# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2003 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 loop_ _publ_author_name _publ_author_address 'Darren W. Johnson' ; Skaggs Institute for Chemical Biology (MB26) The Scripps Research Institute 10550 N. Torrey Pines Road La Jolla, CA 92037 ; 'Fraser Hof' ; Skaggs Institute for Chemical Biology (MB26) The Scripps Research Institute 10550 N. Torrey Pines Road La Jolla, CA 92037 ; 'Liam C. Palmer' ; Skaggs Institute for Chemical Biology (MB26) The Scripps Research Institute 10550 N. Torrey Pines Road La Jolla, CA 92037 ; 'Tomas Martin' ; Skaggs Institute for Chemical Biology (MB26) The Scripps Research Institute 10550 N. Torrey Pines Road La Jolla, CA 92037 ; 'Ulrike Obst' ; Skaggs Institute for Chemical Biology (MB26) The Scripps Research Institute 10550 N. Torrey Pines Road La Jolla, CA 92037 ; 'Rebek Junior,J.' ; Skaggs Institute for Chemical Biology (MB26) The Scripps Research Institute 10550 N. Torrey Pines Road La Jolla, CA 92037 ; _publ_contact_author_name 'Prof Julius Rebek' _publ_contact_author_address ; Julius Rebek, Jr. Skaggs Institute for Chemical Biology (MB26) The Scripps Research Institute 10550 N. Torrey Pines Road La Jolla, CA 92037 ; _publ_contact_author_email jrebek@scripps.edu _publ_contact_author_fax 858-784-2876 _publ_contact_author_phone 858-784-2250 _publ_section_title ; Glycoluril Ribbons Tethered by Complementary Hydrogen Bonds ; data_tetsxm _database_code_CSD 203373 _publ_section_references ; Altomare, A., Burla, M. C., Camalli, M., Cascarano, M., Giacovazzo, C., Guagliardi, A., Polidori, G. (1993). J. Appl. Cryst., 26, 343-350. Siemens Industrial Automation, Inc. (1995). SMART. Area Detector Software Package, Madison, WI, USA. Siemens Industrial Automation, Inc. (1995). SAINT. SAX Area Detector Integration Program (v. 4.024), Madison, WI, USA. Siemens Industrial Automation, Inc. (1993). SHELXL. SHELXTL Crystal Structure Determination Software Package, Madison, WI, USA. ; _audit_creation_method SHELXL-97 _computing_data_collection 'SMART (Siemens, 1995)' _computing_cell_refinement ; SMART (Siemens, 1995), SAINT (Siemens, 1995) ; _computing_data_reduction ; SAINT (Siemens, 1995), XPREP (Siemens, 1995) ; _computing_structure_solution 'SIR92 (Altomare, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _chemical_formula_sum 'C28 H28 Cl2 N6 O4 S' _chemical_formula_weight 615.52 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' N N 0.0311 0.0180 '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' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 '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(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' #--------------------------------------------------------- _cell_length_a 10.875(6) _cell_length_b 11.278(7) _cell_length_c 22.289(12) _cell_angle_alpha 90.00 _cell_angle_beta 96.48(3) _cell_angle_gamma 90.00 _cell_volume 2716(3) _cell_formula_units_Z 4 _cell_measurement_temperature 158(2) _cell_measurement_reflns_used 1456 _cell_measurement_theta_min 4.40 _cell_measurement_theta_max 42.53 _exptl_crystal_description block _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.01 _exptl_crystal_density_diffrn 1.505 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1280 _exptl_absorpt_coefficient_mu 3.275 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.67 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_process_details ? #-------------------------------------------------------- _diffrn_ambient_temperature 158(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator 'mirror optics' _diffrn_radiation_detector 'CCD area detector' _diffrn_measurement_device_type '3 circle diffractometer' _diffrn_measurement_method ; omega scans with profile analysis ; _diffrn_reflns_number 9468 _diffrn_reflns_av_R_equivalents 0.0614 _diffrn_reflns_av_sigmaI/netI 0.0532 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 4.40 _diffrn_reflns_theta_max 42.53 _reflns_number_total 1832 _reflns_number_gt 1456 _reflns_threshold_expression >2sigma(I) _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^)+(0.1481P)^2^+8.2552P] 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 none _refine_ls_number_reflns 1832 _refine_ls_number_parameters 230 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0964 _refine_ls_R_factor_gt 0.0781 _refine_ls_wR_factor_ref 0.2394 _refine_ls_wR_factor_gt 0.2127 _refine_ls_goodness_of_fit_ref 1.128 _refine_ls_restrained_S_all 1.128 _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 S1 S -0.1024(2) 0.2730(2) 0.60375(12) 0.0311(10) Uani 1 1 d . . . O4 O -0.0765(5) 0.2625(5) 0.6674(3) 0.0277(17) Uani 1 1 d . . . O6 O 0.0725(5) 0.4854(6) 0.3306(2) 0.0327(18) Uani 1 1 d . . . O7 O 0.0293(5) 0.0033(5) 0.3390(2) 0.0301(18) Uani 1 1 d . . . O8 O -0.2269(5) 0.2917(6) 0.5817(3) 0.042(2) Uani 1 1 d . . . N5 N 0.2140(6) 0.3378(7) 0.3467(3) 0.023(2) Uani 1 1 d . . . N11 N -0.0453(6) 0.1623(6) 0.5700(3) 0.024(2) Uani 1 1 d . . . H11A H -0.0652 0.0895 0.5754 0.029 Uiso 1 1 calc R . . N18 N 0.1972(6) 0.1275(6) 0.3502(3) 0.0185(19) Uani 1 1 d . . . N19 N 0.0716(6) 0.1323(6) 0.2661(3) 0.025(2) Uani 1 1 d . . . H19A H 0.0149 0.1085 0.2388 0.029 Uiso 1 1 calc R . . N21 N -0.0164(6) 0.3694(7) 0.5746(3) 0.034(2) Uani 1 1 d . . . H21A H -0.0145 0.4436 0.5835 0.040 Uiso 1 1 calc R . . N27 N 0.0940(6) 0.3414(6) 0.2604(3) 0.026(2) Uani 1 1 d . . . H27A H 0.0466 0.3717 0.2309 0.031 Uiso 1 1 calc R . . Cl1 Cl -0.3998(2) 0.0857(3) 0.46823(12) 0.0600(11) Uani 1 1 d . . . Cl2 Cl -0.1478(3) 0.3155(3) 0.39323(14) 0.0807(13) Uani 1 1 d . . . C9 C 0.3630(8) 0.1885(9) 0.1084(4) 0.036(3) Uiso 1 1 d . . . C10 C 0.4449(8) 0.3120(9) 0.2979(4) 0.028(3) Uiso 1 1 d . . . H10A H 0.4112 0.3876 0.2995 0.034 Uiso 1 1 calc R . . C12 C 0.2525(8) 0.3099(9) 0.1702(4) 0.031(3) Uiso 1 1 d . . . H12A H 0.2283 0.3857 0.1803 0.037 Uiso 1 1 calc R . . C13 C 0.5628(8) 0.2964(9) 0.2812(4) 0.034(3) Uiso 1 1 d . . . H13A H 0.6083 0.3624 0.2720 0.040 Uiso 1 1 calc R . . C14 C 0.3783(7) 0.2140(8) 0.3121(4) 0.019(2) Uiso 1 1 d . . . C15 C 0.0392(8) 0.1978(8) 0.5315(4) 0.024(3) Uiso 1 1 d . . . C16 C 0.2355(8) 0.1066(8) 0.4128(4) 0.026(3) Uiso 1 1 d . . . H16A H 0.3242 0.1187 0.4203 0.031 Uiso 1 1 calc R . . H16B H 0.2191 0.0243 0.4218 0.031 Uiso 1 1 calc R . . C17 C 0.2564(8) 0.3642(8) 0.4084(4) 0.028(3) Uiso 1 1 d . . . H17A