# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Susumu Kitagawa' _publ_contact_author_email KITAGAWA@SBCHEM.KYOTO-U.AC.JP _publ_section_title ; Periodic molecular boxes in entangled enantiomorphic lcy nets ; loop_ _publ_author_name 'Susumu Kitagawa' 'Charlotte Bonneau' 'Shuhei Furukawa' 'Ryotaro Matsuda' 'Yohei Takashima' # Attachment 'Framework1.cif' data_thiophene _database_code_depnum_ccdc_archive 'CCDC 766017' #TrackingRef 'Framework1.cif' _audit_creation_date 2010-02-05T18:50:49-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C19 H9 O15 S3 Zn4' _chemical_formula_weight 834.92 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting cubic _symmetry_space_group_name_H-M 'P a -3' _symmetry_space_group_name_Hall '-P 2ac 2ab ' _symmetry_Int_Tables_number 205 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' 'z, x, y' 'y, z, x' '-z+1/2, -x, y+1/2' '-y, z+1/2, -x+1/2' 'z+1/2, -x+1/2, -y' '-y+1/2, -z, x+1/2' '-z, x+1/2, -y+1/2' 'y+1/2, -z+1/2, -x' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' '-z, -x, -y' '-y, -z, -x' 'z-1/2, x, -y-1/2' 'y, -z-1/2, x-1/2' '-z-1/2, x-1/2, y' 'y-1/2, z, -x-1/2' 'z, -x-1/2, y-1/2' '-y-1/2, z-1/2, x' _cell_length_a 19.025(3) _cell_length_b 19.025(3) _cell_length_c 19.025(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 6886.1(19) _cell_formula_units_Z 8 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 20294 _cell_measurement_theta_min 3.0286 _cell_measurement_theta_max 27.4971 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.611 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3288 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 2.994 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.358 _exptl_absorpt_correction_T_max 0.418 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_measurement_device_type 'Rigaku Saturn' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.31 _diffrn_radiation_monochromator confocal _diffrn_reflns_av_R_equivalents 0.0624 _diffrn_reflns_av_unetI/netI 0.0235 _diffrn_reflns_number 54017 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_full 27.5 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 2643 _reflns_number_gt 2552 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution SIR92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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. The diffused electron densities resulting from residual solvent molecules were removed from the data set using the SQUEEZE routine of PLATON and refined further using the data generated. The contents of the solvent region are not represented in the unit cell contents in crystal data. Although the Fourier peak with high intensity (2.62 eA-3) was observed near the Zn cluster, no assignable atoms were found in the result of elemental analysis. Methanol atom at special position was refined with disordered model using part -1 instruction. ; _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^)+(0.0923P)^2^+36.9661P] 