) -0.0084(8) -0.0059(7) F1 0.0208(7) 0.0369(8) 0.0411(8) 0.0042(6) -0.0076(6) -0.0076(6) F2 0.0395(8) 0.0220(7) 0.0420(8) 0.0056(6) -0.0122(6) -0.0110(6) F3 0.0213(7) 0.0374(8) 0.0361(8) 0.0054(6) -0.0082(5) -0.0079(6) F4 0.0388(8) 0.0210(7) 0.0475(9) 0.0047(6) -0.0133(6) -0.0118(6) O1 0.0228(10) 0.0413(11) 0.0961(17) 0.0105(11) -0.0129(10) -0.0124(8) O2 0.0306(9) 0.0271(9) 0.0405(10) 0.0053(7) -0.0124(7) -0.0137(7) O3 0.0252(9) 0.0410(11) 0.0790(14) 0.0150(10) -0.0210(9) -0.0152(8) O4 0.0312(9) 0.0257(9) 0.0414(10) 0.0046(7) -0.0088(7) -0.0143(7) C1 0.0254(12) 0.0322(13) 0.0299(12) 0.0033(10) -0.0070(9) -0.0090(10) C2 0.0422(14) 0.0355(14) 0.0477(15) 0.0096(12) -0.0170(12) -0.0243(12) C3 0.0225(11) 0.0258(11) 0.0224(11) -0.0001(9) -0.0052(8) -0.0073(9) C4 0.0246(11) 0.0208(11) 0.0267(11) 0.0004(9) -0.0064(9) -0.0041(9) C5 0.0189(10) 0.0247(11) 0.0292(11) -0.0009(9) -0.0054(9) -0.0041(9) C6 0.0224(11) 0.0247(11) 0.0212(10) 0.0008(8) -0.0060(8) -0.0070(9) C7 0.0247(11) 0.0192(10) 0.0294(12) 0.0009(9) -0.0077(9) -0.0024(9) C8 0.0172(10) 0.0278(12) 0.0282(12) -0.0004(9) -0.0047(9) -0.0025(9) C9 0.0185(10) 0.0190(10) 0.0311(12) 0.0012(9) -0.0058(9) -0.0016(8) C10 0.0189(10) 0.0204(10) 0.0303(12) 0.0002(9) -0.0042(9) -0.0037(8) C11 0.0216(11) 0.0270(11) 0.0302(12) 0.0002(9) -0.0064(9) -0.0060(9) C12 0.0298(12) 0.0366(13) 0.0257(12) 0.0021(10) -0.0069(9) -0.0097(10) C13 0.0254(11) 0.0282(12) 0.0321(13) 0.0039(10) -0.0047(9) -0.0063(9) C14 0.0221(11) 0.0253(11) 0.0352(13) -0.0014(9) -0.0095(9) -0.0048(9) C15 0.0280(12) 0.0311(12) 0.0286(12) -0.0004(9) -0.0104(9) -0.0054(10) C16 0.0224(11) 0.0254(11) 0.0290(12) 0.0005(9) -0.0070(9) -0.0013(9) C17 0.0192(10) 0.0195(10) 0.0298(12) 0.0023(9) -0.0049(9) -0.0052(8) C18 0.0331(13) 0.0360(13) 0.0321(13) -0.0001(10) -0.0101(10) -0.0149(11) C19 0.0401(14) 0.0389(14) 0.0307(13) 0.0073(11) -0.0064(11) -0.0168(11) C20 0.0340(13) 0.0309(13) 0.0430(14) 0.0012(11) -0.0165(11) -0.0117(10) C21 0.0315(12) 0.0318(12) 0.0283(12) 0.0031(10) -0.0055(10) -0.0100(10) C22 0.0262(12) 0.0306(12) 0.0235(11) 0.0047(9) -0.0077(9) -0.0112(10) C23 0.0455(15) 0.0375(14) 0.0435(15) 0.0072(11) -0.0133(12) -0.0270(12) C24 0.0234(11) 0.0265(11) 0.0200(10) 0.0003(9) -0.0047(8) -0.0079(9) C25 0.0245(11) 0.0213(11) 0.0274(11) 0.0014(9) -0.0075(9) -0.0047(9) C26 0.0180(10) 0.0241(11) 0.0293(11) 0.0001(9) -0.0068(9) -0.0039(8) C27 0.0216(11) 0.0230(11) 0.0217(10) 0.0008(8) -0.0066(8) -0.0076(9) C28 0.0236(11) 0.0197(10) 0.0295(12) 0.0029(9) -0.0086(9) -0.0033(9) C29 0.0179(10) 0.0278(12) 0.0283(11) 0.0013(9) -0.0081(9) -0.0033(9) C30 0.0192(10) 0.0182(10) 0.0291(11) 0.0007(8) -0.0081(9) -0.0017(8) C31 0.0207(10) 0.0206(10) 