# Electronic Supplementary Material (ESI) for Green Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Green Chemistry' _journal_coden_cambridge 1048 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email rkpedfcy@iitr.ernet.in _publ_contact_author_name 'Rama Krishna Peddinti' loop_ _publ_author_name 'Rama Krishna Peddinti' 'Garima Choudhary' data_nag _database_code_depnum_ccdc_archive 'CCDC 827294' #TrackingRef 'X-Ray-GC-Paper-Peddinti-IITR.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic 'give the name of the compound' _chemical_name_common 'give the name of the compound' _chemical_melting_point ? _chemical_formula_moiety 'C16 H19 N1 O4' _chemical_formula_sum 'C16 H19 N O4' _chemical_formula_weight 289.32 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.236(2) _cell_length_b 9.233(2) _cell_length_c 12.061(3) _cell_angle_alpha 85.83(4) _cell_angle_beta 82.48(4) _cell_angle_gamma 73.52(4) _cell_volume 765.5(3) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Blocks _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.36 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.255 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 308 _exptl_absorpt_coefficient_mu 0.090 _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 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 'Bruker, APEX CCD area detector' _diffrn_measurement_method SMART _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7501 _diffrn_reflns_av_R_equivalents 0.0214 _diffrn_reflns_av_sigmaI/netI 0.0225 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 25.25 _reflns_number_total 2758 _reflns_number_gt 2362 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SMART _computing_data_reduction SAINTPLUS _computing_structure_solution 'SHELXTL (Sheldrick, 1990)' _computing_structure_refinement 'SHELXTL (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^)+(0.0590P)^2^+0.2322P] 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 2758 _refine_ls_number_parameters 194 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0701 _refine_ls_R_factor_gt 0.0597 _refine_ls_wR_factor_ref 0.1495 _refine_ls_wR_factor_gt 0.1436 _refine_ls_goodness_of_fit_ref 1.154 _refine_ls_restrained_S_all 1.154 _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 0.4658(2) 0.24153(16) 0.42346(12) 0.0541(4) Uani 1 1 d . . . O2 O 0.3816(3) 0.3246(2) 0.25774(14) 0.0808(6) Uani 1 1 d . . . O3 O -0.0006(2) 0.78294(16) 0.47411(12) 0.0511(4) Uani 1 1 d . . . O4 O 0.0055(2) 0.85868(16) 0.29224(12) 0.0489(4) Uani 1 1 d . . . N1 N 0.2337(2) 0.50499(18) 0.51676(13) 0.0428(4) Uani 1 1 d . . . H1A H 0.1638 0.5876 0.5464 0.051 Uiso 1 1 d R . . C1 C 0.3661(3) 0.3503(3) 0.35437(18) 0.0524(6) Uani 1 1 d . . . C2 C 0.2467(3) 0.4953(2) 0.40382(16) 0.0417(5) Uani 1 1 d . . . C3 C 0.3271(3) 0.3889(2) 0.58644(16) 0.0391(5) Uani 1 1 d . . . C4 C 0.3053(3) 0.3998(2) 0.70196(17) 0.0428(5) Uani 1 1 d . . . H14A H 0.2269 0.4884 0.7339 0.051 Uiso 1 1 