# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Xuefang Shi' _publ_contact_author_email XUEFANGSHI@126.COM _publ_section_title ; Observation of a quasi-one dimensional tube-like water aggregate in a supramolecular organic host ; loop_ _publ_author_name 'Xuefang Shi' 'Lei He' 'Hai-Bin Song' 'Wenqin Zhang' # Attachment '10-31-Shis.cif' # Supplementary Material (ESI) for Chemical Communications # This journal is ?The Royal Society of Chemistry 2008 data_Shi _database_code_depnum_ccdc_archive 'CCDC 290854' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common bis(3-pyrazinylcarbonylaminopropyl)amine _chemical_melting_point ? _chemical_formula_moiety 'C16 H22 N7 O2, H7 O4, 4(H2 O)' _chemical_formula_sum 'C16 H37 N7 O10' _chemical_formula_weight 487.53 _chemical_absolute_configuration unk 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2 _symmetry_space_group_name_Hall 'P2 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, -z' _cell_length_a 11.016(2) _cell_length_b 25.860(5) _cell_length_c 4.5170(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1286.7(4) _cell_formula_units_Z 2 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 2936 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 27.9 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.258 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 524 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.970 _exptl_absorpt_correction_T_max 0.992 _exptl_absorpt_process_details crystalclear _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type 'Rigaku Saturn' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 9363 _diffrn_reflns_av_R_equivalents 0.0771 _diffrn_reflns_av_sigmaI/netI 0.0517 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 4 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 27.86 _reflns_number_total 1810 _reflns_number_gt 1480 _reflns_threshold_expression >2sigma(I) _computing_data_collection Crystalclear _computing_cell_refinement Crystalclear _computing_data_reduction Crystalclear _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^)+(0.0705P)^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 none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'None, Friedel Pairs merged' _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1810 _refine_ls_number_parameters 186 _refine_ls_number_restraints 11 _refine_ls_R_factor_all 0.0602 _refine_ls_R_factor_gt 0.0469 _refine_ls_wR_factor_ref 0.1168 _refine_ls_wR_factor_gt 0.1105 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.007 _refine_ls_shift/su_max 0.002 _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 O1 O 0.34020(17) 0.31481(8) 1.0022(4) 0.0315(5) Uani 1 1 d . . . N1 N 0.3897(2) 0.19824(8) 0.3855(5) 0.0274(5) Uani 1 1 d . . . N2 N 0.15992(19) 0.23883(8) 0.5139(5) 0.0256(5) Uani 1 1 d . . . N3 N 0.1380(2) 0.31961(8) 0.8959(4) 0.0216(5) Uani 1 1 d . . . H3 H 0.074(3) 0.3081(11) 0.786(7) 0.026 Uiso 1 1 d . . . N4 N 0.0000 0.5000 0.9334(7) 0.0248(7) Uani 1 2 d SD . . H4A H -0.069(2) 0.4908(12) 0.842(6) 0.030 Uiso 1 1 d D . . C1 C 0.2896(2) 0.18039(10) 0.2570(6) 0.0261(6) Uani 1 1 d . . . H1 H 0.2962 0.1532 0.1163 0.031 Uiso 1 1 calc R . . C2 C 0.1759(3) 0.20027(10) 0.3224(6) 0.0290(6) Uani 1 1 d . . . H2 H 0.1069 0.1859 0.2271 