data_global _audit_creation_method 'APEX2 v2011.2-0' _publ_requested_journal ? _ öö publ_contact_author_name Prof. Abdulaziz Alnajjar _publ_contact_author_address ; ; _publ_contact_author_email ? _publ_contact_author_fax ? _publ_contact_author_phone ? _publ_section_title ; ; _publ_section_abstract ; ; _publ_section_references ; ; _publ_section_comment ; ; data_I _chemical_name_systematic ? _chemical_name_common Hamada_M1_16_02_12 _chemical_formula_moiety ? _chemical_formula_sum 'C15 H18 O6' _chemical_formula_iupac ? _chemical_formula_weight 294.29 _chemical_absolute_configuration ? _chemical_melting_point ? _space_group_crystal_system hexagonal _space_group_name_H-M_alt 'P 65' _space_group_name_Hall 'P 65' loop_ _space_group_symop_operation_xyz 'x, y, z' 'x-y, x, z+5/6' 'y, -x+y, z+1/6' '-y, x-y, z+2/3' '-x+y, -x, z+1/3' '-x, -y, z+1/2' _cell_length_a 11.3311(5) _cell_length_b 11.3311(5) _cell_length_c 19.5375(10) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 120 _cell_volume 2172.42(18) _cell_formula_units_Z 6 _cell_measurement_reflns_used 2855 _cell_measurement_theta_min 4.5058 _cell_measurement_theta_max 66.0226 _cell_measurement_temperature 296.(2) _exptl_crystal_description Needle _exptl_crystal_colour 'clear light colourless' _exptl_crystal_size_max 0.340 _exptl_crystal_size_mid 0.070 _exptl_crystal_size_min 0.040 _exptl_crystal_density_diffrn 1.350 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 0.879 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_absorpt_correction_T_min 0.52 _exptl_absorpt_correction_T_max 0.96 _exptl_special_details ; ; _diffrn_ambient_temperature 296.(2) _diffrn_source ? _diffrn_source_type ? _diffrn_radiation_type ? _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_monochromator ? _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 4546 _diffrn_reflns_av_R_equivalents 0.0921 _diffrn_reflns_av_sigmaI/netI 0.0777 _diffrn_reflns_theta_min 4.51 _diffrn_reflns_theta_max 66.48 _diffrn_reflns_theta_full 66.48 _diffrn_measured_fraction_theta_max 0.982 _diffrn_measured_fraction_theta_full 0.982 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 21 _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. ; _reflns_number_total 2271 _reflns_number_gt 1853 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0779 _refine_ls_R_factor_gt 0.0686 _refine_ls_wR_factor_gt 0.1650 _refine_ls_wR_factor_ref 0.1691 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.063 _refine_ls_number_reflns 2271 _refine_ls_number_parameters 193 _refine_ls_number_restraints 1 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1105P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.405 _refine_diff_density_min -0.381 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.1(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'Bruker Instrument Service v2011.2.0.0' _computing_cell_refinement 'SAINT V7.68A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O O1 0.8929(2) -0.1813(2) 0.01993(12) 0.0246(5) Uani d . 1 . . O O2 1.2338(2) 0.45678(19) 0.01680(12) 0.0244(5) Uani d . 