# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_page_first ? _journal_page_last 2 _journal_volume ? _journal_year ? loop_ _publ_author_address '' _publ_contact_author_email ivan.aprahamian@gmail.com _publ_contact_author_name 'Ivan Aprahamian' loop_ _publ_author_name I.Aprahamian 'Xin Su' 'Yin Yang' C.Carroll data_1 _database_code_depnum_ccdc_archive 'CCDC 841442' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C13 H12 B F2 N3' _chemical_formula_sum 'C13 H12 B F2 N3' _chemical_melting_point ? _exptl_crystal_description ? _exptl_crystal_colour ? _diffrn_ambient_temperature 173(2) _chemical_formula_weight 259.07 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' B B 0.0090 0.0039 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_int_tables_number 2 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.41690(10) _cell_length_b 8.37810(10) _cell_length_c 11.0339(2) _cell_angle_alpha 70.2960(10) _cell_angle_beta 73.1310(10) _cell_angle_gamma 71.4410(10) _cell_volume 598.944(15) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.436 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.913 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7552 _exptl_absorpt_correction_T_max 0.8798 _exptl_absorpt_process_details SADABS _exptl_special_details ; Data was collected using a BRUKER CCD (charge coupled device) based diffractometer equipped with an Oxford low-temperature apparatus operating at 173 K. A suitable crystal was chosen and mounted on a glass fiber or nylon loop using Paratone oil for Mo radiation and Mineral oil for Copper radiation. Data were measured using omega and Phi scans of 0.5\% per frame for 30 s. The total number of images were based on results from the program COSMO where redundancy was expected to be 4.0 and completeness to 0.83\%A to 100%. Cell parameters were retrieved using APEX II software and refined using SAINT on all observed reflections. Data reduction was performed using the SAINT software which corrects for Lp. Scaling and absorption corrections were applied using SADABS6 multi-scan technique, supplied by George Sheldrick. The structures are solved by the direct method using the SHELXS-97 program and refined by least squares method on F2, SHELXL-97, incorporated in SHELXTL-PC V 6.14. All H atoms were found by difference Fourier methods and refined isotrpically. ; _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method '\w,and/f 0.5 deg' _diffrn_detector_area_resol_mean 836.6 _diffrn_reflns_number 11932 _diffrn_reflns_av_R_equivalents 0.0231 _diffrn_reflns_av_sigmaI/netI 0.0133 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 4.35 _diffrn_reflns_theta_max 68.02 _reflns_number_total 2112 _reflns_number_gt 2026 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COSMO (BRUKER, V1.58, 2006)' _computing_cell_refinement 'APEX2 (BRUKER, V2008.5-0, 2006)' _computing_data_reduction 'SAINT (BRUKER, V7.34A, 2006)' _computing_structure_solution 'SHELXS (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_structure_refinement 'SHELXL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_molecular_graphics 'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_publication_material 'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _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^)+(0.0503P)^2^+0.2469P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0094(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2112 _refine_ls_number_parameters 221 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0380 _refine_ls_R_factor_gt 0.0368 _refine_ls_wR_factor_ref 0.0981 _refine_ls_wR_factor_gt 0.0968 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F1 F 0.23514(17) 0.76864(14) 0.46598(8) 0.0522(3) Uani 1 1 d . . . F2 F 0.05411(12) 0.97894(13) 0.32783(10) 0.0472(3) Uani 1 1 d . . . B1 B 0.2401(2) 0.8779(2) 0.33963(15) 0.0290(4) Uani 1 1 d . . . N1 N 0.50141(15) 0.78718(14) 0.14959(11) 0.0245(3) Uani 1 1 d . . . N2 N 0.32973(15) 0.77819(14) 0.23567(10) 0.0235(3) Uani 1 1 d . . . N3 N 0.36935(15) 1.00458(14) 0.32103(10) 0.0245(3) Uani 1 1 d . . . C1 C 0.60180(18) 0.88970(17) 0.14831(12) 0.0237(3) Uani 1 1 d . . . C2 C 0.54158(18) 1.00473(16) 0.23413(12) 0.0240(3) Uani 1 1 d . . . C3 C 0.6517(2) 1.11513(19) 0.22968(14) 0.0298(3) Uani 1 1 d . . . H1 H 0.773(3) 1.112(2) 0.1696(18) 0.041(5) Uiso 1 1 d . . . C4 C 0.5839(2) 1.2238(2) 0.31154(15) 0.0340(4) Uani 1 1 d . . . H2 H 0.662(3) 1.297(2) 0.3091(18) 0.045(5) Uiso 1 1 d . . . C5 C 0.4066(2) 1.22290(19) 0.39835(14) 0.0321(3) Uani 1 1 d . . . H3 H 0.355(3) 1.296(2) 0.4582(18) 0.043(5) Uiso 1 1 d . . . C6 C 0.3025(2) 1.11251(19) 0.40103(14) 0.0293(3) Uani 1 1 d . . . H4 H 0.183(3) 1.105(2) 0.4579(17) 0.038(4) Uiso 1 1 d . . . C7 C 0.7893(2) 0.89040(19) 0.04891(15) 0.0292(3) Uani 1 1 d . . . H5 H 0.793(2) 1.008(2) -0.0088(16) 0.031(4) Uiso 1 1 d . . . H6 H 0.902(3) 0.848(2) 0.0906(17) 0.039(4) Uiso 1 1 d . . . H7 H 0.803(3) 0.816(3) -0.0053(18) 0.047(5) Uiso 1 1 d . . . C8 C 0.23355(18) 0.66752(16) 0.21934(13) 0.0235(3) Uani 1 1 d . . . C9 C 0.0718(2) 0.62292(18) 0.31319(13) 0.0280(3) Uani 1 1 d . . . H8 H 0.024(2) 0.666(2) 0.3913(17) 0.034(4) Uiso 1 1 d . . . C10 C -0.0226(2) 0.51458(19) 0.29772(14) 0.0315(3) Uani 1 1 d . . . H9 H -0.134(3) 0.482(2) 0.3639(17) 0.038(4) Uiso 1 1 d . . . C11 C 0.0418(2) 0.44807(19) 0.18894(15) 0.0324(3) Uani 1 1 d . . . H10 H -0.022(2) 0.371(2) 0.1777(16) 0.035(4) Uiso 1 1 d . . . C12 C 0.2003(2) 0.49328(18) 0.09498(15) 0.0305(3) Uani 1 1 d . . . H11 H 0.251(2) 0.449(2) 0.0166(17) 0.035(4) Uiso 1 1 d . . . C13 C 0.2960(2) 0.60227(18) 0.10893(14) 0.0268(3) Uani 1 1 d . . . H12 H 0.401(2) 0.634(2) 0.0451(16) 0.029(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0867(8) 0.0644(7) 0.0223(5) -0.0050(4) -0.0026(4) -0.0557(6) F2 0.0215(4) 0.0577(6) 0.0752(7) -0.0427(5) 0.0007(4) -0.0101(4) B1 0.0272(8) 0.0379(9) 0.0255(8) -0.0107(7) 0.0016(6) -0.0168(7) N1 0.0206(5) 0.0262(6) 0.0246(6) -0.0053(4) -0.0020(4) -0.0070(4) N2 0.0204(5) 0.0271(6) 0.0227(5) -0.0057(4) -0.0007(4) -0.0099(4) N3 0.0235(6) 0.0268(6) 0.0234(5) -0.0057(4) -0.0053(4) -0.0070(5) C1 0.0202(6) 0.0248(6) 0.0243(6) -0.0029(5) -0.0050(5) -0.0069(5) C2 0.0220(6) 0.0254(7) 0.0228(6) -0.0010(5) -0.0076(5) -0.0065(5) C3 0.0271(7) 0.0344(7) 0.0301(7) -0.0057(6) -0.0064(6) -0.0134(6) C4 0.0383(8) 0.0352(8) 0.0352(8) -0.0064(6) -0.0120(7) -0.0174(7) C5 0.0368(8) 0.0309(7) 0.0326(7) -0.0110(6) -0.0102(6) -0.0084(6) C6 0.0277(7) 0.0325(7) 0.0285(7) -0.0102(6) -0.0047(6) -0.0074(6) C7 0.0231(7) 0.0307(7) 0.0322(7) -0.0079(6) -0.0005(6) -0.0101(6) C8 0.0221(6) 0.0217(6) 0.0257(6) -0.0034(5) -0.0065(5) -0.0059(5) C9 0.0296(7) 0.0310(7) 0.0239(7) -0.0051(6) -0.0030(5) -0.0126(6) C10 0.0290(7) 0.0332(7) 0.0309(7) -0.0023(6) -0.0029(6) -0.0156(6) C11 0.0320(7) 0.0293(7) 0.0408(8) -0.0087(6) -0.0089(6) -0.0135(6) C12 0.0297(7) 0.0305(7) 0.0346(8) -0.0131(6) -0.0063(6) -0.0073(6) C13 0.0227(7) 0.0281(7) 0.0279(7) -0.0079(5) -0.0013(6) -0.0073(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 F1 B1 1.3835(18) . ? F2 B1 1.3869(19) . ? B1 N2 1.5185(18) . ? B1 N3 1.5729(19) . ? N1 C1 1.2982(17) . ? N1 N2 1.3565(15) . ? N2 C8 1.4175(17) . ? N3 C2 1.3567(17) . ? N3 C6 1.3570(17) . ? C1 C2 1.4563(18) . ? C1 C7 1.5006(18) . ? C2 C3 1.3972(19) . ? C3 C4 1.377(2) . ? C3 H1 0.950(19) . ? C4 C5 1.385(2) . ? C4 H2 0.961(19) . ? C5 C6 1.369(2) . ? C5 H3 0.968(19) . ? C6 H4 0.932(19) . ? C7 H5 0.983(17) . ? C7 H6 0.977(18) . ? C7 H7 0.97(2) . ? C8 C9 1.3980(19) . ? C8 C13 1.3993(19) . ? C9 C10 1.386(2) . ? C9 H8 0.974(17) . ? C10 C11 1.389(2) . ? C10 H9 0.972(18) . ? C11 C12 1.383(2) . ? C11 H10 0.964(17) . ? C12 C13 1.3899(19) . ? C12 H11 0.983(17) . ? C13 H12 0.925(17) . ? 