Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Agnieszka Szumna' _publ_contact_author_address ; Institute of Organic Chemistry Polish Academy of Sciences Kasprzaka 44/52 Warsaw 01-224 POLAND ; _publ_contact_author_email SZUMNAA@ICHO.EDU.PL _publ_section_title ; Cyclochiral conformers of resorcin[4]arenes stabilized by hydrogen bonds ; _publ_author_name 'Agnieszka Szumna' data_217 _database_code_depnum_ccdc_archive 'CCDC 635229' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C94.69 H126.10 N8.65 O13.38' _chemical_formula_weight 1599.53 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' _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M I4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x, z' '-x, -y, z' 'y, -x, z' 'x+1/2, y+1/2, z+1/2' '-y+1/2, x+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' 'y+1/2, -x+1/2, z+1/2' _cell_length_a 23.3843(6) _cell_length_b 23.3843(6) _cell_length_c 8.2561(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4514.6(2) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.6080 _cell_measurement_theta_max 28.6174 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.177 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1724 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_T_min 0.92344 _exptl_absorpt_correction_T_max 1.04567 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ? _exptl_special_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.28cycle2 beta (release 25-10-2005 CrysAlis171 .NET) (compiled Oct 25 2005,08:50:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 8.6479 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21498 _diffrn_reflns_av_R_equivalents 0.0378 _diffrn_reflns_av_sigmaI/netI 0.1048 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.62 _diffrn_reflns_theta_max 28.72 _reflns_number_total 4767 _reflns_number_gt 1993 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (L. Barbour, 1999)' _computing_publication_material 'X-Seed (L. Barbour, 1999)' _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^)+(0.0786P)^2^+0.0000P] 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 0.0023(4) _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 1.2(16) _refine_ls_number_reflns 4767 _refine_ls_number_parameters 279 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1250 _refine_ls_R_factor_gt 0.0468 _refine_ls_wR_factor_ref 0.1313 _refine_ls_wR_factor_gt 0.1182 _refine_ls_goodness_of_fit_ref 0.776 _refine_ls_restrained_S_all 0.776 _refine_ls_shift/su_max 0.327 _refine_ls_shift/su_mean 0.006 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 0.54415(14) 0.35233(15) 0.6783(4) 0.0808(10) Uani 1 1 d . . . H1 H 0.5558 0.3127 0.7102 0.097 Uiso 1 1 calc R . . C2 C 0.48461(14) 0.36173(14) 0.7532(4) 