# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'RSC Advances' _journal_coden_cambridge 1500 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Kshama Kundu' _publ_contact_author_email kshamaroy@yahoo.com loop_ _publ_author_name 'Kshama Kundu' S.K.Nayak data_barc025 _database_code_depnum_ccdc_archive 'CCDC 828034' #TrackingRef 'web_deposit_cif_file_0_KshamaKundu_1306996724.barc025.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H21 N O2' _chemical_formula_weight 331.40 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 Orthorhombic _symmetry_space_group_name_H-M 'P c a b' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y+1/2, z+1/2' 'x+1/2, -y, -z+1/2' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, y-1/2, -z-1/2' '-x-1/2, y, z-1/2' 'x-1/2, -y-1/2, z' _cell_length_a 8.5808(7) _cell_length_b 46.211(4) _cell_length_c 8.7745(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3479.3(5) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3319 _cell_measurement_theta_min 3.3432 _cell_measurement_theta_max 32.6032 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.265 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1408 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_T_min 0.9747 _exptl_absorpt_correction_T_max 0.9817 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OXFORD DIFFRACTION XCALIBUR-S' _diffrn_measurement_method \w/q-scan _diffrn_detector_area_resol_mean 15.9948 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24296 _diffrn_reflns_av_R_equivalents 0.0859 _diffrn_reflns_av_sigmaI/netI 0.0676 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -54 _diffrn_reflns_limit_k_max 54 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.35 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3063 _reflns_number_gt 1410 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.,' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Ortep3 _computing_publication_material Shelx97 _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^)+(0.0490P)^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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3063 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1316 _refine_ls_R_factor_gt 0.0497 _refine_ls_wR_factor_ref 0.1117 _refine_ls_wR_factor_gt 0.0941 _refine_ls_goodness_of_fit_ref 0.862 _refine_ls_restrained_S_all 0.862 _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 O1 O 0.0091(2) 0.17424(4) 0.6505(2) 0.0650(5) Uani 1 1 d . . . O2 O 0.0413(2) 0.01869(4) 1.2771(2) 0.0802(6) Uani 1 1 d . . . N1 N -0.0428(2) 0.08673(4) 0.7609(2) 0.0591(6) Uani 1 1 d . . . H1 H -0.1066 0.0803 0.6934 0.071 Uiso 1 1 calc R . . C1 C -0.0065(3) 0.15307(6) 0.5416(3) 0.0540(7) Uani 1 1 d . . . C2 C -0.0406(3) 0.16303(7) 0.3961(4) 0.0677(8) Uani 1 1 d . . . H2 H -0.0505 0.1828 0.3786 0.081 Uiso 1 1 calc R . . C3 C -0.0595(3) 0.14398(8) 0.2787(4) 0.0731(9) Uani 1 1 d . . . H3 H -0.0829 0.1507 0.1815 