# Electronic Supplementary Material (ESI) for Organic and Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email sureshe123@rediffmail.com _publ_contact_author_name Dr.Suresh.E. _publ_author_name V.Nair data_rmr152m _database_code_depnum_ccdc_archive 'CCDC 813059' #TrackingRef 'Rmr152m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H10 O2' _chemical_formula_weight 174.19 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' O O 0.0106 0.0060 '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' _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 6.352(3) _cell_length_b 7.033(3) _cell_length_c 10.437(4) _cell_angle_alpha 83.301(7) _cell_angle_beta 77.060(7) _cell_angle_gamma 77.613(7) _cell_volume 442.7(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1545 _cell_measurement_theta_min 2.97 _cell_measurement_theta_max 27.80 _exptl_crystal_description PLATES _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.307 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 184 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_process_details ' BRUKER SADABS' _exptl_absorpt_correction_T_min 0.9720 _exptl_absorpt_correction_T_max 0.9920 _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 'BRUKER MART APEX CCD DIFFRACTOMETER' _diffrn_measurement_method 'OMEGA-PHI SCAN' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3420 _diffrn_reflns_av_R_equivalents 0.0254 _diffrn_reflns_av_sigmaI/netI 0.0343 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 25.99 _reflns_number_total 1718 _reflns_number_gt 1476 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SMART' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP _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^)+(0.0825P)^2^+0.1001P] 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 1718 _refine_ls_number_parameters 147 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0663 _refine_ls_R_factor_gt 0.0602 _refine_ls_wR_factor_ref 0.1636 _refine_ls_wR_factor_gt 0.1584 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.9536(2) 0.2212(2) 0.22862(14) 0.0734(5) Uani 1 d . . . O2 O 0.81059(18) 0.19467(17) 0.44002(11) 0.0519(4) Uani 1 d . . . C1 C 0.6317(3) 0.2094(2) 0.54387(15) 0.0428(4) Uani 1 d . . . C9 C 0.7862(3) 0.2340(2) 0.31146(17) 0.0497(4) Uani 1 d . . . C3 C 0.4981(3) 0.1815(3) 0.77488(18) 0.0567(5) Uani 1 d . . . C2 C 0.6730(3) 0.1631(3) 0.66940(18) 0.0524(5) Uani 1 d . . . C6 C 0.4183(3) 0.2677(2) 0.52243(16) 0.0428(4) Uani 1 d . . . C10 C 0.0904(4) 0.2623(4) 0.8767(2) 0.0806(7) Uani 1 d . . . H10A H -0.0059 0.3865 0.8684 0.121 Uiso 1 calc R . . H10B H 0.1456 0.2526 0.9562 0.121 Uiso 1 calc R . . H10C H 0.0107 0.1597 0.8801 0.121 Uiso 1 calc R . . C11 C 0.5448(4) 0.3166(4) 0.1449(2) 0.0647(6) Uani 1 d . . . C8 C 0.5631(3) 0.2856(2) 0.28664(16) 0.0474(4) Uani 1 d . . . C4 C 0.2808(3) 0.2437(3) 0.75955(17) 0.0554(5) Uani 1 d . . . C5 C 0.2455(3) 0.2841(3) 0.63238(18) 0.0522(5) Uani 1 d . . . C7 C 0.3910(3) 0.3022(2) 0.38798(17) 0.0478(4) Uani 1 d . . . H3 H 0.527(3) 