# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Cehpuri Ramana' _publ_contact_author_email VR.CHEPURI@NCL.RES.IN _publ_section_title ; An expeditious one-step entry to the central core of integrastatins A/B ; loop_ _publ_author_name 'Cehpuri Ramana' 'Rajesh G Gonnade' 'Challa Nageswara Reddy' # Attachment 'COMPOUND6.cif' data_almc _database_code_depnum_ccdc_archive 'CCDC 676602' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H12 O3' _chemical_formula_sum 'C15 H12 O3' _chemical_formula_weight 240.25 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 19.374(18) _cell_length_b 5.222(5) _cell_length_c 24.39(2) _cell_angle_alpha 90.00 _cell_angle_beta 109.910(15) _cell_angle_gamma 90.00 _cell_volume 2320(4) _cell_formula_units_Z 8 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 1576 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 26.52 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.67 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.375 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1008 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9387 _exptl_absorpt_correction_T_max 0.9952 _exptl_absorpt_process_details 'bruker sadabs' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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 'CCD Area Detector' _diffrn_measurement_device 'Bruker Smart APEX' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10305 _diffrn_reflns_av_R_equivalents 0.0486 _diffrn_reflns_av_sigmaI/netI 0.0388 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2034 _reflns_number_gt 1406 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006)' _computing_publication_material 'SHELXTL (Bruker, 2003)' _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. We first considered the space group Cc for this compound before assigning the space group as C2/c thinking that in space group Cc the two symmetry independent molecules will have two different orientation of the central 8 member ring and no disorder to resolve! But, each of the two independent molecules in the asymmetric unit of Cc also exhibits the same disorder. Furthermore, the axis of the two fold orientational disorder of the molecule does not coincide with the crystallographic 2-fold axis in space group C2/c. Other than the above explanation, some more observations made while solving and refining the structure in both space group. 1) E-statistics [N(Z) test] of the intensities suggested that the structure may be centrosymmetric (68% probability for centric structure). 2)The reflections to parameter ratio in both space group is ~ 10. The structure is refined To R-value of 0.0546 for [I>2sigma(I)] in Cc whereas in C2/c the R-value is 0.0755. 