# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Susumu Kitagawa' _publ_contact_author_address ; Department of Synthetic Chemistry and Biological Chemistry Graduate School of Engineering, Kyoto University Katsura, Nishikyo-ku Kyoto 615-8510 JAPAN ; _publ_contact_author_email KITAGAWA@SBCHEM.KYOTO-U.AC.JP _publ_section_title ; Selective Guest Sorption in Interdigitated Porous Framework with Hydrophobic Pore Surfaces ; loop_ _publ_author_name 'Susumu Kitagawa' 'Satoshi Horike' 'Keiji Nakagawa' 'Daisuke Tanaka' # Attachment 'cid1_squeeze_pqn.cif' data_crystalclear _database_code_depnum_ccdc_archive 'CCDC 639850' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C39 H31 N5 O9 Zn2' _chemical_formula_weight 844.43 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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 10.082(5) _cell_length_b 11.384(5) _cell_length_c 15.744(8) _cell_angle_alpha 90.00 _cell_angle_beta 103.917(8) _cell_angle_gamma 90.00 _cell_volume 1753.9(14) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.599 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 1.434 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7624 _exptl_absorpt_correction_T_max 0.7624 _exptl_absorpt_process_details sadab _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type CCD _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9433 _diffrn_reflns_av_R_equivalents 0.0732 _diffrn_reflns_av_sigmaI/netI 0.0758 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3057 _reflns_number_gt 2353 _reflns_threshold_expression >2sigma(I) _computing_data_collection crystalclear _computing_cell_refinement crystalclear _computing_data_reduction teXsan _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material teXsan _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^)+(0.0422P)^2^+5.3254P] 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_number_reflns 3057 _refine_ls_number_parameters 222 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0770 _refine_ls_R_factor_gt 0.0600 _refine_ls_wR_factor_ref 0.1449 _refine_ls_wR_factor_gt 0.1368 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.001 _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 Zn1 Zn 0.62512(6) 0.23565(5) 0.66157(4) 0.0218(2) Uani 1 1 d . . . O1 O -0.1596(4) 0.2273(3) 0.6710(2) 0.0255(8) Uani 1 1 d . . . O4 O 0.4280(4) 0.2308(3) 0.5885(2) 0.0240(8) Uani 1 1 d . . . C1 C 0.3306(5) 0.2285(4) 0.6256(3) 0.0206(11) Uani 1 1 d . . . O3 O 0.3429(4) 0.2486(3) 0.7047(2) 0.0299(9) Uani 1 1 d . . . O2 O -0.2939(4) 0.2166(4) 0.5391(2) 0.0336(9) Uani 1 1 d . . . C11 C 0.7288(6) 0.8648(5) 0.7286(3) 0.0313(14) Uani 1 1 d . . . H17 H 0.7999 0.8266 0.7674 0.038 Uiso 1 1 calc R . . C3 C 0.0766(5) 0.2150(4) 