data_gg4906s _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C15 H18 O3), C H4 O' _chemical_formula_sum 'C31 H40 O7' _chemical_formula_weight 524.63 _Chemical_Absolute_Configuration 'Syn' 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 2' _symmetry_space_group_name_Hall 'P 2 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, -z' _cell_length_a 14.560(9) _cell_length_b 7.622(5) _cell_length_c 12.513(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1388.6(15) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needles _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.252 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 564 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.9472 _exptl_absorpt_correction_T_max 0.9913 _exptl_absorpt_process_details 'Sadabs (Bruker)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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_method '\w and phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12341 _diffrn_reflns_av_R_equivalents 0.0753 _diffrn_reflns_av_sigmaI/netI 0.0483 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.87 _diffrn_reflns_theta_max 28.16 _reflns_number_total 1953 _reflns_number_gt 1066 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1204P)^2^+0.1566P] 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 constr _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 ? _refine_ls_number_reflns 1953 _refine_ls_number_parameters 170 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1277 _refine_ls_R_factor_gt 0.0648 _refine_ls_wR_factor_ref 0.2125 _refine_ls_wR_factor_gt 0.1705 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.006 _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 0.3611(2) 0.8163(5) 0.9084(2) 0.0593(9) Uani 1 1 d . . . O2 O 0.2784(3) 0.9637(6) 1.0273(3) 0.0772(12) Uani 1 1 d . . . O3 O 0.6688(2) 0.7330(6) 0.7004(4) 0.0831(12) Uani 1 1 d . . . C1 C 0.2812(3) 0.8913(6) 0.9418(4) 0.0533(12) Uani 1 1 d . . . C2 C 0.2086(3) 0.8696(7) 0.8589(4) 0.0548(12) Uani 1 1 d . . . H2 H 0.1719 0.7657 0.8762 0.066 Uiso 1 1 calc R . . C3 C 0.2643(3) 0.8322(7) 0.7586(3) 0.0486(11) Uani 1 1 d . . . H3 H 0.2855 0.9432 0.7278 0.058 Uiso 1 1 calc R . . C4 C 0.3460(3) 0.7336(6) 0.8051(3) 0.0452(10) Uani 1 1 d . . . H4 H 0.3287 0.6108 0.8164 0.054 Uiso 1 1 calc R . . C5 C 0.1452(4) 1.0278(10) 0.8526(5) 0.0847(19) Uani 1 1 d . . . H5A H 0.1790 1.1274 0.8269 0.127 Uiso 1 1 calc R . . H5B H 0.1211 1.0530 0.9224 0.127 Uiso 1 1 calc R . . H5C H 0.0954 1.0029 0.8046 0.127 Uiso 1 1 calc R . . C6 C 0.2188(4) 0.7232(10) 0.6722(4) 0.081(2) Uani 1 1 d . . . H6A H 0.2130 0.6041 0.6987 0.097 Uiso 1 1 calc R . . H6B H 0.1571 0.7681 0.6618 0.097 Uiso 1 1 calc R . . C7 C 0.2624(4) 0.7159(12) 0.5708(5) 0.098(3) Uani 1 1 d . . . H7A H 0.2342 0.8077 0.5282 0.118 Uiso 1 1 calc R . . H7B H 0.2433 0.6057 0.5389 0.118 Uiso 1 1 calc R . . C8 C 0.3639(3) 0.7297(7) 0.5507(4) 0.0561(12) Uani 1 1 d . . . C9 C 0.4327(3) 0.7391(6) 0.6221(4) 0.0461(10) Uani 1 1 d . . . C10 C 0.4329(3) 0.7400(6) 0.7401(3) 0.0442(10) Uani 1 1 d . . . C11 C 0.5195(3) 0.7406(7) 0.7806(4) 0.0485(11) Uani 1 1 d . . . C12 C 0.5847(3) 0.7399(6) 0.6920(4) 0.0558(12) Uani 