# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2003 data_global _publ_contact_author_email IYODA-MASAHIKO@C.METRO-U.AC.JP _publ_contact_author_name 'Prof Masahiko Iyoda' _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _audit_creation_date 'Thu Aug 28 14:43:19 2003' _audit_creation_method 'by teXsan' _audit_update_record ? _publ_section_references ; ENTER OTHER REFERENCES Molecular Structure Corporation, Rigaku Corporation. (2000). teXsan. Single Crystal Structure Analysis Software. Version 1.11. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. Rigaku, 3-9-12 Akishima, Tokyo, Japan. Zachariasen, W. H. (1967). Acta Cryst. 23, 558-564. ; _publ_contact_author_address ; Department of Chemistry, Graduate School of Science Tokyo Metropolitan University Minami-osawa Hachioji 192-0397 JAPAN ; _publ_section_title ; Synthesis and Inclusion Properties of a Novel Macrocyclic Hexaketone Monohydrate with a Hemiacetal Structure ; loop_ _publ_author_name 'Masahiko Iyoda' 'Takeru Horino' 'Masanori Ohkoshi' 'Masato Yoshida' #------------------------------------------------------------------------------ data_KOSHIKOSHIMAX _database_code_CSD 215698 #------------------------------------------------------------------------------ # CHEMICAL DATA _chemical_formula_sum 'C25 H18 O8 ' _chemical_formula_moiety ? _chemical_formula_weight 446.41 _chemical_melting_point ? #------------------------------------------------------------------------------ # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,y,1/2-z -x,-y,-z x,-y,1/2+z 1/2+x,1/2+y,z 1/2-x,1/2+y,1/2-z 1/2-x,1/2-y,-z 1/2+x,1/2-y,1/2+z _cell_length_a 20.486(7) _cell_length_b 19.08(1) _cell_length_c 13.742(5) _cell_angle_alpha 90 _cell_angle_beta 131.58(1) _cell_angle_gamma 90 _cell_volume 4018(3) _cell_formula_units_Z 8 _cell_measurement_reflns_used 24 _cell_measurement_theta_min 12.8 _cell_measurement_theta_max 15.0 _cell_measurement_temperature 296.2 #------------------------------------------------------------------------------ _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.100 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.476 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_type none #------------------------------------------------------------------------------ # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku AFC7R' _diffrn_measurement_method \w-2\q _diffrn_reflns_number 4887 _diffrn_reflns_av_R_equivalents 0.038 _diffrn_reflns_theta_max 27.50 _diffrn_measured_fraction_theta_max 0.9994 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.9994 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 17 _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 0.46 #------------------------------------------------------------------------------ # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > 3.0 sigma(F^2^). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F^2^ > 3.