# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2012 data_publication_text _journal_name_full 'RSC Advances' _journal_coden_cambridge 1500 #TrackingRef '- CIF.cif' _publ_contact_author_name 'Dr. Gopal Das' _publ_contact_author_address ;Department of Chemistry Indian Institute of Technology Guwahati Assam 781039 India ; _publ_contact_author_email gdas@iitg.ernet.in _publ_contact_author_phone 00913612582313 _publ_contact_author_fax 00913612582349 loop_ _publ_author_address ;Department of Chemistry Indian Institute of Technology Guwahati Assam 781039 India ; _publ_author_name G.Das data_Dye _database_code_depnum_ccdc_archive 'CCDC 882733' #TrackingRef '- CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H10 N2 O3' _chemical_formula_sum 'C13 H10 N2 O3' _chemical_formula_weight 242.23 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 'P 21/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 14.1104(8) _cell_length_b 4.8957(2) _cell_length_c 16.7631(8) _cell_angle_alpha 90.00 _cell_angle_beta 94.640(4) _cell_angle_gamma 90.00 _cell_volume 1154.20(10) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1281 _cell_measurement_theta_min 4.34 _cell_measurement_theta_max 20.46 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.394 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504.0 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.953 _exptl_absorpt_correction_T_max 0.968 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14306 _diffrn_reflns_av_R_equivalents 0.0718 _diffrn_reflns_av_sigmaI/netI 0.0475 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 4.34 _diffrn_reflns_theta_max 28.36 _reflns_number_total 2839 _reflns_number_gt 2462 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0579P)^2^+0.0697P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.022(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2839 _refine_ls_number_parameters 204 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1267 _refine_ls_R_factor_gt 0.0525 _refine_ls_wR_factor_ref 0.1445 _refine_ls_wR_factor_gt 0.1136 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _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 C5 C 0.70275(16) 0.6495(4) 0.52387(14) 0.0598(6) Uani 1 1 d . . . C6 C 0.66213(14) 0.4834(4) 0.46189(12) 0.0547(5) Uani 1 1 d . . . C3 C 0.79941(19) 0.8702(5) 0.43364(15) 0.0723(7) Uani 1 1 d . . . C4 C 0.77070(16) 0.8397(4) 0.51040(13) 0.0622(6) Uani 1 1 d . . . C1 C 0.69203(16) 0.5177(4) 0.38486(12) 0.0616(6) Uani 1 1 d . . . C2 C 0.76110(19) 0.7143(5) 0.37160(16) 0.0747(7) Uani 1 1 d . . . C7 C 0.90437(17) 1.3216(5) 0.63330(13) 0.0662(6) Uani 1 1 d . . . C14C C 0.9840(2) 1.4785(6) 0.62504(18) 0.0823(8) Uani 1 1 d . . . C9 C 1.0176(2) 1.6483(6) 0.68552(17) 0.0893(8) Uani 1 1 d . . . C12 C 0.8585(2) 1.3381(6) 0.70358(15) 0.0786(7) Uani 1 1 d . . . C11 C 0.8938(2) 1.5143(6) 0.76291(16) 0.0836(8) Uani 1 1 d . . . C10 C 0.9729(2) 1.6683(6) 0.75375(17) 0.0807(8) Uani 1 1 d . . . C13 C 0.59100(15) 0.2796(4) 0.47751(12) 0.0570(5) Uani 1 1 d . . . O2 O 0.55440(11) 0.1263(3) 0.42478(8) 0.0656(4) Uani 1 1 d . . . O1 O 0.65674(13) 0.3688(4) 0.32121(9) 0.0756(5) Uani 1 1 d . . . O3 O 0.56761(12) 0.2679(3) 0.55168(8) 0.0671(5) Uani 1 1 d . . . N1 N 0.87289(14) 1.1540(4) 0.56639(12) 0.0746(6) Uani 1 