# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2001 data_mpc _database_code_CSD 169025 _journal_coden_Cambridge 207 _publ_requested_journal 'Perkin Transactions 1' loop_ _publ_author_name 'Doi, Mitsunobu' 'Iritani, Masashi' 'Ito, Tadayoshi' 'Minoura, Katsuhiko' 'Numata, Atsushi' 'Yamada, Takeshi' _publ_contact_author_name 'Prof Atsushi Numata' _publ_contact_author_address ; Prof Atsushi Numata Osaka University of Pharmaceutical Sciences 4-20-1 Nasahara Takatsuki Osaka 56-1094 JAPAN ; _publ_contact_author_email 'NUMATA@OGLY.OUPS.SC.JP' _publ_section_title ; bsolute stereostructures of cell adhesion inhibitors, macrosphelides C, E-G and I, produced by a Periconia species separated from an Aplysia sea hare ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; Macrosphelide C ; _chemical_name_common mpc _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H22 O7' _chemical_formula_weight 326.34 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 10.514(2) _cell_length_b 28.460(2) _cell_length_c 5.860(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1753.4(7) _cell_formula_units_Z 4 _cell_measurement_temperature 288(2) _cell_measurement_reflns_used 20 _cell_measurement_theta_min 18.89 _cell_measurement_theta_max 21.07 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.236 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 0.817 _exptl_absorpt_correction_type \y-scan _exptl_absorpt_correction_T_min 0.99 _exptl_absorpt_correction_T_max 0.82 _exptl_absorpt_process_details 'North, Phillips & Mathews (1968)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 288(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Rigaku RU200' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku AFC5R' _diffrn_measurement_method 2\q-\w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 1.6 _diffrn_reflns_number 2864 _diffrn_reflns_av_R_equivalents 0.0420 _diffrn_reflns_av_sigmaI/netI 0.0242 _diffrn_reflns_limit_h_min -2 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 67.63 _reflns_number_total 2473 _reflns_number_gt 2185 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'MSC/AFC Diffractmeter Control Software' _computing_cell_refinement 'MSC/AFC Diffractmeter Control Software' _computing_data_reduction 'MSC/AFC Diffractmeter Control Software' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Burnett & Johnson 1996)' _computing_publication_material 'PARST (Nardelli, 1983)' _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^)+(0.0441P)^2^+0.6740P] 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 SHELXL _refine_ls_extinction_coef 0.0075(6) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.2(3) _refine_ls_number_reflns 2473 _refine_ls_number_parameters 210 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0532 _refine_ls_R_factor_gt 0.0437 _refine_ls_wR_factor_ref 0.1135 _refine_ls_wR_factor_gt 0.1055 