0.0692(9) Uani 1 1 d . . . C3 C 0.46570(12) 0.33025(12) 0.8862(4) 0.0605(8) Uani 1 1 d . . . C4 C 0.41248(12) 0.33837(12) 0.9547(4) 0.0592(8) Uani 1 1 d . . . C5 C 0.37655(14) 0.37915(13) 0.8888(5) 0.0681(8) Uani 1 1 d . . . C6 C 0.39187(15) 0.41196(14) 0.7544(4) 0.0726(10) Uani 1 1 d . . . C7 C 0.44727(15) 0.40229(14) 0.6905(4) 0.0716(9) Uani 1 1 d . . . H7 H 0.4594 0.4245 0.6006 0.086 Uiso 1 1 calc R . . O8 O 0.50371(8) 0.29069(9) 0.9470(3) 0.0696(6) Uani 1 1 d D . . H8 H 0.4894(11) 0.2669(11) 1.019(3) 0.064(11) Uiso 1 1 d D . . O9 O 0.32333(9) 0.38557(9) 0.9583(3) 0.0822(7) Uani 1 1 d D . . H9 H 0.3094(13) 0.4195(9) 0.940(5) 0.109(14) Uiso 1 1 d D . . C10 C 0.39348(12) 0.30534(11) 1.1010(4) 0.0678(8) Uani 1 1 d . . . H10A H 0.4252 0.3044 1.1804 0.081 Uiso 1 1 calc R . . H10B H 0.3610 0.3257 1.1520 0.081 Uiso 1 1 calc R . . N11 N 0.37583(9) 0.24618(9) 1.0651(3) 0.0593(6) Uani 1 1 d . . . C12 C 0.41261(12) 0.20317(11) 1.1039(4) 0.0563(7) Uani 1 1 d . . . O13 O 0.46342(8) 0.21242(7) 1.1361(3) 0.0673(6) Uani 1 1 d . . . N14 N 0.39044(8) 0.14967(9) 1.1069(3) 0.0544(6) Uani 1 1 d . . . H14 H 0.3531 0.1463 1.1175 0.065 Uiso 1 1 calc R . . C15 C 0.42424(11) 0.09660(10) 1.0936(4) 0.0553(7) Uani 1 1 d . . . C16 C 0.38087(11) 0.04850(11) 1.0897(4) 0.0647(7) Uani 1 1 d . . . H16A H 0.3597 0.0477 1.1921 0.097 Uiso 1 1 calc R . . H16B H 0.4007 0.0120 1.0744 0.097 Uiso 1 1 calc R . . H16C H 0.3541 0.0547 0.9999 0.097 Uiso 1 1 calc R . . C17 C 0.45828(13) 0.09843(13) 0.9351(4) 0.0709(9) Uani 1 1 d . . . H17A H 0.4864 0.1295 0.9401 0.106 Uiso 1 1 calc R . . H17B H 0.4321 0.1051 0.8443 0.106 Uiso 1 1 calc R . . H17C H 0.4781 0.0619 0.9196 0.106 Uiso 1 1 calc R . . C18 C 0.46358(14) 0.08922(14) 1.2366(5) 0.0794(10) Uani 1 1 d . . . H18A H 0.4918 0.1202 1.2376 0.119 Uiso 1 1 calc R . . H18B H 0.4833 0.0524 1.2284 0.119 Uiso 1 1 calc R . . H18C H 0.4412 0.0903 1.3370 0.119 Uiso 1 1 calc R . . C19 C 0.32056(11) 0.23848(12) 0.9823(4) 0.0658(8) Uani 1 1 d . . . H19 H 0.3102 0.2771 0.9395 0.079 Uiso 1 1 calc R . . C20 C 0.27335(12) 0.22321(14) 1.1010(6) 0.0954(12) Uani 1 1 d . . . H20A H 0.2734 0.2506 1.1908 0.143 Uiso 1 1 calc R . . H20B H 0.2799 0.1846 1.1433 0.143 Uiso 1 1 calc R . . H20C H 0.2363 0.2246 1.0456 0.143 Uiso 1 1 calc R . . C21 C 0.32636(12) 0.20058(12) 0.8344(4) 0.0616(8) Uani 1 1 d . . . C22 C 0.29258(12) 0.15211(14) 0.8084(4) 0.0686(9) Uani 1 1 d . . . H22 H 0.2644 0.1422 0.8863 0.082 Uiso 1 1 calc R . . C23 C 0.29914(15) 0.11825(15) 0.6722(5) 0.0804(10) Uani 1 1 d . . . H23 H 0.2769 0.0846 0.6591 0.096 Uiso 1 1 calc R . . C24 C 0.33826(18) 0.13392(15) 0.5561(5) 0.0862(11) Uani 1 1 d . . . H24 H 0.3423 0.1114 0.4610 0.103 Uiso 1 1 calc R . . C25 C 0.37197(14) 0.18247(14) 0.5764(5) 0.0781(9) Uani 