0.6048(3) 0.0223(11) Uani 1 1 d . . . H2 H 0.0879 0.2381 0.6627 0.027 Uiso 1 1 calc R . . C2 C 0.1898(5) 0.2016(4) 0.5710(3) 0.0233(11) Uani 1 1 d . . . C8 C -0.1760(5) 0.2139(4) 0.5901(3) 0.0248(11) Uani 1 1 d . . . N1 N 0.6290(4) 0.4229(4) 0.6597(3) 0.0253(10) Uani 1 1 d . . . C6 C -0.0546(6) 0.1945(4) 0.5533(3) 0.0248(11) Uani 1 1 d . . . C12 C 0.5224(5) 0.8627(5) 0.6187(3) 0.0274(12) Uani 1 1 d . . . H18 H 0.4506 0.8234 0.5813 0.033 Uiso 1 1 calc R . . C14 C 0.6305(5) 0.6697(4) 0.6687(3) 0.0241(11) Uani 1 1 d . . . C4 C 0.1719(6) 0.1607(5) 0.4850(3) 0.0344(14) Uani 1 1 d . . . H4 H 0.2470 0.1510 0.4611 0.041 Uiso 1 1 calc R . . C10 C 0.5239(6) 0.9827(4) 0.6208(4) 0.0272(12) Uani 1 1 d . . . H19 H 0.4525 1.0226 0.5836 0.033 Uiso 1 1 calc R . . N2 N 0.6217(4) 1.0459(4) 0.6729(3) 0.0223(9) Uani 1 1 d . . . C13 C 0.6274(5) 0.7993(4) 0.6720(3) 0.0218(10) Uani 1 1 d . A . C9 C 0.7234(6) 0.9852(5) 0.7270(3) 0.0322(14) Uani 1 1 d . . . H20 H 0.7926 1.0269 0.7646 0.039 Uiso 1 1 calc R . . C7 C -0.0694(6) 0.1542(5) 0.4683(3) 0.0348(14) Uani 1 1 d . . . H7 H -0.1561 0.1404 0.4329 0.042 Uiso 1 1 calc R . . C5 C 0.0434(6) 0.1350(6) 0.4365(4) 0.0403(16) Uani 1 1 d . . . H8 H 0.0327 0.1038 0.3807 0.048 Uiso 1 1 calc R . . C20 C 0.7284(11) 0.6021(9) 0.7232(7) 0.020(2) Uiso 0.50 1 d P A 1 H9 H 0.7993 0.6383 0.7635 0.024 Uiso 0.50 1 calc PR A 1 C21 C 0.7222(12) 0.4801(9) 0.7185(7) 0.023(2) Uiso 0.50 1 d P A 1 H10 H 0.7866 0.4369 0.7586 0.028 Uiso 0.50 1 calc PR A 1 C22 C 0.5412(11) 0.4879(9) 0.6011(7) 0.024(2) Uiso 0.50 1 d P A 1 H11 H 0.4778 0.4490 0.5575 0.029 Uiso 0.50 1 calc PR A 1 C15 C 0.7398(14) 0.4830(10) 0.6829(8) 0.033(3) Uiso 0.50 1 d P A 2 H12 H 0.8216 0.4415 0.6975 0.039 Uiso 0.50 1 calc PR A 2 C19 C 0.5387(12) 0.6079(10) 0.6012(7) 0.028(2) Uiso 0.50 1 d P A 1 H13 H 0.4776 0.6485 0.5574 0.034 Uiso 0.50 1 calc PR A 1 C16 C 0.5110(15) 0.4860(12) 0.6407(9) 0.042(3) Uiso 0.50 1 d P A 2 H14 H 0.4282 0.4460 0.6252 0.050 Uiso 0.50 1 calc PR A 2 C17 C 0.5095(14) 0.6081(11) 0.6436(8) 0.040(3) Uiso 0.50 1 d P A 2 H15 H 0.4269 0.6483 0.6286 0.048 Uiso 0.50 1 calc PR A 2 C18 C 0.7475(13) 0.6047(10) 0.6879(8) 0.032(3) Uiso 0.50 1 d P A 2 H16 H 0.8320 0.6417 0.7044 0.038 Uiso 0.50 1 calc PR A 2 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 0.0159(4) 0.0233(3) 0.0262(3) 0.0005(2) 0.0048(2) 0.0001(2) O1 0.021(2) 0.032(2) 0.0240(18) -0.0018(15) 0.0077(15) 0.0004(16) O4 0.0156(19) 0.0271(18) 0.0302(18) -0.0011(15) 0.0073(15) -0.0003(15) C1 0.019(3) 0.016(2) 0.028(3) 0.002(2) 0.007(2) 0.000(2) O3 0.020(2) 0.043(2) 0.0252(19) -0.0018(16) 0.0035(16) -0.0005(17) O2 0.010(2) 0.055(3) 0.034(2) -0.0032(18) 0.0013(16) -0.0004(18) C11 0.029(3) 0.024(3) 0.030(3) 0.003(2) -0.013(2) 0.000(2) C3 0.018(3) 