# Electronic Supplementary Material (ESI) for Catalysis Science & Technology # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Cat.Sci.Tech. _journal_coden_cambridge 1486 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Rajakumar Ananthakrishnan' _publ_contact_author_email raja.iitchem@yahoo.com loop_ _publ_author_name S.Gazi R.Ananthakrishnan data_ra_sg_dph6_0m _database_code_depnum_ccdc_archive 'CCDC 818065' #TrackingRef '- ra_sg_dph6_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H17 N O5' _chemical_formula_weight 315.32 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 ? _symmetry_space_group_name_H-M ? 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 8.8191(6) _cell_length_b 17.5507(11) _cell_length_c 20.7531(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3212.2(4) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.304 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1328 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type ? _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 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 42559 _diffrn_reflns_av_R_equivalents 0.0373 _diffrn_reflns_av_sigmaI/netI 0.0226 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 29.49 _reflns_number_total 4345 _reflns_number_gt 3091 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0791P)^2^+1.4852P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4345 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0788 _refine_ls_R_factor_gt 0.0520 _refine_ls_wR_factor_ref 0.1682 _refine_ls_wR_factor_gt 0.1416 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.006 _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 N1 N 0.20650(16) 0.08726(8) 0.38657(6) 0.0364(3) Uani 1 1 d . . . O3 O 0.07965(17) 0.21838(8) 0.54573(6) 0.0473(3) Uani 1 1 d . . . C11 C -0.07236(18) 0.16102(9) 0.40603(8) 0.0336(3) Uani 1 1 d . . . C7 C 0.15956(17) 0.10474(9) 0.44636(7) 0.0308(3) Uani 1 1 d . . . C8 C 0.02261(18) 0.14272(9) 0.45750(7) 0.0318(3) Uani 1 1 d . . . C13 C -0.01999(19) 0.14270(9) 0.34451(7) 0.0344(3) Uani 1 1 d . . . C3 C 0.2028(2) 0.04086(10) 0.55262(8) 0.0382(4) Uani 1 1 d . . . H3 H 0.0997 0.0301 0.5548 0.046 Uiso 1 1 calc R . . C4 C 0.26005(18) 0.08102(9) 0.50020(7) 0.0317(3) Uani 1 1 d . . . O5 O -0.22507(16) 0.11400(9) 0.27840(7) 0.0553(4) Uani 1 1 d . . . O1 O 0.54096(18) 0.00466(10) 0.64709(6) 0.0637(5) Uani 1 1 d . . . H1 H 0.6294 0.0168 0.6405 0.096 Uiso 1 1 calc R . . O2 O -0.12315(16) 0.14281(10) 0.55505(7) 0.0579(4) Uani 1 1 d . . . C6 C 0.50895(19) 0.07458(12) 0.54792(9) 0.0433(4) Uani 1 1 d . . . H6 H 0.6114 0.0871 0.5468 0.052 Uiso 1 1 calc R . . C14 C 0.12023(19) 0.10779(10) 0.33607(7) 0.0362(4) Uani 1 1 d . . . C16 C -0.1148(2) 0.16335(11) 0.28705(8) 0.0406(4) Uani 1 1 d . . . C9 C -0.01865(18) 0.16667(10) 0.52482(8) 0.0354(4) Uani 1 1 d . . . C1 C 0.4512(2) 0.03239(11) 0.59856(8) 0.0418(4) Uani 1 1 d . . . C2 C 0.2978(2) 0.01687(11) 0.60153(8) 0.0427(4) Uani 1 1 d . . . H2 H 0.2584 -0.0097 0.6365 0.051 Uiso 1 1 calc R . . C5 C 0.41369(19) 0.09802(11) 0.49895(8) 0.0380(4) Uani 1 1 d . . . H5 H 0.4532 0.1256 0.4646 0.046 Uiso 1 1 calc R . . O4 O -0.0939(2) 0.21765(11) 0.25405(8) 0.0787(6) Uani 1 1 d . . . C12 C -0.2219(2) 0.20032(13) 0.41602(10) 0.0512(5) Uani 1 1 d . . . H12A H -0.2383 0.2082 0.4613 0.077 Uiso 1 1 calc R . . H12B H -0.3019 0.1693 0.3989 0.077 Uiso 1 1 calc R . . H12C H -0.2210 0.2486 0.3943 0.077 Uiso 1 1 calc R . . C15 C 0.1832(3) 0.09149(14) 0.27013(9) 0.0554(5) Uani 1 1 d . . . H15A H 0.2806 0.0675 0.2742 0.083 Uiso 1 1 calc R . . H15B H 0.1939 0.1384 0.2467 0.083 Uiso 1 1 calc R . . H15C H 0.1155 0.0582 0.2474 0.083 Uiso 1 1 calc R . . C17 C -0.3312(3) 0.12925(17) 0.22682(12) 0.0742(7) Uani 1 1 d . . . H17A H -0.4058 0.0895 0.2253 0.111 Uiso 1 1 calc R . . H17B H -0.2778 0.1312 0.1865 0.111 Uiso 1 1 calc R . . H17C H -0.3804 0.1772 0.2344 0.111 Uiso 1 1 calc R . . C10 C 0.0652(3) 0.24102(15) 0.61238(9) 0.0650(6) Uani 1 1 d . . . H10A H 0.1411 0.2784 0.6224 0.097 Uiso 1 1 calc R . . H10B H 0.0785 0.1973 0.6396 0.097 Uiso 1 1 calc R . . H10C H -0.0336 0.2624 0.6194 0.097 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 N1 0.0362(7) 0.0451(8) 0.0278(6) -0.0021(5) -0.0009(5) 0.0044(6) O3 0.0624(8) 0.0514(8) 0.0283(6) -0.0076(5) 0.0090(6) -0.0141(6) C11 0.0334(7) 0.0371(8) 0.0302(7) 0.0023(6) 0.0001(6) 0.0007(6) C7 0.0317(7) 0.0344(8) 0.0262(7) 0.0005(6) -0.0009(6) -0.0023(6) C8 0.0327(7) 0.0365(8) 0.0260(7) 0.0006(6) 0.0012(6) -0.0027(6) C13 0.0377(8) 0.0396(9) 0.0258(7) 0.0038(6) -0.0039(6) 0.0002(7) C3 0.0353(8) 0.0448(10) 0.0344(8) 0.0050(7) -0.0022(6) -0.0035(7) C4 0.0333(7) 0.0357(8) 0.0262(7) -0.0010(6) -0.0031(6) 0.0004(6) O5 0.0524(8) 0.0649(9) 0.0486(8) 0.0185(7) -0.0215(6) -0.0082(7) O1 0.0554(9) 0.1060(13) 0.0298(7) -0.0036(7) -0.0103(6) 0.0345(9) O2 0.0447(8) 0.0894(12) 0.0396(7) -0.0064(7) 0.0132(6) -0.0155(7) C6 0.0311(8) 0.0597(11) 0.0391(9) -0.0093(8) -0.0053(7) 0.0027(8) C14 0.0400(8) 0.0436(9) 0.0249(7) -0.0008(6) -0.0011(6) 0.0031(7) C16 0.0452(9) 0.0473(10) 0.0292(8) 0.0069(7) -0.0033(7) 0.0037(8) C9 0.0342(8) 0.0444(9) 0.0278(7) 0.0019(6) 0.0016(6) 0.0012(7) C1 0.0442(9) 0.0547(11) 0.0267(7) -0.0082(7) -0.0065(7) 0.0148(8) C2 0.0491(10) 0.0493(10) 0.0295(8) 0.0052(7) -0.0013(7) 0.0044(8) C5 0.0344(8) 0.0466(10) 0.0329(8) -0.0003(7) 0.0009(6) -0.0011(7) O4 0.0952(13) 0.0785(11) 0.0625(10) 0.0398(9) -0.0287(9) -0.0231(10) C12 0.0434(10) 0.0669(13) 0.0432(10) 0.0019(9) 0.0001(8) 0.0187(9) C15 0.0585(12) 0.0800(15) 0.0275(8) -0.0042(8) 0.0017(8) 0.0178(11) C17 0.0673(15) 0.0932(19) 0.0621(14) 0.0162(13) -0.0363(12) -0.0024(14) C10 0.0904(17) 0.0741(15) 0.0303(9) -0.0142(9) 0.0110(10) -0.0201(13) _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 N1 C7 1.344(2) . ? N1 C14 1.344(2) . ? O3 C9 1.328(2) . ? O3 C10 1.445(2) . ? C11 C8 1.395(2) . ? C11 C13 1.395(2) . ? C11 C12 1.503(2) . ? C7 C8 1.399(2) . ? C7 C4 1.486(2) . ? C8 C9 1.504(2) . ? C13 C14 1.391(2) . ? C13 C16 1.501(2) . ? C3 C2 1.381(2) . ? C3 C4 1.391(2) . ? C4 C5 1.388(2) . ? O5 C16 1.314(2) . ? O5 C17 1.447(2) . ? O1 C1 1.370(2) . ? O2 C9 1.191(2) . ? C6 C5 1.381(2) . ? C6 C1 1.383(3) . ? C14 C15 1.504(2) . ? C16 O4 1.188(2) . ? C1 C2 1.382(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 C7 N1 C14 118.98(14) . . ? C9 O3 C10 116.31(15) . . ? C8 C11 C13 116.68(15) . . ? C8 C11 C12 121.80(15) . . ? C13 C11 C12 121.50(15) . . ? N1 C7 C8 121.83(14) . . ? N1 C7 C4 116.54(14) . . ? C8 C7 C4 121.62(13) . . ? C11 C8 C7 120.11(14) . . ? C11 C8 C9 120.12(14) . . ? C7 C8 C9 119.72(14) . . ? C14 C13 C11 120.72(14) . . ? C14 C13 C16 120.11(14) . . ? C11 C13 C16 119.14(15) . . ? C2 C3 C4 120.62(16) . . ? C5 C4 C3 118.54(15) . . ? C5 C4 C7 120.54(14) . . ? C3 C4 C7 120.92(14) . . ? C16 O5 C17 117.24(17) . . ? C5 C6 C1 119.65(16) . . ? N1 C14 C13 121.54(14) . . ? N1 C14 C15 116.69(15) . . ? C13 C14 C15 121.77(15) . . ? O4 C16 O5 124.39(17) . . ? O4 C16 C13 124.41(18) . . ? O5 C16 C13 111.20(14) . . ? O2 C9 O3 124.98(16) . . ? O2 C9 C8 125.34(16) . . ? O3 C9 C8 109.68(13) . . ? O1 C1 C2 117.58(17) . . ? O1 C1 C6 122.41(17) . . ? C2 C1 C6 120.00(16) . . ? C3 C2 C1 120.05(17) . . ? C6 C5 C4 121.07(16) . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 29.49 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.415 _refine_diff_density_min -0.273 _refine_diff_density_rms 0.049