0.088 Uiso 1 1 calc R . . C4 C -0.0439(3) 0.11468(8) 0.3048(3) 0.0703(8) Uani 1 1 d . . . H4 H -0.0558 0.1016 0.2251 0.084 Uiso 1 1 calc R . . C5 C -0.0106(3) 0.10489(6) 0.4497(3) 0.0601(7) Uani 1 1 d . . . H5 H -0.0003 0.0851 0.4664 0.072 Uiso 1 1 calc R . . C6 C 0.0081(2) 0.12376(6) 0.5711(3) 0.0488(7) Uani 1 1 d . . . C7 C 0.0421(3) 0.11340(5) 0.7308(3) 0.0511(7) Uani 1 1 d . . . H7 H 0.1537 0.1092 0.7376 0.061 Uiso 1 1 calc R . . C8 C 0.0050(3) 0.13711(5) 0.8452(3) 0.0552(7) Uani 1 1 d . . . H8A H -0.1071 0.1387 0.8565 0.066 Uiso 1 1 calc R . . H8B H 0.0484 0.1320 0.9436 0.066 Uiso 1 1 calc R . . C9 C 0.0704(3) 0.16585(5) 0.7952(3) 0.0555(7) Uani 1 1 d . . . H9 H 0.1838 0.1640 0.7862 0.067 Uiso 1 1 calc R . . C10 C 0.0350(3) 0.18988(5) 0.9034(3) 0.0527(7) Uani 1 1 d . . . C11 C 0.1342(3) 0.19672(6) 1.0206(3) 0.0669(8) Uani 1 1 d . . . H11 H 0.2285 0.1869 1.0284 0.080 Uiso 1 1 calc R . . C12 C 0.0988(4) 0.21763(7) 1.1271(4) 0.0796(9) Uani 1 1 d . . . H12 H 0.1676 0.2216 1.2062 0.095 Uiso 1 1 calc R . . C13 C -0.0374(4) 0.23234(7) 1.1152(4) 0.0895(10) Uani 1 1 d . . . H13 H -0.0627 0.2465 1.1866 0.107 Uiso 1 1 calc R . . C14 C -0.1381(4) 0.22640(7) 0.9976(4) 0.0983(11) Uani 1 1 d . . . H14 H -0.2309 0.2367 0.9891 0.118 Uiso 1 1 calc R . . C15 C -0.1024(3) 0.20532(7) 0.8924(4) 0.0779(9) Uani 1 1 d . . . H15 H -0.1714 0.2014 0.8132 0.094 Uiso 1 1 calc R . . C16 C -0.0234(3) 0.07127(5) 0.8967(3) 0.0469(6) Uani 1 1 d . . . C17 C -0.1436(3) 0.05420(6) 0.9491(3) 0.0537(7) Uani 1 1 d . . . H17 H -0.2386 0.0546 0.8983 0.064 Uiso 1 1 calc R . . C18 C -0.1273(3) 0.03654(6) 1.0744(3) 0.0562(7) Uani 1 1 d . . . H18 H -0.2106 0.0253 1.1073 0.067 Uiso 1 1 calc R . . C19 C 0.0129(3) 0.03557(5) 1.1512(3) 0.0548(7) Uani 1 1 d . . . C20 C 0.1316(3) 0.05320(6) 1.1030(3) 0.0583(7) Uani 1 1 d . . . H20 H 0.2253 0.0533 1.1564 0.070 Uiso 1 1 calc R . . C21 C 0.1149(3) 0.07066(6) 0.9774(3) 0.0553(7) Uani 1 1 d . . . H21 H 0.1976 0.0822 0.9462 0.066 Uiso 1 1 calc R . . C22 C -0.0638(3) -0.00459(6) 1.3041(3) 0.0724(9) Uani 1 1 d . . . H22A H -0.1621 0.0030 1.3379 0.109 Uiso 1 1 calc R . . H22B H -0.0216 -0.0171 1.3810 0.109 Uiso 1 1 calc R . . H22C H -0.0786 -0.0153 1.2116 0.109 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 O1 0.0885(13) 0.0525(12) 0.0540(12) 0.0111(11) 0.0008(11) 0.0023(10) O2 0.0903(14) 0.0761(15) 0.0743(15) 0.0225(12) -0.0144(11) -0.0179(12) N1 0.0684(14) 0.0502(15) 0.0585(16) 0.0058(12) -0.0151(11) -0.0100(11) C1 0.0490(16) 0.0590(19) 0.0540(19) 0.0056(17) 0.0096(15) 0.0003(14) C2 0.0724(19) 0.072(2) 0.058(2) 0.0154(19) 0.0089(17) 0.0043(16) C3 0.0686(19) 0.098(3) 0.053(2) 0.010(2) 0.0097(16) 0.0024(18) C4 0.0642(19) 0.093(3) 0.054(2) -0.0098(19) 0.0058(16) 0.0018(17) C5 0.0532(16) 0.0616(19) 0.066(2) -0.0025(17) 0.0086(15) 0.0039(13) C6 0.0433(15) 0.0520(18) 0.0511(18) 0.0029(15) 0.0060(14) 0.0058(12) C7 0.0456(14) 0.0454(17) 0.0624(19) 0.0035(15) 0.0013(14) 