0.0284(11) 0.0013(9) -0.0056(9) -0.0059(8) C32 0.0298(12) 0.0302(12) 0.0290(12) 0.0008(9) -0.0090(9) -0.0081(10) C33 0.0368(14) 0.0425(14) 0.0272(12) -0.0046(10) -0.0106(10) -0.0106(11) C34 0.0247(11) 0.0311(12) 0.0356(13) -0.0065(10) -0.0089(10) -0.0070(10) C35 0.0281(12) 0.0316(12) 0.0310(12) 0.0065(10) -0.0096(10) -0.0102(10) C36 0.0334(13) 0.0373(13) 0.0267(12) 0.0043(10) -0.0111(10) -0.0123(11) C37 0.0231(11) 0.0265(11) 0.0287(12) 0.0019(9) -0.0090(9) -0.0059(9) C38 0.0188(10) 0.0194(10) 0.0302(12) 0.0022(8) -0.0068(9) -0.0055(8) C39 0.0519(16) 0.0534(17) 0.0254(13) 0.0034(11) -0.0063(11) -0.0264(14) C40 0.0371(14) 0.0410(14) 0.0428(15) -0.0086(12) -0.0109(11) -0.0178(12) C41 0.0511(16) 0.0537(17) 0.0322(14) 0.0148(12) -0.0103(12) -0.0308(14) C42 0.0368(13) 0.0350(13) 0.0309(13) -0.0007(10) -0.0120(10) -0.0161(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B1 F2 1.375(3) . ? B1 F1 1.397(3) . ? B1 N1 1.545(3) . ? B1 N2 1.553(3) . ? B2 F4 1.382(3) . ? B2 F3 1.392(3) . ? B2 N3 1.548(3) . ? B2 N4 1.545(3) . ? N1 C14 1.342(3) . ? N1 C17 1.399(3) . ? N2 C13 1.343(3) . ? N2 C10 1.395(3) . ? N3 C35 1.340(3) . ? N3 C38 1.396(3) . ? N4 C34 1.345(3) . ? N4 C31 1.403(3) . ? O1 C1 1.202(3) . ? O2 C1 1.338(3) . ? O2 C2 1.447(3) . ? O3 C22 1.208(3) . ? O4 C22 1.336(3) . ? O4 C23 1.442(3) . ? C1 C3 1.486(3) . ? C3 C4 1.391(3) . ? C3 C8 1.400(3) . ? C4 C5 1.384(3) . ? C5 C6 1.391(3) . ? C6 C7 1.396(3) . ? C6 C9 1.487(3) . ? C7 C8 1.380(3) . ? C9 C17 1.400(3) . ? C9 C10 1.400(3) . ? C10 C11 1.427(3) . ? C11 C12 1.383(3) . ? C11 C18 1.501(3) . ? C12 C13 1.402(3) . ? C13 C19 1.493(3) . ? C14 C15 1.403(3) . ? C14 C20 1.485(3) . ? C15 C16 1.378(3) . ? C16 C17 1.431(3) . ? C16 C21 1.495(3) . ? C22 C24 1.484(3) . ? C24 C25 1.393(3) . ? C24 C29 1.394(3) . ? C25 C26 1.385(3) . ? C26 C27 1.395(3) . ? C27 C28 1.389(3) . ? C27 C30 1.491(3) . ? C28 C29 1.385(3) . ? C30 C31 1.392(3) . ? C30 C38 1.397(3) . ? C31 C32 1.431(3) . ? C32 C33 1.377(3) . ? C32 C39 1.494(3) . ? C33 C34 1.396(4) . ? C34 C40 1.493(3) . ? C35 C36 1.399(3) . ? C35 C41 1.492(3) . ? C36 C37 1.382(3) . ? C37 C38 1.424(3) . ? C37 C42 1.500(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag F2 B1 F1 109.67(18) . . ? F2 B1 N1 111.51(19) . . ? F1 B1 N1 109.38(18) . . ? F2 B1 N2 110.78(19) . . ? F1 B1 N2 108.88(19) . . ? N1 B1 N2 106.54(18) . . ? F4 B2 F3 109.47(18) . . ? F4 B2 N3 110.79(18) . . ? F3 B2 N3 108.84(19) . . ? F4 B2 N4 110.76(19) . . ? F3 B2 N4 110.05(18) . . ? N3 B2 N4 106.89(17) . . ? C14 N1 C17 108.50(19) . . ? C14 N1 B1 126.29(19) . . ? C17 N1 B1 124.79(18) . . ? C13 N2 C10 108.85(19) . . ? C13 N2 B1 125.68(19) . . ? C10 N2 B1 125.35(19) . . ? C35 N3 C38 108.70(19) . . ? C35 