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 109.24(12) . . ? F1 B1 N2 112.39(12) . . ? F2 B1 N2 111.90(12) . . ? F1 B1 N3 106.90(11) . . ? F2 B1 N3 107.73(12) . . ? N2 B1 N3 108.45(11) . . ? C1 N1 N2 120.97(11) . . ? N1 N2 C8 113.85(10) . . ? N1 N2 B1 125.01(11) . . ? C8 N2 B1 121.13(11) . . ? C2 N3 C6 120.63(11) . . ? C2 N3 B1 123.20(11) . . ? C6 N3 B1 116.13(11) . . ? N1 C1 C2 124.26(12) . . ? N1 C1 C7 116.75(12) . . ? C2 C1 C7 118.97(11) . . ? N3 C2 C3 119.15(12) . . ? N3 C2 C1 117.80(11) . . ? C3 C2 C1 123.04(12) . . ? C4 C3 C2 120.05(13) . . ? C4 C3 H1 121.9(11) . . ? C2 C3 H1 118.1(11) . . ? C3 C4 C5 119.76(13) . . ? C3 C4 H2 119.3(11) . . ? C5 C4 H2 120.9(11) . . ? C6 C5 C4 118.85(13) . . ? C6 C5 H3 119.0(11) . . ? C4 C5 H3 122.2(11) . . ? N3 C6 C5 121.54(13) . . ? N3 C6 H4 115.7(11) . . ? C5 C6 H4 122.8(11) . . ? C1 C7 H5 111.8(9) . . ? C1 C7 H6 111.9(10) . . ? H5 C7 H6 107.2(14) . . ? C1 C7 H7 108.9(11) . . ? H5 C7 H7 108.1(14) . . ? H6 C7 H7 108.7(15) . . ? C9 C8 C13 118.51(12) . . ? C9 C8 N2 120.37(12) . . ? C13 C8 N2 121.12(12) . . ? C10 C9 C8 120.58(13) . . ? C10 C9 H8 118.4(10) . . ? C8 C9 H8 121.0(10) . . ? C9 C10 C11 120.67(13) . . ? C9 C10 H9 120.4(10) . . ? C11 C10 H9 119.0(10) . . ? C12 C11 C10 119.05(13) . . ? C12 C11 H10 119.5(10) . . ? C10 C11 H10 121.4(10) . . ? C11 C12 C13 120.92(13) . . ? C11 C12 H11 121.7(10) . . ? C13 C12 H11 117.4(10) . . ? C12 C13 C8 120.26(13) . . ? C12 C13 H12 120.8(10) . . ? C8 C13 H12 118.9(10) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 N1 N2 C8 176.70(11) . . . . ? C1 N1 N2 B1 -1.94(19) . . . . ? F1 B1 N2 N1 -112.68(14) . . . . ? F2 B1 N2 N1 123.97(13) . . . . ? N3 B1 N2 N1 5.28(17) . . . . ? F1 B1 N2 C8 68.77(16) . . . . ? F2 B1 N2 C8 -54.57(16) . . . . ? N3 B1 N2 C8 -173.26(10) . . . . ? F1 B1 N3 C2 114.99(13) . . . . ? F2 B1 N3 C2 -127.70(13) . . . . ? N2 B1 N3 C2 -6.41(17) . . . . ? F1 B1 N3 C6 -62.77(16) . . . . ? F2 B1 N3 C6 54.53(15) . . . . ? N2 B1 N3 C6 175.83(11) . . . . ? N2 N1 C1 C2 -1.26(19) . . . . ? N2 N1 C1 C7 -179.77(11) . . . . ? C6 N3 C2 C3 1.27(18) . . . . ? B1 N3 C2 C3 -176.39(12) . . . . ? C6 N3 C2 C1 -178.09(11) . . . . ? B1 N3 C2 C1 4.25(18) . . . . ? N1 C1 C2 N3 0.01(19) . . . . ? C7 C1 C2 N3 178.49(11) . . . . ? N1 C1 C2 C3 -179.32(12) . . . . ? C7 C1 C2 C3 -0.84(19) . . . . ? N3 C2 C3 C4 -0.9(2) . . . . ? C1 C2 C3 C4 178.42(12) . . . . ? C2 C3 C4 C5 0.1(2) . . . . ? C3 C4 C5 C6 0.3(2) . . . . ? C2 N3 C6 C5 -0.9(2) . . . . ? B1 N3 C6 C5 176.94(13) . . . . ? C4 C5 C6 N3 0.1(2) . . . . ? N1 N2 C8 C9 169.73(11) . . . . ? B1 N2 C8 C9 -11.58(18) . . . . ? N1 N2 C8 C13 -11.06(17) . . . . ? B1 N2 C8 C13 167.64(12) . . . . ? C13 C8 C9 C10 0.8(2) . . . . ? N2 C8 C9 C10 -179.93(12) . . . . ? C8 C9 C10 C11 0.1(2) . . . . ? C9 C10 C11 C12 -0.9(2) . . . . ? C10 C11 C12 C13 0.6(2) . . . . ? C11 C12 C13 C8 0.3(2) . . . . ? C9 C8 C13 C12 -1.1(2) . . . . ? N2 C8 C13 C12 179.71(12) . . . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 68.02 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.359 _refine_diff_density_min -0.265 _refine_diff_density_rms 0.041 _publ_contact_Crystallographer_name 'Richard Staples' _contact_Crystallographer_email staples@chemistry.msu.com data_ia1410_0m _database_code_depnum_ccdc_archive 'CCDC 841443' #TrackingRef '6866_web_deposit_cif_file_1_IvanAprahamian_1314131892.2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C13 H9 B F2 N4' _chemical_formula_sum 'C13 H9 B F2 N4' _chemical_melting_point ? _exptl_crystal_description ? _exptl_crystal_colour ? _diffrn_ambient_temperature 173(2) _chemical_formula_weight 270.05 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_int_tables_number 14 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.6822(13) _cell_length_b 6.9729(7) _cell_length_c 13.8314(14) _cell_angle_alpha 90.00 _cell_angle_beta 95.1380(10) _cell_angle_gamma 90.00 _cell_volume 1218.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.472 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.113 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9701 _exptl_absorpt_correction_T_max 0.9908 _exptl_absorpt_process_details SADABS _exptl_special_details ; Data was collected using a BRUKER CCD (charge coupled device) based diffractometer equipped with an Oxford low-temperature apparatus operating at 173 K. A suitable crystal was chosen and mounted on a glass fiber or nylon loop using Paratone oil for Mo radiation and Mineral oil for Copper radiation. Data were measured using omega and phi scans of 0.5\% per frame for 30 s. The total number of images were based on results from the program COSMO where redundancy was expected to be 4 and completeness to 0.83\%A to 100%. Cell parameters were retrieved using APEX II software and refined using SAINT on all observed reflections.Data reduction was performed using the SAINT software which corrects for Lp. Scaling and absorption corrections were applied using SADABS6 multi-scan technique, supplied by George Sheldrick. The structures are solved by the direct method using the SHELXS-97 program and refined by least squares method on F2, SHELXL-97, incorporated in SHELXTL-PC V 6.14. All H atoms were placed in calculated positions and refined using a riding model. C-H(aromatic) = 0.94 \%A and Uiso(H) = 1.2Ueq(C) C-H (alaphatic) = 0.99 \%A and Uiso(H) = 1.2Ueq(C) CH2 = 0.98 \%A and Uiso(H) = 1.2Ueq(C) CH3 = 0.97\%A and Uiso(H) = 1.5Ueq(C) N-H = 0.86 (0.92)\%A and Uiso(H) = 1.2 Ueq(N) O-H(alcohol) = 0.85\%Aand Uiso(H) = 1.2Ueq(O) O-H(acid) = 0.82\%A and Uiso(H) = 1.5Ueq(O) ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method '\w,and/f 0.5 deg' _diffrn_detector_area_resol_mean 836.6 _diffrn_reflns_number 16730 _diffrn_reflns_av_R_equivalents 0.0465 _diffrn_reflns_av_sigmaI/netI 0.0492 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 25.39 _reflns_number_total 2249 _reflns_number_gt 1780 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COSMO (BRUKER, V1.58, 2006)' _computing_cell_refinement 'APEX2 (BRUKER, V2008.5-0, 2006)' _computing_data_reduction 'SAINT (BRUKER, V7.34A, 2006)' _computing_structure_solution 'SHELXS (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_structure_refinement 'SHELXL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_molecular_graphics 'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_publication_material 'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _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^)+(0.0613P)^2^+0.2001P] 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 2249 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0556 _refine_ls_R_factor_gt 0.0444 _refine_ls_wR_factor_ref 0.1288 _refine_ls_wR_factor_gt 0.1172 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 F1 F 0.10335(8) -0.14405(17) 0.64657(7) 0.0646(3) Uani 1 1 d . . . F2 F 0.09461(8) 0.17778(17) 0.66866(7) 0.0653(3) Uani 1 1 d . . . B1 B 0.15821(16) 0.0167(3) 0.68154(15) 0.0498(5) Uani 1 1 d . . . N1 N 0.26126(11) 0.0414(2) 0.63248(10) 0.0458(4) Uani 1 1 d . . . N2 N 0.35638(10) 0.0678(2) 0.67908(10) 0.0480(4) Uani 1 1 d . . . N3 N 0.18724(11) -0.0101(2) 0.79368(10) 0.0475(4) Uani 1 1 d . . . N4 N 0.55899(13) 0.1089(3) 0.85119(11) 0.0685(5) Uani 1 1 d . . . C1 C 0.36737(13) 0.0615(3) 0.77390(12) 0.0476(4) Uani 1 1 d . . . C2 C 0.28588(13) 0.0183(2) 0.83732(12) 0.0469(4) Uani 1 1 d . . . C3 C 0.30532(15) -0.0010(2) 0.93760(13) 0.0514(4) Uani 1 1 d . . . H3 H 0.3742 0.0223 0.9683 0.062 Uiso 1 1 calc R . . C4 C 0.22443(15) -0.0537(3) 0.99188(13) 0.0549(5) Uani 1 1 d . . . H4 H 0.2371 -0.0683 1.0602 0.066 Uiso 1 1 calc R . . C5 C 0.12438(15) -0.0855(3) 0.94608(13) 0.0571(5) Uani 1 1 d . . . H5 H 0.0678 -0.1232 0.9825 0.068 Uiso 1 1 calc R . . C6 C 0.10792(15) -0.0617(3) 0.84757(13) 0.0541(4) Uani 1 1 d . . . H6 H 0.0391 -0.0820 0.8163 0.065 Uiso 1 1 calc R . . C7 C 0.47408(15) 0.0894(3) 0.81628(13) 0.0550(5) Uani 1 1 d . . . C8 C 0.26189(14) 0.0329(2) 0.52917(12) 0.0471(4) Uani 1 1 d . . . C9 C 0.16893(14) 0.0637(3) 0.47008(13) 0.0519(4) Uani 1 1 d . . . H9 H 0.1053 0.0945 0.4980 0.062 Uiso 1 1 calc R . . C10 C 0.16967(15) 0.0492(3) 0.37047(13) 0.0568(5) Uani 1 1 d . . . H10 H 0.1060 0.0697 0.3301 0.068 Uiso 1 1 calc R . . C11 C 0.26188(16) 0.0053(3) 0.32876(13) 0.0576(5) Uani 1 1 d . . . H11 H 0.2616 -0.0042 0.2602 0.069 Uiso 1 1 calc R . . C12 C 0.35445(16) -0.0246(3) 0.38774(13) 0.0555(5) Uani 1 1 d . . . H12 H 0.4182 -0.0535 0.3595 0.067 Uiso 1 1 calc R . . C13 C 0.35459(15) -0.0127(2) 0.48750(13) 0.0511(4) Uani 1 1 d . . . H13 H 0.4181 -0.0357 0.5277 0.061 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 F1 0.0606(7) 0.0829(8) 0.0507(6) -0.0119(5) 0.0075(5) -0.0201(5) F2 0.0620(7) 0.0854(8) 0.0481(6) -0.0009(5) 0.0023(5) 0.0237(6) B1 0.0463(11) 0.0583(12) 0.0442(11) -0.0053(8) 0.0007(8) 0.0004(9) N1 0.0450(8) 0.0522(8) 0.0395(7) -0.0002(6) 0.0010(6) 0.0003(6) N2 0.0454(8) 0.0552(8) 0.0428(8) -0.0031(6) -0.0002(6) 0.0010(6) N3 0.0482(8) 0.0500(8) 0.0446(8) -0.0012(6) 0.0054(6) -0.0024(6) N4 0.0560(10) 0.1010(14) 0.0478(9) -0.0074(9) -0.0001(7) -0.0018(9) C1 0.0471(9) 0.0547(10) 0.0405(9) -0.0026(7) 0.0010(7) 0.0022(7) C2 0.0493(10) 0.0472(9) 0.0439(9) -0.0024(7) 0.0019(7) 0.0030(7) C3 0.0554(10) 0.0550(10) 0.0433(9) -0.0022(7) 0.0014(8) 0.0037(8) C4 0.0654(12) 0.0566(10) 0.0428(10) 0.0015(8) 0.0062(8) 0.0034(8) C5 0.0611(11) 0.0610(11) 0.0506(10) 0.0030(8) 0.0133(8) -0.0029(9) C6 0.0526(10) 0.0588(10) 0.0512(10) -0.0011(8) 0.0065(8) -0.0053(8) C7 0.0524(10) 0.0719(12) 0.0404(9) -0.0036(8) 0.0030(8) 0.0020(9) C8 0.0517(10) 0.0486(9) 0.0405(9) 0.0017(7) 0.0007(7) -0.0036(7) C9 0.0515(10) 0.0569(10) 0.0462(10) 0.0048(8) -0.0010(8) -0.0031(8) C10 0.0594(11) 0.0627(11) 0.0462(10) 0.0066(8) -0.0061(8) -0.0098(9) C11 0.0701(13) 0.0630(11) 0.0390(9) 0.0024(8) 0.0008(9) -0.0107(9) C12 0.0627(11) 0.0621(11) 0.0422(10) 0.0000(8) 0.0069(8) -0.0041(9) C13 0.0525(10) 0.0567(10) 0.0439(10) 0.0006(7) 0.0023(8) -0.0010(8) _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 F1 B1 1.384(2) . ? F2 B1 1.385(2) . ? B1 N1 1.535(2) . ? B1 N3 1.573(2) . ? N1 N2 1.3287(18) . ? N1 C8 1.431(2) . ? N2 C1 1.307(2) . ? N3 C6 1.353(2) . ? N3 C2 1.354(2) . ? N4 C7 1.148(2) . ? C1 C7 1.439(2) . ? C1 C2 1.446(2) . ? C2 C3 1.393(2) . ? C3 C4 1.375(3) . ? C3 H3 0.9500 . ? C4 C5 1.384(3) . ? C4 H4 0.9500 . ? C5 C6 1.370(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C8 C9 1.390(2) . ? C8 C13 1.392(3) . ? C9 C10 1.382(3) . ? C9 H9 0.9500 . ? C10 C11 1.384(3) . ? C10 H10 0.9500 . ? C11 C12 1.384(3) . ? C11 H11 0.9500 . ? C12 C13 1.382(2) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? 