1 1 d . . . H25 H 0.3989 0.1931 0.4959 0.094 Uiso 1 1 calc R . . C26 C 0.36582(13) 0.21478(13) 0.7142(5) 0.0688(9) Uani 1 1 d . . . H26 H 0.3891 0.2477 0.7281 0.083 Uiso 1 1 calc R . . C27 C 0.5464(2) 0.3536(2) 0.4951(5) 0.1327(18) Uani 1 1 d . . . H27A H 0.5302 0.3901 0.4558 0.159 Uiso 1 1 calc R . . H27B H 0.5868 0.3516 0.4593 0.159 Uiso 1 1 calc R . . C28 C 0.5144(2) 0.3057(3) 0.4239(8) 0.189(3) Uani 1 1 d . . . H28A H 0.5162 0.3081 0.3055 0.283 Uiso 1 1 calc R . . H28B H 0.4744 0.3076 0.4590 0.283 Uiso 1 1 calc R . . H28C H 0.5312 0.2695 0.4598 0.283 Uiso 1 1 calc R . . C29 C 0.5000 0.5000 1.0184(13) 0.075(4) Uiso 0.655(6) 4 d SP A 1 H29A H 0.4830 0.4644 0.9789 0.113 Uiso 0.1638(15) 1 calc PR A 1 H29B H 0.5394 0.5031 0.9789 0.113 Uiso 0.1638(15) 1 calc PR A 1 H29C H 0.4777 0.5326 0.9789 0.113 Uiso 0.1638(15) 1 calc PR A 1 C30 C 0.5000 0.5000 1.1910(14) 0.066(3) Uiso 0.655(6) 4 d SP A 1 N31 N 0.5000 0.5000 1.3317(17) 0.127(4) Uiso 0.655(6) 4 d SP A 1 O32 O 0.4793(2) 0.5759(2) 1.1775(8) 0.069(2) Uiso 0.345(6) 1 d P A 2 C33 C 0.5232(4) 0.5388(4) 1.0691(15) 0.087(3) Uiso 0.345(6) 1 d P A 2 H33A H 0.5110 0.4987 1.0682 0.130 Uiso 0.345(6) 1 calc PR A 2 H33B H 0.5617 0.5415 1.1153 0.130 Uiso 0.345(6) 1 calc PR A 2 H33C H 0.5235 0.5536 0.9581 0.130 Uiso 0.345(6) 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 C1 0.084(2) 0.082(2) 0.076(2) -0.0370(19) 0.010(2) -0.0014(19) C2 0.076(2) 0.066(2) 0.066(2) -0.0350(19) -0.0071(19) -0.0032(18) C3 0.0575(19) 0.0542(18) 0.070(2) -0.0283(17) -0.0111(17) 0.0036(16) C4 0.0570(18) 0.0592(17) 0.061(2) -0.0151(16) -0.0055(16) 0.0102(14) C5 0.066(2) 0.069(2) 0.069(2) -0.0144(18) -0.0113(18) 0.0019(17) C6 0.076(2) 0.078(2) 0.064(2) -0.028(2) -0.0308(19) 0.0051(18) C7 0.090(2) 0.074(2) 0.0505(19) -0.0225(17) -0.0135(18) -0.0098(19) O8 0.0624(13) 0.0575(13) 0.0890(18) -0.0165(13) 0.0026(13) 0.0061(11) O9 0.0638(14) 0.0692(15) 0.114(2) 0.0001(14) 0.0007(14) 0.0180(11) C10 0.0646(17) 0.0630(18) 0.076(2) -0.0175(19) -0.0048(19) 0.0164(14) N11 0.0514(13) 0.0505(14) 0.0761(18) -0.0125(12) -0.0059(13) 0.0157(11) C12 0.0522(16) 0.0574(17) 0.0592(18) -0.0142(16) 0.0050(17) 0.0086(14) O13 0.0527(12) 0.0636(12) 0.0856(16) -0.0127(11) -0.0141(11) 0.0065(9) N14 0.0451(12) 0.0612(14) 0.0571(15) -0.0016(13) 0.0019(12) 0.0077(10) C15 0.0515(15) 0.0536(15) 0.0609(18) 0.0023(15) -0.0037(16) 0.0047(13) C16 0.0639(17) 0.0672(17) 0.0630(18) 0.0080(17) 0.0024(17) -0.0026(14) C17 0.0653(19) 0.0615(19) 0.086(3) -0.0048(17) 0.0209(19) 0.0102(15) C18 0.069(2) 0.068(2) 0.101(3) 0.0142(19) -0.024(2) -0.0034(16) C19 0.0412(16) 0.0647(18) 0.092(2) -0.0058(18) -0.0080(17) 0.0172(14) C20 0.0575(18) 0.097(2) 0.132(3) -0.030(3) 0.022(2) 0.0203(17) C21 0.0499(17) 0.0589(19) 