# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Fenniri, Hicham' _publ_contact_author_email hicham.fenniri@ualberta.ca _publ_section_title ; Rosette Nanotubes with 1.4 nm Inner Diameter from a Tricyclic Variant of the Lehn\^aMascal G\^a C Base ; loop_ _publ_author_name G.Borzsonyi R.Johnson J.-Y.Cho T.Yamazaki R.Beingessner ; Kovalenko ; H.Fenniri # Attachment '- Mono-allylamine-dichloro.cif' data_11241A _database_code_depnum_ccdc_archive 'CCDC 639261' #TrackingRef '- Mono-allylamine-dichloro.cif' # 5. CRYSTAL DATA _chemical_compound_source ? _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _chemical_name_systematic ; ? ; _exptl_crystal_density_method ? _chemical_formula_sum 'C11 H7 Cl2 N5' _chemical_formula_structural ? _chemical_formula_weight 280.12 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'p 1 21/c 1' 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 11.8814(5) _cell_length_b 7.4778(4) _cell_length_c 13.3827(6) _cell_angle_alpha 90.00 _cell_angle_beta 104.075(3) _cell_angle_gamma 90.00 _cell_volume 1153.31(18) _cell_measurement_reflns_used 6787 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_formula_units_z 4 _exptl_crystal_density_diffrn 1.61 _exptl_crystal_density_meas ? _diffrn_radiation_type MO-K\a _diffrn_radiation_wavelength 0.71073 _exptl_absorpt_coefficient_mu 0.549 _cell_measurement_temperature 150 _exptl_crystal_F_000 568 # 6. DATA COLLECTION _diffrn_ambient_temperature 150 _diffrn_measurement_device_type Nonius_KappaCCD _exptl_absorpt_correction_type refined_empirical_(Otwinowski_&_Minor,_1996 _exptl_absorpt_correction_T_min 0.7217 _exptl_absorpt_correction_T_max 0.9209 _diffrn_reflns_number 6787 _diffrn_measured_fraction_theta_max 0.9790 _diffrn_reflns_theta_full 26.4 _reflns_number_total 2592 _reflns_number_gt 2104 _reflns_threshold_expression >2.0\s(I) _diffrn_reflns_av_R_equivalents 0.049 _diffrn_reflns_theta_min 5.00 _diffrn_reflns_theta_max 27.47 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_max 17 # 7. REFINEMENT DATA _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating R_factor_obs 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_R_factor_gt 0.042 _refine_ls_wR_factor_ref 0.088 _refine_ls_hydrogen_treatment ; Chemically significant hydrogens refined isotropically Others riding ; _refine_ls_number_reflns 2584 _refine_ls_number_parameters 168 _refine_ls_number_restraints 0 _refine_ls_goodness_of_fit_ref 0.998 _refine_ls_weighting_scheme 'calc ' _refine_ls_weighting_details '1/[\s^2^(Fo^2^)+(0.0281P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3 ' _refine_ls_shift/su_max 0.001 _refine_diff_density_max 0.31 _refine_diff_density_min -0.47 _refine_ls_extinction_method SHELXL97_(Sheldrick_1997) _refine_ls_extinction_coef 0.90E-02 _atom_type_scat_source 'International Tables for Crystallography (Vol C)' # 8. COMPUTING DATA _computing_data_collection Collect_(Nonius,_1998) _computing_cell_refinement DENZO/SCALEPACK_(Otwinowski,_1996) _computing_data_reduction DENZO/SCALEPACK_(Otwinowski,_1996) _computing_structure_solution Direct_methods_(SIR97,_Altomare_et_al.,_1997) _computing_structure_refinement SHELX97_(Sheldrick,_1997) _computing_molecular_graphics ; ORTEP (Johnson, 1976) PLUTON (Spek, 1991) ; _computing_publication_material CIF_VAX_MolEN_(Fair,_1990) # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag Cl(6) 0.63917(5) 0.54719(8) 1.08217(4) 0.02586(18) Uani ? Cl(8) 0.92966(5) -0.32397(7) 1.04927(4) 0.02317(16) Uani ? N(1) 0.97936(19) -0.3432(3) 0.79647(15) 0.0327(7) Uani ? N(5) 0.68078(16) 0.4513(2) 0.90859(12) 0.0197(5) Uani ? N(6) 0.74025(15) 0.2542(2) 1.05393(12) 0.0191(5) Uani ? N(7) 0.82912(15) -0.0151(2) 1.04068(12) 0.0188(5) Uani ? N(8) 0.71484(16) 