# Electronic Supplementary Material (ESI) for Green Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Green Chemistry' _journal_coden_cambridge 1048 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Mr. Rambabu' _publ_contact_author_email rambabu_us@yahoo.com _publ_author_name M.Pal data_iql_012_a _database_code_depnum_ccdc_archive 'CCDC 864149' #TrackingRef 'IQL_012_A.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H18 F3 N O4' _chemical_formula_weight 405.37 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' F F 0.0171 0.0103 '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, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.6247(14) _cell_length_b 8.6852(8) _cell_length_c 17.0833(19) _cell_angle_alpha 90.00 _cell_angle_beta 112.949(2) _cell_angle_gamma 90.00 _cell_volume 1861.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 273(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 1.450 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 844 _exptl_absorpt_coefficient_mu 0.120 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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_reflns_number 18259 _diffrn_reflns_av_R_equivalents 0.0430 _diffrn_reflns_av_sigmaI/netI 0.0373 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4264 _reflns_number_gt 3202 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0401P)^2^+0.7713P] 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 SHELXL _refine_ls_extinction_coef 0.0020(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4264 _refine_ls_number_parameters 266 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0582 _refine_ls_R_factor_gt 0.0394 _refine_ls_wR_factor_ref 0.1007 _refine_ls_wR_factor_gt 0.0906 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.001 _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 0.04939(12) 0.79339(19) 0.76885(10) 0.0218(3) Uani 1 1 d . . . C2 C 0.10272(12) 0.78846(17) 0.70688(10) 0.0172(3) Uani 1 1 d . . . C3 C 0.20231(12) 0.71868(18) 0.73155(9) 0.0178(3) Uani 1 1 d . . . H3 H 0.2327 0.6707 0.7842 0.021 Uiso 1 1 calc R . . C4 C 0.25600(12) 0.72109(18) 0.67712(9) 0.0177(3) Uani 1 1 d . . . H4 H 0.3229 0.6756 0.6941 0.021 Uiso 1 1 calc R . . C5 C 0.21094(11) 0.79077(17) 0.59738(9) 0.0151(3) Uani 1 1 d . . . C6 C 0.26981(11) 0.80308(17) 0.53979(9) 0.0149(3) Uani 1 1 d . . . C7 C 0.33645(11) 0.68402(17) 0.52958(9) 0.0156(3) Uani 1 1 d . . . C8 C 0.39817(11) 0.71620(17) 0.48390(9) 0.0159(3) Uani 1 1 d . . . H8 H 0.4455 0.6426 0.4798 0.019 Uiso 1 1 calc R . . C9 C 0.39002(11) 0.85931(17) 0.44359(9) 0.0140(3) Uani 1 1 d . . . C10 C 0.44728(11) 0.89651(17) 0.39197(9) 0.0148(3) Uani 1 1 d . . . H10 H 0.4965 0.8272 0.3870 0.018 Uiso 1 1 calc R . . C11 C 0.43002(11) 1.03399(17) 0.34973(9) 0.0158(3) Uani 1 1 d . . . C12 C 0.54816(12) 0.97456(18) 0.28130(10) 0.0200(3) Uani 1 1 d . . . H12A H 0.6097 0.9600 0.3330 0.030 Uiso 1 1 calc R . . H12B H 0.5699 1.0152 0.2383 0.030 Uiso 1 1 calc R . . H12C H 0.5130 0.8776 0.2627 0.030 Uiso 1 1 calc R . . C13 C 0.11077(12) 0.85906(18) 0.57361(10) 0.0199(3) Uani 1 1 d . . . H13 H 0.0798 0.9062 0.5207 0.024 Uiso 1 1 calc R . . C14 C 0.05637(12) 0.85800(19) 0.62753(10) 0.0214(3) Uani 1 1 d . . . H14 H -0.0105 0.9035 0.6107 0.026 