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 110.07(15) . . ? F1 B1 N1 110.94(15) . . ? F2 B1 N1 111.18(15) . . ? F1 B1 N3 108.33(15) . . ? F2 B1 N3 107.78(14) . . ? N1 B1 N3 108.41(14) . . ? N2 N1 C8 113.83(13) . . ? N2 N1 B1 124.96(13) . . ? C8 N1 B1 121.20(14) . . ? C1 N2 N1 119.52(14) . . ? C6 N3 C2 119.74(15) . . ? C6 N3 B1 117.06(15) . . ? C2 N3 B1 123.20(14) . . ? N2 C1 C7 114.58(15) . . ? N2 C1 C2 126.72(15) . . ? C7 C1 C2 118.57(14) . . ? N3 C2 C3 120.25(16) . . ? N3 C2 C1 116.24(14) . . ? C3 C2 C1 123.48(16) . . ? C4 C3 C2 119.69(17) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C3 C4 C5 119.42(17) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? C6 C5 C4 119.19(17) . . ? C6 C5 H5 120.4 . . ? C4 C5 H5 120.4 . . ? N3 C6 C5 121.69(17) . . ? N3 C6 H6 119.2 . . ? C5 C6 H6 119.2 . . ? N4 C7 C1 178.8(2) . . ? C9 C8 C13 119.69(16) . . ? C9 C8 N1 120.04(16) . . ? C13 C8 N1 120.23(15) . . ? C10 C9 C8 119.59(18) . . ? C10 C9 H9 120.2 . . ? C8 C9 H9 120.2 . . ? C9 C10 C11 120.87(17) . . ? C9 C10 H10 119.6 . . ? C11 C10 H10 119.6 . . ? C10 C11 C12 119.44(17) . . ? C10 C11 H11 120.3 . . ? C12 C11 H11 120.3 . . ? C13 C12 C11 120.30(18) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C12 C13 C8 120.10(17) . . ? C12 C13 H13 120.0 . . ? C8 C13 H13 120.0 . . ? 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 N2 -129.14(16) . . . . ? F2 B1 N1 N2 108.01(17) . . . . ? N3 B1 N1 N2 -10.3(2) . . . . ? F1 B1 N1 C8 49.4(2) . . . . ? F2 B1 N1 C8 -73.47(19) . . . . ? N3 B1 N1 C8 168.22(14) . . . . ? C8 N1 N2 C1 -174.17(15) . . . . ? B1 N1 N2 C1 4.5(2) . . . . ? F1 B1 N3 C6 -50.2(2) . . . . ? F2 B1 N3 C6 68.90(19) . . . . ? N1 B1 N3 C6 -170.65(15) . . . . ? F1 B1 N3 C2 130.65(16) . . . . ? F2 B1 N3 C2 -110.27(17) . . . . ? N1 B1 N3 C2 10.2(2) . . . . ? N1 N2 C1 C7 179.19(15) . . . . ? N1 N2 C1 C2 3.4(3) . . . . ? C6 N3 C2 C3 -1.6(2) . . . . ? B1 N3 C2 C3 177.56(14) . . . . ? C6 N3 C2 C1 176.30(16) . . . . ? B1 N3 C2 C1 -4.5(2) . . . . ? N2 C1 C2 N3 -3.2(3) . . . . ? C7 C1 C2 N3 -178.86(16) . . . . ? N2 C1 C2 C3 174.63(17) . . . . ? C7 C1 C2 C3 -1.0(3) . . . . ? N3 C2 C3 C4 1.7(3) . . . . ? C1 C2 C3 C4 -176.05(17) . . . . ? C2 C3 C4 C5 -0.6(3) . . . . ? C3 C4 C5 C6 -0.6(3) . . . . ? C2 N3 C6 C5 0.4(3) . . . . ? B1 N3 C6 C5 -178.82(17) . . . . ? C4 C5 C6 N3 0.7(3) . . . . ? N2 C1 C7 N4 -134(10) . . . . ? C2 C1 C7 N4 42(10) . . . . ? N2 N1 C8 C9 -160.67(16) . . . . ? B1 N1 C8 C9 20.7(2) . . . . ? N2 N1 C8 C13 21.6(2) . . . . ? B1 N1 C8 C13 -157.09(16) . . . . ? C13 C8 C9 C10 -0.2(3) . . . . ? N1 C8 C9 C10 -177.95(15) . . . . ? C8 C9 C10 C11 -0.3(3) . . . . ? C9 C10 C11 C12 0.1(3) . . . . ? C10 C11 C12 C13 0.7(3) . . . . ? C11 C12 C13 C8 -1.1(3) . . . . ? C9 C8 C13 C12 0.9(3) . . . . ? N1 C8 C13 C12 178.66(15) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.39 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.144 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.042 _contact_Crystallographer_name 'Richard Staples' _contact_Crystallographer_email staples@chemistry.msu.com # Attachment '6867_web_deposit_cif_file_2_IvanAprahamian_1314131892.3.cif' data_3 _database_code_depnum_ccdc_archive 'CCDC 841444' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C14 H12 B F2 N3 O' _chemical_formula_sum 'C14 H12 B F2 N3 O' _exptl_crystal_recrystallization_method 'ethyl acetate/hexane' _chemical_melting_point ? _exptl_crystal_description chunk _exptl_crystal_colour yellow _diffrn_ambient_temperature 173(2) _chemical_formula_weight 287.08 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_int_tables_number 14 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.5890(18) _cell_length_b 11.4482(15) _cell_length_c 8.7135(11) _cell_angle_alpha 90.00 _cell_angle_beta 105.5190(10) _cell_angle_gamma 90.00 _cell_volume 1306.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5526 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 25.28 _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.460 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 0.113 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9529 _exptl_absorpt_correction_T_max 0.9832 _exptl_absorpt_process_details SADABS _exptl_special_details ; Data was collected using a BRUKER CCD (charge coupled device) based diffractometer equipped with an Oxford low-temperature apparatus operating at 173 K. A suitable crystal was chosen and mounted on a glass fiber or nylon loop using Paratone oil for Mo radiation and Mineral oil for Copper radiation. Data were measured using omega and phi scans of 0.5\% per frame for 30 s. The total number of images were based on results from the program COSMO where redundancy was expected to be 4 and completeness to 0.83\%A to 100%. Cell parameters were retrieved using APEX II software and refined using SAINT on all observed reflections.Data reduction was performed using the SAINT software which corrects for Lp. Scaling and absorption corrections were applied using SADABS6 multi-scan technique, supplied by George Sheldrick. The structures are solved by the direct method using the SHELXS-97 program and refined by least squares method on F2, SHELXL-97, incorporated in SHELXTL-PC V 6.14. All H atoms were placed in calculated positions and refined using a riding model. C-H(aromatic) = 0.94 \%A and Uiso(H) = 1.2Ueq(C) C-H (alaphatic) = 0.99 \%A and Uiso(H) = 1.2Ueq(C) CH2 = 0.98 \%A and Uiso(H) = 1.2Ueq(C) CH3 = 0.97\%A and Uiso(H) = 1.5Ueq(C) N-H = 0.86 (0.92)\%A and Uiso(H) = 1.2 Ueq(N) O-H(alcohol) = 0.85\%Aand Uiso(H) = 1.2Ueq(O) O-H(acid) = 0.82\%A and Uiso(H) = 1.5Ueq(O) ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\w,and/f 0.5 deg' _diffrn_detector_area_resol_mean 836.6 _diffrn_reflns_number 8857 _diffrn_reflns_av_R_equivalents 0.0221 _diffrn_reflns_av_sigmaI/netI 0.0188 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 25.28 _reflns_number_total 2378 _reflns_number_gt 2010 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COSMO (BRUKER, V1.61, 2009)' _computing_cell_refinement 'APEX2 (BRUKER, V2010.11-3, 2010)' _computing_data_reduction 'SAINT (BRUKER, V7.68A, 2010)' _computing_structure_solution 'SHELXS (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_structure_refinement 'SHELXL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_molecular_graphics 'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_publication_material 'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _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^)+(0.0359P)^2^+0.3747P] 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 2378 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0400 _refine_ls_R_factor_gt 0.0315 _refine_ls_wR_factor_ref 0.0809 _refine_ls_wR_factor_gt 0.0758 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _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 F1 F 0.56444(6) 0.10673(7) 0.16762(10) 0.0378(2) Uani 1 1 d . . . F2 F 0.58754(6) 0.12707(7) 0.43418(10) 0.0384(2) Uani 1 1 d . . . O1 O 0.92590(8) 0.27635(10) 0.09714(14) 0.0445(3) Uani 1 1 d . . . N1 N 0.80410(8) 0.07339(9) 0.27841(13) 0.0260(3) Uani 1 1 d . . . N2 N 0.72657(8) 0.05035(9) 0.33889(13) 0.0263(3) Uani 1 1 d . . . N3 N 0.67509(8) 0.25893(9) 0.30383(13) 0.0257(3) Uani 1 1 d . . . B1 B 0.63389(12) 0.13126(14) 0.31207(19) 0.0278(3) Uani 1 1 d . . . C1 C 0.81774(10) 0.17899(11) 0.22854(15) 0.0250(3) Uani 1 1 d . . . C2 C 0.76017(10) 0.28055(11) 0.25461(15) 0.0247(3) Uani 1 1 d . . . C3 C 0.79065(10) 0.39618(12) 0.24448(16) 0.0295(3) Uani 1 1 d . . . H3 H 0.8502 0.4126 0.2111 0.035 Uiso 1 1 calc R . . C4 C 0.73465(11) 0.48607(12) 0.28274(17) 0.0337(3) Uani 1 1 d . . . H4 H 0.7554 0.5647 0.2756 0.040 Uiso 1 1 calc R . . C5 C 0.64810(11) 0.46218(13) 0.33155(18) 0.0359(4) Uani 1 1 d . . . H5 H 0.6086 0.5237 0.3579 0.043 Uiso 1 1 calc R . . C6 C 0.62046(11) 0.34815(13) 0.34111(17) 0.0328(3) Uani 1 1 d . . . H6 H 0.5611 0.3311 0.3749 0.039 Uiso 1 1 calc R . . C7 C 0.90543(10) 0.18700(13) 0.15878(16) 0.0300(3) Uani 1 1 d . . . C8 C 0.96891(12) 0.07935(14) 0.1628(2) 0.0405(4) Uani 1 1 d . . . H8A H 0.9279 0.0191 0.0948 0.061 Uiso 1 1 calc R . . H8B H 0.9920 0.0504 0.2724 0.061 Uiso 1 1 calc R . . H8C H 1.0283 0.0982 0.1238 0.061 Uiso 1 1 calc R . . C9 C 0.73155(11) -0.06335(11) 0.40868(16) 0.0281(3) Uani 1 1 d . . . C10 C 0.64323(12) -0.11664(13) 0.42578(18) 0.0356(3) Uani 1 1 d . . . H10 H 0.5790 -0.0789 0.3885 0.043 Uiso 1 1 calc R . . C11 C 0.64983(13) -0.22549(13) 0.49784(19) 0.0426(4) Uani 1 1 d . . . H11 H 0.5896 -0.2621 0.5098 0.051 Uiso 1 1 calc R . . C12 C 0.74242(14) -0.28111(13) 0.55226(19) 0.0439(4) Uani 1 1 d . . . H12 H 0.7462 -0.3553 0.6024 0.053 Uiso 1 1 calc R . . C13 C 0.82964(13) -0.22844(13) 0.53360(18) 0.0403(4) Uani 1 1 d . . . H13 H 0.8935 -0.2671 0.5699 0.048 Uiso 1 1 calc R . . C14 C 0.82500(12) -0.11947(12) 0.46217(17) 0.0334(3) Uani 1 1 d . . . H14 H 0.8855 -0.0835 0.4500 0.040 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 F1 0.0313(4) 0.0386(5) 0.0383(5) 0.0028(4) 0.0003(4) -0.0068(4) F2 0.0401(5) 0.0385(5) 0.0433(5) 0.0084(4) 0.0227(4) 0.0050(4) O1 0.0442(6) 0.0435(7) 0.0535(7) 0.0112(5) 0.0261(5) 0.0015(5) N1 0.0266(6) 0.0265(6) 0.0246(6) -0.0023(4) 0.0064(5) -0.0010(4) N2 0.0281(6) 0.0237(6) 0.0279(6) 0.0002(5) 0.0087(5) -0.0017(4) N3 0.0251(6) 0.0267(6) 0.0249(6) 0.0005(4) 0.0059(5) 0.0025(5) B1 0.0265(8) 0.0303(8) 0.0280(8) 0.0033(6) 0.0097(6) 0.0001(6) C1 0.0252(7) 0.0250(7) 0.0242(7) -0.0007(5) 0.0054(5) 0.0000(5) C2 0.0241(7) 0.0272(7) 0.0212(6) 0.0013(5) 0.0035(5) 0.0005(5) C3 0.0301(7) 0.0282(7) 0.0294(7) 0.0020(6) 0.0064(6) -0.0013(6) C4 0.0393(8) 0.0248(7) 0.0333(8) 0.0003(6) 0.0031(6) 0.0001(6) C5 0.0388(8) 0.0292(8) 0.0381(8) -0.0042(6) 0.0076(7) 0.0076(6) C6 0.0303(7) 0.0344(8) 0.0344(8) -0.0016(6) 0.0101(6) 0.0064(6) C7 0.0283(7) 0.0350(8) 0.0266(7) -0.0014(6) 0.0072(6) -0.0007(6) C8 0.0342(8) 0.0430(9) 0.0484(10) -0.0034(7) 0.0183(7) 0.0051(7) C9 0.0378(7) 0.0219(7) 0.0240(7) -0.0028(5) 0.0072(6) -0.0027(6) C10 0.0403(8) 0.0302(8) 0.0360(8) -0.0031(6) 0.0097(6) -0.0066(6) C11 0.0569(10) 0.0326(8) 0.0407(9) -0.0040(7) 0.0173(8) -0.0154(7) C12 0.0732(12) 0.0243(7) 0.0337(9) -0.0009(6) 0.0135(8) -0.0065(8) C13 0.0549(10) 0.0275(8) 0.0356(9) 0.0000(6) 0.0070(7) 0.0046(7) C14 0.0410(8) 0.0271(7) 0.0315(8) -0.0013(6) 0.0086(6) 0.0000(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 F1 B1 1.3850(18) . ? F2 B1 1.3747(17) . ? O1 C7 1.2216(17) . ? N1 C1 1.3145(17) . ? N1 N2 1.3245(15) . ? N2 C9 1.4307(17) . ? N2 B1 1.5301(18) . ? N3 C6 1.3524(18) . ? N3 C2 1.3591(17) . ? N3 B1 1.5736(19) . ? C1 C2 1.4527(18) . ? C1 C7 1.4782(19) . ? C2 C3 1.3969(19) . ? C3 C4 1.373(2) . ? C3 H3 0.9500 . ? C4 C5 1.381(2) . ? C4 H4 0.9500 . ? C5 C6 1.367(2) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.499(2) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C14 1.388(2) . ? C9 C10 1.389(2) . ? C10 C11 1.387(2) . ? C10 H10 0.9500 . ? C11 C12 1.376(2) . ? C11 H11 0.9500 . ? C12 C13 1.378(2) . ? C12 H12 0.9500 . ? C13 C14 1.388(2) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 N2 120.81(11) . . ? N1 N2 C9 113.46(11) . . ? N1 N2 B1 121.90(11) . . ? C9 N2 B1 123.99(11) . . ? C6 N3 C2 120.41(12) . . ? C6 N3 B1 117.75(11) . . ? C2 N3 B1 121.77(11) . . ? F2 B1 F1 110.76(11) . . ? F2 B1 N2 112.92(11) . . ? F1 B1 N2 110.42(12) . . ? F2 B1 N3 108.06(12) . . ? F1 B1 N3 108.13(11) . . ? N2 B1 N3 106.31(11) . . ? N1 C1 C2 123.70(12) . . ? N1 C1 C7 113.17(12) . . ? C2 C1 C7 122.80(12) . . ? N3 C2 C3 118.96(12) . . ? N3 C2 C1 116.28(11) . . ? C3 C2 C1 124.57(12) . . ? C4 C3 C2 120.13(13) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 C5 119.96(13) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C6 C5 C4 118.59(13) . . ? C6 C5 H5 120.7 . . ? C4 C5 H5 120.7 . . ? N3 C6 C5 121.95(14) . . ? N3 C6 H6 119.0 . . ? C5 C6 H6 119.0 . . ? O1 C7 C1 122.43(13) . . ? O1 C7 C8 120.08(13) . . ? C1 C7 C8 117.49(12) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C14 C9 C10 119.98(13) . . ? C14 C9 N2 119.93(12) . . ? C10 C9 N2 120.08(13) . . ? C11 C10 C9 119.33(15) . . ? C11 C10 H10 120.3 . . ? C9 C10 H10 120.3 . . ? C12 C11 C10 120.92(15) . . ? C12 C11 H11 119.5 . . ? C10 C11 H11 119.5 . . ? C11 C12 C13 119.53(14) . . ? C11 C12 H12 120.2 . . ? C13 C12 H12 120.2 . . ? C12 C13 C14 120.60(15) . . ? C12 C13 H13 119.7 . . ? C14 C13 H13 119.7 . . ? C9 C14 C13 119.63(14) . . ? C9 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 N1 N2 C9 -171.21(11) . . . . ? C1 N1 N2 B1 17.63(18) . . . . ? N1 N2 B1 F2 -151.48(12) . . . . ? C9 N2 B1 F2 38.31(18) . . . . ? N1 N2 B1 F1 83.91(15) . . . . ? C9 N2 B1 F1 -86.31(15) . . . . ? N1 N2 B1 N3 -33.15(16) . . . . ? C9 N2 B1 N3 156.63(11) . . . . ? C6 N3 B1 F2 -33.88(16) . . . . ? C2 N3 B1 F2 148.89(11) . . . . ? C6 N3 B1 F1 86.06(14) . . . . ? C2 N3 B1 F1 -91.18(14) . . . . ? C6 N3 B1 N2 -155.36(11) . . . . ? C2 N3 B1 N2 27.40(16) . . . . ? N2 N1 C1 C2 8.84(19) . . . . ? N2 N1 C1 C7 -177.58(11) . . . . ? C6 N3 C2 C3 0.53(19) . . . . ? B1 N3 C2 C3 177.70(12) . . . . ? C6 N3 C2 C1 175.66(12) . . . . ? B1 N3 C2 C1 -7.17(17) . . . . ? N1 C1 C2 N3 -13.74(19) . . . . ? C7 C1 C2 N3 173.29(12) . . . . ? N1 C1 C2 C3 161.08(13) . . . . ? C7 C1 C2 C3 -11.9(2) . . . . ? N3 C2 C3 C4 -0.5(2) . . . . ? C1 C2 C3 C4 -175.18(13) . . . . ? C2 C3 C4 C5 0.1(2) . . . . ? C3 C4 C5 C6 0.2(2) . . . . ? C2 N3 C6 C5 -0.2(2) . . . . ? B1 N3 C6 C5 -177.47(13) . . . . ? C4 C5 C6 N3 -0.2(2) . . . . ? N1 C1 C7 O1 175.30(13) . . . . ? C2 C1 C7 O1 -11.1(2) . . . . ? N1 C1 C7 C8 -3.49(18) . . . . ? C2 C1 C7 C8 170.15(13) . . . . ? N1 N2 C9 C14 23.93(17) . . . . ? B1 N2 C9 C14 -165.12(13) . . . . ? N1 N2 C9 C10 -157.32(12) . . . . ? B1 N2 C9 C10 13.63(19) . . . . ? C14 C9 C10 C11 0.6(2) . . . . ? N2 C9 C10 C11 -178.17(13) . . . . ? C9 C10 C11 C12 0.0(2) . . . . ? C10 C11 C12 C13 -0.6(2) . . . . ? C11 C12 C13 C14 0.7(2) . . . . ? C10 C9 C14 C13 -0.5(2) . . . . ? N2 C9 C14 C13 178.30(12) . . . . ? C12 C13 C14 C9 -0.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.28 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.156 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.035 _contact_Crystallographer_name 'Richard Staples' _contact_Crystallographer_email staples@chemistry.msu.com # Attachment '6868_web_deposit_cif_file_3_IvanAprahamian_1314131892.4.cif' data_4 _database_code_depnum_ccdc_archive 'CCDC 841445' #TrackingRef '6868_web_deposit_cif_file_3_IvanAprahamian_1314131892.4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C15 H14 B F2 N3 O2' _chemical_formula_sum 'C15 H14 B F2 N3 O2' _chemical_melting_point ? _exptl_crystal_description needle _exptl_crystal_colour white _diffrn_ambient_temperature 173(2) _chemical_formula_weight 317.10 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_int_tables_number 14 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.589(3) _cell_length_b 11.456(2) _cell_length_c 8.6272(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.271(2) _cell_angle_gamma 90.00 _cell_volume 1441.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2583 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 24.82 _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.461 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.115 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9632 _exptl_absorpt_correction_T_max 0.9966 _exptl_absorpt_process_details SADABS _exptl_special_details ; Data was collected using a BRUKER CCD (charge coupled device) based diffractometer equipped with an Oxford low-temperature apparatus operating at 173 K. A suitable crystal was chosen and mounted on a glass fiber or nylon loop using Paratone oil for Mo radiation and Mineral oil for Copper radiation. Data were measured using omega and phi scans of 0.5\% per frame for 30 s. The total number of images were based on results from the program COSMO where redundancy was expected to be 4 and completeness to 0.83\%A to 100%. Cell parameters were retrieved using APEX II software and refined using SAINT on all observed reflections.Data reduction was performed using the SAINT software which corrects for Lp. Scaling and absorption corrections were applied using SADABS6 multi-scan technique, supplied by George Sheldrick. The structures are solved by the direct method using the SHELXS-97 program and refined by least squares method on F2, SHELXL-97, incorporated in SHELXTL-PC V 6.14. All H atoms were placed in calculated positions and refined using a riding model. C-H(aromatic) = 0.94 \%A and Uiso(H) = 1.2Ueq(C) C-H (alaphatic) = 0.99 \%A and Uiso(H) = 1.2Ueq(C) CH2 = 0.98 \%A and Uiso(H) = 1.2Ueq(C) CH3 = 0.97\%A and Uiso(H) = 1.5Ueq(C) N-H = 0.86 (0.92)\%A and Uiso(H) = 1.2 Ueq(N) O-H(alcohol) = 0.85\%Aand Uiso(H) = 1.2Ueq(O) O-H(acid) = 0.82\%A and Uiso(H) = 1.5Ueq(O) ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\w,and/f 0.5 deg' _diffrn_detector_area_resol_mean 836.6 _diffrn_reflns_number 11401 _diffrn_reflns_av_R_equivalents 0.0616 _diffrn_reflns_av_sigmaI/netI 0.0551 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 25.37 _reflns_number_total 2656 _reflns_number_gt 1668 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COSMO (BRUKER, V1.61, 2009)' _computing_cell_refinement 'APEX2 (BRUKER, V2010.11-3, 2010)' _computing_data_reduction 'SAINT (BRUKER, V7.68A, 2010)' _computing_structure_solution 'SHELXS (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_structure_refinement 'SHELXL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_molecular_graphics 'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_publication_material 'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _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^)+(0.0496P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2656 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0834 _refine_ls_R_factor_gt 0.0424 _refine_ls_wR_factor_ref 0.1099 _refine_ls_wR_factor_gt 0.0921 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F1 F 0.42553(9) 0.61369(11) 0.39573(14) 0.0392(4) Uani 1 1 d . . . F2 F 0.44059(9) 0.59366(11) 0.13536(15) 0.0393(4) Uani 1 1 d . . . O1 O 0.11152(10) 0.57273(13) -0.07075(16) 0.0322(4) Uani 1 1 d . . . O2 O 0.10716(12) 0.76737(14) -0.0639(2) 0.0532(5) Uani 1 1 d . . . B1 B 0.38104(18) 0.6190(2) 0.2553(3) 0.0290(6) Uani 1 1 d . . . N1 N 0.22778(12) 0.56161(15) 0.15123(19) 0.0269(4) Uani 1 1 d . . . N2 N 0.29716(12) 0.54045(15) 0.2483(2) 0.0270(4) Uani 1 1 d . . . N3 N 0.34429(12) 0.74649(15) 0.23149(19) 0.0268(4) Uani 1 1 d . . . C1 C 0.21710(14) 0.66653(18) 0.0924(2) 0.0254(5) Uani 1 1 d . . . C2 C 0.26847(14) 0.76864(19) 0.1429(2) 0.0261(5) Uani 1 1 d . . . C3 C 0.24288(15) 0.88441(18) 0.1172(2) 0.0291(5) Uani 1 1 d . . . H3 H 0.1910 0.9014 0.0542 0.035 Uiso 1 1 calc R . . C4 C 0.29229(16) 0.9739(2) 0.1824(2) 0.0324(6) Uani 1 1 d . . . H4 H 0.2742 1.0526 0.1656 0.039 Uiso 1 1 calc R . . C5 C 0.36843(16) 0.9494(2) 0.2724(3) 0.0353(6) Uani 1 1 d . . . H5 H 0.4032 1.0106 0.3181 0.042 Uiso 1 1 calc R . . C6 C 0.39276(16) 0.8354(2) 0.2945(2) 0.0330(6) Uani 1 1 d . . . H6 H 0.4452 0.8181 0.3559 0.040 Uiso 1 1 calc R . . C7 C 0.14012(15) 0.6771(2) -0.0197(2) 0.0292(5) Uani 1 1 d . . . C8 C 0.03722(16) 0.5746(2) -0.1839(3) 0.0351(6) Uani 1 1 d . . . H8A H 0.0497 0.6334 -0.2653 0.042 Uiso 1 1 calc R . . H8B H -0.0213 0.5947 -0.1329 0.042 Uiso 1 1 calc R . . C9 C 0.03179(17) 0.4550(2) -0.2536(3) 0.0424(6) Uani 1 1 d . . . H9A H 0.0905 0.4357 -0.3020 0.064 Uiso 1 1 calc R . . H9B H -0.0169 0.4532 -0.3321 0.064 Uiso 1 1 calc R . . H9C H 0.0183 0.3979 -0.1723 0.064 Uiso 1 1 calc R . . C10 C 0.29103(15) 0.42906(18) 0.3222(2) 0.0273(5) Uani 1 1 d . . . C11 C 0.20572(17) 0.38060(19) 0.3506(3) 0.0349(6) Uani 1 1 d . . . H11 H 0.1516 0.4216 0.3222 0.042 Uiso 1 1 calc R . . C12 C 0.19973(19) 0.2725(2) 0.4203(3) 0.0441(7) Uani 1 1 d . . . H12 H 0.1412 0.2394 0.4397 0.053 Uiso 1 1 calc R . . C13 C 0.2772(2) 0.2120(2) 0.4620(3) 0.0474(7) Uani 1 1 d . . . H13 H 0.2727 0.1370 0.5084 0.057 Uiso 1 1 calc R . . C14 C 0.3617(2) 0.2617(2) 0.4354(3) 0.0465(7) Uani 1 1 d . . . H14 H 0.4156 0.2208 0.4653 0.056 Uiso 1 1 calc R . . C15 C 0.36958(17) 0.3699(2) 0.3660(2) 0.0353(6) Uani 1 1 d . . . H15 H 0.4283 0.4033 0.3486 0.042 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 F1 0.0390(8) 0.0442(8) 0.0342(7) 0.0073(6) -0.0139(6) -0.0059(6) F2 0.0339(8) 0.0439(9) 0.0402(8) 0.0049(6) 0.0066(6) 0.0079(6) O1 0.0333(9) 0.0308(9) 0.0324(9) -0.0005(7) -0.0108(7) -0.0024(7) O2 0.0684(13) 0.0276(10) 0.0632(12) 0.0005(9) -0.0378(10) 0.0077(9) B1 0.0279(15) 0.0337(15) 0.0255(13) 0.0033(12) -0.0039(11) 0.0008(12) N1 0.0305(11) 0.0266(10) 0.0236(9) -0.0006(8) -0.0035(8) 0.0038(8) N2 0.0295(11) 0.0258(10) 0.0256(9) 0.0015(8) -0.0057(8) 0.0035(8) N3 0.0270(10) 0.0299(10) 0.0237(10) 0.0004(8) -0.0008(8) -0.0025(9) C1 0.0281(13) 0.0234(12) 0.0248(11) 0.0008(10) -0.0014(10) 0.0015(10) C2 0.0268(13) 0.0312(13) 0.0203(11) 0.0012(10) 0.0031(10) -0.0022(10) C3 0.0315(13) 0.0293(13) 0.0266(12) 0.0018(10) 0.0011(10) -0.0001(11) C4 0.0387(15) 0.0274(13) 0.0311(12) 0.0002(10) 0.0065(11) -0.0031(11) C5 0.0377(15) 0.0323(14) 0.0358(14) -0.0055(11) 0.0008(12) -0.0091(11) C6 0.0312(14) 0.0379(15) 0.0298(12) -0.0019(11) -0.0021(10) -0.0079(11) C7 0.0335(14) 0.0274(13) 0.0266(12) 0.0009(11) -0.0015(10) -0.0014(11) C8 0.0319(14) 0.0415(14) 0.0319(13) -0.0022(11) -0.0129(11) 0.0020(11) C9 0.0405(16) 0.0460(16) 0.0408(14) -0.0089(12) -0.0073(12) -0.0048(12) C10 0.0379(14) 0.0213(12) 0.0227(11) -0.0028(9) -0.0050(10) 0.0024(11) C11 0.0428(15) 0.0298(13) 0.0321(13) 0.0015(11) -0.0075(11) -0.0040(12) C12 0.0597(18) 0.0343(15) 0.0383(15) 0.0042(12) -0.0049(13) -0.0102(14) C13 0.082(2) 0.0260(14) 0.0339(14) 0.0034(11) -0.0071(14) 0.0046(15) C14 0.068(2) 0.0370(15) 0.0344(14) 0.0013(12) -0.0106(13) 0.0194(15) C15 0.0413(15) 0.0334(14) 0.0311(13) 0.0003(11) -0.0047(11) 0.0085(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 F1 B1 1.373(3) . ? F2 B1 1.385(3) . ? O1 C7 1.340(2) . ? O1 C8 1.456(3) . ? O2 C7 1.202(2) . ? B1 N2 1.520(3) . ? B1 N3 1.569(3) . ? N1 C1 1.313(3) . ? N1 N2 1.333(2) . ? N2 C10 1.430(3) . ? N3 C6 1.353(3) . ? N3 C2 1.365(3) . ? C1 C2 1.455(3) . ? C1 C7 1.484(3) . ? C2 C3 1.395(3) . ? C3 C4 1.373(3) . ? C3 H3 0.9500 . ? C4 C5 1.381(3) . ? C4 H4 0.9500 . ? C5 C6 1.366(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C8 C9 1.498(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C15 1.382(3) . ? C10 C11 1.386(3) . ? C11 C12 1.380(3) . ? C11 H11 0.9500 . ? C12 C13 1.372(4) . ? C12 H12 0.9500 . ? C13 C14 1.378(4) . ? C13 H13 0.9500 . ? C14 C15 1.381(3) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? 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 C7 O1 C8 115.92(17) . . ? F1 B1 F2 110.75(19) . . ? F1 B1 N2 112.69(19) . . ? F2 B1 N2 110.7(2) . . ? F1 B1 N3 108.44(19) . . ? F2 B1 N3 108.22(18) . . ? N2 B1 N3 105.75(18) . . ? C1 N1 N2 119.82(18) . . ? N1 N2 C10 113.18(17) . . ? N1 N2 B1 121.74(17) . . ? C10 N2 B1 124.26(18) . . ? C6 N3 C2 120.37(19) . . ? C6 N3 B1 118.10(19) . . ? C2 N3 B1 121.44(18) . . ? N1 C1 C2 124.08(19) . . ? N1 C1 C7 114.49(19) . . ? C2 C1 C7 121.10(19) . . ? N3 C2 C3 118.76(19) . . ? N3 C2 C1 115.65(19) . . ? C3 C2 C1 125.4(2) . . ? C4 C3 C2 120.4(2) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 119.8(2) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C6 C5 C4 118.7(2) . . ? C6 C5 H5 120.6 . . ? C4 C5 H5 120.6 . . ? N3 C6 C5 121.9(2) . . ? N3 C6 H6 119.0 . . ? C5 C6 H6 119.0 . . ? O2 C7 O1 122.7(2) . . ? O2 C7 C1 125.3(2) . . ? O1 C7 C1 112.01(18) . . ? O1 C8 C9 107.08(18) . . ? O1 C8 H8A 110.3 . . ? C9 C8 H8A 110.3 . . ? O1 C8 H8B 110.3 . . ? C9 C8 H8B 110.3 . . ? H8A C8 H8B 108.6 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C15 C10 C11 120.0(2) . . ? C15 C10 N2 120.4(2) . . ? C11 C10 N2 119.64(19) . . ? C12 C11 C10 119.7(2) . . ? C12 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? C13 C12 C11 120.9(2) . . ? C13 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? C12 C13 C14 118.9(2) . . ? C12 C13 H13 120.5 . . ? C14 C13 H13 120.5 . . ? C13 C14 C15 121.3(2) . . ? C13 C14 H14 119.3 . . ? C15 C14 H14 119.3 . . ? C14 C15 C10 119.2(2) . . ? C14 C15 H15 120.4 . . ? C10 C15 H15 120.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 N1 N2 C10 170.13(17) . . . . ? C1 N1 N2 B1 -19.8(3) . . . . ? F1 B1 N2 N1 155.48(18) . . . . ? F2 B1 N2 N1 -79.8(2) . . . . ? N3 B1 N2 N1 37.2(3) . . . . ? F1 B1 N2 C10 -35.6(3) . . . . ? F2 B1 N2 C10 89.1(2) . . . . ? N3 B1 N2 C10 -153.90(17) . . . . ? F1 B1 N3 C6 31.4(3) . . . . ? F2 B1 N3 C6 -88.8(2) . . . . ? N2 B1 N3 C6 152.50(18) . . . . ? F1 B1 N3 C2 -152.14(18) . . . . ? F2 B1 N3 C2 87.7(2) . . . . ? N2 B1 N3 C2 -31.0(3) . . . . ? N2 N1 C1 C2 -9.4(3) . . . . ? N2 N1 C1 C7 177.16(17) . . . . ? C6 N3 C2 C3 0.8(3) . . . . ? B1 N3 C2 C3 -175.55(19) . . . . ? C6 N3 C2 C1 -174.79(18) . . . . ? B1 N3 C2 C1 8.8(3) . . . . ? N1 C1 C2 N3 14.5(3) . . . . ? C7 C1 C2 N3 -172.52(18) . . . . ? N1 C1 C2 C3 -160.8(2) . . . . ? C7 C1 C2 C3 12.2(3) . . . . ? N3 C2 C3 C4 -1.2(3) . . . . ? C1 C2 C3 C4 174.0(2) . . . . ? C2 C3 C4 C5 0.8(3) . . . . ? C3 C4 C5 C6 0.0(3) . . . . ? C2 N3 C6 C5 -0.1(3) . . . . ? B1 N3 C6 C5 176.4(2) . . . . ? C4 C5 C6 N3 -0.3(3) . . . . ? C8 O1 C7 O2 -0.1(3) . . . . ? C8 O1 C7 C1 -178.80(17) . . . . ? N1 C1 C7 O2 164.8(2) . . . . ? C2 C1 C7 O2 -8.8(3) . . . . ? N1 C1 C7 O1 -16.5(3) . . . . ? C2 C1 C7 O1 169.80(18) . . . . ? C7 O1 C8 C9 166.28(18) . . . . ? N1 N2 C10 C15 150.15(19) . . . . ? B1 N2 C10 C15 -19.6(3) . . . . ? N1 N2 C10 C11 -30.1(3) . . . . ? B1 N2 C10 C11 160.1(2) . . . . ? C15 C10 C11 C12 -1.0(3) . . . . ? N2 C10 C11 C12 179.2(2) . . . . ? C10 C11 C12 C13 -0.1(3) . . . . ? C11 C12 C13 C14 1.0(4) . . . . ? C12 C13 C14 C15 -0.9(4) . . . . ? C13 C14 C15 C10 -0.2(4) . . . . ? C11 C10 C15 C14 1.1(3) . . . . ? N2 C10 C15 C14 -179.13(19) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.172 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.047 _contact_Crystallographer_name 'Richard Staples' _contact_Crystallographer_email staples@chemistry.msu.com # Attachment '6869_web_deposit_cif_file_4_IvanAprahamian_1314131892.5.cif' data_5 _database_code_depnum_ccdc_archive 'CCDC 841446' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C17 H11 B F2 N4' _chemical_formula_sum 'C17 H11 B F2 N4' _chemical_melting_point ? _exptl_crystal_description ? _exptl_crystal_colour ? _diffrn_ambient_temperature 173(2) _chemical_formula_weight 320.11 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_int_tables_number 2 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.7978(7) _cell_length_b 8.4159(11) _cell_length_c 25.529(2) _cell_angle_alpha 91.862(2) _cell_angle_beta 95.4460(10) _cell_angle_gamma 117.2480(10) _cell_volume 1477.