N3 B2 125.50(19) . . ? C38 N3 B2 125.49(18) . . ? C34 N4 C31 108.17(19) . . ? C34 N4 B2 126.84(19) . . ? C31 N4 B2 124.98(18) . . ? C1 O2 C2 115.78(19) . . ? C22 O4 C23 115.70(19) . . ? O1 C1 O2 123.1(2) . . ? O1 C1 C3 124.5(2) . . ? O2 C1 C3 112.41(19) . . ? C4 C3 C8 119.2(2) . . ? C4 C3 C1 122.1(2) . . ? C8 C3 C1 118.62(19) . . ? C5 C4 C3 120.6(2) . . ? C4 C5 C6 120.1(2) . . ? C5 C6 C7 119.6(2) . . ? C5 C6 C9 121.12(19) . . ? C7 C6 C9 119.31(19) . . ? C8 C7 C6 120.4(2) . . ? C7 C8 C3 120.2(2) . . ? C17 C9 C10 121.0(2) . . ? C17 C9 C6 119.83(19) . . ? C10 C9 C6 119.03(19) . . ? N2 C10 C9 120.4(2) . . ? N2 C10 C11 107.79(19) . . ? C9 C10 C11 131.8(2) . . ? C12 C11 C10 105.8(2) . . ? C12 C11 C18 124.2(2) . . ? C10 C11 C18 130.0(2) . . ? C11 C12 C13 108.9(2) . . ? N2 C13 C12 108.6(2) . . ? N2 C13 C19 123.0(2) . . ? C12 C13 C19 128.4(2) . . ? N1 C14 C15 108.9(2) . . ? N1 C14 C20 123.4(2) . . ? C15 C14 C20 127.8(2) . . ? C16 C15 C14 109.0(2) . . ? C15 C16 C17 105.8(2) . . ? C15 C16 C21 125.0(2) . . ? C17 C16 C21 129.0(2) . . ? N1 C17 C9 120.21(19) . . ? N1 C17 C16 107.76(19) . . ? C9 C17 C16 131.8(2) . . ? O3 C22 O4 123.1(2) . . ? O3 C22 C24 124.4(2) . . ? O4 C22 C24 112.50(19) . . ? C25 C24 C29 119.5(2) . . ? C25 C24 C22 121.98(19) . . ? C29 C24 C22 118.53(19) . . ? C26 C25 C24 120.6(2) . . ? C25 C26 C27 119.63(19) . . ? C28 C27 C26 119.9(2) . . ? C28 C27 C30 119.61(19) . . ? C26 C27 C30 120.46(19) . . ? C29 C28 C27 120.4(2) . . ? C28 C29 C24 119.99(19) . . ? C31 C30 C38 121.5(2) . . ? C31 C30 C27 119.6(2) . . ? C38 C30 C27 118.92(19) . . ? C30 C31 N4 120.5(2) . . ? C30 C31 C32 131.7(2) . . ? N4 C31 C32 107.68(19) . . ? C33 C32 C31 105.9(2) . . ? C33 C32 C39 125.1(2) . . ? C31 C32 C39 129.0(2) . . ? C32 C33 C34 109.1(2) . . ? N4 C34 C33 109.1(2) . . ? N4 C34 C40 123.3(2) . . ? C33 C34 C40 127.5(2) . . ? N3 C35 C36 109.0(2) . . ? N3 C35 C41 123.1(2) . . ? C36 C35 C41 127.9(2) . . ? C37 C36 C35 108.6(2) . . ? C36 C37 C38 106.1(2) . . ? C36 C37 C42 123.9(2) . . ? C38 C37 C42 130.0(2) . . ? N3 C38 C30 120.08(19) . . ? N3 C38 C37 107.64(19) . . ? C30 C38 C37 132.3(2) . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.584 _refine_diff_density_min -0.525 _refine_diff_density_rms 0.090 _database_code_depnum_ccdc_archive 'CCDC 939165' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_939166 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H21 B F2 N2 O2' _chemical_formula_weight 382.21 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 8.3318(13) _cell_length_b 12.0855(17) _cell_length_c 18.610(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1874.0(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.355 