0.035 Uiso 1 1 calc R . . C3 C 0.2606(2) 0.25666(9) 0.6450(5) 0.0209(5) Uani 1 1 d . . . C4 C 0.3736(2) 0.23647(10) 0.5836(6) 0.0255(5) Uani 1 1 d . . . H4 H 0.4423 0.2500 0.6845 0.031 Uiso 1 1 calc R . . C5 C 0.2491(2) 0.30005(9) 0.8656(5) 0.0210(5) Uani 1 1 d . . . C6 C 0.1090(2) 0.36279(9) 1.0919(5) 0.0225(5) Uani 1 1 d . . . H6A H 0.1796 0.3702 1.2208 0.027 Uiso 1 1 calc R . . H6B H 0.0397 0.3532 1.2202 0.027 Uiso 1 1 calc R . . C7 C 0.0769(2) 0.41103(10) 0.9155(5) 0.0232(5) Uani 1 1 d . . . H7A H 0.1482 0.4217 0.7970 0.028 Uiso 1 1 calc R . . H7B H 0.0102 0.4028 0.7766 0.028 Uiso 1 1 calc R . . C8 C 0.0384(2) 0.45553(9) 1.1137(6) 0.0224(5) Uani 1 1 d . . . H8A H -0.0296 0.4444 1.2421 0.027 Uiso 1 1 calc R . . H8B H 0.1070 0.4658 1.2425 0.027 Uiso 1 1 calc R . . O2 O 0.22876(19) 0.53588(8) 0.7059(5) 0.0320(5) Uani 1 1 d D . . H2A H 0.279(3) 0.5104(11) 0.673(8) 0.048 Uiso 1 1 d D . . H2B H 0.247(3) 0.5527(12) 0.860(7) 0.048 Uiso 1 1 d D . . O3 O 0.2955(2) 0.59027(9) 0.2025(5) 0.0372(5) Uani 1 1 d D . . H3A H 0.371(2) 0.5930(14) 0.194(10) 0.056 Uiso 1 1 d D . . H3B H 0.266(3) 0.5768(15) 0.351(7) 0.056 Uiso 1 1 d D . . O4 O 0.4497(2) 0.40449(9) 0.1741(5) 0.0377(5) Uani 1 1 d D . . H4B H 0.408(3) 0.3758(11) 0.160(9) 0.057 Uiso 1 1 d D . . H4C H 0.437(8) 0.423(3) 0.020(12) 0.057 Uiso 0.50 1 d PD . . H4D H 0.425(7) 0.420(3) 0.328(12) 0.057 Uiso 0.50 1 d PD . . O5 O 0.4098(2) 0.46264(8) 0.6728(5) 0.0351(5) Uani 1 1 d D . . H5A H 0.412(8) 0.441(2) 0.530(12) 0.053 Uiso 0.50 1 d PD . . H5B H 0.425(7) 0.444(3) 0.826(12) 0.053 Uiso 0.50 1 d PD . . H5C H 0.468(5) 0.485(2) 0.663(16) 0.053 Uiso 0.50 1 d PD . . 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 0.0246(10) 0.0307(10) 0.0393(10) -0.0094(9) -0.0063(9) 0.0000(8) N1 0.0260(12) 0.0249(11) 0.0312(10) -0.0038(9) 0.0034(10) 0.0051(10) N2 0.0231(11) 0.0236(11) 0.0301(10) -0.0033(9) -0.0041(9) 0.0009(9) N3 0.0231(11) 0.0188(10) 0.0229(9) -0.0028(8) -0.0028(9) 0.0029(9) N4 0.0340(18) 0.0178(15) 0.0225(14) 0.000 0.000 0.0040(14) C1 0.0313(14) 0.0214(12) 0.0257(12) -0.0033(10) 0.0016(11) 0.0035(12) C2 0.0301(15) 0.0245(13) 0.0325(13) -0.0059(11) -0.0064(12) -0.0004(11) C3 0.0201(12) 0.0199(12) 0.0228(11) 0.0008(9) -0.0024(10) -0.0011(10) C4 0.0203(12) 0.0253(12) 0.0310(12) -0.0038(10) -0.0011(11) 0.0004(11) C5 0.0235(13) 0.0164(11) 0.0230(11) 0.0009(9) -0.0012(10) 0.0011(10) C6 0.0273(13) 0.0201(11) 0.0200(10) -0.0017(9) 0.0001(10) 0.0039(11) C7 0.0281(13) 0.0212(11) 0.0204(10) 0.0004(9) 0.0019(11) 0.0020(11) C8 0.0282(13) 0.0179(11) 0.0212(10) 0.0019(9) -0.0003(10) 0.0057(10) O2 0.0308(11) 0.0350(12) 0.0303(9) -0.0009(9) 0.0009(9) 0.0008(9) O3 0.0412(12) 0.0400(12) 0.0303(10) 0.0051(9) -0.0016(10) 0.0008(11) O4 0.0474(13) 0.0316(12) 0.0341(10) -0.0058(9) 0.0014(10) -0.0117(10) O5 0.0362(12) 0.0333(12) 0.0359(10) -0.0035(9) 0.0012(11) -0.0024(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. H atoms of O4, O5 are disordered due to symmetry in different places. H atom of O4 is disordered over different places, one of them (H4b) is of occupancy 1, two others are of occupancy 0.5 each. The O5 shows a disorder of H2O and OHC, while the H5A, H5B and H5C of O5 are of occupancy 0.5, respectively. ; 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 C5 