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.439 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9637 _exptl_absorpt_correction_T_max 0.9952 _exptl_absorpt_process_details SADABS _exptl_special_details ; Data was collected using a BRUKER CCD (charge coupled device) based diffractometer equipped with an Oxford low-temperature apparatus operating at 173 K. A suitable crystal was chosen and mounted on a glass fiber or nylon loop using Paratone oil for Mo radiation and Mineral oil for Copper radiation. Data were measured using omega and phi scans of 0.5\% per frame for 30 s. The total number of images were based on results from the program COSMO where redundancy was expected to be 4 and completeness to 0.83\%A to 100%. Cell parameters were retrieved using APEX II software and refined using SAINT on all observed reflections.Data reduction was performed using the SAINT software which corrects for Lp. Scaling and absorption corrections were applied using SADABS6 multi-scan technique, supplied by George Sheldrick. The structures are solved by the direct method using the SHELXS-97 program and refined by least squares method on F2, SHELXL-97, incorporated in SHELXTL-PC V 6.14. All H atoms were placed in calculated positions and refined using a riding model. C-H(aromatic) = 0.94 \%A and Uiso(H) = 1.2Ueq(C) C-H (alaphatic) = 0.99 \%A and Uiso(H) = 1.2Ueq(C) CH2 = 0.98 \%A and Uiso(H) = 1.2Ueq(C) CH3 = 0.97\%A and Uiso(H) = 1.5Ueq(C) N-H = 0.86 (0.92)\%A and Uiso(H) = 1.2 Ueq(N) O-H(alcohol) = 0.85\%Aand Uiso(H) = 1.2Ueq(O) O-H(acid) = 0.82\%A and Uiso(H) = 1.5Ueq(O) ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method '\w,and/f 0.5 deg' _diffrn_detector_area_resol_mean 836.6 _diffrn_reflns_number 23953 _diffrn_reflns_av_R_equivalents 0.0412 _diffrn_reflns_av_sigmaI/netI 0.0366 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 25.28 _reflns_number_total 5349 _reflns_number_gt 3603 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COSMO (BRUKER, V1.61, 2009)' _computing_cell_refinement 'APEX2 (BRUKER, V2010.11-3, 2010)' _computing_data_reduction 'SAINT (BRUKER, V7.68A, 2010)' _computing_structure_solution 'SHELXS (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_structure_refinement 'SHELXL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_molecular_graphics 'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_publication_material 'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0546P)^2^+0.5672P] 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 5349 _refine_ls_number_parameters 368 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0812 _refine_ls_R_factor_gt 0.0492 _refine_ls_wR_factor_ref 0.1350 _refine_ls_wR_factor_gt 0.1187 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 F1A F 0.8840(3) 0.9330(2) 0.07750(8) 0.0613(6) Uani 0.783(2) 1 d P A 1 F2A F 1.0100(2) 0.7643(3) 0.11564(6) 0.0522(6) Uani 0.783(2) 1 d P A 1 F1C F 0.9840(9) 0.8825(8) 0.1198(2) 0.0442(18) Uani 0.217(2) 1 d P A 2 F2C F 0.7776(11) 0.7667(9) 0.0439(3) 0.056(2) Uani 0.217(2) 1 d P A 2 B1A B 0.8519(4) 0.7566(4) 0.08654(12) 0.0431(7) Uani 1 1 d . . . N1A N 0.6663(3) 0.6480(2) 0.11211(8) 0.0410(5) Uani 1 1 d . A . N2A N 0.5595(3) 0.4721(2) 0.10237(7) 0.0391(5) Uani 1 1 d . . . N3A N 0.8314(3) 0.6622(3) 0.02958(9) 0.0329(6) Uani 0.783(2) 1 d P A 1 N4A N 0.3855(4) 0.0478(3) 0.04898(9) 0.0626(6) Uani 1 1 d . A . C1A C 0.4766(4) 0.1998(3) 0.05613(10) 0.0468(6) Uani 1 1 d . . . C2A C 0.5967(4) 0.3912(3) 0.06294(11) 0.0520(7) Uani 1 1 d . A . C3A C 0.7181(4) 0.4820(4) 0.02042(10) 0.0319(6) Uani 0.783(2) 1 d P A 1 N3C N 0.92729(11) 0.59823(10) 0.081337(18) 0.036(2) Uani 0.217(2) 1 d PG A 2 C3C C 0.80119(12) 0.42015(10) 0.070442(16) 0.036(2) Uani 0.217(2) 1 d PG A 2 C4C C 0.87049(13) 0.30002(11) 0.056329(16) 0.039(3) Uani 0.217(2) 1 d PG A 2 H4CA H 0.7749 0.1794 0.0467 0.047 Uiso 0.217(2) 1 calc PR A 2 C5C C 1.06338(14) 0.33636(12) 0.054740(18) 0.0475(6) Uani 0.217(2) 1 d PG . . H5CA H 1.1079 0.2506 0.0481 0.057 Uiso 0.217(2) 1 calc PR A 2 C6C C 1.17751(13) 0.51897(12) 0.06445(2) 0.0458(6) Uani 0.217(2) 1 d PG . . H6CA H 1.3117 0.5618 0.0615 0.055 Uiso 0.217(2) 1 calc PR A 2 C7C C 1.11799(12) 0.66091(11) 0.07927(2) 0.041(3) Uani 0.217(2) 1 d PG A 2 H7CA H 1.2086 0.7843 0.0865 0.050 Uiso 0.217(2) 1 calc PR A 2 C4A C 0.71592(16) 0.39128(13) -0.026758(16) 0.0386(7) Uani 0.783(2) 1 d PG . 1 H4AA H 0.6374 0.2635 -0.0323 0.046 Uiso 0.783(2) 1 d PR A 1 C5A C 0.82270(18) 0.48120(15) -0.064415(17) 0.0458(6) Uani 0.783(2) 1 d PG . 1 H5AA H 0.8194 0.4197 -0.0971 0.055 Uiso 0.783(2) 1 d PR A 1 C6A C 0.93683(17) 0.66380(15) -0.05470(2) 0.0475(6) Uani 0.783(2) 1 d PG . 1 H6AA H 1.0170 0.7296 -0.0807 0.057 Uiso 0.783(2) 1 d PR A 1 C7A C 0.93842(15) 0.75484(13) -0.00815(2) 0.0402(7) Uani 0.783(2) 1 d PG . 1 H7AA H 1.0151 0.8828 -0.0027 0.048 Uiso 0.783(2) 1 d PR A 1 C8A C 0.61454(10) 0.72505(8) 0.15521(2) 0.0356(5) Uani 1 1 d G . . C9A C 0.59975(11) 0.87836(9) 0.14757(2) 0.0416(6) Uani 1 1 d G A . H9AA H 0.6191 0.9271 0.1143 0.050 Uiso 1 1 calc R . . C10A C 0.55616(12) 0.96487(9) 0.18836(3) 0.0481(6) Uani 1 1 d G . . H10A H 0.5481 1.0723 0.1826 0.058 Uiso 1 1 calc R A . C11A C 0.52578(11) 0.89639(9) 0.23557(3) 0.0476(6) Uani 1 1 d G A . H11A H 0.4966 0.9564 0.2628 0.057 Uiso 1 1 calc R . . C12A C 0.53677(9) 0.73573(8) 0.24522(2) 0.0428(6) Uani 1 1 d G . . C13A C 0.58330(8) 0.64738(8) 0.20446(2) 0.0383(5) Uani 1 1 d G A . C14A C 0.60176(7) 0.49190(7) 0.216223(19) 0.0484(6) Uani 1 1 d G . . H14A H 0.6389 0.4340 0.1903 0.058 Uiso 1 1 calc R A . C15A C 0.56719(7) 0.42486(7) 0.263820(19) 0.0624(8) Uani 1 1 d G A . H15A H 0.5767 0.3186 0.2705 0.075 Uiso 1 1 calc R . . C16A C 0.51752(8) 0.51045(8) 0.30331(2) 0.0680(8) Uani 1 1 d G . . H16A H 0.4934 0.4619 0.3365 0.082 Uiso 1 1 calc R A . C17A C 0.50375(9) 0.66319(9) 0.29421(2) 0.0593(7) Uani 1 1 d G A . H17A H 0.4715 0.7211 0.3213 0.071 Uiso 1 1 calc R . . F1B F 1.12299(9) 0.17846(7) 0.408033(18) 0.0673(5) Uani 1 1 d G . . F2B F 0.80498(9) -0.01745(7) 0.39385(2) 0.0672(5) Uani 1 1 d G . . N1B N 0.91126(7) 0.26027(6) 0.354095(16) 0.0415(5) Uani 1 1 d G . . N2B N 0.94790(6) 0.33430(5) 0.308638(16) 0.0408(5) Uani 1 1 d G . . N3B N 0.99478(8) 0.02329(6) 0.32195(2) 0.0368(4) Uani 1 1 d G . . N4B N 1.04094(8) 0.41134(8) 0.184771(17) 0.0665(7) Uani 1 1 d G . . B1B B 0.95596(8) 0.11004(6) 0.372091(18) 0.0442(7) Uani 1 1 d G . . C1B C 1.02554(7) 0.34436(7) 0.223469(17) 0.0439(6) Uani 1 1 d G . . C2B C 1.00150(7) 0.25906(6) 0.271976(17) 0.0362(5) Uani 1 1 d G . . C3B C 1.02260(8) 0.09863(7) 0.275412(19) 0.0337(5) Uani 1 1 d G . . C4B C 1.06302(10) 0.01609(8) 0.23324(2) 0.0381(5) Uani 1 1 d G . . H4BA H 1.0838 0.0686 0.2005 0.046 Uiso 1 1 calc R . . C5B C 1.07252(11) -0.14141(8) 0.23944(2) 0.0411(6) Uani 1 1 d G . . H5BA H 1.0986 -0.1989 0.2109 0.049 Uiso 1 1 calc R . . C6B C 1.04417(11) -0.21566(8) 0.28704(2) 0.0443(6) Uani 1 1 d G . . H6BA H 1.0509 -0.3243 0.2917 0.053 Uiso 1 1 calc R . . C7B C 1.00623(10) -0.13132(7) 0.32760(2) 0.0438(6) Uani 1 1 d G . . H7BA H 0.9874 -0.1822 0.3606 0.053 Uiso 1 1 calc R . . C8B C 0.85179(8) 0.35405(7) 0.390808(16) 0.0439(6) Uani 1 1 d G . . C9B C 0.66526(9) 0.27532(8) 0.401715(19) 0.0540(7) Uani 1 1 d G . . H9BA H 0.5757 0.1599 0.3854 0.065 Uiso 1 1 calc R . . C10B C 0.60393(11) 0.36589(10) 0.43772(2) 0.0677(8) Uani 1 1 d G . . H10B H 0.4739 0.3100 0.4459 0.081 Uiso 1 1 calc R . . C11B C 0.73130(12) 0.53230(10) 0.460432(18) 0.0657(8) Uani 1 1 d G . . H11B H 0.6879 0.5935 0.4834 0.079 Uiso 1 1 calc R . . C12B C 0.92673(11) 0.61561(9) 0.450394(16) 0.0536(7) Uani 1 1 d G . . C13B C 0.98901(9) 0.52452(7) 0.414852(16) 0.0432(6) Uani 1 1 d G . . C14B C 1.18810(9) 0.60751(7) 0.406355(18) 0.0496(6) Uani 1 1 d G . . H14B H 1.2337 0.5468 0.3839 0.060 Uiso 1 1 calc R . . C15B C 1.31415(10) 0.77383(7) 0.43025(2) 0.0617(8) Uani 1 1 d G . . H15B H 1.4465 0.8287 0.4241 0.074 Uiso 1 1 calc R . . C16B C 1.24851(12) 0.86366(8) 0.46386(2) 0.0701(9) Uani 1 1 d G . . H16B H 1.3366 0.9801 0.4798 0.084 Uiso 1 1 calc R . . C17B C 1.06422(13) 0.78801(9) 0.473789(19) 0.0685(9) Uani 1 1 d G . . H17B H 1.0240 0.8512 0.4971 0.082 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 F1A 0.0897(15) 0.0298(10) 0.0640(13) 0.0092(9) 0.0383(11) 0.0217(10) F2A 0.0369(10) 0.0703(15) 0.0356(10) -0.0083(9) -0.0007(8) 0.0149(10) F1C 0.052(4) 0.025(3) 0.048(4) 0.001(3) 0.013(3) 0.011(3) F2C 0.078(5) 0.057(5) 0.043(4) 0.014(3) 0.011(4) 0.037(4) B1A 0.0475(17) 0.0386(16) 0.0398(17) -0.0062(13) 0.0068(14) 0.0173(14) N1A 0.0361(11) 0.0310(10) 0.0509(12) -0.0103(9) 0.0038(9) 0.0125(9) N2A 0.0401(11) 0.0326(10) 0.0434(11) -0.0042(9) -0.0053(9) 0.0182(9) N3A 0.0352(13) 0.0343(14) 0.0303(13) 0.0010(10) 0.0012(10) 0.0175(11) N4A 0.0783(17) 0.0375(13) 0.0666(16) -0.0015(11) 0.0032(13) 0.0235(12) C1A 0.0519(15) 0.0376(15) 0.0511(15) -0.0054(12) -0.0037(12) 0.0234(13) C2A 0.0432(14) 0.0345(14) 0.0726(18) -0.0157(13) 0.0042(13) 0.0150(12) C3A 0.0362(15) 0.0312(15) 0.0315(15) -0.0006(12) -0.0018(12) 0.0196(13) N3C 0.041(5) 0.033(5) 0.033(5) -0.004(4) 0.002(4) 0.018(4) C3C 