# Electronic Supplementary Material (ESI) for Analyst # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'The Analyst' _journal_coden_cambridge 0091 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Pinaki Talukdar' _publ_contact_author_email 'ptalukdar@iiserpune.ac.in, ptalukdar@gmail.com' loop_ _publ_author_name 'Dnyaneshwar Kand' 'Pratyush Mishra' 'Pinaki Talukdar' data_trail2 _database_code_depnum_ccdc_archive 'CCDC 863628' #TrackingRef '- 05 Analyst Talukdar CCDC 863628.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety C16H12BF2N3 _chemical_formula_sum 'C16 H12 B F2 N3' _chemical_formula_weight 295.10 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' 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 P21/c 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 15.746(3) _cell_length_b 8.9776(18) _cell_length_c 10.2886(19) _cell_angle_alpha 90.00 _cell_angle_beta 99.120(4) _cell_angle_gamma 90.00 _cell_volume 1436.1(5) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needles _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.035 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.365 _exptl_crystal_density_method calcd _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9652 _exptl_absorpt_correction_T_max 0.9965 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 9884 _diffrn_reflns_av_R_equivalents 0.0430 _diffrn_reflns_av_sigmaI/netI 0.0571 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.31 _diffrn_reflns_theta_max 28.49 _reflns_number_total 3567 _reflns_number_gt 1835 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0981P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.038(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3567 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1222 _refine_ls_R_factor_gt 0.0589 _refine_ls_wR_factor_ref 0.1907 _refine_ls_wR_factor_gt 0.1476 _refine_ls_goodness_of_fit_ref 0.990 _refine_ls_restrained_S_all 0.990 _refine_ls_shift/su_max 0.035 _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 B1 B 0.10172(19) 0.4684(3) 0.7099(3) 0.0498(7) Uani 1 1 d . . . C1 C 0.54563(18) 0.0553(4) 1.2076(3) 0.0719(9) Uani 1 1 d . . . H1A H 0.5254 -0.0066 1.2724 0.108 Uiso 1 1 calc R . . H1B H 0.5817 0.1326 1.2509 0.108 Uiso 1 1 calc R . . H1C H 0.5780 -0.0040 1.1552 0.108 Uiso 1 1 calc R . . F1 F 0.02393(9) 0.46586(18) 0.75936(18) 0.0770(6) Uani 1 1 d . . . N1 N 0.17032(13) 0.5481(2) 0.8048(2) 0.0494(6) Uani 1 1 d . . . C2 C 0.24082(15) 0.4825(2) 0.8799(2) 0.0427(6) Uani 1 1 d . . . F2 F 0.08742(12) 0.53709(18) 0.58764(16) 0.0793(6) Uani 1 1 d . . . N2 N 0.13299(11) 0.3083(2) 0.69581(18) 0.0419(5) Uani 1 1 d . . . C3 C 0.25578(14) 0.3257(2) 0.8700(2) 0.0387(5) Uani 1 1 d . . . N3 N 0.03596(13) 0.2287(3) 0.5094(2) 0.0597(6) Uani 1 1 d . . . H3A