Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Dr Nikolai Kuhnert' _publ_contact_author_address ; Chemistry The University of Surrey Chemistry SBMS C4 GUILDFORD Surrey GU2 7XH UNITED KINGDOM ; _publ_contact_author_email N.KUHNERT@SURREY.AC.UK _publ_section_title ; Tuning the Size of Macrocyclic Cavities Trianglimine Macrocycles for Applications in Nanomachines ; loop_ _publ_author_name 'Nikolai Kuhnert' 'Nicolai I. Burzlaff' 'Ana Lopez-Periago' 'Chirag Patel' data_nkbu03 _database_code_depnum_ccdc_archive 'CCDC 249596' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common "'4,4`-diformylphenyl ether'" _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H10 O3' _chemical_formula_weight 226.22 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' O O 0.0106 0.0060 '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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.543(6) _cell_length_b 7.122(3) _cell_length_c 12.956(6) _cell_angle_alpha 90.00 _cell_angle_beta 102.40(3) _cell_angle_gamma 90.00 _cell_volume 1130.4(9) _cell_formula_units_Z 4 _cell_measurement_temperature 188(2) _cell_measurement_reflns_used 28 _cell_measurement_theta_min 4.36 _cell_measurement_theta_max 12.51 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.329 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 188(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 2834 _diffrn_reflns_av_R_equivalents 0.0456 _diffrn_reflns_av_sigmaI/netI 0.0373 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 27.00 _reflns_number_total 2450 _reflns_number_gt 1760 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0668P)^2^+0.3822P] 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 0.045(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2450 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0744 _refine_ls_R_factor_gt 0.0495 _refine_ls_wR_factor_ref 0.1366 _refine_ls_wR_factor_gt 0.1211 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _refine_ls_shift/su_max 0.288 _refine_ls_shift/su_mean 0.002 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 O1 O -0.09858(15) 0.3285(2) -0.16808(13) 0.0583(5) Uani 1 1 d . . . C1 C -0.00908(19) 0.3105(3) -0.11185(17) 0.0409(5) Uani 1 1 d . . . O2 O 0.07834(12) 0.0776(2) 0.31466(10) 0.0429(4) Uani 1 1 d . . . C2 C 0.01251(15) 0.2537(2) 0.00042(15) 0.0308(4) Uani 1 1 d . . . O3 O 0.19675(13) 0.7508(2) 0.65041(11) 0.0450(4) Uani 1 1 d . . . C3 C 0.12059(16) 0.2381(3) 0.05748(16) 0.0369(5) Uani 1 1 d . . . H3 H 0.1787 0.2665 0.0236 0.044 Uiso 1 1 calc R . . C4 C 0.14407(16) 0.1820(3) 0.16207(17) 0.0397(5) Uani 1 1 d . . . H4 H 0.2175 0.1702 0.2000 0.048 Uiso 1 1 calc R . . C5 C 0.05792(16) 0.1432(3) 0.21048(14) 0.0332(4) Uani 1 1 d . . . C6 C -0.05000(16) 0.1590(3) 0.15580(15) 0.0345(4) Uani 1 1 d . . . H6 H -0.1079 0.1322 0.1903 0.041 Uiso 1 1 calc R . . C7 C -0.07245(15) 0.2139(3) 0.05098(15) 0.0340(4) Uani 1 1 d . . . H7 H -0.1460 0.2245 0.0133 0.041 Uiso 1 1 calc R . . C8 C 0.10185(15) 0.2088(3) 0.39517(14) 0.0303(4) Uani 1 1 d . . . C9 C 0.11941(15) 0.1382(3) 0.49808(14) 0.0323(4) Uani 1 1 d . . . H9 H 0.1157 0.0070 0.5100 0.039 Uiso 1 1 calc R . . C10 C 0.14235(14) 0.2620(3) 0.58256(14) 0.0317(4) Uani 1 1 d . . . H10 H 0.1533 0.2150 0.6527 0.038 Uiso 1 1 calc R . . C11 C 0.14962(13) 0.4560(3) 0.56583(13) 0.0276(4) Uani 1 1 d . . . C12 C 0.13064(13) 0.5228(3) 0.46190(14) 0.0272(4) Uani 1 1 d . . . H12 H 0.1343 0.6540 0.4498 0.033 Uiso 1 1 calc R . . C13 C 0.10660(14) 0.4016(3) 0.37622(14) 0.0294(4) Uani 1 1 d . . . H13 H 0.0936 0.4486 0.3060 0.035 Uiso 1 1 calc R . . C14 C 0.17749(16) 0.5838(3) 0.65650(15) 0.0352(4) Uani 1 1 d . . . H1 H 0.0477(11) 0.343(2) -0.1569(11) 0.000(3) Uiso 1 1 d . . . H14 H 0.1803(16) 0.527(3) 0.7303(16) 0.042(6) 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 O1 0.0710(11) 0.0486(10) 0.0448(9) 0.0072(8) -0.0112(8) -0.0014(9) C1 0.0546(13) 