# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Manojit Pal' _publ_contact_author_email manojitpal@rediffmail.com _publ_author_name M.Pal data_cqsd_5d_1 _database_code_depnum_ccdc_archive 'CCDC 828186' #TrackingRef 'CQSD_5D_1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H16 N2 O' _chemical_formula_sum 'C22 H16 N2 O' _chemical_formula_weight 324.37 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/n ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.388(6) _cell_length_b 11.595(8) _cell_length_c 15.005(10) _cell_angle_alpha 90.00 _cell_angle_beta 94.983(9) _cell_angle_gamma 90.00 _cell_volume 1627.3(19) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 688 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 22.58 _exptl_crystal_description plate _exptl_crystal_colour transparant _exptl_crystal_size_max 0.005 _exptl_crystal_size_mid 0.0024 _exptl_crystal_size_min 0.0016 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.324 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 1.000 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'Multiscan absorption correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker Kappa APEX-II CCD DUO' _diffrn_measurement_method '\ f and \ w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 6728 _diffrn_reflns_av_R_equivalents 0.0793 _diffrn_reflns_av_sigmaI/netI 0.1175 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 27.00 _reflns_number_total 3152 _reflns_number_gt 1525 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1525P)^2^+2.2812P] 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 3152 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1540 _refine_ls_R_factor_gt 0.0661 _refine_ls_wR_factor_ref 0.2361 _refine_ls_wR_factor_gt 0.1633 _refine_ls_goodness_of_fit_ref 0.765 _refine_ls_restrained_S_all 0.765 _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 C1 C 0.2686(4) 0.7279(4) 0.1231(2) 0.0214(9) Uani 1 1 d . . . C2 C 0.3801(4) 0.6681(4) 0.1702(3) 0.0284(10) Uani 1 1 d . . . H2 H 0.3648 0.5950 0.1931 0.034 Uiso 1 1 calc R . . C3 C 0.5150(4) 0.7194(4) 0.1826(3) 0.0345(11) Uani 1 1 d . . . H3 H 0.5889 0.6805 0.2152 0.041 Uiso 1 1 calc R . . C4 C 0.5410(4) 0.8266(4) 0.1476(3) 0.0349(12) Uani 1 1 d . . . H4 H 0.6327 0.8577 0.1536 0.042 Uiso 1 1 calc R . . C5 C 0.4290(4) 0.8875(4) 0.1036(3) 0.0308(10) Uani 1 1 d . . . H5 H 0.4446 0.9613 0.0820 0.037 Uiso 1 1 calc R . . C6 C 0.2935(4) 0.8386(4) 0.0914(3) 0.0242(9) Uani 1 1 d . . . C7 C 0.1750(4) 0.9068(4) 0.0462(3) 0.0257(9) Uani 1 1 d . . . C8 C 0.0112(4) 0.7581(3) 0.0949(3) 0.0235(9) Uani 1 1 d . . . H8 H -0.0653 0.7193 0.0576 0.028 Uiso 1 1 calc R . . C9 