3) Most of the atoms in Cc showed high atomic displacement parameters (ADP's) and some atoms even showed non-positive definite values, whereas all the atoms in space group C2/c behave with normal thermal parameters. 4) Structure solved and refined in Cc checked through 'ADDSYM' in PLATON and 'checkcif' program,both detected center of symmetry and suggested C2/c as a new space group. Therefore, we preferred to report the structure in C2/c rather than Cc, inspite higher R-index in space group C2/c. The ESDs in molecular geometry parameters also are lower in the centrosymmetric space group ; _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^)+(0.0271P)^2^+4.8105P] 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 2034 _refine_ls_number_parameters 203 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1136 _refine_ls_R_factor_gt 0.0755 _refine_ls_wR_factor_ref 0.1496 _refine_ls_wR_factor_gt 0.1330 _refine_ls_goodness_of_fit_ref 1.095 _refine_ls_restrained_S_all 1.096 _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 0.2157(3) 0.9778(12) 0.0404(2) 0.0589(14) Uani 0.50 1 d P A 1 O1' O 0.1463(3) 0.9715(13) 0.0308(2) 0.0590(13) Uani 0.50 1 d P A 2 O2 O 0.19097(14) 0.5786(4) 0.07530(10) 0.0637(7) Uani 1 1 d . . . O3 O 0.2415(2) 0.7458(6) 0.22881(11) 0.0916(11) Uani 1 1 d . . . C1 C 0.1620(6) 0.802(2) 0.0489(4) 0.054(2) Uani 0.50 1 d P A 1 H1 H 0.1285 0.7573 0.0099 0.065 Uiso 0.50 1 calc PR A 1 C1' C 0.2069(6) 0.799(2) 0.0507(4) 0.062(3) Uani 0.50 1 d PD A 2 H1' H 0.2183 0.7465 0.0162 0.074 Uiso 0.50 1 calc PR A 2 C2 C 0.27561(18) 0.9630(8) 0.09031(15) 0.0637(11) Uani 1 1 d D . . C3 C 0.3193(3) 1.1387(12) 0.0772(2) 0.110(2) Uani 1 1 d . A . H3 H 0.3058 1.2034 0.0395 0.132 Uiso 1 1 calc R . . C4 C 0.3803(3) 1.2190(10) 0.1169(4) 0.117(2) Uani 1 1 d . . . H4 H 0.4094 1.3388 0.1068 0.140 Uiso 1 1 calc R A . C5 C 0.4011(2) 1.1303(12) 0.1718(3) 0.1047(19) Uani 1 1 d . A . H5 H 0.4437 1.1905 0.1999 0.126 Uiso 1 1 calc R . . C6 C 0.3581(2) 0.9479(10) 0.18589(16) 0.0835(14) Uani 1 1 d . . . H6 H 0.3720 0.8841 0.2237 0.100 Uiso 1 1 calc R A . C7 C 0.29462(17) 0.8602(6) 0.14408(15) 0.0518(9) Uani 1 1 d . A . C8 C 0.2407(5) 0.6289(14) 0.1354(4) 0.0490(18) Uani 0.50 1 d P A 1 H8 H 0.2695 0.4739 0.1503 0.059 Uiso 0.50 1 calc PR A 1 C8' C 0.2551(5) 0.6771(13) 0.1725(3) 0.052(2) Uani 0.50 1 d P A 2 H8' H 0.2799 0.5107 0.1778 0.062 Uiso 0.50 1 calc PR A 2 C9 C 0.1876(4) 0.6693(13) 0.1689(3) 0.0453(17) Uani 0.50 1 d P A 1 H9 H 0.1627 0.5087 0.1715 0.054 Uiso 0.50 1 calc PR A 1 C9' C 0.1794(5) 0.6457(14) 0.1298(4) 0.055(2) Uani 0.50 1 d P A 2 H9' H 0.1582 0.4947 0.1420 0.066 Uiso 0.50 1 calc PR A 2 C10 C 0.13054(18) 0.8737(7) 0.1315(2) 0.0656(11) Uani 1 1 d . . . C11 C 0.0921(2) 0.9662(9) 0.16526(18) 0.0738(12) Uani 1 1 d . A . H11 H 0.1013 0.8994 0.2024 0.089 Uiso 1 1 calc R . . C12 C 