Uiso 1 1 calc R . . C15 C 0.35594(11) 1.14323(17) 0.35924(9) 0.0151(3) Uani 1 1 d . . . C16 C 0.27813(13) 1.39139(18) 0.32514(11) 0.0243(4) Uani 1 1 d . . . H16A H 0.2069 1.3516 0.3064 0.037 Uiso 1 1 calc R . . H16B H 0.2788 1.4803 0.2919 0.037 Uiso 1 1 calc R . . H16C H 0.3025 1.4198 0.3840 0.037 Uiso 1 1 calc R . . C17 C 0.30142(11) 1.10961(17) 0.40943(9) 0.0154(3) Uani 1 1 d . . . H17 H 0.2539 1.1811 0.4153 0.019 Uiso 1 1 calc R . . C18 C 0.31673(11) 0.96674(17) 0.45250(9) 0.0143(3) Uani 1 1 d . . . C19 C 0.33954(12) 0.52218(18) 0.55987(9) 0.0176(3) Uani 1 1 d . . . C20 C 0.24322(14) 0.32575(19) 0.59615(11) 0.0261(4) Uani 1 1 d . . . H20A H 0.2997 0.3177 0.6523 0.031 Uiso 1 1 calc R . . H20B H 0.2526 0.2448 0.5606 0.031 Uiso 1 1 calc R . . C21 C 0.13589(16) 0.3122(2) 0.60150(14) 0.0399(5) Uani 1 1 d . . . H21A H 0.1296 0.3889 0.6397 0.060 Uiso 1 1 calc R . . H21B H 0.1287 0.2117 0.6221 0.060 Uiso 1 1 calc R . . H21C H 0.0809 0.3272 0.5461 0.060 Uiso 1 1 calc R . . F1 F 0.05482(10) 0.65994(14) 0.80857(8) 0.0482(3) Uani 1 1 d . . . F2 F 0.09414(10) 0.89713(15) 0.83032(7) 0.0475(3) Uani 1 1 d . . . F3 F -0.05353(8) 0.82948(15) 0.73246(7) 0.0414(3) Uani 1 1 d . . . N1 N 0.26008(9) 0.93908(14) 0.50169(8) 0.0156(3) Uani 1 1 d . . . O1 O 0.47628(8) 1.08053(12) 0.29606(7) 0.0197(2) Uani 1 1 d . . . O2 O 0.34697(8) 1.27602(12) 0.31488(7) 0.0197(2) Uani 1 1 d . . . O3 O 0.41740(9) 0.43987(13) 0.57936(7) 0.0255(3) Uani 1 1 d . . . O4 O 0.24558(9) 0.47664(12) 0.55919(7) 0.0216(3) 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 0.0233(8) 0.0223(9) 0.0230(8) 0.0001(7) 0.0124(7) -0.0034(6) C2 0.0206(7) 0.0148(8) 0.0188(7) -0.0022(6) 0.0105(6) -0.0041(6) C3 0.0204(7) 0.0177(8) 0.0143(7) 0.0009(6) 0.0057(6) -0.0011(6) C4 0.0174(7) 0.0180(8) 0.0175(7) 0.0003(6) 0.0068(6) 0.0020(6) C5 0.0188(7) 0.0121(7) 0.0164(7) -0.0005(6) 0.0089(6) -0.0007(5) C6 0.0165(7) 0.0152(8) 0.0131(7) -0.0005(5) 0.0057(6) -0.0007(5) C7 0.0175(7) 0.0148(8) 0.0129(7) 0.0003(6) 0.0043(6) 0.0020(6) C8 0.0167(7) 0.0148(8) 0.0154(7) -0.0005(6) 0.0053(6) 0.0029(6) C9 0.0138(6) 0.0143(7) 0.0126(7) -0.0022(6) 0.0039(5) -0.0002(5) C10 0.0139(6) 0.0147(8) 0.0164(7) -0.0023(6) 0.0066(6) 0.0010(5) C11 0.0164(7) 0.0164(8) 0.0157(7) -0.0021(6) 0.0076(6) -0.0025(6) C12 0.0206(7) 0.0185(8) 0.0262(8) -0.0003(6) 0.0150(7) 0.0018(6) C13 0.0215(7) 0.0197(8) 0.0189(8) 0.0064(6) 0.0084(6) 0.0039(6) C14 0.0193(7) 0.0227(9) 0.0250(8) 0.0050(7) 0.0116(6) 0.0047(6) C15 0.0170(7) 0.0115(7) 0.0161(7) 0.0009(6) 0.0056(6) 0.0003(5) C16 0.0298(9) 0.0151(8) 0.0365(10) 0.0062(7) 0.0220(8) 0.0059(6) C17 0.0161(7) 0.0155(8) 0.0156(7) -0.0007(6) 0.0071(6) 0.0032(5) C18 0.0157(7) 0.0143(8) 0.0121(7) -0.0005(5) 0.0047(5) 0.0003(5) C19 0.0247(8) 0.0171(8) 0.0136(7) -0.0002(6) 0.0104(6) 0.0020(6) C20 0.0438(10) 0.0139(8) 0.0263(9) 0.0004(6) 0.0200(8) -0.0038(7) C21 0.0490(12) 0.0308(11) 0.0484(12) -0.0001(9) 0.0282(10) -0.0140(9) F1 0.0744(9) 0.0364(7) 0.0596(8) 0.0204(6) 0.0541(7) 0.0116(6) F2 0.0538(7) 0.0634(8) 0.0407(7) -0.0311(6) 0.0352(6) -0.0301(6) F3 0.0245(5) 0.0710(9) 0.0360(6) 0.0093(6) 0.0198(5) 0.0078(5) N1 0.0176(6) 0.0159(7) 0.0142(6) 0.0007(5) 0.0072(5) 0.0017(5) O1 0.0234(6) 0.0172(6) 0.0256(6) 0.0027(4) 0.0175(5) 0.0027(4) O2 