1 1 d . . . C13 C 0.5323(3) 0.7479(8) 0.5899(4) 0.0610(13) Uani 1 1 d . . . H13A H 0.5482 0.6498 0.5441 0.073 Uiso 1 1 calc R . . H13B H 0.5452 0.8563 0.5522 0.073 Uiso 1 1 calc R . . C14 C 0.5531(3) 0.7354(9) 0.8935(4) 0.0682(15) Uani 1 1 d . . . H14A H 0.5063 0.6867 0.9387 0.102 Uiso 1 1 calc R . . H14B H 0.5674 0.8523 0.9168 0.102 Uiso 1 1 calc R . . H14C H 0.6073 0.6639 0.8975 0.102 Uiso 1 1 calc R . . C15 C 0.3853(4) 0.7348(11) 0.4329(4) 0.0860(19) Uani 1 1 d . . . H15A H 0.3861 0.6174 0.4051 0.129 Uiso 1 1 calc R . . H15B H 0.4443 0.7882 0.4221 0.129 Uiso 1 1 calc R . . H15C H 0.3391 0.8020 0.3965 0.129 Uiso 1 1 calc R . . O1S O 0.0757(9) 0.453(2) 0.8090(12) 0.162 Uiso 0.50 1 d PD . . H1SA H 0.1029 0.5358 0.7813 0.194 Uiso 0.50 1 calc PR . . C1S C 0.0000 0.5000 0.8359(14) 0.184 Uiso 1 2 d SD . . H1A H -0.0445 0.4581 0.7853 0.221 Uiso 0.50 1 calc PR . . H1B H -0.0021 0.6258 0.8385 0.221 Uiso 0.50 1 calc PR . . H1C H -0.0137 0.4533 0.9053 0.221 Uiso 0.50 1 calc PR . . 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 0.0511(18) 0.081(2) 0.0453(18) -0.0095(17) 0.0028(15) 0.0066(17) O2 0.076(3) 0.098(3) 0.058(2) -0.020(2) 0.0157(19) -0.005(2) O3 0.0456(19) 0.102(3) 0.102(3) 0.000(3) 0.0090(18) -0.005(2) C1 0.056(3) 0.056(3) 0.048(3) -0.002(2) 0.014(2) -0.008(2) C2 0.042(2) 0.068(3) 0.054(3) -0.004(2) 0.007(2) 0.004(2) C3 0.039(2) 0.061(3) 0.045(2) -0.001(2) 0.0052(19) 0.005(2) C4 0.048(2) 0.044(2) 0.044(2) -0.001(2) 0.0036(18) -0.0005(19) C5 0.078(4) 0.103(5) 0.073(4) -0.003(4) 0.010(3) 0.035(4) C6 0.052(3) 0.128(6) 0.063(3) -0.019(4) -0.003(2) -0.011(3) C7 0.055(3) 0.165(8) 0.075(4) -0.044(5) -0.003(3) -0.008(4) C8 0.059(3) 0.063(3) 0.047(2) -0.002(2) 0.000(2) 0.006(2) C9 0.048(2) 0.045(2) 0.046(2) 0.003(2) 0.0067(19) 0.005(2) C10 0.042(2) 0.040(2) 0.051(2) -0.002(2) 0.0042(19) 0.000(2) C11 0.043(2) 0.048(3) 0.055(3) -0.002(2) 0.0010(19) -0.001(2) C12 0.042(2) 0.049(3) 0.077(3) -0.002(3) 0.005(2) -0.002(2) C13 0.056(3) 0.068(3) 0.059(3) 0.008(3) 0.011(2) 0.003(3) C14 0.050(2) 0.082(4) 0.073(3) -0.007(3) -0.013(2) 0.004(3) C15 0.088(4) 0.121(5) 0.050(3) 0.002(4) 0.002(3) 0.023(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 O1 C1 1.361(6) . ? O1 C4 1.455(5) . ? O2 C1 1.204(5) . ? O3 C12 1.230(5) . ? C1 C2 1.491(7) . ? C2 C3 1.520(6) . ? C2 C5 1.521(8) . ? C2 H2 0.9800 . ? C3 C6 1.516(7) . ? C3 C4 1.522(6) . ? C3 H3 0.9800 . ? C4 C10 1.505(6) . ? C4 H4 0.9800 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 C7 1.420(8) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.503(7) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.344(7) . ? C8 C15 1.507(7) . ? C9 C10 1.477(6) . ? C9 C13 1.507(6) . ? C10 C11 1.359(6) . ? C11 C12 1.459(7) . ? C11 C14 1.496(7) . ? C12 C13 1.489(7) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? O1S C1S 1.206(12) . ? O1S H1SA 0.8200 . ? C1S H1A 0.9600 . ? C1S H1B 0.9600 . ? C1S H1C 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 C1 O1 C4 109.0(3) . . ? O2 C1 O1 119.6(5) . . ? O2 C1 C2 130.1(5) . . ? O1 C1 C2 110.2(4) . . ? C1 C2 C3 102.5(3) . . ? C1 C2 C5 112.2(5) . . ? C3 C2 C5 115.5(4) . . ? C1 C2 H2 108.8 . . ? C3 C2 H2 108.8 . . ? C5 C2 H2 108.8 . . ? C6 C3 C2 117.3(4) . . ? C6 C3 C4 110.1(4) . . ? C2 C3 C4 101.2(3) . . ? C6 C3 H3 109.3 . . ? C2 C3 H3 109.3 . . ? C4 C3 H3 109.3 . . ? O1 C4 C10 109.8(3) . . ? O1 C4 C3 104.1(4) . . ? C10 C4 C3 115.8(4) . . ? O1 C4 H4 109.0 . . ? C10 C4 H4 109.0 . . ? C3 C4 H4 109.0 . . ? C2 C5 H5A 109.5 . . ? C2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C7 C6 C3 117.7(5) . . ? C7 C6 H6A 107.9 . . ? C3 C6 H6A 107.9 . . ? C7 C6 H6B 107.9 . . ? C3 C6 H6B 107.9 . . ? H6A C6 H6B 107.2 . . ? C6 C7 C8 125.9(5) . . ? C6 C7 H7A 105.9 . . ? C8 C7 H7A 105.9 . . ? C6 C7 H7B 105.9 . . ? C8 C7 H7B 105.9 . . ? H7A C7 H7B 106.2 . . ? C9 C8 C7 128.7(5) . . ? C9 C8 C15 119.7(5) . . ? C7 C8 C15 111.6(5) . . ? C8 C9 C10 131.8(4) . . ? C8 C9 C13 122.8(4) . . ? C10 C9 C13 105.3(4) . . ? C11 C10 C9 112.1(4) . . ? C11 C10 C4 125.3(4) . . ? C9 C10 C4 122.6(4) . . ? C10 C11 C12 108.6(4) . . ? C10 C11 C14 131.0(4) . . ? C12 C11 C14 120.3(4) . . ? O3 C12 C11 125.6(5) . . ? O3 C12 C13 125.8(5) . . ? C11 C12 C13 108.6(4) . . ? C12 C13 C9 105.2(4) . . ? C12 C13 H13A 110.7 . . ? C9 C13 H13A 110.7 . . ? C12 C13 H13B 110.7 . . ? C9 C13 H13B 110.7 . . ? H13A C13 H13B 108.8 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C8 C15 H15A 109.5 . . ? C8 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C8 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C1S O1S H1SA 109.5 . . ? O1S C1S H1A 109.5 . . ? O1S C1S H1B 109.5 . . ? H1A C1S H1B 109.5 . . ? O1S C1S H1C 109.5 . . ? H1A C1S H1C 109.5 . . ? H1B C1S H1C 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 C4 O1 C1 O2 178.3(5) . . . . ? C4 O1 C1 C2 -2.7(5) . . . . ? O2 C1 C2 C3 159.1(6) . . . . ? O1 C1 C2 C3 -19.7(5) . . . . ? O2 C1 C2 C5 34.6(8) . . . . ? O1 C1 C2 C5 -144.3(4) . . . . ? C1 C2 C3 C6 152.3(5) . . . . ? C5 C2 C3 C6 -85.4(7) . . . . ? C1 C2 C3 C4 32.5(5) . . . . ? C5 C2 C3 C4 154.9(5) . . . . ? C1 O1 C4 C10 148.7(4) . . . . ? C1 O1 C4 C3 24.1(5) . . . . ? C6 C3 C4 O1 -159.6(4) . . . . ? C2 C3 C4 O1 -34.8(4) . . . . ? C6 C3 C4 C10 79.8(5) . . . . ? C2 C3 C4 C10 -155.5(4) . . . . ? C2 C3 C6 C7 168.0(6) . . . . ? C4 C3 C6 C7 -77.0(7) . . . . ? C3 C6 C7 C8 30.1(11) . . . . ? C6 C7 C8 C9 5.0(13) . . . . ? C6 C7 C8 C15 -174.3(7) . . . . ? C7 C8 C9 C10 -0.4(11) . . . . ? C15 C8 C9 C10 178.9(6) . . . . ? C7 C8 C9 C13 178.4(6) . . . . ? C15 C8 C9 C13 -2.4(8) . . . . ? C8 C9 C10 C11 176.3(6) . . . . ? C13 C9 C10 C11 -2.6(6) . . . . ? C8 C9 C10 C4 -1.5(9) . . . . ? C13 C9 C10 C4 179.6(5) . . . . ? O1 C4 C10 C11 29.2(6) . . . . ? C3 C4 C10 C11 146.8(5) . . . . ? O1 C4 C10 C9 -153.3(4) . . . . ? C3 C4 C10 C9 -35.8(7) . . . . ? C9 C10 C11 C12 -0.1(6) . . . . ? C4 C10 C11 C12 177.6(5) . . . . ? C9 C10 C11 C14 -177.6(6) . . . . ? C4 C10 C11 C14 0.1(9) . . . . ? C10 C11 C12 O3 -176.8(5) . . . . ? C14 C11 C12 O3 1.0(8) . . . . ? C10 C11 C12 C13 2.8(6) . . . . ? C14 C11 C12 C13 -179.4(5) . . . . ? O3 C12 C13 C9 175.4(5) . . . . ? C11 C12 C13 C9 -4.3(6) . . . . ? C8 C9 C13 C12 -174.9(5) . . . . ? C10 C9 C13 C12 4.1(6) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 28.16 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.434 _refine_diff_density_min -0.303 _refine_diff_density_rms 0.042