0.0408(2) 1.1533(9) 0.1456(2) 0.0831(14) Uani 1 1 d . . . H12 H 0.0158 1.2142 0.1694 0.100 Uiso 1 1 calc R A . C13 C 0.0262(2) 1.2511(9) 0.0914(3) 0.0945(15) Uani 1 1 d . A . H13 H -0.0097 1.3764 0.0776 0.113 Uiso 1 1 calc R . . C14 C 0.0643(2) 1.1648(11) 0.05706(19) 0.0988(17) Uani 1 1 d . . . H14 H 0.0548 1.2327 0.0200 0.119 Uiso 1 1 calc R A . C15 C 0.1166(2) 0.9775(10) 0.07754(19) 0.0781(14) Uani 1 1 d . A . H3A H 0.245(2) 0.613(8) 0.2462(19) 0.091(15) Uiso 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 O1 0.068(4) 0.063(4) 0.050(3) 0.004(3) 0.026(3) -0.003(3) O1' 0.058(4) 0.069(4) 0.052(3) -0.004(3) 0.021(2) -0.006(3) O2 0.0932(18) 0.0414(14) 0.0606(15) -0.0202(12) 0.0316(14) -0.0093(14) O3 0.178(3) 0.0426(16) 0.0485(15) 0.0024(13) 0.0317(18) 0.0086(19) C1 0.071(6) 0.039(5) 0.041(5) -0.014(4) 0.006(5) -0.015(6) C1' 0.076(7) 0.055(7) 0.057(5) -0.013(5) 0.027(6) -0.013(7) C2 0.048(2) 0.101(3) 0.047(2) -0.012(2) 0.0229(17) 0.013(2) C3 0.071(3) 0.166(5) 0.116(4) 0.073(4) 0.061(3) 0.041(3) C4 0.082(4) 0.076(4) 0.219(7) 0.028(4) 0.087(5) 0.008(3) C5 0.038(2) 0.128(5) 0.140(5) -0.066(4) 0.020(3) -0.011(3) C6 0.056(2) 0.136(4) 0.058(2) 0.008(3) 0.020(2) 0.028(3) C7 0.051(2) 0.042(2) 0.069(2) 0.0053(17) 0.0297(18) 0.0117(16) C8 0.060(5) 0.039(4) 0.055(5) 0.001(4) 0.028(4) 0.002(4) C8' 0.087(7) 0.026(4) 0.057(5) 0.002(3) 0.042(5) 0.010(4) C9 0.050(5) 0.037(4) 0.051(5) 0.000(3) 0.020(4) -0.008(3) C9' 0.081(6) 0.036(4) 0.057(5) -0.008(4) 0.036(5) -0.012(4) C10 0.045(2) 0.042(2) 0.110(3) -0.011(2) 0.026(2) -0.0132(17) C11 0.056(2) 0.086(3) 0.081(3) 0.004(2) 0.026(2) -0.023(2) C12 0.057(3) 0.085(3) 0.119(4) -0.035(3) 0.045(3) -0.014(2) C13 0.046(2) 0.083(3) 0.141(5) 0.008(3) 0.015(3) 0.005(2) C14 0.048(2) 0.160(5) 0.072(3) 0.017(3) 0.000(2) -0.016(3) C15 0.046(2) 0.112(4) 0.076(3) -0.052(3) 0.019(2) -0.033(2) _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 C2 1.369(6) . ? O1 C1 1.452(12) . ? O1' C1' 1.427(13) . ? O1' C15 1.440(6) . ? O2 C1 1.360(12) . ? O2 C1' 1.383(12) . ? O2 C9' 1.464(9) . ? O2 C8 1.478(9) . ? O3 C8' 1.526(8) . ? O3 C9 1.532(8) . ? C1 C15 1.587(11) . ? C1' C2 1.599(10) . ? C2 C7 1.347(5) . ? C2 C3 1.358(6) . ? C3 C4 1.316(7) . ? C4 C5 1.342(7) . ? C5 C6 1.384(7) . ? C6 C7 1.381(5) . ? C7 C8' 1.531(8) . ? C7 C8 1.564(8) . ? C8 C9 1.531(10) . ? C8' C9' 1.490(11) . ? C9 C10 1.583(8) . ? C9' C10 1.531(9) . ? C10 C15 1.363(6) . ? C10 C11 1.373(5) . ? C11 C12 1.358(6) . ? C12 C13 1.354(6) . ? C13 C14 1.368(6) . ? C14 C15 1.375(6) . ? 