calc R . . C5 C 0.3975(3) 0.2819(2) 0.77077(17) 0.0456(5) Uani 1 1 d . . . C6 C 0.5138(3) 0.1507(2) 0.71910(19) 0.0519(6) Uani 1 1 d . . . H7A H 0.5762 0.0694 0.7633 0.062 Uiso 1 1 calc R . . C7 C 0.5385(3) 0.1386(2) 0.60444(19) 0.0503(5) Uani 1 1 d . . . H12A H 0.6180 0.0509 0.5717 0.060 Uiso 1 1 calc R . . C8 C 0.4436(3) 0.2580(2) 0.53949(17) 0.0424(5) Uani 1 1 d . . . C9 C 0.3689(4) 0.2914(3) 0.89832(18) 0.0576(6) Uani 1 1 d . . . C10 C 0.5641(5) 0.2337(4) 0.9453(2) 0.0932(10) Uani 1 1 d . . . H2A H 0.6493 0.2920 0.9122 0.140 Uiso 1 1 calc R . . H2B H 0.6209 0.1293 0.9282 0.140 Uiso 1 1 calc R . . H2C H 0.5448 0.2435 1.0250 0.140 Uiso 1 1 calc R . . C11 C 0.2354(6) 0.1960(5) 0.9466(3) 0.1133(13) Uani 1 1 d . . . H3A H 0.1127 0.2338 0.9174 0.170 Uiso 1 1 calc R . . H3B H 0.2160 0.2010 1.0266 0.170 Uiso 1 1 calc R . . H3C H 0.2930 0.0930 0.9262 0.170 Uiso 1 1 calc R . . C12 C 0.2791(5) 0.4534(3) 0.9354(2) 0.0905(10) Uani 1 1 d . . . H1B H 0.1489 0.4889 0.9160 0.136 Uiso 1 1 calc R . . H1C H 0.3546 0.5169 0.8984 0.136 Uiso 1 1 calc R . . H1D H 0.2774 0.4562 1.0149 0.136 Uiso 1 1 calc R . . C13 C 0.1613(3) 0.6095(2) 0.33447(17) 0.0443(5) Uani 1 1 d . . . H11A H 0.1756 0.5938 0.2582 0.053 Uiso 1 1 calc R . . C14 C 0.0488(3) 0.7549(2) 0.37530(17) 0.0419(5) Uani 1 1 d . . . C15 C -0.1019(4) 1.0106(2) 0.3241(2) 0.0601(6) Uani 1 1 d . . . H5A H -0.0518 1.0377 0.3881 0.072 Uiso 1 1 calc R . . H5B H -0.2378 1.0161 0.3447 0.072 Uiso 1 1 calc R . . C16 C -0.0807(5) 1.1154(3) 0.2284(3) 0.0985(11) Uani 1 1 d . . . H4A H -0.1619 1.2149 0.2455 0.148 Uiso 1 1 calc R . . H4B H -0.1185 1.0820 0.1635 0.148 Uiso 1 1 calc R . . H4C H 0.0521 1.1176 0.2139 0.148 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 0.0604(10) 0.0476(9) 0.0457(9) -0.0060(7) -0.0055(7) -0.0002(7) O2 0.1105(15) 0.0701(12) 0.0434(10) -0.0128(8) -0.0127(9) 0.0092(11) O3 0.0613(10) 0.0468(8) 0.0419(9) -0.0008(6) -0.0051(7) -0.0103(7) O4 0.0533(9) 0.0443(8) 0.0449(8) 0.0056(6) -0.0066(7) -0.0081(7) N1 0.0463(10) 0.0394(9) 0.0389(9) -0.0008(7) -0.0042(7) -0.0064(7) C1 0.0572(13) 0.0508(13) 0.0437(13) -0.0023(10) -0.0048(10) -0.0067(11) C2 0.0416(11) 0.0445(11) 0.0398(11) -0.0019(9) -0.0020(9) -0.0143(9) C3 0.0355(10) 0.0384(10) 0.0447(11) 0.0019(8) -0.0051(8) -0.0128(8) C4 0.0418(11) 0.0430(11) 0.0433(11) -0.0010(9) -0.0026(9) -0.0122(9) C5 0.0457(11) 0.0484(12) 0.0456(12) 0.0070(9) -0.0079(9) -0.0188(10) C6 0.0527(13) 0.0450(12) 0.0569(14) 0.0103(10) -0.0140(10) -0.0114(10) C7 0.0485(12) 0.0410(11) 0.0579(14) -0.0033(10) -0.0074(10) -0.0059(10) C8 0.0404(11) 0.0438(11) 0.0430(11) -0.0025(9) -0.0038(9) -0.0117(9) C9 0.0664(15) 0.0635(15) 0.0421(13) 0.0076(11) -0.0073(11) -0.0187(12) C10 0.095(2) 0.119(3) 0.0561(17) 0.0004(17) -0.0292(16) -0.006(2) C11 0.152(3) 0.150(3) 0.0602(19) 0.014(2) 0.009(2) -0.092(3) C12 0.130(3) 0.084(2) 0.0431(15) -0.0043(14) -0.0125(16) -0.0053(19) C13 0.0463(11) 0.0496(12) 0.0366(11) 0.0025(9) -0.0043(9) -0.0138(9) C14 