# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_jp0312 _database_code_depnum_ccdc_archive 'CCDC 908022' #TrackingRef 'jp0312_deposited.cif' # ========================================================================= # _audit_creation_method 'SHELXL-97, manual editing plus enCIFer' _audit_creation_date '18 October 2012' # ========================================================================= # _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 triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.1190(5) _cell_length_b 7.4620(5) _cell_length_c 12.5730(9) _cell_angle_alpha 76.093(3) _cell_angle_beta 85.589(3) _cell_angle_gamma 73.234(3) _cell_volume 620.74(7) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2592 _cell_measurement_theta_min 2.93 _cell_measurement_theta_max 26.78 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.446 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 284 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9846 _exptl_absorpt_correction_T_max 0.9979 _exptl_absorpt_process_details ; SADABS (Sheldrick, 1997) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 X8 Kappa CCD APEX II' _diffrn_measurement_method '\w / \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8835 _diffrn_reflns_av_R_equivalents 0.0281 _diffrn_reflns_av_sigmaI/netI 0.0302 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.69 _diffrn_reflns_theta_max 25.68 _reflns_number_total 2334 _reflns_number_gt 1783 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2006)' _computing_cell_refinement 'APEX2 (Bruker, 2006)' _computing_data_reduction 'SAINT+ (Bruker, 2005)' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL (Sheldrick, 2008)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 2009)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0473P)^2^+0.1438P] 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 2334 _refine_ls_number_parameters 188 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0560 _refine_ls_R_factor_gt 0.0380 _refine_ls_wR_factor_ref 0.0988 _refine_ls_wR_factor_gt 0.0900 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.029 _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 0.08113(16) 0.62357(15) 0.13572(9) 0.0280(3) Uani 1 1 d D . . H1 H 0.065(3) 0.694(2) 0.1909(12) 0.042 Uiso 1 1 d D . . O2 O 0.08288(16) 0.71732(14) 0.31544(9) 0.0278(3) Uani 1 1 d . . . O3 O 0.16704(16) 0.97151(14) 0.61260(8) 0.0251(3) Uani 1 1 d D . . H6 H 0.111(2) 1.063(2) 0.6533(13) 0.038 Uiso 1 1 d D . . O4 O 0.22972(16) 0.95532(14) 0.82067(8) 0.0257(3) Uani 1 1 d . . . C1 C 0.1544(2) 0.4398(2) 0.19249(12) 0.0219(4) Uani 1 1 d . . . C2 C 0.1777(2) 0.2942(2) 0.13638(13) 0.0261(4) Uani 1 1 d . . . H2 H 0.1441 0.3255 0.0612 0.031 Uiso 1 1 calc R . . C3 C 0.2497(2) 0.1049(2) 0.19081(13) 0.0278(4) Uani 1 1 d . . . H3 H 0.2635 0.0059 0.1529 0.033 Uiso 1 1 calc R . . C4 C 0.3024(2) 0.0564(2) 0.30055(13) 0.0271(4) Uani 1 1 d . . . H4 H 0.3524 -0.0747 0.3371 0.033 Uiso 1 1 calc R . . C5 C 0.2818(2) 0.1994(2) 0.35569(13) 0.0237(4) Uani 1 1 d . . . H5 H 0.3192 0.1656 0.4304 0.028 Uiso 1 1 calc R . . C6 C 0.2066(2) 0.3943(2) 0.30403(12) 0.0201(3) Uani 1 1 d . . . C7 C 