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.831 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8192 _exptl_absorpt_correction_T_max 0.9365 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies Version 1.171.35.21 ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'SuperNova (Cu) X-ray source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6851 _diffrn_reflns_av_R_equivalents 0.0480 _diffrn_reflns_av_sigmaI/netI 0.0540 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 4.36 _diffrn_reflns_theta_max 65.78 _reflns_number_total 3129 _reflns_number_gt 2740 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.1(2) _refine_ls_number_reflns 3129 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0591 _refine_ls_R_factor_gt 0.0504 _refine_ls_wR_factor_ref 0.1479 _refine_ls_wR_factor_gt 0.1372 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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 0.6008(4) 0.8335(3) 0.62809(19) 0.0269(8) Uani 1 1 d . . . N1 N 0.5384(3) 0.8899(2) 0.55820(13) 0.0273(6) Uani 1 1 d . . . N2 N 0.7736(3) 0.8762(2) 0.63977(12) 0.0265(6) Uani 1 1 d . . . O1 O 1.2640(3) 1.2254(2) 0.30749(13) 0.0390(6) Uani 1 1 d . . . O2 O 1.0665(3) 1.35232(17) 0.30996(11) 0.0314(5) Uani 1 1 d . . . F1 F 0.5032(2) 0.85960(16) 0.68624(9) 0.0357(5) Uani 1 1 d . . . F2 F 0.6025(2) 0.71904(14) 0.61880(9) 0.0334(5) Uani 1 1 d . . . C1 C 1.1376(4) 1.2584(2) 0.33101(16) 0.0265(7) Uani 1 1 d . . . C2 C 1.1473(5) 1.4100(3) 0.25217(16) 0.0362(8) Uani 1 1 d . . . H2A H 1.0876 1.4774 0.2402 0.054 Uiso 1 1 calc R . . H2B H 1.1527 1.3619 0.2098 0.054 Uiso 1 1 calc R . . H2C H 1.2562 1.4297 0.2674 0.054 Uiso 1 1 calc R . . C3 C 1.0426(4) 1.1978(2) 0.38614(16) 0.0258(7) Uani 1 1 d . . . C4 C 0.9393(4) 1.2498(2) 0.43475(16) 0.0270(7) Uani 1 1 d . . . H4A H 0.9269 1.3279 0.4335 0.032 Uiso 1 1 calc R . . C5 C 0.8549(4) 1.1879(3) 0.48482(17) 0.0282(7) Uani 1 1 d . . . H5A H 0.7857 1.2240 0.5179 0.034 Uiso 1 1 calc R . . C6 C 0.8709(4) 1.0728(2) 0.48702(16) 0.0240(6) Uani 1 1 d . . . C7 C 0.9752(4) 1.0210(3) 0.43814(16) 0.0289(7) Uani 1 1 d . . . H7A H 0.9868 0.9428 0.4390 0.035 Uiso 1 1 calc R . . C8 C 1.0611(4) 1.0829(2) 0.38880(16) 0.0284(7) Uani 1 1 d . . . H8A H 1.1330 1.0473 0.3566 0.034 Uiso 1 1 calc R . . C9 C 0.7765(4) 1.0005(2) 0.53657(15) 0.0253(7) Uani 1 1 d . . . C10 C 0.8503(4) 0.9591(3) 0.59885(15) 0.0258(6) Uani 1 1 d . . . C11 C 1.0039(4) 0.9792(2) 0.63018(16) 0.0280(7) Uani 1 1 d . . . C12 C 1.0160(4) 0.9077(3) 0.68769(16) 0.0311(7) Uani 1 1 d . . . H12A H 1.1057 0.9016 0.7190 0.037 Uiso 1 1 calc R . . C13 C 0.8749(4) 0.8458(2) 0.69234(16) 0.0282(7) Uani 1 1 d . . . C14 C 0.4006(4) 0.8635(3) 0.52360(17) 