0.3891(3) 0.75095(13) 0.0199(5) Uani ? C(1) 0.9344(2) -0.2357(3) 0.83349(16) 0.0231(7) Uani ? C(2) 0.87815(19) -0.1038(3) 0.88291(16) 0.0189(6) Uani ? C(3) 0.83039(18) 0.0508(3) 0.83480(15) 0.0184(6) Uani ? C(4) 0.77998(17) 0.1744(3) 0.88877(15) 0.0163(6) Uani ? C(5) 0.72464(18) 0.3412(3) 0.84813(16) 0.0177(6) Uani ? C(6) 0.69388(18) 0.3982(3) 1.00589(16) 0.0191(6) Uani ? C(7) 0.78302(18) 0.1381(3) 0.99325(15) 0.0172(6) Uani ? C(8) 0.87339(18) -0.1297(3) 0.98726(15) 0.0181(6) Uani ? C(9) 0.6574(2) 0.5529(3) 0.70630(16) 0.0223(6) Uani ? C(10) 0.5326(2) 0.5256(3) 0.65114(17) 0.0276(7) Uani ? C(11) 0.4757(2) 0.3734(4) 0.64102(19) 0.0327(8) Uani ? H(3) 0.8317 0.0727 0.7667 0.0220 Uiso calc H(8) 0.735(2) 0.315(3) 0.7091(18) 0.030(7) Uiso ? H(10) 0.4916 0.6260 0.6213 0.0330 Uiso calc H(9A) 0.6987 0.6015 0.6583 0.0270 Uiso calc H(9B) 0.6615 0.6401 0.7607 0.0270 Uiso calc H(11A) 0.5131 0.2694 0.6696 0.0390 Uiso calc H(11B) 0.3981 0.3696 0.6053 0.0390 Uiso calc loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cl(6) 0.0330(4) 0.0231(3) 0.0226(3) 0.0059(2) 0.0089(2) -0.0051(2) Cl(8) 0.0247(3) 0.0205(3) 0.0237(3) 0.0046(2) 0.0047(2) 0.0021(2) N(1) 0.0413(14) 0.0322(13) 0.0275(10) 0.0131(10) 0.0140(10) 0.0020(9) N(5) 0.0231(10) 0.0188(10) 0.0173(9) -0.0002(8) 0.0052(7) -0.0003(7) N(6) 0.0208(10) 0.0194(10) 0.0183(9) 0.0011(8) 0.0071(8) -0.0016(8) N(7) 0.0190(10) 0.0187(10) 0.0187(8) 0.0004(7) 0.0044(8) 0.0013(7) N(8) 0.0270(11) 0.0176(10) 0.0171(9) 0.0028(8) 0.0094(8) 0.0008(8) C(1) 0.0261(13) 0.0243(13) 0.0193(11) 0.0031(10) 0.0065(9) 0.0020(10) C(2) 0.0159(11) 0.0206(12) 0.0207(10) 0.0008(9) 0.0052(8) -0.0041(9) C(3) 0.0170(11) 0.0233(13) 0.0151(9) -0.0030(9) 0.0045(8) -0.0017(9) C(4) 0.0122(10) 0.0198(12) 0.0165(10) -0.0021(8) 0.0027(8) -0.0020(8) C(5) 0.0169(11) 0.0185(12) 0.0180(10) -0.0025(9) 0.0049(9) -0.0015(9) C(6) 0.0182(11) 0.0199(12) 0.0191(10) 0.0001(9) 0.0043(9) -0.0041(9) C(7) 0.0150(11) 0.0181(12) 0.0185(10) -0.0011(8) 0.0043(9) -0.0012(9) C(8) 0.0156(11) 0.0199(12) 0.0179(10) 0.0002(9) 0.0022(9) -0.0008(9) C(9) 0.0316(13) 0.0167(12) 0.0207(10) 0.0016(10) 0.0105(9) 0.0036(9) C(10) 0.0290(14) 0.0257(14) 0.0278(12) 0.0078(10) 0.0062(10) 0.0072(10) C(11) 0.0278(14) 0.0307(15) 0.0389(14) 0.0023(11) 0.0066(11) 0.0033(12) # 10. MOLECULAR GEOMETRY _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_publ_flag Cl(6) C(6) 1.740(2) YES Cl(8) C(8) 1.725(2) YES N(1) C(1) 1.142(3) YES N(5) C(6) 1.334(3) YES N(5) C(5) 1.345(3) YES N(6) C(6) 1.305(3) YES N(6) C(7) 1.369(3) YES N(7) C(8) 1.305(3) YES N(7) C(7) 1.359(3) YES N(8) H(8) 0.86(3) YES N(8) C(5) 1.326(3) YES N(8) C(9) 1.458(3) YES C(1) C(2) 1.440(3) YES C(2) C(3) 1.377(3) YES C(2) C(8) 1.424(3) YES C(3) C(4) 1.395(3) YES C(4) C(7) 1.416(3) YES C(4) C(5) 1.453(3) YES C(9) C(10) 1.501(3) YES C(10) C(11) 1.314(3) YES loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C(6) N(5) C(5) 115.80(18) YES C(6) N(6) C(7) 113.86(17) YES C(8) N(7) C(7) 117.87(18) YES H(8) N(8) C(5) 119.6(16) YES H(8) N(8) C(9) 116.6(16) YES C(5) N(8) C(9) 123.30(19) YES N(1) C(1) C(2) 178.2(2) YES C(3) C(2) C(8) 117.55(19) YES C(3) C(2) C(1) 123.04(19) YES C(8) C(2) C(1) 119.4(2) YES C(2) C(3) C(4) 119.63(19) YES C(3) C(4) C(7) 118.22(19) YES C(3) C(4) C(5) 125.98(19) YES C(7) C(4) C(5) 115.79(19) YES N(8) C(5) N(5) 118.1(2) YES N(8) C(5) C(4) 121.50(19) YES N(5) C(5) C(4) 120.43(18) YES N(6) C(6) N(5) 131.4(2) YES N(6) C(6) Cl(6) 114.35(15) YES N(5) C(6) Cl(6) 114.25(16) YES N(7) C(7) N(6) 115.06(17) YES N(7) C(7) C(4) 122.26(19) YES N(6) C(7) C(4) 122.68(19) YES N(7) C(8) C(2) 124.41(19) YES N(7) C(8) Cl(8) 116.72(16) YES C(2) C(8) Cl(8) 118.87(16) YES N(8) C(9) C(10) 113.33(19) YES C(11) C(10) C(9) 126.1(2) YES