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 SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.0030(4) _refine_ls_number_reflns 2643 _refine_ls_number_parameters 138 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0593 _refine_ls_R_factor_gt 0.0578 _refine_ls_wR_factor_ref 0.1633 _refine_ls_wR_factor_gt 0.1618 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.063 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 2.624 _refine_diff_density_min -1.156 _refine_diff_density_rms 0.167 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Zn1 Zn 0.23627(3) 0.23627(3) 0.23627(3) 0.0232(3) Uani 1 3 d S . . Zn2 Zn 0.18259(3) 0.07751(3) 0.20033(3) 0.0212(2) Uani 1 1 d . . . S1 S 0.24873(9) 0.00846(7) 0.42938(7) 0.0406(4) Uani 1 1 d . . . O2 O 0.2330(2) 0.06956(19) 0.29053(17) 0.0318(8) Uani 1 1 d . A . O5 O 0.2262(2) 0.01640(19) 0.13104(18) 0.0341(8) Uani 1 1 d . A . O4 O 0.0922(2) 0.0399(2) 0.2295(3) 0.0596(15) Uani 1 1 d . A . C5 C 0.2521(3) 0.0267(3) 0.5175(3) 0.0375(12) Uani 1 1 d . . . O3 O 0.2129(3) 0.18049(19) 0.32488(18) 0.0390(9) Uani 1 1 d . A . O7 O 0.0836(4) 0.0836(4) 0.0836(4) 0.095(4) Uani 1 3 d S . . C3 C 0.2291(4) 0.1351(3) 0.4699(3) 0.0499(17) Uani 1 1 d . . . H3 H 0.2195 0.1841 0.4697 0.06 Uiso 1 1 calc R . . O1 O 0.17493(16) 0.17493(16) 0.17493(16) 0.0196(10) Uani 1 3 d S A . C1 C 0.2258(3) 0.1172(2) 0.3362(2) 0.0273(9) Uani 1 1 d . . . C2 C 0.2335(3) 0.0955(3) 0.4105(2) 0.0330(11) Uani 1 1 d . A . C4 C 0.2404(4) 0.0960(3) 0.5318(3) 0.0475(16) Uani 1 1 d . . . H4 H 0.2399 0.1154 0.5778 0.057 Uiso 1 1 calc R . . C6 C 0.2331(3) 0.0314(3) 0.0671(3) 0.0358(12) Uani 1 1 d . . . O6 O 0.306(2) 0.2906(13) 0.307(2) 0.058(6) Uani 0.33 1 d PU A -1 C7 C 0.3638(7) 0.2602(7) 0.3289(7) 0.024(3) Uani 0.33 1 d PU A -1 H7A H 0.3522 0.2226 0.3622 0.037 Uiso 0.33 1 calc PR A -1 H7B H 0.3938 0.295 0.3522 0.037 Uiso 0.33 1 calc PR A -1 H7C H 0.3888 0.2403 0.2885 0.037 Uiso 0.33 1 calc PR A -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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0232(3) 0.0232(3) 0.0232(3) 0.00221(19) 0.00221(19) 0.00221(19) Zn2 0.0232(3) 0.0219(3) 0.0186(3) 0.00196(18) 0.00183(18) 0.00488(18) S1 0.0756(10) 0.0243(6) 0.0218(6) -0.0003(4) -0.0111(6) 0.0125(6) O2 0.046(2) 0.0323(18) 0.0169(15) -0.0009(13) -0.0046(14) 0.0147(15) O5 0.048(2) 0.0331(18) 0.0215(16) -0.0064(14) -0.0006(15) 0.0135(16) O4 0.027(2) 0.035(2) 0.117(5) 0.026(3) 0.013(2) -0.0005(17) C5 0.062(3) 0.029(2) 0.022(2) 0.0040(19) -0.003(2) 0.010(2) O3 0.072(3) 0.0248(17) 0.0201(16) 0.0032(13) -0.0019(17) 0.0075(18) O7 0.095(4) 0.095(4) 0.095(4) -0.017(4) -0.017(4) -0.017(4) C3 0.099(5) 0.030(3) 0.021(2) -0.002(2) -0.004(3) 0.019(3) O1 0.0196(10) 0.0196(10) 0.0196(10) 0.0041(12) 0.0041(12) 0.0041(12) C1 0.040(3) 0.022(2) 0.020(2) 0.0023(16) -0.0006(18) 0.0025(18) C2 0.058(3) 0.023(2) 0.018(2) 0.0030(17) -0.002(2) 0.008(2) C4 0.090(5) 0.030(3) 