H 0.0124 0.3152 0.4992 0.072 Uiso 1 1 calc R . . H3B H 0.0179 0.1576 0.4560 0.072 Uiso 1 1 calc R . . C4 C 0.32918(14) 0.2562(2) 0.9562(2) 0.0399(5) Uani 1 1 d . . . C5 C 0.31772(15) 0.1340(3) 1.0344(2) 0.0442(6) Uani 1 1 d . . . H5 H 0.2628 0.0954 1.0333 0.053 Uiso 1 1 calc R . . C6 C 0.38707(17) 0.0687(3) 1.1142(2) 0.0501(7) Uani 1 1 d . . . H6 H 0.3779 -0.0139 1.1646 0.060 Uiso 1 1 calc R . . C7 C 0.46982(16) 0.1243(3) 1.1202(2) 0.0510(7) Uani 1 1 d . . . C8 C 0.16862(19) 0.6935(3) 0.8411(3) 0.0674(8) Uani 1 1 d . . . H8 H 0.1270 0.7625 0.8067 0.081 Uiso 1 1 calc R . . C9 C 0.2378(2) 0.7224(3) 0.9365(3) 0.0709(9) Uani 1 1 d . . . H9 H 0.2518 0.8138 0.9768 0.085 Uiso 1 1 calc R . . C10 C 0.28354(17) 0.5900(3) 0.9621(3) 0.0547(7) Uani 1 1 d . . . H10 H 0.3333 0.5764 1.0228 0.066 Uiso 1 1 calc R . . C11 C 0.48064(16) 0.2460(3) 1.0422(2) 0.0535(7) Uani 1 1 d . . . H11 H 0.5355 0.2851 1.0440 0.064 Uiso 1 1 calc R . . C12 C 0.41219(15) 0.3111(3) 0.9618(2) 0.0505(6) Uani 1 1 d . . . H12 H 0.4218 0.3929 0.9105 0.061 Uiso 1 1 calc R . . C13 C 0.20259(14) 0.2429(2) 0.7800(2) 0.0396(5) Uani 1 1 d . . . C14 C 0.10048(14) 0.2047(3) 0.6078(2) 0.0451(6) Uani 1 1 d . . . C15 C 0.14614(16) 0.0681(3) 0.6352(2) 0.0482(6) Uani 1 1 d . . . H15 H 0.1352 -0.0209 0.5893 0.058 Uiso 1 1 calc R . . C16 C 0.20762(15) 0.0916(3) 0.7391(2) 0.0454(6) Uani 1 1 d . . . H16 H 0.2469 0.0211 0.7780 0.055 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 0.0429(16) 0.0467(16) 0.0566(18) 0.0076(14) -0.0023(14) 0.0074(12) C1 0.0610(18) 0.102(2) 0.0481(16) 0.0011(16) -0.0069(14) 0.0284(16) F1 0.0448(10) 0.0706(11) 0.1159(15) -0.0100(10) 0.0139(9) 0.0104(7) N1 0.0470(12) 0.0394(10) 0.0586(13) 0.0065(10) -0.0018(10) 0.0040(9) C2 0.0386(13) 0.0439(13) 0.0446(13) 0.0049(11) 0.0039(10) 0.0008(10) F2 0.0913(13) 0.0635(10) 0.0708(11) 0.0237(9) -0.0248(9) 0.0017(9) N2 0.0328(10) 0.0458(11) 0.0452(11) 0.0041(9) 0.0006(8) 0.0019(8) C3 0.0347(12) 0.0446(12) 0.0361(12) 0.0049(10) 0.0033(9) 0.0032(9) N3 0.0512(13) 0.0605(13) 0.0599(14) -0.0013(11) -0.0146(11) -0.0004(10) C4 0.0362(12) 0.0469(12) 0.0357(12) 0.0011(10) 0.0034(10) 0.0042(10) C5 0.0404(13) 0.0474(13) 0.0446(13) 0.0028(11) 0.0059(11) 0.0060(10) C6 0.0587(16) 0.0519(14) 0.0394(13) 0.0063(11) 0.0068(12) 0.0129(12) C7 0.0453(14) 0.0688(17) 0.0361(13) -0.0051(13) -0.0022(11) 0.0182(12) C8 0.0694(19) 0.0377(14) 0.089(2) 0.0049(14) -0.0063(16) 0.0048(12) C9 0.077(2) 0.0439(15) 0.088(2) -0.0021(15) -0.0002(17) -0.0068(14) C10 0.0493(15) 0.0486(14) 0.0628(17) 0.0028(13) -0.0017(13) -0.0081(11) C11 0.0338(13) 0.0734(17) 0.0514(15) 0.0024(14) 0.0006(11) 0.0023(12) C12 0.0421(14) 0.0614(16) 0.0472(14) 0.0072(12) 0.0049(11) 0.0007(12) C13 0.0332(12) 0.0457(12) 0.0389(12) 0.0072(10) 0.0030(10) 0.0039(9) C14 0.0341(12) 