# Electronic Supplementary Material (ESI) for Analyst # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'The Analyst' _journal_coden_cambridge 0091 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name P.Chattopadhyay 'Sandipan Sarkar' _publ_contact_author_name 'Pabitra Chattopadhyay' _publ_contact_author_email pabitracc@yahoo.com data_2 _database_code_depnum_ccdc_archive 'CCDC 651980' #TrackingRef 'PC-7-cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety C19H14N4 _chemical_formula_sum C19H14N4 _chemical_formula_weight 298.34 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' _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 8.724(11) _cell_length_b 13.085(15) _cell_length_c 13.323(15) _cell_angle_alpha 90.00 _cell_angle_beta 97.447(10) _cell_angle_gamma 90.00 _cell_volume 1508(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description parallelopiped _exptl_crystal_colour white _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.314 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ? _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type Mo _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_standards_number ? _diffrn_measurement_device 'Marresearch Image Plate' _diffrn_measurement_method '95 frames at 2^o intervals, counting time 2 min.' _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7514 _diffrn_reflns_av_R_equivalents 0.0365 _diffrn_reflns_av_sigmaI/netI 0.0408 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 25.75 _reflns_number_total 2829 _reflns_number_gt 2349 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'XDS (Kabsch, 1988)' _computing_cell_refinement XDS _computing_data_reduction XDS _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics PLATON(Spek,2004) _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 ; w=1/[\s^2^(Fo^2^)+(0.0476P)^2^+0.4146P] 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 0.028(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2829 _refine_ls_number_parameters 212 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0684 _refine_ls_R_factor_gt 0.0539 _refine_ls_wR_factor_ref 0.1258 _refine_ls_wR_factor_gt 0.1202 _refine_ls_goodness_of_fit_ref 1.183 _refine_ls_restrained_S_all 1.183 _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 C17 C 1.1375(2) 0.13238(15) 0.07205(15) 0.0388(5) Uani 1 1 d . . . H17 H 1.1351 0.1452 0.1405 0.047 Uiso 1 1 calc R . . C16 C 1.2086(3) 0.04542(17) 0.04263(17) 0.0477(6) Uani 1 1 d . . . H16 H 1.2558 0.0003 0.0910 0.057 Uiso 1 1 calc R . . C15 C 1.2094(2) 0.02535(16) -0.05979(18) 0.0462(5) Uani 1 1 d . . . H15 H 1.2557 -0.0341 -0.0796 0.055 Uiso 1 