0.076(2) -0.0027(17) -0.0136(17) 0.0209(15) C22 0.0558(19) 0.070(2) 0.080(2) 0.0031(19) -0.0199(17) 0.0086(16) C23 0.087(2) 0.072(2) 0.082(3) -0.006(2) -0.032(2) -0.0007(18) C24 0.114(3) 0.082(3) 0.063(2) -0.011(2) -0.026(2) 0.013(2) C25 0.087(2) 0.080(2) 0.068(2) -0.009(2) -0.014(2) 0.0076(19) C26 0.0600(19) 0.0645(19) 0.082(3) -0.0012(19) -0.0198(19) 0.0108(15) C27 0.158(4) 0.154(4) 0.086(3) -0.081(3) 0.011(3) -0.022(3) C28 0.125(4) 0.266(7) 0.175(6) -0.130(6) -0.042(4) 0.038(4) _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 C27 1.514(6) . ? C1 C6 1.518(4) 2_655 ? C1 C2 1.539(5) . ? C2 C7 1.389(4) . ? C2 C3 1.394(4) . ? C3 O8 1.378(3) . ? C3 C4 1.380(4) . ? C4 C5 1.383(4) . ? C4 C10 1.501(5) . ? C5 O9 1.379(4) . ? C5 C6 1.396(5) . ? C6 C7 1.417(5) . ? C6 C1 1.518(4) 4_565 ? C10 N11 1.474(3) . ? N11 C12 1.362(3) . ? N11 C19 1.473(3) . ? C12 O13 1.237(3) . ? C12 N14 1.354(3) . ? N14 C15 1.476(3) . ? C15 C18 1.507(4) . ? C15 C16 1.515(3) . ? C15 C17 1.532(4) . ? C19 C21 1.515(4) . ? C19 C20 1.519(5) . ? C21 C26 1.395(4) . ? C21 C22 1.398(4) . ? C22 C23 1.384(5) . ? C23 C24 1.375(5) . ? C24 C25 1.392(5) . ? C25 C26 1.373(5) . ? C27 C28 1.469(6) . ? C29 C30 1.425(15) . ? C30 N31 1.161(15) . ? O32 C33 1.581(12) 2_655 ? O32 C33 1.615(12) . ? 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 C27 C1 C6 112.2(3) . 2_655 ? C27 C1 C2 115.5(4) . . ? C6 C1 C2 111.0(2) 2_655 . ? C7 C2 C3 117.1(3) . . ? C7 C2 C1 121.1(3) . . ? C3 C2 C1 121.9(3) . . ? O8 C3 C4 121.7(3) . . ? O8 C3 C2 115.9(3) . . ? C4 C3 C2 122.4(3) . . ? C3 C4 C5 118.8(3) . . ? C3 C4 C10 121.7(3) . . ? C5 C4 C10 119.4(3) . . ? O9 C5 C4 117.4(3) . . ? O9 C5 C6 120.2(3) . . ? C4 C5 C6 122.4(3) . . ? C5 C6 C7 116.3(3) . . ? C5 C6 C1 123.0(3) . 4_565 ? C7 C6 C1 120.7(4) . 4_565 ? C2 C7 C6 123.0(3) . . ? N11 C10 C4 113.8(3) . . ? C12 N11 C10 118.0(2) . . ? C12 N11 C19 125.0(2) . . ? C10 N11 C19 117.0(2) . . ? O13 C12 N14 121.7(2) . . ? O13 C12 N11 121.9(2) . . ? N14 C12 N11 116.4(2) . . ? C12 N14 C15 124.8(2) . . ? N14 C15 C18 111.4(2) . . ? N14 C15 C16 105.5(2) . . ? C18 C15 C16 109.9(2) . . ? N14 C15 C17 108.5(2) . . ? C18 C15 C17 110.8(2) . . ? C16 C15 C17 110.5(3) . . ? N11 C19 C21 111.5(2) . . ? N11 C19 C20 111.5(3) . . ? C21 C19 C20 116.6(3) . . ? C26 C21 C22 117.2(3) . . ? C26 C21 C19 119.6(3) . . ? C22 C21 C19 123.2(3) . . ? C23 C22 C21 121.7(3) . . ? C24 C23 C22 119.2(3) . . ? C23 C24 C25 120.6(4) . . ? C26 C25 C24 119.3(4) . . ? C25 C26 C21 121.8(3) . . ? C28 C27 C1 111.5(5) . . ? N31 C30 C29 180.000(12) . . ? C33 O32 C33 55.8(7) 2_655 . ? _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 28.72 _diffrn_measured_fraction_theta_full 0.962 _refine_diff_density_max 0.443 _refine_diff_density_min -0.251 _refine_diff_density_rms 0.036