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 4616 _reflns_number_gt 1850 _reflns_threshold_expression F^2^>3.0\s(F^2^) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.0442 _refine_ls_wR_factor_ref 0.0535 _refine_ls_hydrogen_treatment ? _refine_ls_number_reflns 1850 _refine_ls_number_parameters 311 _refine_ls_goodness_of_fit_ref 1.140 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00063|Fo|^2^]' _refine_ls_shift/su_max 0.0061 _refine_diff_density_max 0.23 _refine_diff_density_min -0.31 _refine_ls_extinction_method 'Zachariasen(1967) type 2 Gaussian isotropic' _refine_ls_extinction_coef 0.0011(3) _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H H 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; O O 0.011 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O(1) O 0.8941(2) 0.1557(1) 1.0087(3) 0.0205(8) Uani 1.00 d . . . O(2) O 0.7248(2) 0.0320(1) 0.8278(3) 0.0143(7) Uani 1.00 d . . . O(3) O 0.7765(2) 0.0919(1) 0.7416(3) 0.0143(7) Uani 1.00 d . . . O(4) O 0.6331(2) 0.2176(2) 0.5056(3) 0.0253(9) Uani 1.00 d . . . O(5) O 0.7418(2) 0.1128(1) 0.5511(3) 0.0182(8) Uani 1.00 d . . . O(6) O 0.7997(2) -0.0766(1) 0.7112(3) 0.0224(8) Uani 1.00 d . . . O(7) O 0.7192(2) -0.0854(1) 0.8334(3) 0.0195(8) Uani 1.00 d . . . O(8) O 0.8472(2) 0.2234(2) 0.6593(3) 0.036(1) Uani 1.00 d . . . C(1) C 0.8620(3) -0.0314(2) 0.9582(4) 0.017(1) Uani 1.00 d . . . C(2) C 0.9061(3) -0.0947(2) 1.0112(4) 0.020(1) Uani 1.00 d . . . C(3) C 0.9946(3) -0.0949(2) 1.1207(4) 0.025(1) Uani 1.00 d . . . C(4) C 1.0392(3) -0.0323(3) 1.1752(4) 0.023(1) Uani 1.00 d . . . C(5) C 0.9960(3) 0.0309(2) 1.1240(4) 0.019(1) Uani 1.00 d . . . C(6) C 0.9067(3) 0.0312(2) 1.0160(4) 0.017(1) Uani 1.00 d . . . C(7) C 0.8609(2) 0.0991(2) 0.9618(4) 0.015(1) Uani 1.00 d . . . C(8) C 0.7647(3) 0.0942(2) 0.8330(4) 0.014(1) Uani 1.00 d . . . C(9) C 0.7074(2) 0.1528(2) 0.8114(4) 0.014(1) Uani 1.00 d . . . C(10) C 0.6989(3) 0.1649(2) 0.9024(4) 0.018(1) Uani 1.00 d . . . C(11) C 0.6447(3) 0.2177(2) 0.8815(4) 0.020(1) Uani 1.00 d . . . C(12) C 0.5986(3) 0.2595(2) 0.7704(5) 0.024(1) Uani 1.00 d . . . C(13) C 0.6057(3) 0.2474(2) 0.6789(4) 0.019(1) Uani 1.00 d . . . C(14) C 0.6599(3) 0.1933(2) 0.6985(4) 0.015(1) Uani 1.00 d . . . C(15) C 0.6635(3) 0.1779(2) 0.5968(4) 0.019(1) Uani 1.00 d . . . C(16) C 0.7036(2) 0.1075(2) 0.6059(4) 0.013(1) Uani 1.00 d . . . C(17) C 0.6376(3) 0.0484(2) 0.5395(4) 0.017(1) Uani 1.00 d . . . C(18) C 0.5523(3) 0.0615(2) 0.4253(4) 0.022(1) Uani 1.00 d . . . C(19) C 0.4918(3) 0.0082(3) 0.3576(4) 0.025(1) Uani 1.00 d . . . C(20) C 0.5161(3) -0.0594(3) 0.4018(4) 0.026(1) Uani 1.00 d . . . C(21) C 0.6005(3) -0.0742(2) 0.5152(4) 0.022(1) Uani 1.00 d . . . C(22) C 0.6612(3) -0.0207(2) 0.5853(4) 0.017(1) Uani 1.00 d . . . C(23) C 0.7495(3) -0.0427(2) 0.7104(4) 0.016(1) Uani 1.00 d . . . C(24) C 0.7667(2) -0.0310(2) 0.8379(4) 0.014(1) Uani 1.00 d . . . C(25) C 0.8779(4) 0.2607(2) 0.7713(5) 0.040(2) Uani 1.00 d . . . H(1) H 0.8758 -0.1377 0.9728 0.0243 Uiso 1.00 calc . . . H(2) H 1.0245 -0.1383 1.1582 0.0303 Uiso 1.00 calc . . . H(3) H 1.1001 -0.0329 1.2483 0.0283 Uiso 1.00 calc . . . H(4) H 1.0270 0.0738 1.1624 0.0229 Uiso 1.00 calc . . . H(5) H 0.7305 0.1371 0.9786 0.0217 Uiso 1.00 calc . . . H(6) H 0.6385 0.2254 0.9437 0.0244 Uiso 1.00 calc . . . H(7) H 0.5625 0.2963 0.7580 0.0288 Uiso 1.00 calc . . . H(8) H 0.5740 0.2756 0.6029 0.0228 Uiso 1.00 calc . . . H(9) H 0.5353 0.1083 0.3933 0.0261 Uiso 1.00 calc . . . H(10) H 0.4337 0.0183 0.2808 0.0301 Uiso 1.00 calc . . . H(11) H 0.4750 -0.0965 0.3547 0.0316 Uiso 1.00 calc . . . H(12) H 0.6169 -0.1211 0.5452 0.0273 Uiso 1.00 calc . . . H(13) H 0.783(4) 0.158(4) 0.594(7) 0.11(3) Uiso 1.00 calc . . . H(14) H 0.724(3) -0.085(3) 0.899(5) 0.05(2) Uiso 1.00 calc . . . H(15) H 0.8713 0.2335 0.8220 0.0468 Uiso 1.00 calc . . . H(16) H 0.9383 0.2718 0.8225 0.0468 Uiso 1.00 calc . . . H(17) H 0.8460 0.3034 0.7467 0.0468 Uiso 1.00 calc . . . H(18) H 0.854(3) 0.247(3) 0.617(5) 0.05(2) Uiso 1.00 calc . . . 