0.045(6) 0.035(6) 0.027(5) -0.001(4) -0.003(4) 0.019(5) C4C 0.054(7) 0.036(6) 0.029(6) 0.003(4) 0.004(5) 0.023(5) C5C 0.0395(14) 0.0702(18) 0.0306(13) 0.0016(12) 0.0060(10) 0.0235(13) C6C 0.0462(14) 0.0654(17) 0.0343(13) -0.0030(12) 0.0005(11) 0.0343(13) C7C 0.051(7) 0.039(6) 0.029(6) 0.007(5) 0.010(5) 0.015(5) C4A 0.0445(17) 0.0397(17) 0.0365(17) -0.0024(13) -0.0025(13) 0.0254(14) C5A 0.0462(14) 0.0654(17) 0.0343(13) -0.0030(12) 0.0005(11) 0.0343(13) C6A 0.0395(14) 0.0702(18) 0.0306(13) 0.0016(12) 0.0060(10) 0.0235(13) C7A 0.0358(16) 0.0419(17) 0.0366(17) 0.0030(13) 0.0055(13) 0.0124(14) C8A 0.0294(12) 0.0339(12) 0.0414(13) -0.0064(10) 0.0014(10) 0.0141(10) C9A 0.0437(14) 0.0345(13) 0.0471(14) 0.0002(11) 0.0041(11) 0.0190(11) C10A 0.0501(15) 0.0410(14) 0.0595(17) -0.0030(12) 0.0048(12) 0.0272(12) C11A 0.0416(14) 0.0488(15) 0.0532(16) -0.0081(12) 0.0082(12) 0.0218(12) C12A 0.0331(12) 0.0434(14) 0.0448(14) 0.0004(11) 0.0043(10) 0.0121(11) C13A 0.0276(11) 0.0355(13) 0.0464(14) -0.0019(10) -0.0027(10) 0.0117(10) C14A 0.0481(15) 0.0405(14) 0.0524(16) 0.0029(12) -0.0049(12) 0.0190(12) C15A 0.0667(19) 0.0476(16) 0.0646(19) 0.0092(14) -0.0087(15) 0.0222(14) C16A 0.0641(19) 0.072(2) 0.0520(17) 0.0233(15) 0.0012(14) 0.0181(16) C17A 0.0514(16) 0.0677(19) 0.0487(16) 0.0047(14) 0.0104(13) 0.0182(14) F1B 0.0982(12) 0.0717(11) 0.0456(9) -0.0149(7) -0.0203(8) 0.0577(10) F2B 0.1018(13) 0.0507(9) 0.0634(10) 0.0203(8) 0.0420(9) 0.0407(9) N1B 0.0606(13) 0.0392(11) 0.0319(11) 0.0072(9) 0.0096(9) 0.0283(10) N2B 0.0559(12) 0.0357(11) 0.0326(11) 0.0063(8) 0.0054(9) 0.0225(10) N3B 0.0493(12) 0.0324(10) 0.0320(10) 0.0025(8) 0.0015(8) 0.0224(9) N4B 0.0978(19) 0.0624(15) 0.0448(14) 0.0188(12) 0.0189(13) 0.0391(14) B1B 0.0651(19) 0.0368(15) 0.0368(15) 0.0038(12) 0.0048(14) 0.0291(14) C1B 0.0565(16) 0.0374(13) 0.0376(14) 0.0047(11) 0.0095(11) 0.0207(12) C2B 0.0451(13) 0.0321(12) 0.0304(12) 0.0025(10) 0.0047(10) 0.0170(11) C3B 0.0347(12) 0.0326(12) 0.0308(12) 0.0024(9) 0.0016(9) 0.0136(10) C4B 0.0389(13) 0.0406(13) 0.0311(12) 0.0013(10) 0.0019(10) 0.0159(11) C5B 0.0438(14) 0.0427(14) 0.0387(13) -0.0058(11) -0.0019(11) 0.0236(11) C6B 0.0561(15) 0.0395(14) 0.0438(14) -0.0024(11) -0.0029(12) 0.0298(12) C7B 0.0588(16) 0.0397(14) 0.0407(14) 0.0057(11) 0.0024(11) 0.0300(12) C8B 0.0636(17) 0.0454(14) 0.0349(13) 0.0130(11) 0.0112(12) 0.0340(13) C9B 0.0621(17) 0.0594(17) 0.0528(16) 0.0164(13) 0.0180(13) 0.0359(15) C10B 0.083(2) 0.088(2) 0.0629(19) 0.0297(17) 0.0375(16) 0.0586(19) C11B 0.106(3) 0.077(2) 0.0462(17) 0.0168(15) 0.0283(16) 0.065(2) C12B 0.097(2) 0.0607(17) 0.0300(13) 0.0128(12) 0.0138(13) 0.0577(17) C13B 0.0713(17) 0.0417(14) 0.0277(12) 0.0089(10) 0.0061(11) 0.0352(13) C14B 0.0716(18) 0.0452(15) 0.0357(14) 0.0037(11) 0.0028(12) 0.0309(14) C15B 0.077(2) 0.0500(17) 0.0515(17) -0.0042(13) -0.0091(14) 0.0275(15) C16B 0.100(2) 0.0567(18) 0.0497(18) -0.0068(14) -0.0151(17) 0.0376(18) C17B 0.129(3) 0.064(2) 0.0341(15) -0.0016(13) -0.0001(17) 0.065(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 F1A B1A 1.419(3) . ? F2A B1A 1.351(3) . ? F1C B1A 1.296(6) . ? F2C B1A 1.208(7) . ? B1A N1A 1.537(3) . ? B1A N3A 1.593(3) . ? B1A N3C 1.691(3) . ? N1A N2A 1.325(2) . ? N1A C8A 1.4393(19) . ? N2A C2A 1.324(3) . ? N3A C7A 1.355(2) . ? N3A C3A 1.359(3) . ? N4A C1A 1.141(3) . ? C1A C2A 1.440(3) . ? C2A C3C 1.491(3) . ? C2A C3A 1.499(4) . ? C3A C4A 1.399(3) . ? N3C C7C 1.3381 . ? N3C C3C 1.3646 . ? C3C C4C 1.3991 . ? C4C C5C 1.3959 . ? C4C H4CA 0.9500 . ? C5C C6A 0.002(3) 2_765 ? C5C C5A 1.3756(19) 2_765 ? C5C C6C 1.3771 . ? C5C C7A 1.3899(11) 2_765 ? C5C H5CA 0.9500 . ? C6C C5A 0.002(3) 2_765 ? C6C C4A 1.3460(11) 2_765 ? C6C C6A 1.3784(19) 2_765 ? C6C C7C 1.5156 . ? C6C H6CA 0.9500 . ? C7C H7CA 0.9500 . ? C4A C5A 1.3463 . ? C4A C6C 1.3459(17) 2_765 ? C4A H4AA 0.9600 . ? C5A C6C 0.002(4) 2_765 ? C5A C5C 1.376(2) 2_765 ? C5A C6A 1.3770 . ? C5A H5AA 0.9600 . ? C6A C5C 0.002(4) 2_765 ? C6A C6C 1.378(2) 2_765 ? C6A C7A 1.3889 . ? C6A H6AA 0.9601 . ? C7A C5C 1.3899(15) 2_765 ? C7A H7AA 0.9601 . ? C8A C9A 1.3655 . ? C8A C13A 1.4258 . ? C9A C10A 1.4050 . ? C9A H9AA 0.9500 . ? C10A C11A 1.3475 . ? C10A H10A 0.9500 . ? C11A C12A 1.4212 . ? C11A H11A 0.9500 . ? C12A C17A 1.4035 . ? C12A C13A 1.4268 . ? C13A C14A 1.4188 . ? C14A C15A 1.3546 . ? C14A H14A 0.9500 . ? C15A C16A 1.4028 . ? C15A H15A 0.9500 . ? C16A C17A 1.3634 . ? C16A H16A 0.9500 . ? C17A H17A 0.9500 . ? F1B B1B 1.3863 . ? F2B B1B 1.3609 . ? N1B N2B 1.3279 . ? N1B C8B 1.4442 . ? N1B B1B 1.5304 . ? N2B C2B 1.3152 . ? N3B C3B 1.3537 . ? N3B C7B 1.3558 . ? N3B B1B 1.5743 . ? N4B C1B 1.1423 . ? C1B C2B 1.4362 . ? C2B C3B 1.4374 . ? C3B C4B 1.3990 . ? C4B C5B 1.3743 . ? C4B H4BA 0.9500 . ? C5B C6B 1.3749 . ? C5B H5BA 0.9500 . ? C6B C7B 1.3661 . ? C6B H6BA 0.9500 . ? C7B H7BA 0.9500 . ? C8B C9B 1.3560 . ? C8B C13B 1.4115 . ? C9B C10B 1.4234 . ? C9B H9BA 0.9500 . ? C10B C11B 1.3595 . ? C10B H10B 0.9500 . ? C11B C12B 1.4096 . ? C11B H11B 0.9500 . ? C12B C17B 1.4174 . ? C12B C13B 1.4234 . ? C13B C14B 1.4234 . ? C14B C15B 1.3669 . ? C14B H14B 0.9500 . ? C15B C16B 1.4019 . ? C15B H15B 0.9500 . ? C16B C17B 1.3329 . ? C16B H16B 0.9500 . ? C17B H17B 0.9500 . ? 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 F2C B1A F1C 129.7(5) . . ? F2C B1A F2A 147.7(4) . . ? F1C B1A F2A 49.4(3) . . ? F2C B1A F1A 66.5(4) . . ? F1C B1A F1A 64.8(3) . . ? F2A B1A F1A 109.4(2) . . ? F2C B1A N1A 98.8(4) . . ? F1C B1A N1A 111.1(3) . . ? F2A B1A N1A 111.3(2) . . ? F1A B1A N1A 113.4(2) . . ? F2C B1A N3A 48.2(3) . . ? F1C B1A N3A 139.1(4) . . ? F2A B1A N3A 108.2(2) . . ? F1A B1A N3A 105.1(2) . . ? N1A B1A N3A 109.1(2) . . ? F2C B1A N3C 109.4(4) . . ? F1C B1A N3C 105.1(4) . . ? F2A B1A N3C 55.92(15) . . ? F1A B1A N3C 148.0(2) . . ? N1A B1A N3C 98.59(17) . . ? N3A B1A N3C 61.45(13) . . ? N2A N1A C8A 114.40(16) . . ? N2A N1A B1A 122.95(18) . . ? C8A N1A B1A 121.82(16) . . ? C2A N2A N1A 118.1(2) . . ? C7A N3A C3A 119.4(2) . . ? C7A N3A B1A 121.29(19) . . ? C3A N3A B1A 119.0(2) . . ? N4A C1A C2A 177.1(3) . . ? N2A C2A C1A 114.2(2) . . ? N2A C2A C3C 111.63(19) . . ? C1A C2A C3C 105.77(18) . . ? N2A C2A C3A 125.9(2) . . ? C1A C2A C3A 118.7(2) . . ? C3C C2A C3A 64.09(14) . . ? N3A C3A C4A 120.6(2) . . ? N3A C3A C2A 116.0(2) . . ? C4A C3A C2A 123.4(2) . . ? C7C N3C C3C 121.1 . . ? C7C N3C B1A 115.25(10) . . ? C3C N3C B1A 122.63(10) . . ? N3C C3C C4C 120.0 . . ? N3C C3C C2A 110.46(9) . . ? C4C C3C C2A 127.79(9) . . ? C5C C4C C3C 127.7 . . ? C5C C4C H4CA 116.1 . . ? C3C C4C H4CA 116.1 . . ? C6A C5C C5A 141(10) 2_765 2_765 ? C6A C5C C6C 141(10) 2_765 . ? C5A C5C C6C 0.04(8) 2_765 . ? C6A C5C C7A 56(10) 2_765 2_765 ? C5A C5C C7A 121.41(10) 2_765 2_765 ? C6C C5C C7A 121.43(9) . 2_765 ? C6A C5C C4C 50(10) 2_765 . ? C5A C5C C4C 107.64(6) 2_765 . ? C6C C5C C4C 107.7 . . ? C7A C5C C4C 105.04(9) 2_765 . ? C6A C5C H5CA 83.4 2_765 . ? C5A C5C H5CA 126.2 2_765 . ? C6C C5C H5CA 126.2 . . ? C7A C5C H5CA 48.6 2_765 . ? C4C C5C H5CA 126.2 . . ? C5A C6C C4A 98(10) 2_765 2_765 ? C5A C6C C5C 36(10) 2_765 . ? C4A C6C C5C 118.10(9) 2_765 . ? C5A C6C C6A 36(10) 2_765 2_765 ? C4A C6C C6A 118.08(9) 2_765 2_765 ? C5C C6C C6A 0.04(8) . 2_765 ? C5A C6C C7C 106(10) 2_765 . ? C4A C6C C7C 95.22(7) 2_765 . ? C5C C6C C7C 128.8 . . ? C6A C6C C7C 128.74(6) 2_765 . ? C5A C6C H6CA 127.0 2_765 . ? C4A C6C H6CA 49.5 2_765 . ? C5C C6C H6CA 115.6 . . ? C6A C6C H6CA 115.6 2_765 . ? C7C C6C H6CA 115.6 . . ? N3C C7C C6C 114.5 . . ? N3C C7C H7CA 122.7 . . ? C6C C7C H7CA 122.7 . . ? C5A C4A C6C 0.08(14) . 2_765 ? C5A C4A C3A 120.71(12) . . ? C6C C4A C3A 120.77(16) 2_765 . ? C5A C4A H4AA 119.6 . . ? C6C C4A H4AA 119.6 2_765 . ? C3A C4A H4AA 119.7 . . ? C6C C5A C4A 80(10) 2_765 . ? C6C C5A C5C 144(10) 2_765 2_765 ? C4A C5A C5C 118.2 . 2_765 ? C6C C5A C6A 144(10) 2_765 . ? C4A C5A C6A 118.2 . . ? C5C C5A C6A 0.04(9) 2_765 . ? C6C C5A H5AA 51.6 2_765 . ? C4A C5A H5AA 120.9 . . ? C5C C5A H5AA 120.9 2_765 . ? C6A C5A H5AA 120.9 . . ? C5C C6A C5A 37(10) 2_765 . ? C5C C6A C6C 36(10) 2_765 2_765 ? C5A C6A C6C 0.04(8) . 2_765 ? C5C C6A C7A 126(10) 2_765 . ? C5A C6A C7A 121.4 . . ? C6C C6A C7A 121.4 2_765 . ? C5C C6A H6AA 102.3 2_765 . ? C5A C6A H6AA 119.3 . . ? C6C C6A H6AA 119.3 2_765 . ? C7A C6A H6AA 119.3 . . ? N3A C7A C6A 119.71(10) . . ? N3A C7A C5C 119.67(15) . 2_765 ? C6A C7A C5C 0.06(13) . 