0.028(3) 0.022(2) -0.001(2) 0.006(2) -0.002(2) C2 0.017(3) 0.026(3) 0.026(2) -0.001(2) 0.003(2) -0.002(2) C8 0.019(3) 0.023(3) 0.035(3) -0.001(2) 0.012(2) -0.002(2) N1 0.019(2) 0.027(2) 0.028(2) 0.0021(19) 0.0030(19) -0.0011(19) C6 0.026(3) 0.026(3) 0.023(2) 0.002(2) 0.007(2) 0.001(2) C12 0.016(3) 0.028(3) 0.035(3) -0.004(2) -0.001(2) -0.002(2) C14 0.023(3) 0.021(2) 0.028(2) 0.003(2) 0.006(2) -0.004(2) C4 0.027(3) 0.048(4) 0.029(3) -0.005(3) 0.009(3) 0.003(3) C10 0.017(3) 0.023(3) 0.036(3) -0.002(2) -0.004(2) 0.001(2) N2 0.016(2) 0.024(2) 0.026(2) -0.0005(17) 0.0031(18) -0.0001(18) C13 0.020(3) 0.025(3) 0.022(2) 0.000(2) 0.007(2) -0.001(2) C9 0.033(4) 0.028(3) 0.029(3) -0.002(2) -0.006(3) -0.004(2) C7 0.023(3) 0.055(4) 0.025(3) -0.007(3) 0.003(2) -0.003(3) C5 0.019(3) 0.072(5) 0.027(3) -0.015(3) 0.000(2) -0.003(3) _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 O4 2.044(4) . ? Zn1 O3 2.057(4) 2_656 ? Zn1 N1 2.132(4) . ? Zn1 O1 2.142(4) 1_655 ? Zn1 N2 2.169(4) 1_545 ? Zn1 O2 2.278(4) 1_655 ? Zn1 C8 2.536(5) 1_655 ? O1 C8 1.253(6) . ? O1 Zn1 2.142(4) 1_455 ? O4 C1 1.259(6) . ? C1 O3 1.242(6) . ? C1 C2 1.503(7) . ? O3 Zn1 2.057(4) 2_656 ? O2 C8 1.265(6) . ? O2 Zn1 2.279(4) 1_455 ? C11 C9 1.372(7) . ? C11 C13 1.399(7) . ? C11 H17 0.9300 . ? C3 C2 1.379(7) . ? C3 C6 1.395(7) . ? C3 H2 0.9300 . ? C2 C4 1.401(7) . ? C8 C6 1.492(7) . ? C8 Zn1 2.536(5) 1_455 ? N1 C15 1.286(13) . ? N1 C21 1.322(12) . ? N1 C22 1.338(11) . ? N1 C16 1.360(14) . ? C6 C7 1.388(7) . ? C12 C10 1.367(7) . ? C12 C13 1.385(7) . ? C12 H18 0.9300 . ? C14 C18 1.363(13) . ? C14 C20 1.377(11) . ? C14 C17 1.379(14) . ? C14 C19 1.416(12) . ? C14 C13 1.478(7) . ? C4 C5 1.368(8) . ? C4 H4 0.9300 . ? C10 N2 1.332(6) . ? C10 H19 0.9300 . ? N2 C9 1.354(7) . ? N2 Zn1 2.169(4) 1_565 ? C9 H20 0.9300 . ? C7 C5 1.366(8) . ? C7 H7 0.9300 . ? C5 H8 0.9300 . ? C20 C21 1.390(15) . ? C20 H9 0.9300 . ? C21 H10 0.9300 . ? C22 C19 1.365(15) . ? C22 H11 0.9300 . ? C15 C18 1.388(16) . ? C15 H12 0.9300 . ? C19 H13 0.9300 . ? C16 C17 1.391(18) . ? C16 H14 0.9300 . ? C17 H15 0.9300 . ? C18 H16 0.9300 . ? 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 O4 Zn1 O3 118.03(15) . 2_656 ? O4 Zn1 N1 92.15(15) . . ? O3 Zn1 N1 86.77(16) 2_656 . ? O4 Zn1 O1 150.44(14) . 1_655 ? O3 Zn1 O1 91.47(14) 2_656 1_655 ? N1 Zn1 O1 91.37(16) . 1_655 ? O4 Zn1 N2 89.26(15) . 1_545 ? O3 Zn1 N2 89.35(16) 2_656 1_545 ? N1 Zn1 N2 176.09(16) . 1_545 ? O1 Zn1 N2 89.20(15) 1_655 1_545 ? O4 Zn1 O2 91.08(14) . 1_655 ? O3 Zn1 O2 150.84(14) 2_656 1_655 ? N1 Zn1 O2 94.15(16) . 1_655 ? O1 Zn1 O2 59.38(12) 1_655 1_655 ? N2 Zn1 O2 89.47(16) 1_545 1_655 ? O4 Zn1 C8 120.89(16) . 1_655 ? O3 Zn1 C8 120.98(16) 2_656 1_655 ? N1 Zn1 C8 94.16(17) . 