0.022(2) -0.001(2) -0.005(3) 0.016(3) C6 0.051(3) 0.030(2) 0.027(2) -0.007(2) 0.003(2) 0.010(2) O6 0.059(7) 0.057(7) 0.058(7) -0.007(5) -0.002(4) -0.006(5) C7 0.021(4) 0.033(4) 0.019(4) 0.000(4) -0.017(3) -0.001(4) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 Zn1 O1 2.021(5) . ? Zn1 O3 2.041(4) . ? Zn1 O3 2.041(4) 6 ? Zn1 O3 2.041(4) 5 ? Zn1 O6 2.157(11) 6 ? Zn1 O6 2.157(11) . ? Zn1 O6 2.157(11) 5 ? Zn2 O1 1.921(2) . ? Zn2 O5 1.943(3) . ? Zn2 O4 1.944(4) . ? Zn2 O2 1.971(3) . ? Zn2 Zn2 3.0939(9) 6 ? Zn2 Zn2 3.0939(10) 5 ? S1 C5 1.713(5) . ? S1 C2 1.719(5) . ? O2 C1 1.262(6) . ? O5 C6 1.256(6) . ? O4 C6 1.269(7) 6 ? C5 C4 1.364(8) . ? C5 C6 1.482(7) 2 ? O3 C1 1.248(6) . ? C3 C2 1.361(7) . ? C3 C4 1.410(7) . ? C3 H3 0.95 . ? O1 Zn2 1.921(2) 6 ? O1 Zn2 1.921(2) 5 ? C1 C2 1.480(6) . ? C4 H4 0.95 . ? C6 O4 1.269(7) 5 ? C6 C5 1.482(7) 2_554 ? O6 C7 1.31(4) . ? C7 H7A 0.98 . ? C7 H7B 0.98 . ? C7 H7C 0.98 . ? 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 Zn1 O3 92.91(12) . . ? O1 Zn1 O3 92.91(12) . 6 ? O3 Zn1 O3 119.75(2) . 6 ? O1 Zn1 O3 92.91(12) . 5 ? O3 Zn1 O3 119.75(2) . 5 ? O3 Zn1 O3 119.75(2) 6 5 ? O1 Zn1 O6 173.3(8) . 6 ? O3 Zn1 O6 85.7(16) . 6 ? O3 Zn1 O6 82.2(12) 6 6 ? O3 Zn1 O6 93.4(9) 5 6 ? O1 Zn1 O6 173.3(8) . . ? O3 Zn1 O6 82.2(12) . . ? O3 Zn1 O6 93.4(9) 6 . ? O3 Zn1 O6 85.7(16) 5 . ? O6 Zn1 O6 11.5(13) 6 . ? O1 Zn1 O6 173.3(8) . 5 ? O3 Zn1 O6 93.4(9) . 5 ? O3 Zn1 O6 85.7(16) 6 5 ? O3 Zn1 O6 82.2(12) 5 5 ? O6 Zn1 O6 11.5(13) 6 5 ? O6 Zn1 O6 11.5(13) . 5 ? O1 Zn2 O5 116.03(13) . . ? O1 Zn2 O4 111.12(14) . . ? O5 Zn2 O4 110.5(2) . . ? O1 Zn2 O2 109.26(18) . . ? O5 Zn2 O2 109.72(15) . . ? O4 Zn2 O2 98.8(2) . . ? O1 Zn2 Zn2 36.37(8) . 6 ? O5 Zn2 Zn2 130.80(11) . 6 ? O4 Zn2 Zn2 74.80(13) . 6 ? O2 Zn2 Zn2 117.84(10) . 6 ? O1 Zn2 Zn2 36.37(8) . 5 ? O5 Zn2 Zn2 80.07(11) . 5 ? O4 Zn2 Zn2 123.40(15) . 5 ? O2 Zn2 Zn2 130.85(12) . 5 ? Zn2 Zn2 Zn2 60 6 5 ? C5 S1 C2 90.9(2) . . ? C1 O2 Zn2 119.4(3) . . ? C6 O5 Zn2 124.4(3) . . ? C6 O4 Zn2 132.1(4) 6 . ? C4 C5 C6 128.7(5) . 2 ? C4 C5 S1 112.7(4) . . ? C6 C5 S1 118.7(4) 2 . ? C1 O3 Zn1 127.0(3) . . ? C2 C3 C4 113.1(5) . . ? C2 C3 H3 123.5 . . ? C4 C3 H3 123.5 . . ? Zn2 O1 Zn2 107.27(16) 6 . ? Zn2 O1 Zn2 107.27(16) 6 5 ? Zn2 O1 Zn2 107.27(16) . 5 ? Zn2 O1 Zn1 111.59(15) 6 . ? Zn2 O1 Zn1 111.59(15) . . ? Zn2 O1 Zn1 111.59(15) 5 . ? O3 C1 O2 126.5(4) . . ? O3 C1 C2 116.9(4) . . ? O2 C1 C2 116.5(4) . . ? C3 C2 C1 129.2(5) . . ? C3 C2 S1 111.7(4) . . ? C1 C2 S1 119.0(4) . . ? C5 C4 C3 111.6(5) . . ? C5 C4 H4 124.2 . . ? C3 C4 H4 124.2 . . ? O5 C6 O4 126.7(5) . 5 ? O5 C6 C5 117.8(5) . 2_554 ? O4 C6 C5 115.5(5) 5 2_554 ? C7 O6 Zn1 120(2) . . ? # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.000 0.000 186 6 ' ' 2 -0.001 0.000 0.500 213 5 ' ' 3 -0.001 0.500 0.000 213 5 ' ' 4 0.000 0.500 0.500 186 6 ' ' 5 0.499 0.000 1.000 213 5 ' ' 6 0.499 0.500 0.500 213 5 ' ' 7 0.500 0.000 0.500 186 6 ' ' 8 0.500 0.500 0.000 186 6 ' ' _platon_squeeze_details ; ;