2_765 ? N3A C7A H7AA 120.2 . . ? C6A C7A H7AA 120.1 . . ? C5C C7A H7AA 120.2 2_765 . ? C9A C8A C13A 120.9 . . ? C9A C8A N1A 117.38(8) . . ? C13A C8A N1A 121.76(8) . . ? C8A C9A C10A 120.8 . . ? C8A C9A H9AA 119.6 . . ? C10A C9A H9AA 119.6 . . ? C11A C10A C9A 120.4 . . ? C11A C10A H10A 119.8 . . ? C9A C10A H10A 119.8 . . ? C10A C11A C12A 121.0 . . ? C10A C11A H11A 119.5 . . ? C12A C11A H11A 119.5 . . ? C17A C12A C11A 121.1 . . ? C17A C12A C13A 119.5 . . ? C11A C12A C13A 119.4 . . ? C14A C13A C8A 124.5 . . ? C14A C13A C12A 117.9 . . ? C8A C13A C12A 117.7 . . ? C15A C14A C13A 120.9 . . ? C15A C14A H14A 119.5 . . ? C13A C14A H14A 119.5 . . ? C14A C15A C16A 120.8 . . ? C14A C15A H15A 119.6 . . ? C16A C15A H15A 119.6 . . ? C17A C16A C15A 120.2 . . ? C17A C16A H16A 119.9 . . ? C15A C16A H16A 119.9 . . ? C16A C17A C12A 120.7 . . ? C16A C17A H17A 119.7 . . ? C12A C17A H17A 119.7 . . ? N2B N1B C8B 113.5 . . ? N2B N1B B1B 125.7 . . ? C8B N1B B1B 120.1 . . ? C2B N2B N1B 118.8 . . ? C3B N3B C7B 120.1 . . ? C3B N3B B1B 123.2 . . ? C7B N3B B1B 116.7 . . ? F2B B1B F1B 109.7 . . ? F2B B1B N1B 111.5 . . ? F1B B1B N1B 110.7 . . ? F2B B1B N3B 109.6 . . ? F1B B1B N3B 107.8 . . ? N1B B1B N3B 107.4 . . ? N4B C1B C2B 178.7 . . ? N2B C2B C1B 113.8 . . ? N2B C2B C3B 126.3 . . ? C1B C2B C3B 119.7 . . ? N3B C3B C4B 119.7 . . ? N3B C3B C2B 116.7 . . ? C4B C3B C2B 123.6 . . ? C5B C4B C3B 119.6 . . ? C5B C4B H4BA 120.2 . . ? C3B C4B H4BA 120.2 . . ? C4B C5B C6B 119.9 . . ? C4B C5B H5BA 120.1 . . ? C6B C5B H5BA 120.1 . . ? C7B C6B C5B 119.2 . . ? C7B C6B H6BA 120.4 . . ? C5B C6B H6BA 120.4 . . ? N3B C7B C6B 121.6 . . ? N3B C7B H7BA 119.2 . . ? C6B C7B H7BA 119.2 . . ? C9B C8B C13B 121.5 . . ? C9B C8B N1B 119.1 . . ? C13B C8B N1B 119.4 . . ? C8B C9B C10B 119.9 . . ? C8B C9B H9BA 120.1 . . ? C10B C9B H9BA 120.1 . . ? C11B C10B C9B 120.1 . . ? C11B C10B H10B 120.0 . . ? C9B C10B H10B 120.0 . . ? C10B C11B C12B 121.1 . . ? C10B C11B H11B 119.5 . . ? C12B C11B H11B 119.5 . . ? C11B C12B C17B 122.7 . . ? C11B C12B C13B 119.0 . . ? C17B C12B C13B 118.3 . . ? C8B C13B C14B 123.1 . . ? C8B C13B C12B 118.5 . . ? C14B C13B C12B 118.4 . . ? C15B C14B C13B 120.5 . . ? C15B C14B H14B 119.7 . . ? C13B C14B H14B 119.7 . . ? C14B C15B C16B 120.1 . . ? C14B C15B H15B 119.9 . . ? C16B C15B H15B 119.9 . . ? C17B C16B C15B 120.9 . . ? C17B C16B H16B 119.5 . . ? C15B C16B H16B 119.5 . . ? C16B C17B C12B 121.6 . . ? C16B C17B H17B 119.2 . . ? C12B C17B H17B 119.2 . . ? 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 F2C B1A N1A N2A 79.2(4) . . . . ? F1C B1A N1A N2A -142.0(4) . . . . ? F2A B1A N1A N2A -88.8(3) . . . . ? F1A B1A N1A N2A 147.3(2) . . . . ? N3A B1A N1A N2A 30.6(3) . . . . ? N3C B1A N1A N2A -32.1(3) . . . . ? F2C B1A N1A C8A -111.8(4) . . . . ? F1C B1A N1A C8A 27.0(5) . . . . ? F2A B1A N1A C8A 80.2(3) . . . . ? F1A B1A N1A C8A -43.7(3) . . . . ? N3A B1A N1A C8A -160.46(17) . . . . ? N3C B1A N1A C8A 136.88(15) . . . . ? C8A N1A N2A C2A 179.31(18) . . . . ? B1A N1A N2A C2A -11.0(3) . . . . ? F2C B1A N3A C7A 73.1(5) . . . . ? F1C B1A N3A C7A -32.9(7) . . . . ? F2A B1A N3A C7A -81.0(3) . . . . ? F1A B1A N3A C7A 35.8(3) . . . . ? N1A B1A N3A C7A 157.78(19) . . . . ? N3C B1A N3A C7A -112.7(2) . . . . ? F2C B1A N3A C3A -113.1(5) . . . . ? F1C B1A N3A C3A 140.9(6) . . . . ? F2A B1A N3A C3A 92.8(3) . . . . ? F1A B1A N3A C3A -150.4(2) . . . . ? N1A B1A N3A C3A -28.4(3) . . . . ? N3C B1A N3A C3A 61.1(2) . . . . ? N1A N2A C2A C1A 178.6(2) . . . . ? N1A N2A C2A C3C 58.7(3) . . . . ? N1A N2A C2A C3A -14.3(4) . . . . ? N4A C1A C2A N2A 180(100) . . . . ? N4A C1A C2A C3C -57(6) . . . . ? N4A C1A C2A C3A 12(6) . . . . ? C7A N3A C3A C4A 2.0(3) . . . . ? B1A N3A C3A C4A -171.9(2) . . . . ? C7A N3A C3A C2A -176.92(19) . . . . ? B1A N3A C3A C2A 9.2(3) . . . . ? N2A C2A C3A N3A 14.7(4) . . . . ? C1A C2A C3A N3A -178.7(2) . . . . ? C3C C2A C3A N3A -84.2(2) . . . . ? N2A C2A C3A C4A -164.2(2) . . . . ? C1A C2A C3A C4A 2.5(4) . . . . ? C3C C2A C3A C4A 97.0(2) . . . . ? F2C B1A N3C C7C 101.6(4) . . . . ? F1C B1A N3C C7C -41.2(3) . . . . ? F2A B1A N3C C7C -45.87(15) . . . . ? F1A B1A N3C C7C 25.1(5) . . . . ? N1A B1A N3C C7C -155.83(11) . . . . ? N3A B1A N3C C7C 97.01(12) . . . . ? F2C B1A N3C C3C -67.0(4) . . . . ? F1C B1A N3C C3C 150.2(3) . . . . ? F2A B1A N3C C3C 145.50(10) . . . . ? F1A B1A N3C C3C -143.5(4) . . . . ? N1A B1A N3C C3C 35.5(2) . . . . ? N3A B1A N3C C3C -71.63(14) . . . . ? C7C N3C C3C C4C -0.6 . . . . ? B1A N3C C3C C4C 167.36(12) . . . . ? C7C N3C C3C C2A -166.59(12) . . . . ? B1A N3C C3C C2A 1.40(17) . . . . ? N2A C2A C3C N3C -50.6(2) . . . . ? C1A C2A C3C N3C -175.34(15) . . . . ? C3A C2A C3C N3C 69.95(14) . . . . ? N2A C2A C3C C4C 144.84(13) . . . . ? C1A C2A C3C C4C 20.1(3) . . . . ? C3A C2A C3C C4C -94.63(15) . . . . ? N3C C3C C4C C5C 4.5 . . . . ? C2A C3C C4C C5C 167.76(14) . . . . ? C3C C4C C5C C6A -150(92) . . . 2_765 ? C3C C4C C5C C5A -6.2 . . . 2_765 ? C3C C4C C5C C6C -6.2 . . . . ? C3C C4C C5C C7A -136.86(7) . . . 2_765 ? C6A C5C C6C C5A -10(24) 2_765 . . 2_765 ? C7A C5C C6C C5A 64(94) 2_765 . . 2_765 ? C4C C5C C6C C5A -57(71) . . . 2_765 ? C6A C5C C6C C4A -72(100) 2_765 . . 2_765 ? C5A C5C C6C C4A -62(94) 2_765 . . 2_765 ? C7A C5C C6C C4A 1.9 2_765 . . 2_765 ? C4C C5C C6C C4A -119.02(8) . . . 2_765 ? C5A C5C C6C C6A 10(23) 2_765 . . 2_765 ? C7A C5C C6C C6A 74(100) 2_765 . . 2_765 ? C4C C5C C6C C6A -47(77) . . . 2_765 ? C6A C5C C6C C7C 52(77) 2_765 . . . ? C5A C5C C6C C7C 62(71) 2_765 . . . ? C7A C5C C6C C7C 126.02(8) 2_765 . . . ? C4C C5C C6C C7C 5.1 . . . . ? C3C N3C C7C C6C -0.3 . . . . ? B1A N3C C7C C6C -169.15(11) . . . . ? C5A C6C C7C N3C 31(62) 2_765 . . . ? C4A C6C C7C N3C 130.50(9) 2_765 . . . ? C5C C6C C7C N3C -2.3 . . . . ? C6A C6C C7C N3C -2.29(5) 2_765 . . . ? N3A C3A C4A C5A -1.4(3) . . . . ? C2A C3A C4A C5A 177.41(17) . . . . ? N3A C3A C4A C6C -1.5(3) . . . 2_765 ? C2A C3A C4A C6C 177.36(19) . . . 2_765 ? C3A C4A C5A C6C -146(100) . . . 2_765 ? C6C C4A C5A C5C 147(100) 2_765 . . 2_765 ? C3A C4A C5A C5C 1.30(13) . . . 2_765 ? C6C C4A C5A C6A 147(100) 2_765 . . . ? C3A C4A C5A C6A 1.34(13) . . . . ? C6C C5A C6A C5C 2(22) 2_765 . . 2_765 ? C4A C5A C6A C5C -112(100) . . . 2_765 ? C4A C5A C6A C6C -114(100) . . . 2_765 ? C5C C5A C6A C6C -2(22) 2_765 . . 2_765 ? C6C C5A C6A C7A 112(100) 2_765 . . . ? C4A C5A C6A C7A -1.9 . . . . ? C5C C5A C6A C7A 110(100) 2_765 . . . ? C3A N3A C7A C6A -2.5(3) . . . . ? B1A N3A C7A C6A 171.24(17) . . . . ? C3A N3A C7A C5C -2.5(3) . . . 2_765 ? B1A N3A C7A C5C 171.29(19) . . . 2_765 ? C5C C6A C7A N3A 47(100) 2_765 . . . ? C5A C6A C7A N3A 2.52(11) . . . . ? C6C C6A C7A N3A 2.57(12) 2_765 . . . ? C5A C6A C7A C5C -44(100) . . . 2_765 ? C6C C6A C7A C5C -44(100) 2_765 . . 2_765 ? N2A N1A C8A C9A -134.50(14) . . . . ? B1A N1A C8A C9A 55.6(2) . . . . ? N2A N1A C8A C13A 46.69(18) . . . . ? B1A N1A C8A C13A -123.16(18) . . . . ? C13A C8A C9A C10A 0.9 . . . . ? N1A C8A C9A C10A -177.87(8) . . . . ? C8A C9A C10A C11A -0.8 . . . . ? C9A C10A C11A C12A -0.1 . . . . ? C10A C11A C12A C17A -179.5 . . . . ? C10A C11A C12A C13A 0.9 . . . . ? C9A C8A C13A C14A -177.9 . . . . ? N1A C8A C13A C14A 0.84(9) . . . . ? C9A C8A C13A C12A -0.2 . . . . ? N1A C8A C13A C12A 178.62(9) . . . . ? C17A C12A C13A C14A -2.5 . . . . ? C11A C12A C13A C14A 177.2 . . . . ? C17A C12A C13A C8A 179.6 . . . . ? C11A C12A C13A C8A -0.7 . . . . ? C8A C13A C14A C15A -179.2 . . . . ? C12A C13A C14A C15A 3.1 . . . . ? C13A C14A C15A C16A -1.8 . . . . ? C14A C15A C16A C17A -0.1 . . . . ? C15A C16A C17A C12A 0.7 . . . . ? C11A C12A C17A C16A -179.0 . . . . ? C13A C12A C17A C16A 0.6 . . . . ? C8B N1B N2B C2B -179.4 . . . . ? B1B N1B N2B C2B 10.3 . . . . ? N2B N1B B1B F2B -136.1 . . . . ? C8B N1B B1B F2B 54.2 . . . . ? N2B N1B B1B F1B 101.5 . . . . ? C8B N1B B1B F1B -68.2 . . . . ? N2B N1B B1B N3B -16.0 . . . . ? C8B N1B B1B N3B 174.3 . . . . ? C3B N3B B1B F2B 133.8 . . . . ? C7B N3B B1B F2B -48.4 . . . . ? C3B N3B B1B F1B -106.8 . . . . ? C7B N3B B1B F1B 71.0 . . . . ? C3B N3B B1B N1B 12.6 . . . . ? C7B N3B B1B N1B -169.6 . . . . ? N1B N2B C2B C1B 176.4 . . . . ? N1B N2B C2B C3B 1.1 . . . . ? N4B C1B C2B N2B -63.0 . . . . ? N4B C1B C2B C3B 112.7 . . . . ? C7B N3B C3B C4B 0.0 . . . . ? B1B N3B C3B C4B 177.8 . . . . ? C7B N3B C3B C2B 177.9 . . . . ? B1B N3B C3B C2B -4.3 . . . . ? N2B C2B C3B N3B -3.8 . . . . ? C1B C2B C3B N3B -178.9 . . . . ? N2B C2B C3B C4B 174.0 . . . . ? C1B C2B C3B C4B -1.1 . . . . ? N3B C3B C4B C5B 0.5 . . . . ? C2B C3B C4B C5B -177.2 . . . . ? C3B C4B C5B C6B -0.6 . . . . ? C4B C5B C6B C7B 0.2 . . . . ? C3B N3B C7B C6B -0.5 . . . . ? B1B N3B C7B C6B -178.4 . . . . ? C5B C6B C7B N3B 0.4 . . . . ? N2B N1B C8B C9B 110.2 . . . . ? B1B N1B C8B C9B -78.9 . . . . ? N2B N1B C8B C13B -70.3 . . . . ? B1B N1B C8B C13B 100.6 . . . . ? C13B C8B C9B C10B 0.7 . . . . ? N1B C8B C9B C10B -179.9 . . . . ? C8B C9B C10B C11B 1.1 . . . . ? C9B C10B C11B C12B -2.2 . . . . ? C10B C11B C12B C17B -179.3 . . . . ? C10B C11B C12B C13B 1.5 . . . . ? C9B C8B C13B C14B 176.9 . . . . ? N1B C8B C13B C14B -2.6 . . . . ? C9B C8B C13B C12B -1.3 . . . . ? N1B C8B C13B C12B 179.2 . . . . ? C11B C12B C13B C8B 0.3 . . . . ? C17B C12B C13B C8B -179.0 . . . . ? C11B C12B C13B C14B -178.0 . . . . ? C17B C12B C13B C14B 2.7 . . . . ? C8B C13B C14B C15B 179.3 . . . . ? C12B C13B C14B C15B -2.5 . . . . ? C13B C14B C15B C16B 0.6 . . . . ? C14B C15B C16B C17B 1.1 . . . . ? C15B C16B C17B C12B -0.9 . . . . ? C11B C12B C17B C16B 179.7 . . . . ? C13B C12B C17B C16B -1.1 . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.368 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.039 _contact_Crystallographer_name 'Richard Staples' _contact_Crystallographer_email staples@chemistry.msu.com