0.0287(7) Uani 1 1 d . . . C15 C 0.3945(4) 0.9214(3) 0.45873(17) 0.0311(7) Uani 1 1 d . . . H15A H 0.3100 0.9176 0.4245 0.037 Uiso 1 1 calc R . . C16 C 0.5309(4) 0.9850(2) 0.45240(16) 0.0292(7) Uani 1 1 d . . . C17 C 0.6238(4) 0.9653(2) 0.51615(16) 0.0266(6) Uani 1 1 d . . . C18 C 1.1310(4) 1.0595(3) 0.60673(16) 0.0298(7) Uani 1 1 d . . . H18A H 1.2234 1.0542 0.6391 0.045 Uiso 1 1 calc R . . H18B H 1.0877 1.1349 0.6081 0.045 Uiso 1 1 calc R . . H18C H 1.1648 1.0418 0.5576 0.045 Uiso 1 1 calc R . . C19 C 0.8363(5) 0.7562(3) 0.74559(17) 0.0371(8) Uani 1 1 d . . . H19A H 0.7285 0.7273 0.7360 0.056 Uiso 1 1 calc R . . H19B H 0.8403 0.7866 0.7944 0.056 Uiso 1 1 calc R . . H19C H 0.9149 0.6963 0.7411 0.056 Uiso 1 1 calc R . . C20 C 0.2794(4) 0.7847(3) 0.55323(19) 0.0342(7) Uani 1 1 d . . . H20A H 0.3164 0.7568 0.5998 0.051 Uiso 1 1 calc R . . H20B H 0.2657 0.7226 0.5199 0.051 Uiso 1 1 calc R . . H20C H 0.1766 0.8229 0.5594 0.051 Uiso 1 1 calc R . . C21 C 0.5674(5) 1.0601(3) 0.39002(18) 0.0387(8) Uani 1 1 d . . . H21A H 0.4804 1.0555 0.3547 0.058 Uiso 1 1 calc R . . H21B H 0.6685 1.0373 0.3675 0.058 Uiso 1 1 calc R . . H21C H 0.5771 1.1365 0.4072 0.058 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(19) 0.0280(18) 0.0298(16) -0.0003(14) 0.0015(15) -0.0030(15) N1 0.0217(13) 0.0282(13) 0.0321(12) -0.0019(10) 0.0017(12) 0.0001(11) N2 0.0234(13) 0.0273(13) 0.0288(12) -0.0008(11) 0.0008(11) -0.0011(11) O1 0.0292(13) 0.0433(13) 0.0443(12) 0.0044(11) 0.0068(11) 0.0051(11) O2 0.0311(12) 0.0291(10) 0.0340(10) 0.0053(9) 0.0031(10) 0.0003(10) F1 0.0294(10) 0.0440(10) 0.0338(9) -0.0029(8) 0.0066(8) -0.0038(9) F2 0.0324(10) 0.0270(9) 0.0407(10) 0.0029(8) -0.0024(9) -0.0045(8) C1 0.0201(15) 0.0291(16) 0.0301(14) -0.0026(13) 0.0005(13) -0.0018(13) C2 0.048(2) 0.0313(16) 0.0290(14) 0.0052(14) 0.0039(17) -0.0030(16) C3 0.0181(15) 0.0297(15) 0.0296(15) 0.0001(12) -0.0014(13) 0.0003(12) C4 0.0237(16) 0.0239(15) 0.0335(15) -0.0013(12) 0.0013(13) 0.0007(12) C5 0.0248(16) 0.0283(15) 0.0316(15) -0.0028(13) 0.0025(14) 0.0059(13) C6 0.0155(14) 0.0299(16) 0.0265(13) 0.0005(12) -0.0019(12) 0.0002(12) C7 0.0282(18) 0.0264(15) 0.0321(15) -0.0044(12) 0.0026(14) 0.0005(14) C8 0.0265(17) 0.0282(15) 0.0306(15) -0.0006(13) 0.0049(14) 0.0038(14) C9 0.0238(17) 0.0212(13) 0.0307(15) -0.0065(12) 0.0022(13) 0.0020(12) C10 0.0213(15) 0.0257(14) 0.0303(14) -0.0010(13) -0.0008(13) -0.0030(13) C11 0.0242(16) 0.0310(16) 0.0288(14) -0.0052(13) 0.0002(13) -0.0039(14) C12 0.0253(16) 0.0381(16) 0.0298(15) -0.0009(14) -0.0011(14) -0.0005(14) C13 0.0243(16) 0.0323(16) 0.0280(14) -0.0010(13) 0.0000(13) 0.0024(14) C14 0.0178(15) 0.0286(14) 0.0397(16) -0.0051(14) -0.0002(13) 