0.1726(2) 0.5497(2) 0.36287(12) 0.0211(3) Uani 1 1 d . . . C8 C 0.2415(2) 0.5104(2) 0.47502(12) 0.0236(4) Uani 1 1 d . . . H8 H 0.3092 0.3826 0.5102 0.028 Uiso 1 1 calc R . . C9 C 0.2113(2) 0.6506(2) 0.52917(12) 0.0216(4) Uani 1 1 d . . . H9 H 0.1464 0.7768 0.4902 0.026 Uiso 1 1 calc R . . C10 C 0.2673(2) 0.6302(2) 0.64155(12) 0.0200(3) Uani 1 1 d . . . C11 C 0.3434(2) 0.4508(2) 0.71353(13) 0.0243(4) Uani 1 1 d . . . H11 H 0.3675 0.3365 0.6877 0.029 Uiso 1 1 calc R . . C12 C 0.3833(2) 0.4386(2) 0.82041(13) 0.0258(4) Uani 1 1 d . . . H12 H 0.4360 0.3161 0.8675 0.031 Uiso 1 1 calc R . . C13 C 0.3471(2) 0.6045(2) 0.86084(13) 0.0245(4) Uani 1 1 d . . . H13 H 0.3728 0.5949 0.9353 0.029 Uiso 1 1 calc R . . C14 C 0.2741(2) 0.7819(2) 0.79171(12) 0.0206(3) Uani 1 1 d . . . C15 C 0.2353(2) 0.7963(2) 0.68148(12) 0.0197(3) Uani 1 1 d . . . C16 C 0.2611(2) 0.9502(2) 0.93241(12) 0.0278(4) Uani 1 1 d . . . H16A H 0.1865 0.8704 0.9804 0.042 Uiso 1 1 calc R . . H16B H 0.2171 1.0810 0.9444 0.042 Uiso 1 1 calc R . . H16C H 0.4011 0.8956 0.9491 0.042 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 0.0373(7) 0.0243(6) 0.0211(6) -0.0051(5) -0.0013(5) -0.0062(5) O2 0.0367(7) 0.0200(6) 0.0243(6) -0.0071(5) -0.0034(5) -0.0018(5) O3 0.0340(7) 0.0196(6) 0.0187(6) -0.0059(4) -0.0019(5) -0.0013(5) O4 0.0337(6) 0.0236(6) 0.0192(6) -0.0077(4) -0.0038(5) -0.0039(5) C1 0.0193(8) 0.0225(8) 0.0241(9) -0.0051(6) 0.0037(6) -0.0071(6) C2 0.0265(9) 0.0322(9) 0.0225(9) -0.0113(7) 0.0042(7) -0.0099(7) C3 0.0279(9) 0.0281(9) 0.0325(10) -0.0170(7) 0.0074(7) -0.0097(7) C4 0.0273(9) 0.0199(8) 0.0331(10) -0.0073(7) 0.0045(7) -0.0051(6) C5 0.0223(8) 0.0246(8) 0.0238(9) -0.0064(7) 0.0015(7) -0.0058(6) C6 0.0178(8) 0.0228(8) 0.0215(8) -0.0076(6) 0.0030(6) -0.0074(6) C7 0.0196(8) 0.0213(8) 0.0230(9) -0.0055(6) 0.0034(7) -0.0073(6) C8 0.0238(8) 0.0216(8) 0.0242(9) -0.0064(6) -0.0003(7) -0.0035(6) C9 0.0180(8) 0.0231(8) 0.0225(8) -0.0046(6) 0.0008(6) -0.0044(6) C10 0.0153(8) 0.0244(8) 0.0206(8) -0.0068(6) 0.0020(6) -0.0050(6) C11 0.0213(8) 0.0224(8) 0.0284(9) -0.0072(7) 0.0007(7) -0.0041(6) C12 0.0245(9) 0.0225(8) 0.0260(9) -0.0009(7) -0.0029(7) -0.0029(6) C13 0.0234(8) 0.0293(8) 0.0193(8) -0.0040(7) -0.0019(7) -0.0062(7) C14 0.0192(8) 0.0231(8) 0.0214(8) -0.0088(6) 0.0015(6) -0.0059(6) C15 0.0161(8) 0.0205(8) 0.0202(8) -0.0028(6) 0.0002(6) -0.0030(6) C16 0.0336(9) 0.0310(9) 0.0206(9) -0.0112(7) -0.0011(7) -0.0073(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 C1 1.3549(18) . ? O1 H1 0.948(9) . ? O2 C7 1.2521(17) . ? O3 C15 1.3600(17) . ? O3 H6 0.930(9) . ? O4 C14 1.3713(17) . ? O4 C16 1.4290(18) . ? C1 C2 1.397(2) . ? C1 C6 1.414(2) . ? C2 C3 1.378(2) . ? C2 H2 0.9500 . ? C3 C4 1.392(2) . ? C3 H3 0.9500 . ? C4 C5 1.375(2) . ? C4 H4 0.9500 . ? C5 C6 1.405(2) . ? C5 H5 0.9500 . ? C6 C7 1.474(2) . ? C7 C8 1.463(2) . ? C8 C9 1.340(2) . ? C8 H8 0.9500 . ? C9 C10 1.458(2) . ? C9 H9 0.9500 . ? C10 C15 1.399(2) . ? C10 C11 1.407(2) . ? C11 C12 1.371(2) . ? C11 H11 0.9500 . ? C12 C13 1.399(2) . ? C12 H12 0.9500 . ? C13 C14 1.378(2) . ? C13 H13 0.9500 . ? C14 C15 1.407(2) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? 