0.0284(10) 0.0376(11) -0.0016(8) 0.0050(10) 0.0028(9) O2 0.0649(10) 0.0284(7) 0.0294(7) -0.0020(6) -0.0030(6) -0.0040(7) C2 0.0352(10) 0.0249(9) 0.0305(9) -0.0050(8) 0.0028(7) 0.0036(7) O3 0.0589(10) 0.0347(8) 0.0376(8) -0.0056(6) 0.0018(7) -0.0039(7) C3 0.0314(10) 0.0399(11) 0.0394(11) -0.0020(9) 0.0074(8) 0.0057(8) C4 0.0294(9) 0.0417(11) 0.0431(11) -0.0040(9) -0.0033(8) 0.0047(8) C5 0.0436(10) 0.0253(9) 0.0277(9) -0.0056(7) 0.0011(8) 0.0004(8) C6 0.0360(10) 0.0328(10) 0.0345(10) -0.0052(8) 0.0074(8) -0.0032(8) C7 0.0298(9) 0.0297(10) 0.0387(11) -0.0046(8) -0.0011(8) 0.0010(8) C8 0.0297(9) 0.0298(10) 0.0281(9) -0.0043(7) -0.0011(7) -0.0020(7) C9 0.0340(9) 0.0260(9) 0.0349(10) 0.0047(8) 0.0031(8) -0.0013(7) C10 0.0302(9) 0.0362(10) 0.0272(9) 0.0057(8) 0.0027(7) 0.0006(8) C11 0.0213(8) 0.0322(10) 0.0283(9) -0.0018(7) 0.0035(7) 0.0002(7) C12 0.0232(8) 0.0253(9) 0.0319(9) 0.0012(7) 0.0029(6) -0.0008(7) C13 0.0306(9) 0.0307(9) 0.0251(9) 0.0031(7) 0.0016(7) -0.0014(8) C14 0.0379(10) 0.0383(11) 0.0277(10) -0.0010(8) 0.0035(8) 0.0013(8) _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 O1 C1 1.207(3) . ? C1 C2 1.478(3) . ? C1 H1 1.039(14) . ? O2 C8 1.384(2) . ? O2 C5 1.399(2) . ? C2 C7 1.395(3) . ? C2 C3 1.402(3) . ? O3 C14 1.220(3) . ? C3 C4 1.382(3) . ? C3 H3 0.9500 . ? C4 C5 1.389(3) . ? C4 H4 0.9500 . ? C5 C6 1.391(3) . ? C6 C7 1.383(3) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C9 1.397(3) . ? C8 C13 1.399(3) . ? C9 C10 1.387(3) . ? C9 H9 0.9500 . ? C10 C11 1.405(3) . ? C10 H10 0.9500 . ? C11 C12 1.399(2) . ? C11 C14 1.467(3) . ? C12 C13 1.388(3) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 H14 1.03(2) . ? 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 C1 C2 125.0(2) . . ? O1 C1 H1 107.3(8) . . ? C2 C1 H1 127.7(8) . . ? C8 O2 C5 117.86(15) . . ? C7 C2 C3 119.08(18) . . ? C7 C2 C1 121.40(18) . . ? C3 C2 C1 119.53(19) . . ? C4 C3 C2 121.21(19) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? C3 C4 C5 118.52(18) . . ? C3 C4 H4 120.7 . . ? C5 C4 H4 120.7 . . ? C4 C5 C6 121.36(18) . . ? C4 C5 O2 120.21(18) . . ? C6 C5 O2 118.35(18) . . ? C7 C6 C5 119.58(18) . . ? C7 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? C6 C7 C2 120.25(17) . . ? C6 C7 H7 119.9 . . ? C2 C7 H7 119.9 . . ? O2 C8 C9 116.16(17) . . ? O2 C8 C13 122.72(17) . . ? C9 C8 C13 121.12(17) . . ? C10 C9 C8 119.20(18) . . ? C10 C9 H9 120.4 . . ? C8 C9 H9 120.4 . . ? C9 C10 C11 120.87(17) . . ? C9 C10 H10 119.6 . . ? C11 C10 H10 119.6 . . ? C12 C11 C10 118.66(17) . . ? C12 C11 C14 121.43(17) . . ? C10 C11 C14 119.90(17) . . ? C13 C12 C11 121.40(17) . . ? C13 C12 H12 119.3 . . ? C11 C12 H12 119.3 . . ? C12 C13 C8 118.74(17) . . ? C12 C13 H13 120.6 . . ? C8 C13 H13 120.6 . . ? O3 C14 C11 124.70(18) . . ? O3 C14 H14 118.4(13) . . ? C11 C14 H14 116.9(13) . . ? 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 O1 C1 C2 C7 0.6(3) . . . . ? O1 C1 C2 C3 -179.9(2) . . . . ? C7 C2 C3 C4 0.8(3) . . . . ? C1 C2 C3 C4 -178.79(19) . . . . ? C2 C3 C4 C5 -0.8(3) . . . . ? C3 C4 C5 C6 0.3(3) . . . . ? C3 C4 C5 O2 177.00(18) . . . . ? C8 O2 C5 C4 83.3(2) . . . . ? C8 O2 C5 C6 -99.9(2) . . . . ? C4 C5 C6 C7 0.2(3) . . . . ? O2 C5 C6 C7 -176.59(16) . . . . ? C5 C6 C7 C2 -0.2(3) . . . . ? C3 C2 C7 C6 -0.3(3) . . . . ? C1 C2 C7 C6 179.26(18) . . . . ? C5 O2 C8 C9 178.65(16) . . . . ? C5 O2 C8 C13 -0.5(3) . . . . ? O2 C8 C9 C10 -179.40(16) . . . . ? C13 C8 C9 C10 -0.3(3) . . . . ? C8 C9 C10 C11 -0.9(3) . . . . ? C9 C10 C11 C12 1.5(3) . . . . ? C9 C10 C11 C14 -178.02(17) . . . . ? C10 C11 C12 C13 -0.9(2) . . . . ? C14 C11 C12 C13 178.60(16) . . . . ? C11 C12 C13 C8 -0.2(3) . . . . ? O2 C8 C13 C12 179.92(16) . . . . ? C9 C8 C13 C12 0.8(3) . . . . ? C12 C11 C14 O3 -7.5(3) . . . . ? C10 C11 C14 O3 172.05(19) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.254 _refine_diff_density_min -0.287 _refine_diff_density_rms 0.061