0.0004(13) C15 0.0241(16) 0.0331(16) 0.0361(16) 0.0004(13) -0.0052(14) 0.0025(14) C16 0.0244(17) 0.0313(16) 0.0320(14) 0.0000(13) -0.0020(14) 0.0046(13) C17 0.0223(15) 0.0247(15) 0.0329(14) 0.0009(13) 0.0017(13) 0.0005(13) C18 0.0266(16) 0.0341(17) 0.0289(14) -0.0019(13) -0.0018(14) -0.0049(14) C19 0.0349(19) 0.0386(18) 0.0378(17) 0.0075(15) -0.0048(16) -0.0044(15) C20 0.0243(17) 0.0348(18) 0.0434(17) -0.0039(15) -0.0008(16) -0.0024(14) C21 0.034(2) 0.047(2) 0.0356(17) 0.0096(15) -0.0041(15) 0.0007(17) _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 1.390(4) . ? B1 F2 1.394(4) . ? B1 N2 1.545(4) . ? B1 N1 1.558(4) . ? N1 C14 1.354(4) . ? N1 C17 1.396(4) . ? N2 C13 1.344(4) . ? N2 C10 1.411(4) . ? O1 C1 1.208(4) . ? O2 C1 1.339(4) . ? O2 C2 1.448(4) . ? C1 C3 1.488(4) . ? C3 C4 1.398(4) . ? C3 C8 1.398(4) . ? C4 C5 1.387(5) . ? C5 C6 1.397(4) . ? C6 C7 1.405(4) . ? C6 C9 1.495(4) . ? C7 C8 1.384(4) . ? C9 C17 1.394(5) . ? C9 C10 1.404(4) . ? C10 C11 1.427(4) . ? C11 C12 1.379(4) . ? C11 C18 1.501(4) . ? C12 C13 1.397(5) . ? C13 C19 1.502(4) . ? C14 C15 1.397(5) . ? C14 C20 1.494(5) . ? C15 C16 1.377(5) . ? C16 C17 1.436(4) . ? C16 C21 1.505(4) . ? 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 F2 109.1(3) . . ? F1 B1 N2 111.1(3) . . ? F2 B1 N2 109.9(3) . . ? F1 B1 N1 110.8(3) . . ? F2 B1 N1 109.5(3) . . ? N2 B1 N1 106.4(2) . . ? C14 N1 C17 108.6(3) . . ? C14 N1 B1 125.2(3) . . ? C17 N1 B1 125.7(3) . . ? C13 N2 C10 107.6(3) . . ? C13 N2 B1 126.6(3) . . ? C10 N2 B1 125.7(2) . . ? C1 O2 C2 114.8(3) . . ? O1 C1 O2 124.0(3) . . ? O1 C1 C3 123.5(3) . . ? O2 C1 C3 112.5(3) . . ? C4 C3 C8 119.4(3) . . ? C4 C3 C1 123.6(3) . . ? C8 C3 C1 117.0(3) . . ? C5 C4 C3 120.3(3) . . ? C4 C5 C6 120.6(3) . . ? C5 C6 C7 118.9(3) . . ? C5 C6 C9 123.4(3) . . ? C7 C6 C9 117.7(3) . . ? C8 C7 C6 120.6(3) . . ? C7 C8 C3 120.2(3) . . ? C17 C9 C10 121.0(3) . . ? C17 C9 C6 119.4(3) . . ? C10 C9 C6 119.2(3) . . ? C9 C10 N2 120.0(3) . . ? C9 C10 C11 132.0(3) . . ? N2 C10 C11 107.9(2) . . ? C12 C11 C10 106.0(3) . . ? C12 C11 C18 125.4(3) . . ? C10 C11 C18 128.6(3) . . ? C11 C12 C13 108.8(3) . . ? N2 C13 C12 109.7(3) . . ? N2 C13 C19 122.9(3) . . ? C12 C13 C19 127.4(3) . . ? N1 C14 C15 108.9(3) . . ? N1 C14 C20 123.2(3) . . ? C15 C14 C20 127.9(3) . . ? C16 C15 C14 108.9(3) . . ? C15 C16 C17 106.4(3) . . ? C15 C16 C21 124.7(3) . . ? C17 C16 C21 128.9(3) . . ? C9 C17 N1 120.8(3) . . ? C9 C17 C16 131.8(3) . . ? N1 C17 C16 107.3(3) . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 65.78 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.299 _refine_diff_density_min -0.313 _refine_diff_density_rms 0.056 _database_code_depnum_ccdc_archive 'CCDC 939166'