C -0.0445(4) 0.7752(4) 0.1863(3) 0.0239(9) Uani 1 1 d . . . C10 C -0.0798(4) 0.8798(4) 0.2226(3) 0.0326(10) Uani 1 1 d . . . H10 H -0.0629 0.9483 0.1930 0.039 Uiso 1 1 calc R . . C11 C -0.1413(4) 0.8815(4) 0.3044(3) 0.0359(11) Uani 1 1 d . . . H11 H -0.1655 0.9513 0.3296 0.043 Uiso 1 1 calc R . . C12 C -0.1656(5) 0.7795(4) 0.3471(3) 0.0374(11) Uani 1 1 d . . . H12 H -0.2087 0.7812 0.4006 0.045 Uiso 1 1 calc R . . C13 C -0.1275(4) 0.6742(4) 0.3126(3) 0.0300(10) Uani 1 1 d . . . H13 H -0.1445 0.6060 0.3426 0.036 Uiso 1 1 calc R . . C14 C -0.0636(4) 0.6720(4) 0.2323(3) 0.0258(9) Uani 1 1 d . . . C15 C -0.0066(4) 0.5664(4) 0.1949(3) 0.0255(9) Uani 1 1 d . . . H15 H -0.0426 0.4954 0.2109 0.031 Uiso 1 1 calc R . . C16 C 0.0960(4) 0.5694(3) 0.1381(3) 0.0230(9) Uani 1 1 d . . . C17 C 0.1721(4) 0.4681(3) 0.1054(3) 0.0231(9) Uani 1 1 d . . . C18 C 0.1736(4) 0.3640(4) 0.1513(3) 0.0289(10) Uani 1 1 d . . . H18 H 0.1259 0.3579 0.2029 0.035 Uiso 1 1 calc R . . C19 C 0.2453(5) 0.2692(4) 0.1212(3) 0.0304(10) Uani 1 1 d . . . H19 H 0.2420 0.1992 0.1512 0.037 Uiso 1 1 calc R . . C20 C 0.3215(4) 0.2779(4) 0.0470(3) 0.0305(10) Uani 1 1 d . . . H20 H 0.3718 0.2148 0.0278 0.037 Uiso 1 1 calc R . . C21 C 0.3223(4) 0.3813(4) 0.0015(3) 0.0327(11) Uani 1 1 d . . . H21 H 0.3734 0.3878 -0.0486 0.039 Uiso 1 1 calc R . . C22 C 0.2474(4) 0.4755(4) 0.0300(3) 0.0290(10) Uani 1 1 d . . . H22 H 0.2477 0.5444 -0.0017 0.035 Uiso 1 1 calc R . . N1 N 0.0442(3) 0.8618(3) 0.0481(2) 0.0280(8) Uani 1 1 d . . . H1 H -0.0255 0.8975 0.0191 0.034 Uiso 1 1 calc R . . N2 N 0.1317(3) 0.6788(3) 0.1027(2) 0.0228(8) Uani 1 1 d . . . O1 O 0.1954(3) 0.9992(3) 0.0076(2) 0.0369(8) 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 C1 0.0237(17) 0.027(2) 0.013(2) -0.0013(16) 0.0018(14) 0.0029(17) C2 0.031(2) 0.029(2) 0.025(2) -0.0061(18) 0.0022(17) 0.0085(19) C3 0.029(2) 0.041(3) 0.032(3) -0.021(2) -0.0023(18) 0.008(2) C4 0.0199(18) 0.049(3) 0.036(3) -0.025(2) 0.0056(17) -0.001(2) C5 0.032(2) 0.029(3) 0.033(3) -0.0110(19) 0.0090(18) -0.0019(19) C6 0.0266(19) 0.026(2) 0.021(2) -0.0031(17) 0.0033(16) 0.0002(17) C7 0.0280(19) 0.023(2) 0.026(2) -0.0010(18) 0.0014(17) -0.0028(18) C8 0.0192(17) 0.020(2) 0.030(2) 0.0037(17) -0.0039(15) -0.0023(16) C9 0.0207(17) 0.024(2) 0.026(2) -0.0018(18) -0.0040(16) 0.0011(17) C10 0.0250(19) 0.031(3) 0.040(3) -0.002(2) -0.0068(18) -0.0002(19) C11 0.033(2) 0.035(3) 0.038(3) -0.008(2) -0.0019(19) 0.008(2) C12 0.032(2) 0.052(3) 0.028(3) -0.009(2) 0.0003(18) 0.008(2) C13 0.032(2) 0.036(3) 0.021(2) 0.0020(19) 0.0001(17) 0.004(2) C14 0.0237(18) 0.025(2) 0.028(2) -0.0028(18) -0.0028(16) 0.0013(17) C15 0.0295(19) 0.026(2) 