1 d . . . N2 N 0.80492(13) 1.0022(4) 0.57921(10) 0.0657(5) Uani 1 1 d . . . H1 H 0.7771(15) 0.723(4) 0.3177(14) 0.064(6) Uiso 1 1 d . . . H2 H 0.8499(16) 1.000(5) 0.4270(12) 0.072(7) Uiso 1 1 d . . . H4C H 1.0134(17) 1.447(5) 0.5780(16) 0.092(8) Uiso 1 1 d . . . H6C H 0.9977(19) 1.805(6) 0.7963(17) 0.107(9) Uiso 1 1 d . . . H7C H 0.8581(19) 1.534(5) 0.8140(16) 0.105(8) Uiso 1 1 d . . . H5C H 1.075(2) 1.750(7) 0.6800(18) 0.131(11) Uiso 1 1 d . . . H8C H 0.8043(18) 1.234(5) 0.7124(15) 0.089(8) Uiso 1 1 d . . . H10C H 0.6799(13) 0.624(4) 0.5772(12) 0.060(6) Uiso 1 1 d . . . H11H H 0.610(2) 0.248(6) 0.3390(18) 0.113(11) Uiso 1 1 d . . . H12O H 0.523(2) 0.128(6) 0.5559(17) 0.112(10) 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 C5 0.0667(14) 0.0557(13) 0.0576(13) 0.0075(10) 0.0089(11) 0.0077(11) C6 0.0615(12) 0.0506(12) 0.0528(11) 0.0055(9) 0.0089(9) 0.0118(10) C3 0.0749(17) 0.0644(15) 0.0791(17) 0.0047(13) 0.0148(13) -0.0012(13) C4 0.0681(14) 0.0589(13) 0.0602(13) 0.0056(11) 0.0082(11) 0.0103(11) C1 0.0779(14) 0.0536(13) 0.0542(13) 0.0008(10) 0.0120(11) 0.0114(11) C2 0.0943(18) 0.0714(16) 0.0617(15) 0.0053(13) 0.0265(13) 0.0046(14) C7 0.0711(15) 0.0660(14) 0.0603(14) 0.0002(11) -0.0027(11) 0.0059(12) C14C 0.0761(17) 0.101(2) 0.0708(17) 0.0081(15) 0.0146(14) -0.0065(15) C9 0.0865(19) 0.101(2) 0.0784(19) 0.0095(16) -0.0034(16) -0.0252(17) C12 0.0741(17) 0.0914(19) 0.0709(16) -0.0017(14) 0.0097(13) -0.0144(15) C11 0.0852(18) 0.101(2) 0.0647(16) -0.0072(14) 0.0095(14) -0.0108(16) C10 0.0894(19) 0.0832(19) 0.0682(17) 0.0046(13) -0.0007(15) -0.0110(15) C13 0.0664(13) 0.0545(12) 0.0507(12) 0.0017(10) 0.0080(10) 0.0137(11) O2 0.0831(10) 0.0630(9) 0.0513(8) -0.0022(7) 0.0097(7) -0.0028(8) O1 0.1019(13) 0.0724(10) 0.0543(9) -0.0030(8) 0.0173(8) -0.0003(10) O3 0.0856(11) 0.0670(10) 0.0499(9) 0.0010(7) 0.0132(7) -0.0051(9) N1 0.0703(13) 0.0774(13) 0.0766(13) 0.0023(10) 0.0096(10) 0.0040(11) N2 0.0679(12) 0.0593(11) 0.0694(12) 0.0036(9) 0.0020(9) 0.0014(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 C5 C4 1.368(3) . ? C5 C6 1.405(3) . ? C6 C1 1.401(3) . ? C6 C13 1.454(3) . ? C3 C2 1.366(4) . ? C3 C4 1.388(3) . ? C4 N2 1.451(3) . ? C1 O1 1.353(2) . ? C1 C2 1.400(3) . ? C7 C14C 1.378(3) . ? C7 C12 1.392(3) . ? C7 N1 1.431(3) . ? C14C C9 1.366(4) . ? C9 C10 1.353(4) . ? C12 C11 1.379(3) . ? C11 C10 1.365(3) . ? C13 O2 1.240(2) . ? C13 O3 1.313(2) . ? N1 N2 1.246(2) . ? 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 C4 C5 C6 121.4(2) . . ? C1 C6 C5 118.5(2) . . ? C1 C6 C13 120.80(19) . . ? C5 C6 C13 120.69(19) . . ? C2 C3 C4 121.3(3) . . ? C5 C4 C3 119.1(2) . . ? C5 C4 N2 115.7(2) . . ? C3 C4 N2 125.1(2) . . ? O1 C1 C2 117.5(2) . . ? O1 C1 C6 122.9(2) . . ? C2 C1 C6 119.6(2) . . ? C3 C2 C1 120.0(2) . . ? C14C C7 C12 119.5(2) . . ? C14C C7 N1 116.4(2) . . ? C12 C7 N1 124.1(2) . . ? C9 C14C C7 120.1(3) . . ? C10 C9 C14C 121.0(3) . . ? C11 C12 C7 118.8(3) . . ? C10 C11 C12 121.0(3) . . ? C9 C10 C11 119.7(3) . . ? O2 C13 O3 121.8(2) . . ? O2 C13 C6 122.73(18) . . ? O3 C13 C6 115.49(19) . . ? N2 N1 C7 113.66(19) . . ? N1 N2 C4 113.64(19) . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 28.36 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.219 _refine_diff_density_min -0.122 _refine_diff_density_rms 0.030