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 C2 O1 C1 105.6(6) . . ? C1' O1' C15 104.4(6) . . ? C1 O2 C1' 36.3(4) . . ? C1 O2 C9' 93.4(5) . . ? C1' O2 C9' 108.7(5) . . ? C1 O2 C8 110.0(5) . . ? C1' O2 C8 96.6(5) . . ? C9' O2 C8 46.1(4) . . ? C8' O3 C9 49.6(4) . . ? O2 C1 O1 114.2(10) . . ? O2 C1 C15 119.2(7) . . ? O1 C1 C15 103.3(6) . . ? O2 C1' O1' 113.1(9) . . ? O2 C1' C2 116.5(7) . . ? O1' C1' C2 106.8(7) . . ? C7 C2 C3 120.8(4) . . ? C7 C2 O1 139.1(4) . . ? C3 C2 O1 99.2(4) . . ? C7 C2 C1' 105.7(5) . . ? C3 C2 C1' 132.5(6) . . ? O1 C2 C1' 38.1(4) . . ? C4 C3 C2 121.2(5) . . ? C3 C4 C5 120.9(5) . . ? C4 C5 C6 118.9(4) . . ? C7 C6 C5 120.3(4) . . ? C2 C7 C6 117.8(4) . . ? C2 C7 C8' 132.6(4) . . ? C6 C7 C8' 109.2(4) . . ? C2 C7 C8 103.2(4) . . ? C6 C7 C8 137.9(4) . . ? C8' C7 C8 33.3(3) . . ? O2 C8 C9 103.0(7) . . ? O2 C8 C7 116.8(5) . . ? C9 C8 C7 111.2(6) . . ? C9' C8' O3 103.0(7) . . ? C9' C8' C7 106.1(6) . . ? O3 C8' C7 121.8(5) . . ? C8 C9 O3 100.4(6) . . ? C8 C9 C10 104.5(6) . . ? O3 C9 C10 119.3(5) . . ? O2 C9' C8' 104.0(7) . . ? O2 C9' C10 119.9(6) . . ? C8' C9' C10 111.5(6) . . ? C15 C10 C11 118.0(4) . . ? C15 C10 C9' 101.8(5) . . ? C11 C10 C9' 139.2(5) . . ? C15 C10 C9 134.0(5) . . ? C11 C10 C9 107.9(5) . . ? C9' C10 C9 34.3(3) . . ? C12 C11 C10 121.5(4) . . ? C13 C12 C11 120.1(4) . . ? C12 C13 C14 119.7(4) . . ? C13 C14 C15 119.8(4) . . ? C10 C15 C14 120.8(4) . . ? C10 C15 O1' 139.0(5) . . ? C14 C15 O1' 99.9(5) . . ? C10 C15 C1 103.8(5) . . ? C14 C15 C1 134.5(6) . . ? O1' C15 C1 37.7(4) . . ? 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 C1' O2 C1 O1 -8.7(7) . . . . ? C9' O2 C1 O1 108.8(7) . . . . ? C8 O2 C1 O1 64.7(8) . . . . ? C1' O2 C1 C15 -131.4(13) . . . . ? C9' O2 C1 C15 -14.0(8) . . . . ? C8 O2 C1 C15 -58.1(9) . . . . ? C2 O1 C1 O2 -40.5(8) . . . . ? C2 O1 C1 C15 90.5(7) . . . . ? C1 O2 C1' O1' 1.5(6) . . . . ? C9' O2 C1' O1' -67.7(8) . . . . ? C8 O2 C1' O1' -113.4(7) . . . . ? C1 O2 C1' C2 125.9(14) . . . . ? C9' O2 C1' C2 56.6(9) . . . . ? C8 O2 C1' C2 10.9(8) . . . . ? C15 O1' C1' O2 44.9(8) . . . . ? C15 O1' C1' C2 -84.6(8) . . . . ? C1 O1 C2 C7 -9.2(9) . . . . ? C1 O1 C2 C3 -178.2(6) . . . . ? C1 O1 C2 C1' 27.5(7) . . . . ? O2 C1' C2 C7 -10.1(9) . . . . ? O1' C1' C2 C7 117.4(7) . . . . ? O2 C1' C2 C3 158.4(6) . . . . ? O1' C1' C2 C3 -74.1(9) . . . . ? O2 C1' C2 O1 -166.2(14) . . . . ? O1' C1' C2 O1 -38.6(6) . . . . ? C7 C2 C3 C4 -1.9(7) . . . . ? O1 C2 C3 C4 169.7(5) . . . . ? C1' C2 C3 C4 -169.0(7) . . . . ? C2 C3 C4 C5 -0.3(8) . . . . ? C3 C4 C5 C6 1.4(8) . . . . ? C4 C5 C6 C7 -0.3(7) . . . . ? C3 C2 C7 C6 2.9(6) . . . . ? O1 C2 C7 C6 -164.5(6) . . . . ? C1' C2 C7 C6 173.0(5) . . . . ? C3 C2 C7 C8' 174.9(5) . . . . ? O1 C2 C7 C8' 7.6(9) . . . . ? C1' C2 C7 C8' -14.9(7) . . . . ? C3 C2 C7 C8 -167.0(5) . . . . ? O1 C2 C7 C8 25.7(7) . . . . ? C1' C2 C7 C8 3.1(6) . . . . ? C5 C6 C7 C2 -1.7(6) . . . . ? C5 C6 C7 C8' -175.6(4) . . . . ? C5 C6 C7 C8 163.4(5) . . . . ? C1 O2 C8 C9 78.3(7) . . . . ? C1' O2 C8 C9 113.2(6) . . . . ? C9' O2 C8 C9 