1 . . O O3 0.59333(19) 0.15568(19) 0.01580(11) 0.0246(5) Uani d . 1 . . O O4 0.5341(2) -0.0650(2) 0.02648(12) 0.0329(6) Uani d . 1 . . O O5 1.11531(19) -0.0228(2) 0.01497(14) 0.0289(5) Uani d . 1 . . O O6 1.0748(2) 0.5201(2) 0.01404(14) 0.0303(5) Uani d . 1 . . C C1 0.8011(3) -0.4192(3) 0.0341(2) 0.0409(10) Uani d . 1 . . H H1A 0.7613 -0.4138 0.0765 0.061 Uiso calc R 1 . . H H1B 0.8216 -0.4918 0.0366 0.061 Uiso calc R 1 . . H H1C 0.7381 -0.4368 -0.0026 0.061 Uiso calc R 1 . . C C2 0.9288(3) -0.2881(3) 0.02134(19) 0.0269(7) Uani d . 1 . . H H2A 0.9944 -0.2705 0.0574 0.032 Uiso calc R 1 . . H H2B 0.9688 -0.2915 -0.022 0.032 Uiso calc R 1 . . C C3 0.9971(3) -0.0534(3) 0.01753(16) 0.0210(6) Uani d . 1 . . C C4 0.9489(3) 0.0477(3) 0.01781(15) 0.0203(6) Uani d . 1 . . C C5 1.0460(3) 0.1859(3) 0.01488(15) 0.0218(6) Uani d . 1 . . H H5 1.1382 0.2134 0.0126 0.026 Uiso calc R 1 . . C C6 1.0043(3) 0.2824(3) 0.01538(15) 0.0217(6) Uani d . 1 . . C C7 1.1055(3) 0.4322(3) 0.01515(15) 0.0210(6) Uani d . 1 . . C C8 1.3414(3) 0.5992(3) 0.01821(19) 0.0279(7) Uani d . 1 . . H H8A 1.3265 0.6466 0.0556 0.034 Uiso calc R 1 . . H H8B 1.3426 0.6438 -0.0244 0.034 Uiso calc R 1 . . C C9 1.4732(3) 0.6011(3) 0.02783(19) 0.0297(7) Uani d . 1 . . H H9A 1.4703 0.5556 0.0698 0.045 Uiso calc R 1 . . H H9B 1.5466 0.6938 0.0297 0.045 Uiso calc R 1 . . H H9C 1.4875 0.5553 -0.0098 0.045 Uiso calc R 1 . . C C10 0.4422(3) 0.2418(3) -0.0018(2) 0.0369(9) Uani d . 1 . . H H10A 0.4912 0.3095 0.0326 0.055 Uiso calc R 1 . . H H10B 0.3486 0.2198 -0.002 0.055 Uiso calc R 1 . . H H10C 0.482 0.2765 -0.0458 0.055 Uiso calc R 1 . . C C11 0.4496(3) 0.1161(3) 0.01375(19) 0.0294(7) Uani d . 1 . . H H11A 0.4068 0.0782 0.0575 0.035 Uiso calc R 1 . . H H11B 0.4028 0.0479 -0.0214 0.035 Uiso calc R 1 . . C C12 0.6201(3) 0.0536(3) 0.02136(16) 0.0228(6) Uani d . 1 . . C C13 0.7697(3) 0.1039(3) 0.02038(16) 0.0209(7) Uani d . 1 . . C C14 0.8116(3) 0.0072(3) 0.02113(16) 0.0223(6) Uani d . 1 . . H H14 0.7471 -0.085 0.0239 0.027 Uiso calc R 1 . . C C15 0.8672(3) 0.2415(3) 0.01808(16) 0.0218(6) Uani d . 1 . . H H15 0.8399 0.3065 0.0184 0.026 Uiso calc R 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0193(10) 0.0151(11) 0.0413(11) 0.0099(9) -0.0011(10) -0.0011(9) O2 0.0132(10) 0.0153(10) 0.0430(12) 0.0059(8) 0.0023(9) 0.0016(10) O3 0.0153(10) 0.0184(11) 0.0399(12) 0.0084(9) -0.0012(10) 0.0002(9) O4 0.0193(12) 0.0167(11) 0.0580(15) 0.0055(10) 0.0020(11) 0.0000(10) O5 0.0180(12) 0.0208(12) 0.0485(13) 0.0101(9) -0.0003(10) -0.0002(10) O6 0.0210(11) 0.0181(11) 0.0549(14) 0.0120(9) -0.0026(11) -0.0004(11) C1 0.035(2) 0.0230(18) 0.073(3) 0.0205(17) 0.0146(16) 0.0025(15) C2 0.0216(17) 0.0152(15) 0.0465(18) 0.0112(13) -0.0024(15) -0.0027(13) C3 0.0166(14) 0.0172(16) 0.0288(15) 0.0081(14) 0.0014(11) 0.0012(12) C4 0.0200(15) 0.0175(15) 0.0233(14) 0.0094(13) -0.0016(12) -0.0024(12) C5 0.0154(15) 0.0205(15) 0.0283(14) 0.0081(12) 0.0004(12) 0.0003(13) C6 0.0182(15) 0.0216(16) 0.0241(14) 0.0091(13) 0.0000(11) 0.0003(13) C7 0.0174(15) 0.0182(14) 0.0267(14) 