Supplementary Material (ESI) for Chemical Communications This journal is (C) The Royal Society of Chemistry 2001 data_lss286at _database_code_CSD 166911 _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Hughes, Andrew D.' 'Shimizu, Ken D.' 'Shimizu, Linda S.' 'Smith, Mark D.' _publ_contact_author_name 'Dr Linda S. Shimizu' _publ_contact_author_address ; Department of Chemistry and Biochemistry University of South Carolina Columbia South Carolina 29208 UNITED STATES OF AMERICA ; _publ_contact_author_email 'SHIMIZUL@MAIL.CHEM.SC.EDU' _publ_section_title ; Self-assembly of a bis-urea macrocycle into a columnar nanotube ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H20 N4 O2' _chemical_formula_weight 324.38 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 monoclinic _symmetry_space_group_name_H-M P21/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 12.808(3) _cell_length_b 4.6145(10) _cell_length_c 13.950(3) _cell_angle_alpha 90.00 _cell_angle_beta 103.193(4) _cell_angle_gamma 90.00 _cell_volume 802.7(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 929 _cell_measurement_theta_min 2.456 _cell_measurement_theta_max 23.198 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.342 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 0.090 _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 293(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 SMART APEX CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 4211 _diffrn_reflns_av_R_equivalents 0.0676 _diffrn_reflns_av_sigmaI/netI 0.0821 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 23.29 _reflns_number_total 1155 _reflns_number_gt 618 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART NT V5.619 (Bruker, 2000)' _computing_cell_refinement 'SAINT+ NT V6.02a (Bruker, 1998)' _computing_data_reduction 'SAINT+ NT V6.02a' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL V5.1 (Sheldrick, 1997)' _computing_publication_material 'SHELXTL V5.1' _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 [0.00000+1.00000exp(3.35(sin\q/\l)^2^)]/ [\s^2^(Fo^2^)+0.0000+0.0000*P+(0.0235P)^2^+0.0000sin\q/\l] where P = 0.33333Fo^2^ + 0.66667Fc^2^ ; _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_extinction_coef ? _refine_ls_number_reflns 1155 _refine_ls_number_parameters 117 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0833 _refine_ls_R_factor_gt 0.0386 _refine_ls_wR_factor_ref 0.0826 _refine_ls_wR_factor_gt 0.0695 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _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 C1 C -0.0936(2) 0.8006(5) 0.3471(2) 0.0414(7) Uani 1 1 d . . . C2 C 0.0756(2) 0.7505(6) 0.2946(2) 0.0549(8) Uani 1 1 d . . . H2A H 0.0543 0.9355 0.2632 0.066 Uiso 1 1 calc R . . H2B H 0.0911 0.6208 0.2449 0.066 Uiso 1 1 calc R . . C3 C 0.1764(2) 0.7934(5) 0.3729(2) 0.0436(7) Uani 1 1 d . . . C4 C 0.1769(2) 0.9674(5) 0.4541(2) 0.0440(7) Uani 1 1 d . . . H4 H 