0.0539(14) 0.0463(14) 0.0025(12) 0.0029(10) -0.0045(10) C15 0.0444(14) 0.0452(13) 0.0545(15) -0.0054(12) 0.0062(12) -0.0008(11) C16 0.0423(13) 0.0437(13) 0.0502(14) 0.0007(11) 0.0070(11) 0.0059(10) _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 1.386(3) . ? B1 F1 1.399(3) . ? B1 N1 1.516(3) . ? B1 N2 1.534(3) . ? C1 C7 1.509(3) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? N1 C8 1.359(3) . ? N1 C2 1.380(3) . ? C2 C10 1.386(3) . ? C2 C3 1.433(3) . ? N2 C14 1.341(3) . ? N2 C13 1.413(3) . ? C3 C13 1.366(3) . ? C3 C4 1.479(3) . ? N3 C14 1.334(3) . ? N3 H3A 0.8600 . ? N3 H3B 0.8600 . ? C4 C12 1.389(3) . ? C4 C5 1.389(3) . ? C5 C6 1.388(3) . ? C5 H5 0.9300 . ? C6 C7 1.387(4) . ? C6 H6 0.9300 . ? C7 C11 1.382(4) . ? C8 C9 1.371(4) . ? C8 H8 0.9300 . ? C9 C10 1.392(4) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.381(3) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C16 1.428(3) . ? C14 C15 1.427(3) . ? C15 C16 1.340(3) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag F2 B1 F1 108.2(2) . . ? F2 B1 N1 111.8(2) . . ? F1 B1 N1 110.4(2) . . ? F2 B1 N2 109.8(2) . . ? F1 B1 N2 109.3(2) . . ? N1 B1 N2 107.25(19) . . ? C7 C1 H1A 109.5 . . ? C7 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C7 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C8 N1 C2 107.8(2) . . ? C8 N1 B1 126.0(2) . . ? C2 N1 B1 125.9(2) . . ? N1 C2 C10 108.3(2) . . ? N1 C2 C3 120.4(2) . . ? C10 C2 C3 131.2(2) . . ? C14 N2 C13 107.56(18) . . ? C14 N2 B1 128.28(19) . . ? C13 N2 B1 124.1(2) . . ? C13 C3 C2 119.5(2) . . ? C13 C3 C4 120.9(2) . . ? C2 C3 C4 119.6(2) . . ? C14 N3 H3A 120.0 . . ? C14 N3 H3B 120.0 . . ? H3A N3 H3B 120.0 . . ? C12 C4 C5 117.6(2) . . ? C12 C4 C3 121.1(2) . . ? C5 C4 C3 121.3(2) . . ? C6 C5 C4 120.9(2) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C7 C6 C5 121.3(2) . . ? C7 C6 H6 119.3 . . ? C5 C6 H6 119.3 . . ? C11 C7 C6 117.4(2) . . ? C11 C7 C1 120.8(3) . . ? C6 C7 C1 121.8(3) . . ? N1 C8 C9 109.3(2) . . ? N1 C8 H8 125.3 . . ? C9 C8 H8 125.3 . . ? C8 C9 C10 107.6(2) . . ? C8 C9 H9 126.2 . . ? C10 C9 H9 126.2 . . ? C2 C10 C9 107.0(2) . . ? C2 C10 H10 126.5 . . ? C9 C10 H10 126.5 . . ? C12 C11 C7 121.8(2) . . ? C12 C11 H11 119.1 . . ? C7 C11 H11 119.1 . . ? C11 C12 C4 121.0(2) . . ? C11 C12 H12 119.5 . . ? C4 C12 H12 119.5 . . ? C3 C13 N2 121.5(2) . . ? C3 C13 C16 131.4(2) . . ? N2 C13 C16 106.77(19) . . ? N3 C14 N2 124.3(2) . . ? N3 C14 C15 126.0(2) . . ? N2 C14 C15 109.7(2) . . ? C16 C15 C14 107.4(2) . . ? C16 C15 H15 126.3 . . ? C14 C15 H15 126.3 . . ? C15 C16 C13 108.5(2) . . ? C15 C16 H16 125.7 . . ? C13 C16 H16 125.7 . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 28.49 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.350 _refine_diff_density_min -0.304 _refine_diff_density_rms 0.111