3.6(5) . . . . ? C1 O2 C8 C7 -43.8(8) . . . . ? C1' O2 C8 C7 -8.9(7) . . . . ? C9' O2 C8 C7 -118.6(8) . . . . ? C2 C7 C8 O2 3.6(6) . . . . ? C6 C7 C8 O2 -163.0(4) . . . . ? C8' C7 C8 O2 159.0(12) . . . . ? C2 C7 C8 C9 -114.2(6) . . . . ? C6 C7 C8 C9 79.3(8) . . . . ? C8' C7 C8 C9 41.3(7) . . . . ? C9 O3 C8' C9' 4.9(5) . . . . ? C9 O3 C8' C7 123.5(8) . . . . ? C2 C7 C8' C9' -7.2(9) . . . . ? C6 C7 C8' C9' 165.3(5) . . . . ? C8 C7 C8' C9' -40.6(7) . . . . ? C2 C7 C8' O3 -124.2(6) . . . . ? C6 C7 C8' O3 48.4(7) . . . . ? C8 C7 C8' O3 -157.5(12) . . . . ? O2 C8 C9 O3 -174.7(4) . . . . ? C7 C8 C9 O3 -48.9(7) . . . . ? O2 C8 C9 C10 -50.6(6) . . . . ? C7 C8 C9 C10 75.2(7) . . . . ? C8' O3 C9 C8 0.3(5) . . . . ? C8' O3 C9 C10 -112.9(7) . . . . ? C1 O2 C9' C8' -112.5(6) . . . . ? C1' O2 C9' C8' -78.8(7) . . . . ? C8 O2 C9' C8' 2.2(5) . . . . ? C1 O2 C9' C10 12.9(7) . . . . ? C1' O2 C9' C10 46.6(8) . . . . ? C8 O2 C9' C10 127.6(8) . . . . ? O3 C8' C9' O2 -179.8(4) . . . . ? C7 C8' C9' O2 51.2(6) . . . . ? O3 C8' C9' C10 49.7(7) . . . . ? C7 C8' C9' C10 -79.3(8) . . . . ? O2 C9' C10 C15 -7.1(7) . . . . ? C8' C9' C10 C15 114.7(7) . . . . ? O2 C9' C10 C11 160.5(5) . . . . ? C8' C9' C10 C11 -77.7(9) . . . . ? O2 C9' C10 C9 -169.4(12) . . . . ? C8' C9' C10 C9 -47.6(6) . . . . ? C8 C9 C10 C15 10.1(8) . . . . ? O3 C9 C10 C15 121.1(6) . . . . ? C8 C9 C10 C11 -165.6(5) . . . . ? O3 C9 C10 C11 -54.6(6) . . . . ? C8 C9 C10 C9' 34.5(6) . . . . ? O3 C9 C10 C9' 145.5(10) . . . . ? C15 C10 C11 C12 0.9(5) . . . . ? C9' C10 C11 C12 -165.3(6) . . . . ? C9 C10 C11 C12 177.4(4) . . . . ? C10 C11 C12 C13 0.7(6) . . . . ? C11 C12 C13 C14 -1.4(7) . . . . ? C12 C13 C14 C15 0.7(7) . . . . ? C11 C10 C15 C14 -1.6(6) . . . . ? C9' C10 C15 C14 169.3(4) . . . . ? C9 C10 C15 C14 -177.0(5) . . . . ? C11 C10 C15 O1' 170.6(5) . . . . ? C9' C10 C15 O1' -18.6(7) . . . . ? C9 C10 C15 O1' -4.8(9) . . . . ? C11 C10 C15 C1 -172.8(4) . . . . ? C9' C10 C15 C1 -2.0(5) . . . . ? C9 C10 C15 C1 11.8(7) . . . . ? C13 C14 C15 C10 0.8(6) . . . . ? C13 C14 C15 O1' -174.0(4) . . . . ? C13 C14 C15 C1 168.8(6) . . . . ? C1' O1' C15 C10 1.0(10) . . . . ? C1' O1' C15 C14 174.2(6) . . . . ? C1' O1' C15 C1 -26.0(7) . . . . ? O2 C1 C15 C10 11.7(8) . . . . ? O1 C1 C15 C10 -116.3(6) . . . . ? O2 C1 C15 C14 -157.7(6) . . . . ? O1 C1 C15 C14 74.4(8) . . . . ? O2 C1 C15 O1' 173.9(13) . . . . ? O1 C1 C15 O1' 45.9(6) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.185 _refine_diff_density_min -0.203 _refine_diff_density_rms 0.037 # Attachment 'COMPOUND16.cif' data_nr_o_vac_mc _database_code_depnum_ccdc_archive 'CCDC 676603' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H14 O4' _chemical_formula_sum 'C16 H14 O4' _chemical_formula_weight 270.27 