0.1133 1.0560 0.4596 0.053 Uiso 1 1 calc R . . C5 C 0.2675(2) 1.0142(5) 0.5266(2) 0.0434(7) Uani 1 1 d . . . C6 C 0.3621(2) 0.8824(6) 0.5162(2) 0.0605(9) Uani 1 1 d . . . H6 H 0.4251 0.9108 0.5638 0.073 Uiso 1 1 calc R . . C7 C 0.3627(3) 0.7108(7) 0.4359(3) 0.0689(10) Uani 1 1 d . . . H7 H 0.4264 0.6244 0.4297 0.083 Uiso 1 1 calc R . . C8 C 0.2708(2) 0.6649(6) 0.3648(2) 0.0565(9) Uani 1 1 d . . . H8 H 0.2723 0.5469 0.3111 0.068 Uiso 1 1 calc R . . C9 C 0.2708(2) 1.1970(6) 0.6164(2) 0.0552(8) Uani 1 1 d . . . H9A H 0.2921 1.0748 0.6742 0.066 Uiso 1 1 calc R . . H9B H 0.3260 1.3434 0.6199 0.066 Uiso 1 1 calc R . . N1 N -0.17160(18) 0.6592(5) 0.37926(18) 0.0462(7) Uani 1 1 d . . . N2 N -0.01372(17) 0.6334(5) 0.3302(2) 0.0510(7) Uani 1 1 d . . . H1N H -0.168(2) 0.465(6) 0.379(2) 0.068(10) Uiso 1 1 d . . . H2N H -0.0231(17) 0.441(6) 0.3319(17) 0.044(8) Uiso 1 1 d . . . O1 O -0.09664(14) 1.0659(4) 0.33466(14) 0.0535(6) Uani 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 C1 0.0473(17) 0.0355(15) 0.0380(17) -0.0036(14) 0.0028(15) -0.0073(15) C2 0.0548(19) 0.063(2) 0.0497(19) -0.0149(16) 0.0182(18) -0.0065(15) C3 0.0461(18) 0.0433(15) 0.0440(19) -0.0003(14) 0.0157(16) -0.0067(14) C4 0.0410(18) 0.0435(16) 0.0493(18) 0.0000(15) 0.0138(16) -0.0013(13) C5 0.0372(17) 0.0450(17) 0.0489(19) 0.0004(14) 0.0116(16) -0.0080(13) C6 0.0417(19) 0.074(2) 0.065(2) 0.0035(19) 0.0096(17) 0.0008(17) C7 0.050(2) 0.085(2) 0.076(3) -0.006(2) 0.024(2) 0.0171(18) C8 0.057(2) 0.0581(19) 0.060(2) -0.0058(16) 0.025(2) 0.0049(16) C9 0.0463(19) 0.0593(18) 0.058(2) -0.0059(17) 0.0086(17) -0.0113(15) N1 0.0495(16) 0.0355(14) 0.0558(17) -0.0043(12) 0.0169(13) -0.0061(12) N2 0.0458(15) 0.0323(14) 0.077(2) -0.0087(14) 0.0192(14) -0.0073(12) O1 0.0626(13) 0.0285(9) 0.0705(14) 0.0025(10) 0.0178(11) -0.0040(10) _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 O1 1.236(3) . ? C1 N2 1.344(3) . ? C1 N1 1.353(3) . ? C2 N2 1.451(3) . ? C2 C3 1.501(3) . ? C3 C8 1.375(4) . ? C3 C4 1.386(3) . ? C4 C5 1.371(3) . ? C5 C6 1.392(4) . ? C5 C9 1.503(4) . ? C6 C7 1.373(4) . ? C7 C8 1.372(4) . ? C9 N1 1.447(3) 3_576 ? N1 C9 1.447(3) 3_576 ? 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 N2 123.0(3) . . ? O1 C1 N1 121.5(3) . . ? N2 C1 N1 115.5(2) . . ? N2 C2 C3 114.5(2) . . ? C8 C3 C4 118.5(3) . . ? C8 C3 C2 120.6(3) . . ? C4 C3 C2 120.9(2) . . ? C5 C4 C3 122.7(2) . . ? C4 C5 C6 117.6(3) . . ? C4 C5 C9 124.2(2) . . ? C6 C5 C9 118.2(3) . . ? C7 C6 C5 120.3(3) . . ? C8 C7 C6 121.0(3) . . ? C7 C8 C3 120.0(3) . . ? N1 C9 C5 115.7(2) 3_576 . ? C1 N1 C9 121.0(2) . 3_576 ? C1 N2 C2 122.5(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O1 0.90(3) 2.21(3) 3.013(3) 149(2) 1_545 N2 H2N O1 0.90(2) 1.98(3) 2.832(3) 159(2) 1_545 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 23.29 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.123 _refine_diff_density_min -0.126 _refine_diff_density_rms 0.030 #END