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _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 C1 C 0.6396(3) 0.06086(10) 0.2130(5) 0.0579(7) Uani 1 1 d . . . O1 O 0.6759(2) 0.04823(10) 0.0286(4) 0.0867(8) Uani 1 1 d . . . C2 C 0.7213(3) 0.06531(12) 0.4230(6) 0.0689(8) Uani 1 1 d . . . H2A H 0.6893 0.0910 0.5154 0.083 Uiso 1 1 calc R . . H2B H 0.7136 0.0367 0.5120 0.083 Uiso 1 1 calc R . . C3 C 0.8589(3) 0.07385(12) 0.3742(6) 0.0707(9) Uani 1 1 d . . . H3 H 0.8916 0.0496 0.2707 0.085 Uiso 1 1 calc R . . O4 O 0.86158(18) 0.11965(8) 0.2625(4) 0.0742(6) Uani 1 1 d . . . C5 C 0.9612(3) 0.12974(16) 0.1327(6) 0.0823(11) Uani 1 1 d . . . O5 O 1.0529(2) 0.10485(14) 0.1130(5) 0.1155(11) Uani 1 1 d . . . C7 C 0.8445(3) 0.20053(13) 0.0158(6) 0.0771(10) Uani 1 1 d . . . H7 H 0.7781 0.1901 0.1073 0.093 Uiso 1 1 calc R . . C8 C 0.8223(4) 0.24498(14) -0.1189(7) 0.0877(11) Uani 1 1 d . . . H8A H 0.9036 0.2578 -0.1660 0.105 Uiso 1 1 calc R . . H8B H 0.7810 0.2680 -0.0217 0.105 Uiso 1 1 calc R . . C9 C 0.7409(3) 0.23659(12) -0.3275(6) 0.0710(9) Uani 1 1 d . . . H9 H 0.7888 0.2176 -0.4374 0.085 Uiso 1 1 calc R . . O10 O 0.63285(19) 0.20971(7) -0.2454(3) 0.0627(5) Uani 1 1 d . . . C11 C 0.5677(3) 0.18504(10) -0.3997(5) 0.0564(7) Uani 1 1 d . . . O11 O 0.5860(2) 0.18825(9) -0.6026(4) 0.0819(7) Uani 1 1 d . . . C12 C 0.4720(3) 0.15393(10) -0.2985(5) 0.0563(7) Uani 1 1 d . . . H12 H 0.4105 0.1415 -0.3953 0.068 Uiso 1 1 calc R . . C13 C 0.4662(2) 0.14223(10) -0.0826(5) 0.0521(6) Uani 1 1 d . . . H13 H 0.5274 0.1545 0.0154 0.063 Uiso 1 1 calc R . . C14 C 0.3674(2) 0.11044(11) 0.0160(5) 0.0582(7) Uani 1 1 d . . . H14 H 0.3284 0.1261 0.1475 0.070 Uiso 1 1 calc R . . O14 O 0.27180(18) 0.10168(11) -0.1490(4) 0.0830(7) Uani 1 1 d . . . H14A H 0.2019 0.1019 -0.0871 0.125 Uiso 1 1 calc R . . C15 C 0.4212(2) 0.06325(10) 0.0939(5) 0.0590(7) Uani 1 1 d . . . H15 H 0.4559 0.0459 -0.0365 0.071 Uiso 1 1 calc R . . O16 O 0.52021(17) 0.07225(7) 0.2606(4) 0.0597(5) Uani 1 1 d . . . C17 C 0.3222(3) 0.03377(12) 0.2170(8) 0.0870(11) Uani 1 1 d . . . H17A H 0.3594 0.0045 0.2631 0.130 Uiso 1 1 calc R . . H17B H 0.2519 0.0278 0.1164 0.130 Uiso 1 1 calc R . . H17C H 0.2925 0.0504 0.3493 0.130 Uiso 1 1 calc R . . C18 C 0.6972(5) 0.28140(13) -0.4423(7) 0.0972(13) Uani 1 1 d . . . H18A H 0.6467 0.2738 -0.5736 0.146 Uiso 1 1 calc R . . H18B H 0.7699 0.2994 -0.4889 0.146 Uiso 1 1 calc R . . H18C H 0.6472 0.2995 -0.3371 0.146 Uiso 1 1 calc R . . C19 C 0.9382(4) 0.07557(16) 0.5878(7) 0.1025(14) Uani 1 1 d . . . H19A H 1.0255 0.0809 0.5480 0.154 Uiso 1 1 calc R . . H19B H 0.9308 0.0463 0.6678 0.154 Uiso 1 1 calc R . . H19C H 0.9087 0.1006 0.6838 0.154 Uiso 1 1 calc R . . C6 C 0.9490(3) 0.17529(18) 0.0157(7) 0.0934(13) Uani 1 1 d . . . H6 H 1.0193 0.1868 -0.0627 0.112 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 C1 0.0548(15) 0.0586(15) 0.0603(17) 0.0031(14) 0.0040(14) 0.0077(14) O1 0.0567(12) 0.129(2) 0.0740(15) -0.0239(15) 0.0063(11) 0.0164(13) C2 