0.0401(11) 0.0475(12) 0.0403(11) 0.0031(9) -0.0063(9) -0.0162(9) C15 0.0679(15) 0.0425(12) 0.0639(15) 0.0019(11) -0.0020(12) -0.0089(11) C16 0.127(3) 0.0532(16) 0.092(2) 0.0199(15) 0.0111(19) -0.0037(17) _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 1.359(3) . ? O1 C8 1.402(2) . ? O2 C1 1.191(3) . ? O3 C14 1.223(2) . ? O4 C14 1.339(2) . ? O4 C15 1.449(3) . ? N1 C2 1.361(3) . ? N1 C3 1.385(2) . ? N1 H1A 0.8599 . ? C1 C2 1.490(3) . ? C2 C13 1.353(3) . ? C3 C8 1.374(3) . ? C3 C4 1.389(3) . ? C4 C5 1.386(3) . ? C4 H14A 0.9300 . ? C5 C6 1.399(3) . ? C5 C9 1.531(3) . ? C6 C7 1.380(3) . ? C6 H7A 0.9300 . ? C7 C8 1.373(3) . ? C7 H12A 0.9300 . ? C9 C11 1.520(4) . ? C9 C12 1.526(4) . ? C9 C10 1.529(4) . ? C10 H2A 0.9600 . ? C10 H2B 0.9600 . ? C10 H2C 0.9600 . ? C11 H3A 0.9600 . ? C11 H3B 0.9600 . ? C11 H3C 0.9600 . ? C12 H1B 0.9600 . ? C12 H1C 0.9600 . ? C12 H1D 0.9600 . ? C13 C14 1.441(3) . ? C13 H11A 0.9300 . ? C15 C16 1.472(4) . ? C15 H5A 0.9700 . ? C15 H5B 0.9700 . ? C16 H4A 0.9600 . ? C16 H4B 0.9600 . ? C16 H4C 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 C8 121.52(16) . . ? C14 O4 C15 116.88(16) . . ? C2 N1 C3 123.51(17) . . ? C2 N1 H1A 118.2 . . ? C3 N1 H1A 118.3 . . ? O2 C1 O1 118.0(2) . . ? O2 C1 C2 124.0(2) . . ? O1 C1 C2 118.00(18) . . ? C13 C2 N1 124.07(19) . . ? C13 C2 C1 118.58(19) . . ? N1 C2 C1 117.33(18) . . ? C8 C3 N1 118.70(18) . . ? C8 C3 C4 119.04(18) . . ? N1 C3 C4 122.25(18) . . ? C5 C4 C3 121.61(19) . . ? C5 C4 H14A 119.2 . . ? C3 C4 H14A 119.2 . . ? C4 C5 C6 117.22(19) . . ? C4 C5 C9 121.8(2) . . ? C6 C5 C9 120.91(19) . . ? C7 C6 C5 121.9(2) . . ? C7 C6 H7A 119.0 . . ? C5 C6 H7A 119.0 . . ? C8 C7 C6 118.9(2) . . ? C8 C7 H12A 120.5 . . ? C6 C7 H12A 120.5 . . ? C7 C8 C3 121.31(19) . . ? C7 C8 O1 117.99(18) . . ? C3 C8 O1 120.68(18) . . ? C11 C9 C12 108.8(3) . . ? C11 C9 C10 110.0(3) . . ? C12 C9 C10 107.1(2) . . ? C11 C9 C5 108.6(2) . . ? C12 C9 C5 112.02(19) . . ? C10 C9 C5 110.3(2) . . ? C9 C10 H2A 109.5 . . ? C9 C10 H2B 109.5 . . ? H2A C10 H2B 109.5 . . ? C9 C10 H2C 109.5 . . ? H2A C10 H2C 109.5 . . ? H2B C10 H2C 109.5 . . ? C9 C11 H3A 109.5 . . ? C9 C11 H3B 109.5 . . ? H3A C11 H3B 109.5 . . ? C9 C11 H3C 109.5 . . ? H3A C11 H3C 109.5 . . ? H3B C11 H3C 109.5 . . ? C9 C12 H1B 109.5 . . ? C9 C12 H1C 109.5 . . ? H1B C12 H1C 109.5 . . ? C9 C12 H1D 109.5 . . ? H1B C12 H1D 109.5 . . ? H1C C12 H1D 109.5 . . ? C2 C13 C14 121.98(19) . . ? C2 C13 H11A 119.0 . . ? C14 C13 H11A 119.0 . . ? O3 C14 O4 122.98(19) . . ? O3 C14 C13 124.77(18) . . ? O4 C14 C13 112.24(17) . . ? O4 C15 C16 108.5(2) . . ? O4 C15 H5A 110.0 . . ? C16 C15 H5A 110.0 . . ? O4 C15 H5B 110.0 . . ? C16 C15 H5B 110.0 . . ? H5A C15 H5B 108.4 . . ? C15 C16 H4A 109.5 . . ? C15 C16 H4B 109.5 . . ? H4A C16 H4B 109.5 . . ? C15 C16 H4C 109.5 . . ? H4A C16 H4C 109.5 . . ? H4B C16 H4C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.179 _refine_diff_density_min -0.147 _refine_diff_density_rms 0.036