1.238(3) . ? N1 C1 1.329(3) . ? N1 C4 1.345(3) . ? N2 C2 1.332(3) . ? N2 C3 1.340(3) . ? N3 C5 1.331(3) . ? N3 C6 1.460(3) . ? N3 H3 0.91(3) . ? N4 C8 1.471(3) 2_565 ? N4 C8 1.471(3) . ? N4 H4A 0.90(2) . ? C1 C2 1.386(4) . ? C1 H1 0.9500 . ? C2 H2 0.9500 . ? C3 C4 1.377(4) . ? C3 C5 1.506(3) . ? C4 H4 0.9500 . ? C6 C7 1.522(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.519(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? O2 H2A 0.87(2) . ? O2 H2B 0.84(2) . ? O3 H3A 0.83(2) . ? O3 H3B 0.82(3) . ? O4 H4B 0.88(2) . ? O4 H4C 0.85(3) . ? O4 H4D 0.85(3) . ? O5 H5A 0.85(3) . ? O5 H5B 0.85(3) . ? O5 H5C 0.85(3) . ? 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 C1 N1 C4 115.9(2) . . ? C2 N2 C3 115.8(2) . . ? C5 N3 C6 123.6(2) . . ? C5 N3 H3 122.0(17) . . ? C6 N3 H3 114.3(18) . . ? C8 N4 C8 112.8(3) 2_565 . ? C8 N4 H4A 102(2) 2_565 . ? C8 N4 H4A 106.9(19) . . ? N1 C1 C2 121.9(2) . . ? N1 C1 H1 119.1 . . ? C2 C1 H1 119.1 . . ? N2 C2 C1 122.4(2) . . ? N2 C2 H2 118.8 . . ? C1 C2 H2 118.8 . . ? N2 C3 C4 121.9(2) . . ? N2 C3 C5 118.6(2) . . ? C4 C3 C5 119.5(2) . . ? N1 C4 C3 122.1(2) . . ? N1 C4 H4 118.9 . . ? C3 C4 H4 118.9 . . ? O1 C5 N3 125.2(2) . . ? O1 C5 C3 119.4(2) . . ? N3 C5 C3 115.4(2) . . ? N3 C6 C7 111.10(19) . . ? N3 C6 H6A 109.4 . . ? C7 C6 H6A 109.4 . . ? N3 C6 H6B 109.4 . . ? C7 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? C8 C7 C6 112.17(19) . . ? C8 C7 H7A 109.2 . . ? C6 C7 H7A 109.2 . . ? C8 C7 H7B 109.2 . . ? C6 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? N4 C8 C7 110.3(2) . . ? N4 C8 H8A 109.6 . . ? C7 C8 H8A 109.6 . . ? N4 C8 H8B 109.6 . . ? C7 C8 H8B 109.6 . . ? H8A C8 H8B 108.1 . . ? H2A O2 H2B 113(3) . . ? H3A O3 H3B 118(4) . . ? H4B O4 H4C 109(6) . . ? H4B O4 H4D 107(6) . . ? H4C O4 H4D 111(7) . . ? H5A O5 H5B 104(7) . . ? H5A O5 H5C 112(7) . . ? H5B O5 H5C 105(7) . . ? 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 C4 N1 C1 C2 0.4(4) . . . . ? C3 N2 C2 C1 -1.3(4) . . . . ? N1 C1 C2 N2 1.0(4) . . . . ? C2 N2 C3 C4 0.4(4) . . . . ? C2 N2 C3 C5 -179.6(2) . . . . ? C1 N1 C4 C3 -1.3(4) . . . . ? N2 C3 C4 N1 1.0(4) . . . . ? C5 C3 C4 N1 -179.0(2) . . . . ? C6 N3 C5 O1 1.7(4) . . . . ? C6 N3 C5 C3 -178.1(2) . . . . ? N2 C3 C5 O1 175.6(2) . . . . ? C4 C3 C5 O1 -4.4(3) . . . . ? N2 C3 C5 N3 -4.5(3) . . . . ? C4 C3 C5 N3 175.5(2) . . . . ? C5 N3 C6 C7 110.5(3) . . . . ? N3 C6 C7 C8 176.2(2) . . . . ? C8 N4 C8 C7 -179.9(2) 2_565 . . . ? C6 C7 C8 N4 -175.97(19) . . . . ? 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 O5 H5C O5 0.85(3) 1.92(3) 2.772(4) 175(7) 2_665 O5 H5B O4 0.85(3) 1.90(3) 2.753(3) 176(8) 1_556 O5 H5A O4 0.85(3) 1.91(4) 2.744(3) 165(8) . O4 H4D O5 0.85(3) 1.91(4) 2.744(3) 166(8) . O4 H4C O5 0.85(3) 1.90(3) 2.753(3) 179(9) 1_554 O4 H4B O1 0.88(2) 1.88(3) 2.727(3) 161(4) 1_554 O3 H3B O2 0.82(3) 1.96(3) 2.773(3) 167(4) . O3 H3A O4 0.83(2) 1.98(3) 2.812(3) 177(4) 2_665 O2 H2B O3 0.84(2) 1.91(3) 2.748(3) 177(4) 1_556 O2 H2A O5 0.87(2) 1.90(2) 2.754(3) 166(3) . N4 H4A O2 0.90(2) 1.98(2) 2.875(2) 170(3) 2_565 N3 H3 N1 0.91(3) 2.18(3) 3.051(3) 160(2) 4_456 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.86 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.226 _refine_diff_density_min -0.236 _refine_diff_density_rms 0.050