0.0682(18) 0.0748(19) 0.0638(19) 0.0068(16) -0.0048(16) 0.0171(17) C3 0.0565(16) 0.084(2) 0.072(2) -0.0004(17) -0.0130(16) 0.0201(17) O4 0.0471(10) 0.1000(16) 0.0756(13) -0.0021(14) 0.0014(11) 0.0057(11) C5 0.0393(14) 0.143(3) 0.0650(19) -0.009(2) -0.0042(15) -0.008(2) O5 0.0439(12) 0.205(3) 0.0981(19) -0.005(2) 0.0054(13) 0.0190(17) C7 0.066(2) 0.106(3) 0.0591(18) -0.0087(18) 0.0024(16) -0.0351(19) C8 0.090(2) 0.098(3) 0.075(2) -0.007(2) 0.011(2) -0.039(2) C9 0.080(2) 0.0731(19) 0.0604(19) 0.0004(15) 0.0178(16) -0.0158(17) O10 0.0719(12) 0.0667(11) 0.0494(10) 0.0003(10) 0.0081(10) -0.0139(10) C11 0.0609(16) 0.0611(16) 0.0470(15) -0.0026(13) -0.0044(13) 0.0044(14) O11 0.0955(16) 0.1047(18) 0.0454(12) -0.0023(12) 0.0032(11) -0.0116(15) C12 0.0496(14) 0.0683(17) 0.0510(16) -0.0063(13) -0.0061(12) 0.0018(14) C13 0.0416(12) 0.0634(15) 0.0515(14) -0.0073(13) -0.0045(12) 0.0044(12) C14 0.0415(12) 0.0764(18) 0.0566(15) -0.0082(14) 0.0039(12) 0.0014(14) O14 0.0409(10) 0.134(2) 0.0737(15) -0.0010(14) -0.0056(9) -0.0101(13) C15 0.0453(14) 0.0648(17) 0.0669(18) -0.0090(15) 0.0034(13) -0.0004(13) O16 0.0483(10) 0.0701(12) 0.0608(11) -0.0047(10) 0.0033(9) 0.0091(9) C17 0.069(2) 0.074(2) 0.118(3) 0.003(2) 0.008(2) -0.0155(18) C18 0.126(3) 0.078(2) 0.088(3) 0.019(2) 0.021(3) -0.018(2) C19 0.088(3) 0.124(3) 0.095(3) -0.002(3) -0.040(2) 0.020(3) C6 0.0495(18) 0.156(4) 0.075(2) -0.003(3) 0.0056(17) -0.034(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 C1 O1 1.201(4) . ? C1 O16 1.326(3) . ? C1 C2 1.506(4) . ? C2 C3 1.494(4) . ? C3 O4 1.459(4) . ? C3 C19 1.504(5) . ? O4 C5 1.326(4) . ? C5 O5 1.202(5) . ? C5 C6 1.472(6) . ? C7 C6 1.313(5) . ? C7 C8 1.509(5) . ? C8 C9 1.511(5) . ? C9 O10 1.452(4) . ? C9 C18 1.513(5) . ? O10 C11 1.334(3) . ? C11 O11 1.208(3) . ? C11 C12 1.466(4) . ? C12 C13 1.309(4) . ? C13 C14 1.494(4) . ? C14 O14 1.417(3) . ? C14 C15 1.527(4) . ? C15 O16 1.450(3) . ? C15 C17 1.520(4) . ? 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 O1 C1 O16 124.3(3) . . ? O1 C1 C2 125.3(3) . . ? O16 C1 C2 110.4(3) . . ? C3 C2 C1 114.2(3) . . ? O4 C3 C2 104.5(2) . . ? O4 C3 C19 109.5(3) . . ? C2 C3 C19 112.5(3) . . ? C5 O4 C3 117.8(3) . . ? O5 C5 O4 124.1(4) . . ? O5 C5 C6 123.0(4) . . ? O4 C5 C6 112.9(3) . . ? C6 C7 C8 126.0(3) . . ? C7 C8 C9 112.2(3) . . ? O10 C9 C8 105.0(2) . . ? O10 C9 C18 110.7(3) . . ? C8 C9 C18 113.5(3) . . ? C11 O10 C9 117.0(2) . . ? O11 C11 O10 123.1(3) . . ? O11 C11 C12 123.6(3) . . ? O10 C11 C12 113.3(2) . . ? C13 C12 C11 125.2(3) . . ? C12 C13 C14 124.1(3) . . ? O14 C14 C13 109.6(2) . . ? O14 C14 C15 108.2(2) . . ? C13 C14 C15 113.0(2) . . ? O16 C15 C17 105.6(3) . . ? O16 C15 C14 108.2(2) . . ? C17 C15 C14 111.9(2) . . ? C1 O16 C15 119.6(2) . . ? C7 C6 C5 123.7(3) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 67.63 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.124 _refine_diff_density_min -0.123 _refine_diff_density_rms 0.032