0.021(2) 0.0021(17) -0.0002(16) 0.0030(18) C16 0.0299(19) 0.017(2) 0.022(2) 0.0031(16) 0.0008(16) 0.0009(17) C17 0.0279(19) 0.023(2) 0.018(2) 0.0003(16) 0.0012(15) 0.0012(17) C18 0.036(2) 0.028(2) 0.024(2) 0.0051(18) 0.0092(17) 0.007(2) C19 0.043(2) 0.025(2) 0.024(2) 0.0051(18) 0.0020(18) 0.006(2) C20 0.036(2) 0.032(3) 0.024(2) -0.0051(19) 0.0027(18) 0.007(2) C21 0.039(2) 0.033(3) 0.027(3) -0.008(2) 0.0103(19) -0.002(2) C22 0.041(2) 0.025(2) 0.021(2) -0.0006(17) 0.0063(18) -0.0056(19) N1 0.0264(16) 0.0220(19) 0.035(2) 0.0078(16) -0.0017(14) -0.0037(15) N2 0.0261(16) 0.0178(18) 0.0245(19) 0.0044(14) 0.0018(13) -0.0016(14) O1 0.0363(16) 0.0265(18) 0.048(2) 0.0114(15) 0.0023(14) -0.0055(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.395(6) . ? C1 C2 1.396(5) . ? C1 N2 1.414(5) . ? C2 C3 1.397(6) . ? C3 C4 1.379(7) . ? C4 C5 1.386(6) . ? C5 C6 1.391(6) . ? C6 C7 1.480(6) . ? C7 O1 1.241(5) . ? C7 N1 1.337(5) . ? C8 N1 1.441(5) . ? C8 N2 1.455(5) . ? C8 C9 1.522(6) . ? C9 C10 1.381(6) . ? C9 C14 1.401(6) . ? C10 C11 1.402(6) . ? C11 C12 1.373(7) . ? C12 C13 1.386(6) . ? C13 C14 1.392(6) . ? C14 C15 1.468(6) . ? C15 C16 1.340(5) . ? C16 N2 1.426(5) . ? C16 C17 1.481(6) . ? C17 C22 1.388(5) . ? C17 C18 1.389(6) . ? C18 C19 1.386(6) . ? C19 C20 1.378(6) . ? C20 C21 1.380(6) . ? C21 C22 1.387(6) . ? 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 C6 C1 C2 119.3(4) . . ? C6 C1 N2 118.2(3) . . ? C2 C1 N2 122.5(4) . . ? C1 C2 C3 119.1(4) . . ? C4 C3 C2 121.5(4) . . ? C3 C4 C5 119.3(4) . . ? C4 C5 C6 120.1(4) . . ? C5 C6 C1 120.6(4) . . ? C5 C6 C7 119.0(4) . . ? C1 C6 C7 120.4(3) . . ? O1 C7 N1 121.7(4) . . ? O1 C7 C6 122.4(3) . . ? N1 C7 C6 115.9(4) . . ? N1 C8 N2 111.5(3) . . ? N1 C8 C9 115.9(3) . . ? N2 C8 C9 109.6(3) . . ? C10 C9 C14 120.7(4) . . ? C10 C9 C8 125.6(4) . . ? C14 C9 C8 113.7(4) . . ? C9 C10 C11 119.3(4) . . ? C12 C11 C10 119.6(4) . . ? C11 C12 C13 121.7(4) . . ? C12 C13 C14 118.9(4) . . ? C13 C14 C9 119.6(4) . . ? C13 C14 C15 123.1(4) . . ? C9 C14 C15 117.2(4) . . ? C16 C15 C14 121.8(4) . . ? C15 C16 N2 117.7(4) . . ? C15 C16 C17 125.7(4) . . ? N2 C16 C17 116.5(3) . . ? C22 C17 C18 118.3(4) . . ? C22 C17 C16 121.1(4) . . ? C18 C17 C16 120.6(4) . . ? C19 C18 C17 120.8(4) . . ? C20 C19 C18 120.4(4) . . ? C19 C20 C21 119.3(4) . . ? C20 C21 C22 120.5(4) . . ? C21 C22 C17 120.7(4) . . ? C7 N1 C8 125.0(3) . . ? C1 N2 C16 121.1(3) . . ? C1 N2 C8 116.7(3) . . ? C16 N2 C8 112.6(3) . . ? _diffrn_measured_fraction_theta_max 0.889 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.889 _refine_diff_density_max 0.223 _refine_diff_density_min -0.274 _refine_diff_density_rms 0.061