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.896(2) _cell_length_b 12.117(3) _cell_length_c 13.238(4) _cell_angle_alpha 90.00 _cell_angle_beta 97.439(5) _cell_angle_gamma 90.00 _cell_volume 1255.8(6) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 1707 _cell_measurement_theta_min 2.85 _cell_measurement_theta_max 23.09 _exptl_crystal_description PLATE _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.430 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9547 _exptl_absorpt_correction_T_max 0.9969 _exptl_absorpt_process_details 'BRUKER SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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 'CCD Area Detector' _diffrn_measurement_device 'Bruker Smart APEX' _diffrn_measurement_method 'Phi and Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8909 _diffrn_reflns_av_R_equivalents 0.0336 _diffrn_reflns_av_sigmaI/netI 0.0301 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2215 _reflns_number_gt 1757 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006)' _computing_publication_material 'SHELXTL (Bruker, 2003)' _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^)+(0.0377P)^2^+0.3703P] 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 2215 _refine_ls_number_parameters 186 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0635 _refine_ls_R_factor_gt 0.0464 _refine_ls_wR_factor_ref 0.1006 _refine_ls_wR_factor_gt 0.0939 _refine_ls_goodness_of_fit_ref 1.104 _refine_ls_restrained_S_all 1.104 _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 0.16212(17) 0.21481(10) 0.36404(9) 0.0360(3) Uani 1 1 d . . . O2 O 0.37429(17) 0.31815(11) 0.45755(10) 0.0418(4) Uani 1 1 d . . . O3 O 0.3475(2) 0.25446(13) 0.72459(11) 0.0545(5) Uani 1 1 d . . . O4 O 0.04858(18) 0.02387(11) 0.29811(10) 0.0424(4) Uani 1 1 d . . . C1 C 0.2020(2) 0.31792(15) 0.41512(14) 0.0345(5) Uani 1 1 d . . . H1 H 0.1866 0.3765 0.3637 0.041 Uiso 1 1 calc R . . C2 C 0.0806(3) 0.34075(15) 0.49235(14) 0.0325(5) Uani 1 1 d . . . C3 C -0.0886(3) 0.36576(15) 0.45945(15) 0.0377(5) Uani 1 1 d . . . H3 H -0.1269 0.3678 0.3900 0.045 Uiso 1 1 calc R . . C4 C -0.2008(3) 0.38761(17) 0.52826(17) 0.0452(6) Uani 1 1 d . . . H4 H -0.3140 0.4050 0.5054 0.054 Uiso 1 1 calc R . . C5 C -0.1449(3) 0.38364(17) 0.63135(18) 0.0493(6) Uani 1 1 d . . . H5 H -0.2206 0.3976 0.6781 0.059 Uiso 1 1 calc R . . C6 C 0.0243(3) 0.35889(16) 0.66519(16) 0.0448(6) Uani 1 1 d . . . H6 H 0.0616 0.3568 0.7348 0.054 Uiso 1 1 calc R . . C7 C 0.1389(3) 0.33715(15) 0.59657(14) 0.0352(5) Uani 1 1 d . . . C8 C 0.3254(3) 0.31152(17) 0.62992(14) 0.0419(5) Uani 1 1 d . . . H8 H 0.3876 0.3816 0.6390 0.050 Uiso 1 1 calc R . . C9 C 0.3955(3) 0.24681(17) 0.54578(15) 0.0403(5) Uani 1 1 d . . . H9 H 0.5181 0.2353 0.5660 0.048 Uiso 1 1 calc R . . C10 C 0.3143(2) 0.13624(16) 