0.146(3) 0.861(2) 0.063(5) Uiso 1 d . . . H2 H 0.819(3) 0.120(3) 0.6794(18) 0.060(5) Uiso 1 d . . . H11A H 0.398(4) 0.337(3) 0.141(2) 0.085(7) Uiso 1 d . . . H11B H 0.607(4) 0.424(4) 0.103(2) 0.097(8) Uiso 1 d . . . H11C H 0.613(4) 0.201(4) 0.100(3) 0.106(9) Uiso 1 d . . . H5 H 0.106(4) 0.320(3) 0.617(2) 0.069(6) Uiso 1 d . . . H7 H 0.248(3) 0.329(3) 0.3749(18) 0.056(5) Uiso 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 O1 0.0563(8) 0.0933(11) 0.0563(8) -0.0001(7) 0.0061(6) -0.0050(7) O2 0.0440(7) 0.0604(8) 0.0484(7) -0.0002(5) -0.0092(5) -0.0058(5) C1 0.0462(9) 0.0388(8) 0.0441(9) -0.0030(6) -0.0086(7) -0.0109(7) C9 0.0509(10) 0.0489(9) 0.0449(9) -0.0020(7) -0.0037(7) -0.0070(7) C3 0.0816(13) 0.0536(10) 0.0409(9) 0.0004(7) -0.0173(9) -0.0228(9) C2 0.0589(11) 0.0512(10) 0.0511(10) 0.0003(7) -0.0200(8) -0.0122(8) C6 0.0467(9) 0.0396(8) 0.0442(9) -0.0039(6) -0.0092(7) -0.0123(6) C10 0.0903(16) 0.0945(16) 0.0521(12) -0.0130(11) 0.0117(11) -0.0305(13) C11 0.0779(15) 0.0730(14) 0.0455(11) 0.0012(10) -0.0175(10) -0.0178(12) C8 0.0587(10) 0.0423(9) 0.0422(9) -0.0014(7) -0.0120(7) -0.0115(7) C4 0.0703(12) 0.0524(10) 0.0446(9) -0.0085(7) -0.0003(8) -0.0236(8) C5 0.0476(10) 0.0555(10) 0.0537(10) -0.0081(8) -0.0042(8) -0.0143(8) C7 0.0462(10) 0.0508(10) 0.0497(10) -0.0022(7) -0.0154(8) -0.0111(7) _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 C9 1.205(2) . ? O2 C9 1.374(2) . ? O2 C1 1.3785(19) . ? C1 C2 1.382(2) . ? C1 C6 1.390(2) . ? C9 C8 1.459(3) . ? C3 C2 1.373(3) . ? C3 C4 1.395(3) . ? C3 H3 0.95(2) . ? C2 H2 0.938(19) . ? C6 C5 1.395(2) . ? C6 C7 1.439(2) . ? C10 C4 1.511(2) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C8 1.497(3) . ? C11 H11A 0.92(3) . ? C11 H11B 0.95(3) . ? C11 H11C 0.96(3) . ? C8 C7 1.336(2) . ? C4 C5 1.382(3) . ? C5 H5 0.91(2) . ? C7 H7 0.92(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 C9 O2 C1 121.79(13) . . ? O2 C1 C2 117.48(15) . . ? O2 C1 C6 121.01(15) . . ? C2 C1 C6 121.52(16) . . ? O1 C9 O2 116.28(16) . . ? O1 C9 C8 125.74(17) . . ? O2 C9 C8 117.98(14) . . ? C2 C3 C4 122.32(17) . . ? C2 C3 H3 118.3(12) . . ? C4 C3 H3 119.3(12) . . ? C3 C2 C1 118.68(17) . . ? C3 C2 H2 122.5(12) . . ? C1 C2 H2 118.8(12) . . ? C1 C6 C5 117.87(16) . . ? C1 C6 C7 117.53(15) . . ? C5 C6 C7 124.58(15) . . ? C4 C10 H10A 109.5 . . ? C4 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C4 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C8 C11 H11A 108.3(15) . . ? C8 C11 H11B 111.1(15) . . ? H11A C11 H11B 110(2) . . ? C8 C11 H11C 110.8(16) . . ? H11A C11 H11C 106(2) . . ? H11B C11 H11C 110(2) . . ? C7 C8 C9 119.73(16) . . ? C7 C8 C11 124.23(18) . . ? C9 C8 C11 116.04(17) . . ? C5 C4 C3 117.36(17) . . ? C5 C4 C10 121.03(19) . . ? C3 C4 C10 121.59(18) . . ? C4 C5 C6 122.21(17) . . ? C4 C5 H5 120.6(13) . . ? C6 C5 H5 117.2(13) . . ? C8 C7 C6 121.85(16) . . ? C8 C7 H7 121.3(12) . . ? C6 C7 H7 116.7(12) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.235 _refine_diff_density_min -0.301 _refine_diff_density_rms 0.076