H 0.2530 0.4494 0.4139 0.033 Uiso 1 1 calc R . . H17B H 0.3424 0.3404 0.4163 0.033 Uiso 1 1 calc R . . C20 C 0.2157(8) 0.2140(8) 0.2008(4) 0.023(2) Uiso 1 1 d . . . C22 C 0.1529(8) 0.2296(8) 0.2575(4) 0.024(3) Uiso 1 1 d . . . C23 C 0.5486(8) 0.0928(8) 0.2944(4) 0.031(3) Uiso 1 1 d . . . H23A H 0.5845 0.0179 0.2946 0.038 Uiso 1 1 calc R . . C24 C 0.1732(8) 0.1843(8) 0.4553(4) 0.025(2) Uiso 1 1 d . . . C25 C 0.6129(8) 0.1874(9) 0.2782(4) 0.033(3) Uiso 1 1 d . . . C26 C 0.2403(7) 0.2264(8) 0.3193(4) 0.021(2) Uiso 1 1 d . . . C28 C 0.4305(8) 0.1049(8) 0.3108(4) 0.024(3) Uiso 1 1 d . . . H28A H 0.3868 0.0383 0.3211 0.029 Uiso 1 1 calc R . . C29 C 0.1843(8) 0.3052(8) 0.4546(4) 0.027(3) Uiso 1 1 d . . . C30 C 0.7360(9) 0.1718(10) 0.2546(5) 0.054(3) Uiso 1 1 d . . . H30A H 0.7574 0.0892 0.2552 0.081 Uiso 1 1 calc R . . H30B H 0.7981 0.2151 0.2797 0.081 Uiso 1 1 calc R . . H30C H 0.7311 0.2011 0.2140 0.081 Uiso 1 1 calc R . . C31 C 0.2501(8) 0.1053(8) 0.1836(4) 0.033(3) Uiso 1 1 d . . . H31A H 0.2244 0.0385 0.2033 0.040 Uiso 1 1 calc R . . C32 C 0.3265(9) 0.2939(10) 0.1238(4) 0.044(3) Uiso 1 1 d . . . H32A H 0.3508 0.3600 0.1032 0.053 Uiso 1 1 calc R . . C33 C 0.0922(9) 0.0825(9) 0.3202(5) 0.026(3) Uiso 1 1 d . . . C34 C 0.0540(8) 0.3176(8) 0.5332(4) 0.027(3) Uiso 1 1 d . . . C35 C -0.3333(10) 0.2169(10) 0.4408(5) 0.067(4) Uiso 1 1 d . . . H35A H -0.3878 0.2504 0.4077 0.081 Uiso 1 1 calc R . . H35B H -0.3201 0.2756 0.4727 0.081 Uiso 1 1 calc R . . C36 C -0.2156(11) 0.1825(11) 0.4203(6) 0.069(4) Uiso 1 1 d . . . H36A H -0.2289 0.1243 0.3882 0.083 Uiso 1 1 calc R . . H36B H -0.1613 0.1483 0.4533 0.083 Uiso 1 1 calc R . . C37 C 0.1260(8) 0.3716(9) 0.4948(4) 0.033(3) Uiso 1 1 d . . . H37A H 0.1357 0.4536 0.4958 0.039 Uiso 1 1 calc R . . C38 C 0.3242(9) 0.0919(9) 0.1364(4) 0.043(3) Uiso 1 1 d . . . H38A H 0.3465 0.0166 0.1245 0.052 Uiso 1 1 calc R . . C39 C 0.4489(10) 0.1708(11) 0.0598(5) 0.068(4) Uiso 1 1 d . . . H39A H 0.4682 0.2463 0.0433 0.102 Uiso 1 1 calc R . . H39B H 0.4088 0.1217 0.0282 0.102 Uiso 1 1 calc R . . H39C H 0.5238 0.1331 0.0771 0.102 Uiso 1 1 calc R . . C40 C 0.1002(7) 0.1303(9) 0.4948(4) 0.030(3) Uiso 1 1 d . . . H40A H 0.0936 0.0481 0.4958 0.036 Uiso 1 1 calc R . . C42 C 0.1200(9) 0.3943(10) 0.3136(5) 0.028(3) Uiso 1 1 d . . . 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 S1 0.0229(18) 0.044(2) 0.027(2) 0.0004(14) 0.0060(14) 0.0007(14) O4 0.034(4) 0.037(5) 0.013(4) 0.001(3) 0.008(3) -0.003(3) O6 0.035(4) 0.040(5) 0.024(4) -0.005(3) 0.006(3) 0.003(4) O7 0.030(4) 0.034(4) 0.025(4) 0.007(3) 0.001(3) -0.010(4) O8 0.016(4) 0.059(5) 0.047(5) -0.007(4) -0.006(3) 0.011(3) N5 0.024(4) 0.038(6) 0.008(5) -0.006(4) 0.003(4) -0.010(4) N11 0.030(4) 0.025(5) 0.021(5) -0.012(4) 0.017(4) -0.005(4) N18 0.022(4) 0.022(5) 0.012(4) 0.005(4) 0.001(4) 0.003(4) N19 0.017(4) 0.039(5) 0.016(5) 0.005(4) -0.003(3) -0.003(4) N21 0.046(5) 0.026(5) 0.033(5) 0.009(4) 0.020(4) 0.016(4) N27 0.031(5) 0.026(5) 0.017(5) -0.011(4) -0.010(4) 0.003(4) Cl1 0.054(2) 0.075(2) 0.049(2) 0.0125(16) -0.0009(14) -0.0095(16) Cl2 0.058(2) 0.092(3) 0.085(3) 0.031(2) -0.0251(18) -0.0282(19) _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 