0.0007(13) C8 0.0580(15) 0.0538(18) 0.0538(17) 0.0150(15) 0.0028(14) 0.0018(14) C9 0.0555(16) 0.0507(19) 0.0604(19) 0.0076(16) 0.0011(14) 0.0014(13) C10 0.0547(16) 0.0443(17) 0.0590(18) 0.0064(14) 0.0016(15) -0.0053(14) C11 0.0718(19) 0.061(2) 0.069(2) 0.0068(17) -0.0058(18) -0.0008(16) C12 0.099(3) 0.073(2) 0.067(2) 0.005(2) -0.013(2) -0.0204(19) C13 0.113(3) 0.071(2) 0.085(3) -0.015(2) 0.009(2) -0.011(2) C14 0.088(2) 0.097(3) 0.110(3) -0.031(2) -0.002(2) 0.025(2) C15 0.0648(19) 0.085(2) 0.084(2) -0.017(2) -0.0032(18) 0.0085(17) C16 0.0479(15) 0.0384(15) 0.0544(17) 0.0021(14) 0.0002(14) 0.0016(13) C17 0.0504(15) 0.0556(17) 0.0550(19) -0.0029(15) -0.0080(14) -0.0021(14) C18 0.0558(17) 0.0569(18) 0.0559(19) 0.0005(15) 0.0065(15) -0.0090(14) C19 0.0652(18) 0.0454(17) 0.0536(18) 0.0089(15) -0.0055(16) -0.0020(15) C20 0.0554(16) 0.0480(17) 0.072(2) 0.0040(17) -0.0159(15) -0.0022(14) C21 0.0468(16) 0.0449(17) 0.074(2) 0.0064(16) -0.0017(15) -0.0051(13) C22 0.087(2) 0.054(2) 0.076(2) 0.0148(17) 0.0079(16) -0.0055(15) _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 O1 C1 1.375(3) . ? O1 C9 1.428(3) . ? O2 C19 1.374(3) . ? O2 C22 1.424(3) . ? N1 C16 1.399(3) . ? N1 C7 1.456(3) . ? N1 H1 0.8600 . ? C1 C6 1.385(3) . ? C1 C2 1.388(3) . ? C2 C3 1.365(4) . ? C2 H2 0.9300 . ? C3 C4 1.380(4) . ? C3 H3 0.9300 . ? C4 C5 1.380(3) . ? C4 H4 0.9300 . ? C5 C6 1.386(3) . ? C5 H5 0.9300 . ? C6 C7 1.509(3) . ? C7 C8 1.520(3) . ? C7 H7 0.9800 . ? C8 C9 1.507(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.492(3) . ? C9 H9 0.9800 . ? C10 C11 1.372(3) . ? C10 C15 1.381(3) . ? C11 C12 1.378(4) . ? C11 H11 0.9300 . ? C12 C13 1.356(4) . ? C12 H12 0.9300 . ? C13 C14 1.373(4) . ? C13 H13 0.9300 . ? C14 C15 1.376(4) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C17 1.377(3) . ? C16 C21 1.382(3) . ? C17 C18 1.376(3) . ? C17 H17 0.9300 . ? C18 C19 1.379(3) . ? C18 H18 0.9300 . ? C19 C20 1.371(3) . ? C20 C21 1.374(3) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? 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 O1 C9 117.4(2) . . ? C19 O2 C22 116.8(2) . . ? C16 N1 C7 121.8(2) . . ? C16 N1 H1 119.1 . . ? C7 N1 H1 119.1 . . ? O1 C1 C6 123.9(2) . . ? O1 C1 C2 115.1(3) . . ? C6 C1 C2 121.1(3) . . ? C3 C2 C1 120.3(3) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C2 C3 C4 119.7(3) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C5 C4 C3 119.7(3) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C4 C5 C6 121.7(3) . . ? C4 C5 H5 119.1 . . ? C6 C5 H5 119.1 . . ? C1 C6 C5 117.4(2) . . ? C1 C6 C7 120.1(2) . . ? C5 C6 C7 122.4(2) . . ? N1 C7 C6 109.9(2) . . ? N1 C7 C8 112.7(2) . . ? C6 C7 C8 110.1(2) . . ? N1 C7 H7 108.0 . . ? C6 C7 H7 108.0 . . ? C8 C7 H7 108.0 . . ? C9 C8 C7 111.4(2) . . ? C9 C8 H8A 109.3 . . ? C7 C8 H8A 109.3 . . ? C9 C8 H8B 109.3 . . ? C7 C8 H8B 109.3 . . ? H8A C8 H8B 108.0 . . ? O1 C9 C10 106.7(2) . . ? O1 C9 C8 111.1(2) . . ? C10 C9 C8 113.3(2) . . ? O1 