0.51823(14) 0.0342(5) Uani 1 1 d . . . C11 C 0.3494(3) 0.04219(17) 0.57813(15) 0.0425(5) Uani 1 1 d . . . H11 H 0.4198 0.0474 0.6400 0.051 Uiso 1 1 calc R . . C12 C 0.2808(3) -0.05814(17) 0.54640(15) 0.0441(5) Uani 1 1 d . . . H12 H 0.3027 -0.1198 0.5879 0.053 Uiso 1 1 calc R . . C13 C 0.1793(3) -0.06859(17) 0.45311(15) 0.0401(5) Uani 1 1 d . . . H13 H 0.1353 -0.1371 0.4318 0.048 Uiso 1 1 calc R . . C14 C 0.1438(2) 0.02298(16) 0.39221(13) 0.0331(5) Uani 1 1 d . . . C15 C 0.2082(2) 0.12550(15) 0.42681(13) 0.0313(4) Uani 1 1 d . . . C16 C -0.0154(3) -0.07971(18) 0.25858(17) 0.0550(6) Uani 1 1 d . . . H16A H 0.0775 -0.1308 0.2584 0.083 Uiso 1 1 calc R . . H16B H -0.0709 -0.0699 0.1903 0.083 Uiso 1 1 calc R . . H16C H -0.0959 -0.1082 0.3005 0.083 Uiso 1 1 calc R . . H3A H 0.432(4) 0.285(2) 0.762(2) 0.085(10) Uiso 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 O1 0.0469(9) 0.0302(7) 0.0292(7) 0.0023(6) -0.0006(6) 0.0010(6) O2 0.0369(8) 0.0444(8) 0.0433(8) 0.0070(7) 0.0024(6) -0.0080(6) O3 0.0626(11) 0.0586(10) 0.0362(8) 0.0059(7) -0.0168(8) -0.0132(9) O4 0.0544(9) 0.0367(8) 0.0337(8) -0.0012(6) -0.0035(7) -0.0071(7) C1 0.0395(12) 0.0294(11) 0.0327(10) 0.0042(8) -0.0025(9) -0.0046(9) C2 0.0403(12) 0.0224(9) 0.0332(10) 0.0006(8) -0.0014(9) -0.0049(8) C3 0.0422(12) 0.0296(11) 0.0389(11) 0.0022(9) -0.0041(10) -0.0014(9) C4 0.0405(13) 0.0356(12) 0.0599(15) 0.0020(10) 0.0073(11) 0.0012(9) C5 0.0582(15) 0.0386(12) 0.0549(14) -0.0026(11) 0.0210(12) 0.0024(11) C6 0.0670(16) 0.0356(12) 0.0318(11) -0.0028(9) 0.0065(11) -0.0018(11) C7 0.0452(12) 0.0247(10) 0.0340(11) -0.0017(8) -0.0017(9) -0.0054(9) C8 0.0506(14) 0.0357(12) 0.0354(11) 0.0016(9) -0.0098(10) -0.0107(10) C9 0.0333(12) 0.0452(12) 0.0397(11) 0.0076(9) -0.0059(9) -0.0046(9) C10 0.0305(11) 0.0379(12) 0.0340(10) 0.0003(9) 0.0030(8) 0.0027(8) C11 0.0425(13) 0.0479(13) 0.0348(11) 0.0051(10) -0.0029(9) 0.0068(10) C12 0.0519(14) 0.0377(12) 0.0422(12) 0.0102(10) 0.0041(10) 0.0086(10) C13 0.0466(13) 0.0316(11) 0.0427(12) 0.0004(9) 0.0081(10) 0.0015(9) C14 0.0349(11) 0.0362(11) 0.0288(10) 0.0000(8) 0.0070(9) 0.0016(9) C15 0.0314(11) 0.0327(11) 0.0304(10) 0.0038(8) 0.0059(8) 0.0036(8) C16 0.0725(17) 0.0441(13) 0.0459(13) -0.0070(11) -0.0021(12) -0.0144(12) _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 C15 1.384(2) . ? O1 C1 1.436(2) . ? O2 C1 1.403(2) . ? O2 C9 1.445(2) . ? O3 C8 1.422(2) . ? O4 C14 1.369(2) . ? O4 C16 1.427(2) . ? C1 C2 1.515(3) . ? C2 C3 1.384(3) . ? C2 C7 1.398(3) . ? C3 C4 1.376(3) . ? C4 C5 1.380(3) . ? C5 C6 1.386(3) . ? C6 C7 1.388(3) . ? C7 C8 1.513(3) . ? C8 C9 1.524(3) . ? C9 C10 1.510(3) . ? C10 C15 1.386(3) . ? C10 C11 1.395(3) . ? C11 C12 1.374(3) . ? C12 C13 1.388(3) . ? C13 C14 1.379(3) . ? C14 C15 1.397(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 