S1 O8 1.403(6) . ? S1 O4 1.420(6) . ? S1 N11 1.617(7) . ? S1 N21 1.618(8) . ? O6 C42 1.229(11) . ? O7 C33 1.227(11) . ? N5 C42 1.352(11) . ? N5 C17 1.430(10) . ? N5 C26 1.439(11) . ? N11 C15 1.387(10) . ? N18 C33 1.355(11) . ? N18 C26 1.418(10) . ? N18 C16 1.430(10) . ? N19 C33 1.326(11) . ? N19 C22 1.435(11) . ? N21 C34 1.391(11) . ? N27 C42 1.329(11) . ? N27 C22 1.418(11) . ? Cl1 C35 1.785(12) . ? Cl2 C36 1.806(12) . ? C9 C32 1.313(12) . ? C9 C38 1.347(12) . ? C9 C39 1.521(13) . ? C10 C14 1.378(11) . ? C10 C13 1.386(12) . ? C12 C20 1.362(11) . ? C12 C32 1.391(12) . ? C13 C25 1.350(12) . ? C14 C28 1.357(11) . ? C14 C26 1.534(12) . ? C15 C40 1.347(11) . ? C15 C34 1.361(12) . ? C16 C24 1.507(12) . ? C17 C29 1.517(12) . ? C20 C31 1.350(11) . ? C20 C22 1.514(12) . ? C22 C26 1.584(12) . ? C23 C25 1.347(12) . ? C23 C28 1.382(12) . ? C24 C29 1.370(12) . ? C24 C40 1.390(11) . ? C25 C30 1.502(12) . ? C29 C37 1.376(12) . ? C31 C38 1.404(12) . ? C34 C37 1.368(12) . ? C35 C36 1.460(15) . ? 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 O8 S1 O4 116.0(4) . . ? O8 S1 N11 111.1(4) . . ? O4 S1 N11 110.9(4) . . ? O8 S1 N21 109.7(4) . . ? O4 S1 N21 113.5(4) . . ? N11 S1 N21 93.6(4) . . ? C42 N5 C17 124.6(8) . . ? C42 N5 C26 110.7(7) . . ? C17 N5 C26 122.1(7) . . ? C15 N11 S1 112.4(6) . . ? C33 N18 C26 111.2(7) . . ? C33 N18 C16 123.8(7) . . ? C26 N18 C16 121.8(7) . . ? C33 N19 C22 113.7(7) . . ? C34 N21 S1 111.7(6) . . ? C42 N27 C22 112.9(8) . . ? C32 C9 C38 119.4(9) . . ? C32 C9 C39 122.3(10) . . ? C38 C9 C39 118.3(9) . . ? C14 C10 C13 119.1(9) . . ? C20 C12 C32 119.7(9) . . ? C25 C13 C10 121.3(9) . . ? C28 C14 C10 119.4(8) . . ? C28 C14 C26 120.1(8) . . ? C10 C14 C26 119.8(8) . . ? C40 C15 C34 121.0(9) . . ? C40 C15 N11 128.3(9) . . ? C34 C15 N11 110.7(8) . . ? N18 C16 C24 114.6(7) . . ? N5 C17 C29 115.2(7) . . ? C31 C20 C12 118.3(8) . . ? C31 C20 C22 120.5(8) . . ? C12 C20 C22 120.7(8) . . ? N27 C22 N19 112.7(7) . . ? N27 C22 C20 112.9(7) . . ? N19 C22 C20 111.5(7) . . ? N27 C22 C26 102.1(7) . . ? N19 C22 C26 100.6(6) . . ? C20 C22 C26 116.2(7) . . ? C25 C23 C28 121.3(9) . . ? C29 C24 C40 120.1(8) . . ? C29 C24 C16 121.7(8) . . ? C40 C24 C16 118.2(8) . . ? C23 C25 C13 118.9(8) . . ? C23 C25 C30 120.8(9) . . ? C13 C25 C30 120.3(9) . . ? N18 C26 N5 112.9(7) . . ? N18 C26 C14 111.1(7) . . ? N5 C26 C14 111.6(7) . . ? N18 C26 C22 104.0(7) . . ? N5 C26 C22 102.8(6) . . ? C14 C26 C22 114.1(7) . . ? C14 C28 C23 119.9(8) . . ? C24 C29 C37 119.1(8) . . ? C24 C29 C17 119.9(8) . . ? C37 C29 C17 121.0(9) . . ? C20 C31 C38 120.7(9) . . ? C9 C32 C12 122.0(10) . . ? O7 C33 N19 125.1(9) . . ? O7 C33 N18 125.1(9) . . ? N19 C33 N18 109.6(9) . . ? C15 C34 C37 119.9(9) . . ? C15 C34 N21 111.3(8) . . ? C37 C34 N21 128.7(9) . . ? C36 C35 Cl1 106.9(8) . . ? C35 C36 Cl2 106.8(8) . . ? C34 C37 C29 120.3(9) . . ? C9 C38 C31 119.9(9) . . ? C15 C40 C24 119.5(9) . . ? O6 C42 N27 126.6(10) . . ? O6 C42 N5 123.0(10) . . ? N27 C42 N5 110.3(9) . . ? _diffrn_measured_fraction_theta_max 0.954 _diffrn_reflns_theta_full 42.53 _diffrn_measured_fraction_theta_full 0.954 _refine_diff_density_max 0.504 _refine_diff_density_min -0.587 _refine_diff_density_rms 0.110