1 calc R . . C14 C 1.1425(2) 0.09220(15) -0.13214(15) 0.0372(5) Uani 1 1 d . . . H14 H 1.1443 0.0776 -0.2003 0.045 Uiso 1 1 calc R . . C13 C 1.0717(2) 0.18215(14) -0.10444(13) 0.0284(4) Uani 1 1 d . . . N12 N 1.01143(18) 0.25306(13) -0.17612(11) 0.0346(4) Uani 1 1 d D . . H12 H 1.004(2) 0.2334(15) -0.2383(13) 0.042 Uiso 1 1 d D . . C11 C 0.8929(2) 0.32644(14) -0.15784(12) 0.0291(4) Uani 1 1 d . . . H11 H 0.9089 0.3889 -0.1957 0.035 Uiso 1 1 calc R . . C31 C 0.7301(2) 0.28746(13) -0.19263(13) 0.0305(4) Uani 1 1 d . . . N32 N 0.6713(2) 0.31588(16) -0.28566(13) 0.0508(5) Uani 1 1 d . . . C33 C 0.5306(3) 0.2789(2) -0.3212(2) 0.0664(8) Uani 1 1 d . . . H33 H 0.4877 0.2979 -0.3860 0.080 Uiso 1 1 calc R . . C34 C 0.4476(3) 0.2154(2) -0.2681(2) 0.0648(8) Uani 1 1 d . . . H34 H 0.3511 0.1916 -0.2964 0.078 Uiso 1 1 calc R . . C35 C 0.5091(3) 0.1870(2) -0.1717(2) 0.0660(8) Uani 1 1 d . . . H35 H 0.4548 0.1440 -0.1334 0.079 Uiso 1 1 calc R . . C36 C 0.6533(3) 0.22387(17) -0.13327(19) 0.0503(6) Uani 1 1 d . . . H36 H 0.6978 0.2061 -0.0684 0.060 Uiso 1 1 calc R . . N27 N 0.91283(17) 0.35153(11) -0.05034(10) 0.0285(4) Uani 1 1 d . . . C26 C 0.8357(2) 0.42845(13) -0.00480(14) 0.0308(4) Uani 1 1 d . . . C25 C 0.7365(2) 0.50577(15) -0.04403(16) 0.0410(5) Uani 1 1 d . . . H25 H 0.7114 0.5151 -0.1134 0.049 Uiso 1 1 calc R . . C24 C 0.6770(3) 0.56813(17) 0.02501(19) 0.0502(6) Uani 1 1 d . . . H24 H 0.6105 0.6209 0.0017 0.060 Uiso 1 1 calc R . . C23 C 0.7147(3) 0.55368(17) 0.12951(19) 0.0519(6) Uani 1 1 d . . . H23 H 0.6728 0.5972 0.1740 0.062 Uiso 1 1 calc R . . C22 C 0.8127(3) 0.47634(16) 0.16782(16) 0.0447(5) Uani 1 1 d . . . H22 H 0.8371 0.4672 0.2373 0.054 Uiso 1 1 calc R . . C21 C 0.8739(2) 0.41234(14) 0.09955(14) 0.0321(4) Uani 1 1 d . . . N20 N 0.97129(19) 0.32750(12) 0.11701(11) 0.0344(4) Uani 1 1 d . . . C19 C 0.9884(2) 0.29286(13) 0.02604(13) 0.0277(4) Uani 1 1 d . . . C18 C 1.0690(2) 0.20138(13) -0.00016(13) 0.0294(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C17 0.0485(11) 0.0404(11) 0.0270(10) 0.0041(8) 0.0037(8) 0.0023(9) C16 0.0536(13) 0.0414(12) 0.0475(13) 0.0087(10) 0.0048(10) 0.0101(10) C15 0.0460(12) 0.0378(11) 0.0570(14) -0.0049(10) 0.0152(10) 0.0047(9) C14 0.0368(10) 0.0437(11) 0.0330(11) -0.0095(9) 0.0109(8) -0.0048(9) C13 0.0257(8) 0.0346(9) 0.0252(9) -0.0016(7) 0.0046(7) -0.0085(7) N12 0.0420(9) 0.0465(10) 0.0158(8) -0.0027(7) 0.0051(6) -0.0002(7) C11 0.0405(10) 0.0314(9) 0.0152(8) 0.0021(7) 0.0028(7) -0.0062(8) C31 0.0363(10) 0.0280(9) 0.0260(10) -0.0028(7) 0.0000(7) 0.0007(8) N32 0.0479(11) 0.0725(13) 0.0289(10) 0.0013(9) -0.0067(8) -0.0031(10) C33 0.0511(14) 0.096(2) 