0.0083(13) 0.0003(12) -0.0006(12) C8 0.0202(16) 0.0150(14) 0.0454(17) 0.0063(12) 0.0025(14) -0.0006(13) C9 0.0199(16) 0.0191(16) 0.0445(18) 0.0055(13) -0.0010(12) -0.0014(13) C10 0.0173(16) 0.034(2) 0.065(3) 0.0167(15) 0.0068(14) 0.0100(15) C11 0.0167(16) 0.0245(17) 0.0460(19) 0.0096(13) -0.0031(13) 0.0009(14) C12 0.0178(15) 0.0178(16) 0.0326(15) 0.0087(13) -0.0002(12) -0.0026(12) C13 0.0162(15) 0.0205(15) 0.0274(15) 0.0102(13) 0.0012(11) 0.0003(12) C14 0.0171(14) 0.0175(15) 0.0292(16) 0.0063(11) 0.0012(12) 0.0000(12) C15 0.0218(16) 0.0177(15) 0.0289(14) 0.0121(13) -0.0010(13) -0.0023(13) _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_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C3 . 1.336(3) ? O1 C2 . 1.456(3) ? O2 C7 . 1.338(3) ? O2 C8 . 1.457(3) ? O3 C12 . 1.339(3) ? O3 C11 . 1.458(3) ? O4 C12 . 1.206(4) ? O5 C3 . 1.205(3) ? O6 C7 . 1.208(3) ? C1 C2 . 1.488(4) ? C1 H1A . 0.96 ? C1 H1B . 0.96 ? C1 H1C . 0.96 ? C2 H2A . 0.97 ? C2 H2B . 0.97 ? C3 C4 . 1.497(4) ? C4 C14 . 1.385(4) ? C4 C5 . 1.394(4) ? C5 C6 . 1.392(4) ? C5 H5 . 0.93 ? C6 C15 . 1.383(4) ? C6 C7 . 1.499(4) ? C8 C9 . 1.495(4) ? C8 H8A . 0.97 ? C8 H8B . 0.97 ? C9 H9A . 0.96 ? C9 H9B . 0.96 ? C9 H9C . 0.96 ? C10 C11 . 1.499(4) ? C10 H10A . 0.96 ? C10 H10B . 0.96 ? C10 H10C . 0.96 ? C11 H11A . 0.97 ? C11 H11B . 0.97 ? C12 C13 . 1.495(4) ? C13 C15 . 1.390(4) ? C13 C14 . 1.395(4) ? C14 H14 . 0.93 ? C15 H15 . 0.93 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C3 O1 C2 . . 116.1(2) ? C7 O2 C8 . . 116.8(2) ? C12 O3 C11 . . 115.9(2) ? C2 C1 H1A . . 109.5 ? C2 C1 H1B . . 109.5 ? H1A C1 H1B . . 109.5 ? C2 C1 H1C . . 109.5 ? H1A C1 H1C . . 109.5 ? H1B C1 H1C . . 109.5 ? O1 C2 C1 . . 107.3(2) ? O1 C2 H2A . . 110.3 ? C1 C2 H2A . . 110.3 ? O1 C2 H2B . . 110.3 ? C1 C2 H2B . . 110.3 ? H2A C2 H2B . . 108.5 ? O5 C3 O1 . . 124.5(3) ? O5 C3 C4 . . 123.9(3) ? O1 C3 C4 . . 111.6(2) ? C14 C4 C5 . . 120.0(2) ? C14 C4 C3 . . 121.7(2) ? C5 C4 C3 . . 118.3(2) ? C6 C5 C4 . . 119.7(3) ? C6 C5 H5 . . 120.2 ? C4 C5 H5 . . 120.2 ? C15 C6 C5 . . 120.2(3) ? C15 C6 C7 . . 118.4(2) ? C5 C6 C7 . . 121.4(3) ? O6 C7 O2 . . 124.0(3) ? O6 C7 C6 . . 124.1(3) ? O2 C7 C6 . . 111.9(2) ? O2 C8 C9 . . 107.2(2) ? O2 C8 H8A . . 110.3 ? C9 C8 H8A . . 110.3 ? O2 C8 H8B . . 110.3 ? C9 C8 H8B . . 110.3 ? H8A C8 H8B . . 108.5 ? C8 C9 H9A . . 109.5 ? C8 C9 H9B . . 109.5 ? H9A C9 H9B . . 109.5 ? C8 C9 H9C . . 109.5 ? H9A C9 H9C . . 109.5 ? H9B C9 H9C . . 109.5 ? C11 C10 H10A . . 109.5 ? C11 C10 H10B . . 109.5 ? H10A C10 H10B . . 109.5 ? C11 C10 H10C . . 109.5 ? H10A C10 H10C . . 109.5 ? H10B C10 H10C . . 109.5 ? O3 C11 C10 . . 107.3(3) ? O3 C11 H11A . . 110.2 ? C10 C11 H11A . . 110.2 ? O3 C11 H11B . . 110.2 ? C10 C11 H11B . . 110.2 ? H11A C11 H11B . . 108.5 ? O4 C12 O3 . . 124.3(2) ? O4 C12 C13 . . 123.8(3) ? O3 C12 C13 . . 111.9(2) ? C15 C13 C14 . . 119.4(3) ? C15 C13 C12 . . 122.8(3) ? C14 C13 C12 . . 117.9(2) ? C4 C14 C13 . . 120.4(2) ? C4 C14 H14 . . 119.8 ? C13 C14 H14 . . 119.8 ? C6 C15 C13 . . 120.4(2) ? C6 C15 H15 . . 119.8 ? C13 C15 H15 . . 119.8 ?