C9 H9 108.5 . . ? C10 C9 H9 108.5 . . ? C8 C9 H9 108.5 . . ? C11 C10 C15 117.6(3) . . ? C11 C10 C9 121.4(2) . . ? C15 C10 C9 120.9(2) . . ? C10 C11 C12 122.2(3) . . ? C10 C11 H11 118.9 . . ? C12 C11 H11 118.9 . . ? C13 C12 C11 119.3(3) . . ? C13 C12 H12 120.4 . . ? C11 C12 H12 120.4 . . ? C12 C13 C14 120.0(3) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C13 C14 C15 120.4(3) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C14 C15 C10 120.5(3) . . ? C14 C15 H15 119.7 . . ? C10 C15 H15 119.7 . . ? C17 C16 C21 117.4(2) . . ? C17 C16 N1 119.2(2) . . ? C21 C16 N1 123.3(2) . . ? C18 C17 C16 122.0(2) . . ? C18 C17 H17 119.0 . . ? C16 C17 H17 119.0 . . ? C17 C18 C19 119.9(2) . . ? C17 C18 H18 120.1 . . ? C19 C18 H18 120.1 . . ? C20 C19 O2 117.0(2) . . ? C20 C19 C18 118.5(2) . . ? O2 C19 C18 124.5(2) . . ? C19 C20 C21 121.2(2) . . ? C19 C20 H20 119.4 . . ? C21 C20 H20 119.4 . . ? C20 C21 C16 120.9(2) . . ? C20 C21 H21 119.6 . . ? C16 C21 H21 119.6 . . ? O2 C22 H22A 109.5 . . ? O2 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O2 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? 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 C9 O1 C1 C6 11.4(3) . . . . ? C9 O1 C1 C2 -169.3(2) . . . . ? O1 C1 C2 C3 -179.7(2) . . . . ? C6 C1 C2 C3 -0.3(4) . . . . ? C1 C2 C3 C4 -0.3(4) . . . . ? C2 C3 C4 C5 0.5(4) . . . . ? C3 C4 C5 C6 -0.1(4) . . . . ? O1 C1 C6 C5 -180.0(2) . . . . ? C2 C1 C6 C5 0.8(4) . . . . ? O1 C1 C6 C7 0.5(3) . . . . ? C2 C1 C6 C7 -178.8(2) . . . . ? C4 C5 C6 C1 -0.6(4) . . . . ? C4 C5 C6 C7 179.0(2) . . . . ? C16 N1 C7 C6 175.2(2) . . . . ? C16 N1 C7 C8 -61.6(3) . . . . ? C1 C6 C7 N1 142.6(2) . . . . ? C5 C6 C7 N1 -37.0(3) . . . . ? C1 C6 C7 C8 17.8(3) . . . . ? C5 C6 C7 C8 -161.7(2) . . . . ? N1 C7 C8 C9 -169.5(2) . . . . ? C6 C7 C8 C9 -46.3(3) . . . . ? C1 O1 C9 C10 -164.66(19) . . . . ? C1 O1 C9 C8 -40.7(3) . . . . ? C7 C8 C9 O1 59.1(3) . . . . ? C7 C8 C9 C10 179.3(2) . . . . ? O1 C9 C10 C11 -146.6(2) . . . . ? C8 C9 C10 C11 90.8(3) . . . . ? O1 C9 C10 C15 35.9(3) . . . . ? C8 C9 C10 C15 -86.7(3) . . . . ? C15 C10 C11 C12 1.6(4) . . . . ? C9 C10 C11 C12 -175.9(2) . . . . ? C10 C11 C12 C13 -1.0(4) . . . . ? C11 C12 C13 C14 -0.2(5) . . . . ? C12 C13 C14 C15 0.7(5) . . . . ? C13 C14 C15 C10 0.0(5) . . . . ? C11 C10 C15 C14 -1.1(4) . . . . ? C9 C10 C15 C14 176.4(3) . . . . ? C7 N1 C16 C17 153.3(2) . . . . ? C7 N1 C16 C21 -31.1(3) . . . . ? C21 C16 C17 C18 -1.6(4) . . . . ? N1 C16 C17 C18 174.3(2) . . . . ? C16 C17 C18 C19 -0.1(4) . . . . ? C22 O2 C19 C20 -164.5(2) . . . . ? C22 O2 C19 C18 17.7(4) . . . . ? C17 C18 C19 C20 2.3(4) . . . . ? C17 C18 C19 O2 -179.9(2) . . . . ? O2 C19 C20 C21 179.4(2) . . . . ? C18 C19 C20 C21 -2.6(4) . . . . ? C19 C20 C21 C16 0.9(4) . . . . ? C17 C16 C21 C20 1.3(4) . . . . ? N1 C16 C21 C20 -174.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.251 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.028