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 H1 102.5(11) . . ? C15 O3 H6 109.5(11) . . ? C14 O4 C16 116.81(11) . . ? O1 C1 C2 117.38(14) . . ? O1 C1 C6 122.14(13) . . ? C2 C1 C6 120.48(13) . . ? C3 C2 C1 119.60(15) . . ? C3 C2 H2 120.2 . . ? C1 C2 H2 120.2 . . ? C2 C3 C4 120.99(14) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C5 C4 C3 119.57(14) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C4 C5 C6 121.47(15) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C5 C6 C1 117.88(14) . . ? C5 C6 C7 122.54(14) . . ? C1 C6 C7 119.52(13) . . ? O2 C7 C8 120.00(13) . . ? O2 C7 C6 118.97(14) . . ? C8 C7 C6 121.03(13) . . ? C9 C8 C7 121.47(14) . . ? C9 C8 H8 119.3 . . ? C7 C8 H8 119.3 . . ? C8 C9 C10 126.96(14) . . ? C8 C9 H9 116.5 . . ? C10 C9 H9 116.5 . . ? C15 C10 C11 118.30(14) . . ? C15 C10 C9 118.56(13) . . ? C11 C10 C9 123.07(14) . . ? C12 C11 C10 120.94(14) . . ? C12 C11 H11 119.5 . . ? C10 C11 H11 119.5 . . ? C11 C12 C13 120.69(14) . . ? C11 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? C14 C13 C12 119.43(14) . . ? C14 C13 H13 120.3 . . ? C12 C13 H13 120.3 . . ? O4 C14 C13 125.55(14) . . ? O4 C14 C15 114.08(12) . . ? C13 C14 C15 120.36(14) . . ? O3 C15 C10 119.35(13) . . ? O3 C15 C14 120.40(13) . . ? C10 C15 C14 120.25(13) . . ? O4 C16 H16A 109.5 . . ? O4 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O4 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? 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 O1 C1 C2 C3 -179.33(13) . . . . ? C6 C1 C2 C3 0.9(2) . . . . ? C1 C2 C3 C4 -1.0(2) . . . . ? C2 C3 C4 C5 0.2(2) . . . . ? C3 C4 C5 C6 0.6(2) . . . . ? C4 C5 C6 C1 -0.7(2) . . . . ? C4 C5 C6 C7 176.48(14) . . . . ? O1 C1 C6 C5 -179.85(13) . . . . ? C2 C1 C6 C5 0.0(2) . . . . ? O1 C1 C6 C7 2.9(2) . . . . ? C2 C1 C6 C7 -177.31(13) . . . . ? C5 C6 C7 O2 -171.16(14) . . . . ? C1 C6 C7 O2 6.0(2) . . . . ? C5 C6 C7 C8 8.7(2) . . . . ? C1 C6 C7 C8 -174.17(13) . . . . ? O2 C7 C8 C9 -0.1(2) . . . . ? C6 C7 C8 C9 -179.98(13) . . . . ? C7 C8 C9 C10 178.22(13) . . . . ? C8 C9 C10 C15 175.55(14) . . . . ? C8 C9 C10 C11 -7.6(2) . . . . ? C15 C10 C11 C12 0.7(2) . . . . ? C9 C10 C11 C12 -176.17(14) . . . . ? C10 C11 C12 C13 0.7(2) . . . . ? C11 C12 C13 C14 -1.2(2) . . . . ? C16 O4 C14 C13 -0.5(2) . . . . ? C16 O4 C14 C15 178.43(13) . . . . ? C12 C13 C14 O4 179.12(13) . . . . ? C12 C13 C14 C15 0.3(2) . . . . ? C11 C10 C15 O3 178.15(13) . . . . ? C9 C10 C15 O3 -4.8(2) . . . . ? C11 C10 C15 C14 -1.6(2) . . . . ? C9 C10 C15 C14 175.39(13) . . . . ? O4 C14 C15 O3 2.4(2) . . . . ? C13 C14 C15 O3 -178.62(13) . . . . ? O4 C14 C15 C10 -177.81(12) . . . . ? C13 C14 C15 C10 1.2(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 O2 0.948(9) 1.635(12) 2.5229(15) 154.3(17) . O3 H6 O2 0.930(9) 1.915(11) 2.7847(14) 154.8(16) 2_576 O3 H6 O4 0.930(9) 2.205(17) 2.6559(15) 108.9(13) . _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.222 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.040 #============================================================================# # Luis Cunha-Silva @ REQUIMTE & DQB FCUP * 28/09/2012 * END # #============================================================================#