C15 O1 C1 111.89(13) . . ? C1 O2 C9 109.12(14) . . ? C14 O4 C16 116.97(15) . . ? O2 C1 O1 109.44(15) . . ? O2 C1 C2 113.27(15) . . ? O1 C1 C2 110.92(15) . . ? C3 C2 C7 119.94(19) . . ? C3 C2 C1 119.82(17) . . ? C7 C2 C1 120.24(18) . . ? C4 C3 C2 120.79(19) . . ? C3 C4 C5 119.8(2) . . ? C4 C5 C6 120.0(2) . . ? C5 C6 C7 120.8(2) . . ? C6 C7 C2 118.72(19) . . ? C6 C7 C8 122.69(18) . . ? C2 C7 C8 118.58(19) . . ? O3 C8 C7 111.13(18) . . ? O3 C8 C9 112.29(17) . . ? C7 C8 C9 108.92(15) . . ? O2 C9 C10 109.54(15) . . ? O2 C9 C8 105.53(16) . . ? C10 C9 C8 116.74(17) . . ? C15 C10 C11 118.22(18) . . ? C15 C10 C9 118.95(17) . . ? C11 C10 C9 122.71(17) . . ? C12 C11 C10 120.47(18) . . ? C11 C12 C13 120.79(19) . . ? C14 C13 C12 119.79(19) . . ? O4 C14 C13 125.75(18) . . ? O4 C14 C15 115.16(16) . . ? C13 C14 C15 119.09(17) . . ? O1 C15 C10 122.22(17) . . ? O1 C15 C14 116.24(15) . . ? C10 C15 C14 121.54(17) . . ? 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 O2 C1 O1 -73.48(18) . . . . ? C9 O2 C1 C2 50.8(2) . . . . ? C15 O1 C1 O2 52.81(19) . . . . ? C15 O1 C1 C2 -72.88(19) . . . . ? O2 C1 C2 C3 166.65(16) . . . . ? O1 C1 C2 C3 -69.8(2) . . . . ? O2 C1 C2 C7 -13.1(2) . . . . ? O1 C1 C2 C7 110.46(18) . . . . ? C7 C2 C3 C4 0.2(3) . . . . ? C1 C2 C3 C4 -179.50(18) . . . . ? C2 C3 C4 C5 -0.6(3) . . . . ? C3 C4 C5 C6 0.7(3) . . . . ? C4 C5 C6 C7 -0.4(3) . . . . ? C5 C6 C7 C2 0.1(3) . . . . ? C5 C6 C7 C8 179.01(19) . . . . ? C3 C2 C7 C6 0.1(3) . . . . ? C1 C2 C7 C6 179.77(17) . . . . ? C3 C2 C7 C8 -178.94(17) . . . . ? C1 C2 C7 C8 0.8(3) . . . . ? C6 C7 C8 O3 32.3(3) . . . . ? C2 C7 C8 O3 -148.69(17) . . . . ? C6 C7 C8 C9 156.56(18) . . . . ? C2 C7 C8 C9 -24.5(2) . . . . ? C1 O2 C9 C10 50.4(2) . . . . ? C1 O2 C9 C8 -76.07(18) . . . . ? O3 C8 C9 O2 -176.21(15) . . . . ? C7 C8 C9 O2 60.3(2) . . . . ? O3 C8 C9 C10 61.9(2) . . . . ? C7 C8 C9 C10 -61.7(2) . . . . ? O2 C9 C10 C15 -12.4(3) . . . . ? C8 C9 C10 C15 107.4(2) . . . . ? O2 C9 C10 C11 163.59(18) . . . . ? C8 C9 C10 C11 -76.6(2) . . . . ? C15 C10 C11 C12 0.3(3) . . . . ? C9 C10 C11 C12 -175.7(2) . . . . ? C10 C11 C12 C13 1.8(3) . . . . ? C11 C12 C13 C14 -1.3(3) . . . . ? C16 O4 C14 C13 -1.9(3) . . . . ? C16 O4 C14 C15 178.19(18) . . . . ? C12 C13 C14 O4 178.71(19) . . . . ? C12 C13 C14 C15 -1.3(3) . . . . ? C1 O1 C15 C10 -13.7(2) . . . . ? C1 O1 C15 C14 167.21(16) . . . . ? C11 C10 C15 O1 177.96(17) . . . . ? C9 C10 C15 O1 -5.8(3) . . . . ? C11 C10 C15 C14 -3.0(3) . . . . ? C9 C10 C15 C14 173.19(18) . . . . ? O4 C14 C15 O1 2.6(2) . . . . ? C13 C14 C15 O1 -177.38(17) . . . . ? O4 C14 C15 C10 -176.52(17) . . . . ? C13 C14 C15 C10 3.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.199 _refine_diff_density_min -0.122 _refine_diff_density_rms 0.036