0.0461(15) -0.0084(14) -0.0166(12) -0.0035(14) C34 0.0380(12) 0.0647(16) 0.088(2) -0.0254(15) -0.0074(13) -0.0062(12) C35 0.0452(14) 0.0545(15) 0.097(2) 0.0072(14) 0.0051(14) -0.0151(12) C36 0.0432(12) 0.0516(13) 0.0541(14) 0.0136(11) -0.0014(10) -0.0112(10) N27 0.0374(8) 0.0313(8) 0.0164(7) 0.0000(6) 0.0020(6) -0.0023(6) C26 0.0371(10) 0.0276(9) 0.0278(10) -0.0019(7) 0.0050(7) -0.0064(8) C25 0.0468(12) 0.0373(11) 0.0380(11) 0.0036(9) 0.0019(9) -0.0002(9) C24 0.0514(13) 0.0369(11) 0.0622(16) -0.0020(11) 0.0072(11) 0.0094(10) C23 0.0591(14) 0.0439(12) 0.0561(15) -0.0152(11) 0.0205(11) 0.0029(11) C22 0.0560(13) 0.0466(12) 0.0335(11) -0.0091(9) 0.0133(9) -0.0006(10) C21 0.0392(10) 0.0321(9) 0.0261(10) -0.0024(8) 0.0084(7) -0.0039(8) N20 0.0473(10) 0.0382(9) 0.0180(8) -0.0009(7) 0.0053(6) -0.0005(7) C19 0.0344(10) 0.0307(9) 0.0176(9) 0.0019(7) 0.0024(7) -0.0047(8) C18 0.0315(9) 0.0313(9) 0.0253(9) -0.0012(7) 0.0037(7) -0.0042(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C17 C16 1.377(3) . ? C17 C18 1.396(3) . ? C16 C15 1.390(3) . ? C15 C14 1.374(3) . ? C14 C13 1.401(3) . ? C13 N12 1.385(3) . ? C13 C18 1.415(3) . ? N12 C11 1.455(3) . ? C11 N27 1.458(3) . ? C11 C31 1.524(3) . ? C31 N32 1.331(3) . ? C31 C36 1.380(3) . ? N32 C33 1.347(3) . ? C33 C34 1.359(4) . ? C34 C35 1.377(4) . ? C35 C36 1.382(3) . ? N27 C19 1.373(2) . ? N27 C26 1.393(3) . ? C26 C25 1.389(3) . ? C26 C21 1.403(3) . ? C25 C24 1.380(3) . ? C24 C23 1.401(4) . ? C23 C22 1.379(3) . ? C22 C21 1.393(3) . ? C21 N20 1.399(3) . ? N20 C19 1.320(3) . ? C19 C18 1.454(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C16 C17 C18 120.4(2) . . ? C17 C16 C15 119.68(19) . . ? C14 C15 C16 120.8(2) . . ? C15 C14 C13 120.8(2) . . ? N12 C13 C14 121.46(18) . . ? N12 C13 C18 120.32(17) . . ? C14 C13 C18 118.16(17) . . ? C13 N12 C11 122.76(16) . . ? N12 C11 N27 108.44(14) . . ? N12 C11 C31 112.52(16) . . ? N27 C11 C31 111.23(15) . . ? N32 C31 C36 123.04(19) . . ? N32 C31 C11 114.89(17) . . ? C36 C31 C11 122.01(17) . . ? C31 N32 C33 116.7(2) . . ? N32 C33 C34 124.0(2) . . ? C33 C34 C35 118.7(2) . . ? C34 C35 C36 118.5(2) . . ? C31 C36 C35 119.0(2) . . ? C19 N27 C26 107.08(16) . . ? C19 N27 C11 125.95(16) . . ? C26 N27 C11 126.01(15) . . ? C25 C26 N27 132.47(18) . . ? C25 C26 C21 122.62(18) . . ? N27 C26 C21 104.88(16) . . ? C24 C25 C26 116.7(2) . . ? C25 C24 C23 121.5(2) . . ? C22 C23 C24 121.4(2) . . ? C23 C22 C21 118.1(2) . . ? C22 C21 N20 130.14(19) . . ? C22 C21 C26 119.65(19) . . ? N20 C21 C26 110.20(16) . . ? C19 N20 C21 104.96(15) . . ? N20 C19 N27 112.83(17) . . ? N20 C19 C18 128.22(16) . . ? N27 C19 C18 118.89(16) . . ? C17 C18 C13 