0.0255(6) 0.0135(6) 0.0264(6) 0.0046(4) 0.0170(5) 0.0048(4) O3 0.0328(6) 0.0204(6) 0.0296(6) 0.0081(5) 0.0190(5) 0.0108(5) O4 0.0278(6) 0.0147(6) 0.0261(6) 0.0031(4) 0.0146(5) -0.0005(4) _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 F1 1.3305(19) . ? C1 F3 1.3309(18) . ? C1 F2 1.3367(19) . ? C1 C2 1.500(2) . ? C2 C14 1.391(2) . ? C2 C3 1.393(2) . ? C3 C4 1.390(2) . ? C3 H3 0.9300 . ? C4 C5 1.395(2) . ? C4 H4 0.9300 . ? C5 C13 1.395(2) . ? C5 C6 1.496(2) . ? C6 N1 1.3301(19) . ? C6 C7 1.431(2) . ? C7 C8 1.381(2) . ? C7 C19 1.493(2) . ? C8 C9 1.404(2) . ? C8 H8 0.9300 . ? C9 C18 1.418(2) . ? C9 C10 1.424(2) . ? C10 C11 1.367(2) . ? C10 H10 0.9300 . ? C11 O1 1.3609(17) . ? C11 C15 1.440(2) . ? C12 O1 1.4360(18) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.389(2) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 O2 1.3591(18) . ? C15 C17 1.367(2) . ? C16 O2 1.4291(18) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 C18 1.416(2) . ? C17 H17 0.9300 . ? C18 N1 1.3658(18) . ? C19 O3 1.2132(18) . ? C19 O4 1.3356(18) . ? C20 O4 1.4604(19) . ? C20 C21 1.505(3) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 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 F1 C1 F3 106.40(13) . . ? F1 C1 F2 105.60(14) . . ? F3 C1 F2 106.44(14) . . ? F1 C1 C2 112.90(13) . . ? F3 C1 C2 112.90(13) . . ? F2 C1 C2 112.06(13) . . ? C14 C2 C3 120.17(14) . . ? C14 C2 C1 120.98(14) . . ? C3 C2 C1 118.79(14) . . ? C4 C3 C2 119.73(14) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C5 120.92(14) . . ? C3 C4 H4 119.5 . . ? C5 C4 H4 119.5 . . ? C4 C5 C13 118.47(14) . . ? C4 C5 C6 121.90(13) . . ? C13 C5 C6 119.50(13) . . ? N1 C6 C7 121.94(13) . . ? N1 C6 C5 114.12(12) . . ? C7 C6 C5 123.84(13) . . ? C8 C7 C6 118.55(13) . . ? C8 C7 C19 116.45(13) . . ? C6 C7 C19 124.87(13) . . ? C7 C8 C9 120.48(13) . . ? C7 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? C8 C9 C18 117.01(13) . . ? C8 C9 C10 123.16(13) . . ? C18 C9 C10 119.75(13) . . ? C11 C10 C9 120.14(13) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? O1 C11 C10 125.84(13) . . ? O1 C11 C15 114.17(13) . . ? C10 C11 C15 119.99(13) . . ? O1 C12 H12A 109.5 . . ? O1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C5 121.22(14) . . ? C14 C13 H13 119.4 . . ? C5 C13 H13 119.4 . . ? C13 C14 C2 119.49(14) . . ? C13 C14 H14 120.3 . . ? C2 C14 H14 120.3 . . ? O2 C15 C17 125.32(13) . . ? O2 C15 C11 114.27(13) . . ? C17 C15 C11 120.41(13) . . ? O2 C16 H16A 109.5 . . ? O2 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O2 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C17 C18 120.47(13) . . ? C15 C17 H17 119.8 . . ? C18 C17 H17 119.8 . . ? N1 C18 C17 118.02(13) . . ? N1 C18 C9 122.76(13) . . ? C17 C18 C9 119.22(13) . . ? O3 C19 O4 124.09(14) . . ? O3 C19 C7 123.60(14) . . ? O4 C19 C7 112.24(12) . . ? O4 C20 C21 106.39(14) . . ? O4 C20 H20A 110.5 . . ? C21 C20 H20A 110.5 . . ? O4 C20 H20B 110.5 . . ? C21 C20 H20B 110.5 . . ? H20A C20 H20B 108.6 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C6 N1 C18 119.00(12) . . ? C11 O1 C12 117.04(12) . . ? C15 O2 C16 116.57(12) . . ? C19 O4 C20 116.39(12) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.374 _refine_diff_density_min -0.260 _refine_diff_density_rms 0.047