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 O(1) 0.019(2) 0.017(2) 0.020(2) -0.003(1) 0.011(1) -0.006(1) O(2) 0.018(1) 0.012(1) 0.014(1) 0.001(1) 0.011(1) -0.001(1) O(3) 0.014(1) 0.018(2) 0.012(1) 0.002(1) 0.009(1) 0.000(1) O(4) 0.034(2) 0.022(2) 0.024(2) 0.007(1) 0.021(2) 0.009(1) O(5) 0.023(2) 0.021(2) 0.017(2) 0.000(1) 0.016(1) 0.000(1) O(6) 0.025(2) 0.023(2) 0.021(2) 0.002(1) 0.016(1) -0.003(1) O(7) 0.027(2) 0.014(2) 0.021(2) -0.006(1) 0.018(2) -0.001(1) O(8) 0.052(2) 0.035(2) 0.031(2) -0.021(2) 0.031(2) -0.005(2) C(1) 0.020(2) 0.018(2) 0.018(2) -0.001(2) 0.015(2) -0.001(2) C(2) 0.028(2) 0.013(2) 0.024(2) 0.002(2) 0.020(2) 0.000(2) C(3) 0.032(3) 0.022(3) 0.024(3) 0.012(2) 0.020(2) 0.008(2) C(4) 0.019(2) 0.036(3) 0.019(2) 0.010(2) 0.015(2) 0.008(2) C(5) 0.021(2) 0.024(2) 0.017(2) 0.004(2) 0.014(2) 0.003(2) C(6) 0.019(2) 0.022(2) 0.015(2) 0.005(2) 0.013(2) 0.002(2) C(7) 0.016(2) 0.021(2) 0.014(2) -0.001(2) 0.012(2) 0.001(2) C(8) 0.018(2) 0.012(2) 0.014(2) 0.000(2) 0.011(2) 0.000(2) C(9) 0.012(2) 0.014(2) 0.016(2) -0.002(2) 0.009(2) -0.005(2) C(10) 0.020(2) 0.018(2) 0.017(2) 0.000(2) 0.012(2) 0.001(2) C(11) 0.026(2) 0.022(2) 0.025(2) -0.001(2) 0.022(2) -0.005(2) C(12) 0.025(2) 0.017(2) 0.037(3) 0.007(2) 0.024(2) 0.004(2) C(13) 0.018(2) 0.017(2) 0.022(2) 0.005(2) 0.013(2) 0.008(2) C(14) 0.017(2) 0.012(2) 0.017(2) -0.001(2) 0.012(2) 0.001(2) C(15) 0.018(2) 0.014(2) 0.022(2) -0.003(2) 0.012(2) 0.001(2) C(16) 0.015(2) 0.017(2) 0.010(2) 0.000(2) 0.010(2) 0.001(2) C(17) 0.017(2) 0.026(2) 0.013(2) 0.001(2) 0.012(2) -0.003(2) C(18) 0.022(2) 0.027(2) 0.019(2) 0.000(2) 0.015(2) 0.001(2) C(19) 0.016(2) 0.043(3) 0.013(2) -0.005(2) 0.009(2) -0.004(2) C(20) 0.024(3) 0.038(3) 0.021(2) -0.017(2) 0.016(2) -0.013(2) C(21) 0.028(3) 0.022(2) 0.022(2) -0.008(2) 0.019(2) -0.008(2) C(22) 0.021(2) 0.022(2) 0.017(2) -0.003(2) 0.015(2) -0.003(2) C(23) 0.021(2) 0.007(2) 0.021(2) -0.006(2) 0.014(2) -0.006(2) C(24) 0.020(2) 0.009(2) 0.017(2) -0.002(2) 0.014(2) -0.002(2) C(25) 0.061(4) 0.018(2) 0.041(3) 0.008(2) 0.034(3) 0.004(2) #------------------------------------------------------------------------------ _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan Ver. 1.11' _computing_structure_solution SIR92 _computing_structure_refinement 'teXsan Ver. 1.10' _computing_publication_material 'teXsan Ver. 1.11' _computing_molecular_graphics ? #------------------------------------------------------------------------------ _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag ? ? ? ? ? ? # -- ENTER BONDS HERE, ONE PER LINE -- # e.g. C1 C2 1.541(1) . . yes #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag # -- ENTER ANGLES HERE, ONE PER LINE -- # e.g. C1 C2 C3 109.4(3) . . . yes ? ? ? ? ? ? ? ? #------------------------------------------------------------------------------ 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 # -- ENTER TORSION ANGLES HERE, ONE PER LINE -- # e.g. C1 C2 C3 C4 109.4(3) . . . . yes ? ? ? ? ? ? ? ? ? ? #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag ? ? ? ? ? ? # -- ENTER BONDS HERE, ONE PER LINE -- # e.g. O1 N1 1.541(1) . . yes #------------------------------------------------------------------------------ #------------------------------------------------------------------------------