1_655 ? O1 Zn1 C8 29.55(15) 1_655 1_655 ? N2 Zn1 C8 88.24(16) 1_545 1_655 ? O2 Zn1 C8 29.86(15) 1_655 1_655 ? C8 O1 Zn1 92.9(3) . 1_455 ? C1 O4 Zn1 120.0(3) . . ? O3 C1 O4 124.1(5) . . ? O3 C1 C2 117.7(5) . . ? O4 C1 C2 118.2(4) . . ? C1 O3 Zn1 165.0(4) . 2_656 ? C8 O2 Zn1 86.4(3) . 1_455 ? C9 C11 C13 120.0(5) . . ? C9 C11 H17 120.0 . . ? C13 C11 H17 120.0 . . ? C2 C3 C6 121.0(5) . . ? C2 C3 H2 119.5 . . ? C6 C3 H2 119.5 . . ? C3 C2 C4 118.9(5) . . ? C3 C2 C1 120.8(4) . . ? C4 C2 C1 120.4(5) . . ? O1 C8 O2 121.1(5) . . ? O1 C8 C6 119.6(5) . . ? O2 C8 C6 119.3(5) . . ? O1 C8 Zn1 57.5(3) . 1_455 ? O2 C8 Zn1 63.7(3) . 1_455 ? C6 C8 Zn1 175.7(4) . 1_455 ? C15 N1 C21 27.9(6) . . ? C15 N1 C22 106.7(8) . . ? C21 N1 C22 116.9(7) . . ? C15 N1 C16 115.9(9) . . ? C21 N1 C16 109.4(8) . . ? C22 N1 C16 32.6(6) . . ? C15 N1 Zn1 123.1(6) . . ? C21 N1 Zn1 119.7(5) . . ? C22 N1 Zn1 123.4(5) . . ? C16 N1 Zn1 120.8(6) . . ? C7 C6 C3 118.9(5) . . ? C7 C6 C8 121.1(5) . . ? C3 C6 C8 120.1(4) . . ? C10 C12 C13 120.2(5) . . ? C10 C12 H18 119.9 . . ? C13 C12 H18 119.9 . . ? C18 C14 C20 26.6(6) . . ? C18 C14 C17 116.5(8) . . ? C20 C14 C17 110.2(8) . . ? C18 C14 C19 105.8(8) . . ? C20 C14 C19 115.5(7) . . ? C17 C14 C19 32.9(6) . . ? C18 C14 C13 124.0(7) . . ? C20 C14 C13 123.6(6) . . ? C17 C14 C13 119.6(7) . . ? C19 C14 C13 120.5(6) . . ? C5 C4 C2 119.7(5) . . ? C5 C4 H4 120.2 . . ? C2 C4 H4 120.2 . . ? N2 C10 C12 123.8(5) . . ? N2 C10 H19 118.1 . . ? C12 C10 H19 118.1 . . ? C10 N2 C9 116.6(4) . . ? C10 N2 Zn1 120.7(3) . 1_565 ? C9 N2 Zn1 122.4(3) . 1_565 ? C12 C13 C11 116.3(5) . . ? C12 C13 C14 121.2(4) . . ? C11 C13 C14 122.5(5) . . ? N2 C9 C11 122.8(5) . . ? N2 C9 H20 118.6 . . ? C11 C9 H20 118.6 . . ? C5 C7 C6 119.9(5) . . ? C5 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C7 C5 C4 121.5(5) . . ? C7 C5 H8 119.3 . . ? C4 C5 H8 119.3 . . ? C14 C20 C21 120.6(9) . . ? C14 C20 H9 119.7 . . ? C21 C20 H9 119.7 . . ? N1 C21 C20 123.0(9) . . ? N1 C21 H10 118.5 . . ? C20 C21 H10 118.5 . . ? N1 C22 C19 124.2(9) . . ? N1 C22 H11 117.9 . . ? C19 C22 H11 117.9 . . ? N1 C15 C18 125.4(11) . . ? N1 C15 H12 117.3 . . ? C18 C15 H12 117.3 . . ? C22 C19 C14 119.3(9) . . ? C22 C19 H13 120.4 . . ? C14 C19 H13 120.4 . . ? N1 C16 C17 122.4(12) . . ? N1 C16 H14 118.8 . . ? C17 C16 H14 118.8 . . ? C14 C17 C16 120.1(11) . . ? C14 C17 H15 119.9 . . ? C16 C17 H15 119.9 . . ? C14 C18 C15 119.7(11) . . ? C14 C18 H16 120.2 . . ? C15 C18 H16 120.2 . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.441 _refine_diff_density_min -0.546 _refine_diff_density_rms 0.103 # SQUEEZE RESULTS (APPEND TO CIF) 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 1 0.000 0.500 0.000 106.7 24.2 2 0.000 0.500 0.500 106.7 24.3 _platon_squeeze_details ; ;