120.12(18) . . ? C17 C18 C19 122.97(18) . . ? C13 C18 C19 116.88(16) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C18 C17 C16 C15 -1.3(3) . . . . ? C17 C16 C15 C14 1.2(3) . . . . ? C16 C15 C14 C13 -0.1(3) . . . . ? C15 C14 C13 N12 176.33(18) . . . . ? C15 C14 C13 C18 -0.9(3) . . . . ? C14 C13 N12 C11 157.72(17) . . . . ? C18 C13 N12 C11 -25.1(3) . . . . ? C13 N12 C11 N27 31.0(2) . . . . ? C13 N12 C11 C31 -92.5(2) . . . . ? N12 C11 C31 N32 -94.3(2) . . . . ? N27 C11 C31 N32 143.76(18) . . . . ? N12 C11 C31 C36 82.9(2) . . . . ? N27 C11 C31 C36 -39.0(3) . . . . ? C36 C31 N32 C33 -0.4(3) . . . . ? C11 C31 N32 C33 176.8(2) . . . . ? C31 N32 C33 C34 0.0(4) . . . . ? N32 C33 C34 C35 0.4(4) . . . . ? C33 C34 C35 C36 -0.4(4) . . . . ? N32 C31 C36 C35 0.5(4) . . . . ? C11 C31 C36 C35 -176.6(2) . . . . ? C34 C35 C36 C31 0.0(4) . . . . ? N12 C11 N27 C19 -21.6(2) . . . . ? C31 C11 N27 C19 102.6(2) . . . . ? N12 C11 N27 C26 171.08(15) . . . . ? C31 C11 N27 C26 -64.7(2) . . . . ? C19 N27 C26 C25 -176.5(2) . . . . ? C11 N27 C26 C25 -7.2(3) . . . . ? C19 N27 C26 C21 1.49(18) . . . . ? C11 N27 C26 C21 170.74(16) . . . . ? N27 C26 C25 C24 178.37(19) . . . . ? C21 C26 C25 C24 0.7(3) . . . . ? C26 C25 C24 C23 -0.2(3) . . . . ? C25 C24 C23 C22 -0.1(4) . . . . ? C24 C23 C22 C21 0.0(3) . . . . ? C23 C22 C21 N20 -178.06(19) . . . . ? C23 C22 C21 C26 0.4(3) . . . . ? C25 C26 C21 C22 -0.8(3) . . . . ? N27 C26 C21 C22 -179.02(18) . . . . ? C25 C26 C21 N20 177.97(17) . . . . ? N27 C26 C21 N20 -0.27(19) . . . . ? C22 C21 N20 C19 177.5(2) . . . . ? C26 C21 N20 C19 -1.1(2) . . . . ? C21 N20 C19 N27 2.1(2) . . . . ? C21 N20 C19 C18 -175.08(17) . . . . ? C26 N27 C19 N20 -2.3(2) . . . . ? C11 N27 C19 N20 -171.61(16) . . . . ? C26 N27 C19 C18 175.13(15) . . . . ? C11 N27 C19 C18 5.9(3) . . . . ? C16 C17 C18 C13 0.3(3) . . . . ? C16 C17 C18 C19 178.14(19) . . . . ? N12 C13 C18 C17 -176.44(17) . . . . ? C14 C13 C18 C17 0.8(3) . . . . ? N12 C13 C18 C19 5.6(2) . . . . ? C14 C13 C18 C19 -177.19(16) . . . . ? N20 C19 C18 C17 2.8(3) . . . . ? N27 C19 C18 C17 -174.28(17) . . . . ? N20 C19 C18 C13 -179.30(17) . . . . ? N27 C19 C18 C13 3.7(2) . . . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.75 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.241 _refine_diff_density_min -0.173 _refine_diff_density_rms 0.053 _publ_section_references ; Kabsch, W. (1988), J.Appl.Cryst 21 916-932. Sheldrick, G.M. (1997) SHELX97 program for crystallography refinement. University of Gottingen, Germany. Spek, A.L., (2004) PLATON-94 program, Utrecht University, The Netherlands Walker, N. and Stuart, D., Acta Crystl 1983 A39 158 ;