# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2007 data_global _journal_name_full 'New J.Chem.(Nouv.J.Chim.)' _journal_coden_Cambridge 0440 _publ_contact_author_name 'Marina Fonari' _publ_contact_author_address ; Institute of Applied Physics Academy of Sciences of Moldova Academy str., 5 Chisinau MD2028 MOLDOVA ; _publ_contact_author_email FONARI.XRAY@PHYS.ASM.MD _publ_section_title ; Supramolecular associates of p-aminobenzoic acid with N- and N,O-heterocyclic molecules ; loop_ _publ_author_name M.Fonari S.S.Basok E.V.Ganin V.Kravtsov B.S.Luisi B.Moulton # Attachment 'B618207K_msad.cif' data_msad _database_code_depnum_ccdc_archive 'CCDC 626905' _audit_creation_method SHELXL-97 _chemical_name_systematic ; piperazinediium bis(4-aminobenzoate) dihydrate ; _chemical_name_common 'piperazinediium bis(4-aminobenzoate) dihydrate' _chemical_melting_point '189-190 \oC' _chemical_formula_moiety 'C4 H12 N2, 2(C7 H6 N O2), 2(H2 O)' _chemical_formula_sum 'C18 H28 N4 O6' _chemical_formula_weight 396.44 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 'P2(1)/c ' 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 6.5739(13) _cell_length_b 11.597(2) _cell_length_c 12.604(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.13(3) _cell_angle_gamma 90.00 _cell_volume 960.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 2883 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 27.91 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_min 0.22 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_max 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.370 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.737459 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS - Area Detector Absorption Correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 90(2) _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7319 _diffrn_reflns_av_R_equivalents 0.0287 _diffrn_reflns_av_sigmaI/netI 0.0243 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 25.99 _reflns_number_total 1891 _reflns_number_gt 1685 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0715P)^2^+0.2156P] 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_number_reflns 1891 _refine_ls_number_parameters 151 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0420 _refine_ls_R_factor_gt 0.0373 _refine_ls_wR_factor_ref 0.1073 _refine_ls_wR_factor_gt 0.1039 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _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 O1 O 0.89746(14) 0.38265(8) 0.18777(7) 0.0193(2) Uani 1 1 d . . . O2 O 1.16687(14) 0.49908(8) 0.18044(7) 0.0211(3) Uani 1 1 d . . . N1 N 1.2260(2) 0.33186(11) 0.66211(9) 0.0226(3) Uani 1 1 d . . . H1N1 H 1.131(3) 0.2934(16) 0.6987(14) 0.032(5) Uiso 1 1 d . . . H2N1 H 1.354(3) 0.3229(16) 0.6832(15) 0.034(5) Uiso 1 1 d . . . C1 C 1.05215(19) 0.42985(11) 0.22941(10) 0.0158(3) Uani 1 1 d . . . C2 C 1.10103(19) 0.40050(11) 0.34192(10) 0.0158(3) Uani 1 1 d . . . C3 C 1.29829(19) 0.41070(11) 0.38215(10) 0.0167(3) Uani 1 1 d . . . H3 H 1.4025 0.4351 0.3377 0.020 Uiso 1 1 calc R . . C4 C 1.3413(2) 0.38514(11) 0.48721(10) 0.0172(3) Uani 1 1 d . . . H4 H 1.4743 0.3908 0.5120 0.021 Uiso 1 1 calc R . . C5 C 1.1862(2) 0.35081(11) 0.55627(10) 0.0165(3) Uani 1 1 d . . . C6 C 0.9876(2) 0.34071(11) 0.51581(10) 0.0173(3) Uani 1 1 d . . . H6 H 0.8825 0.3179 0.5604 0.021 Uiso 1 1 calc R . . C7 C 0.9470(2) 0.36427(11) 0.41054(10) 0.0165(3) Uani 1 1 d . . . H7 H 0.8151 0.3559 0.3849 0.020 Uiso 1 1 calc R . . N2 N 0.70874(17) 0.46818(10) 0.02109(9) 0.0164(3) Uani 1 1 d . . . H1N2 H 0.773(3) 0.4827(14) -0.0425(15) 0.028(4) Uiso 1 1 d . . . H2N2 H 0.803(3) 0.4375(16) 0.0710(14) 0.034(5) Uiso 1 1 d . . . C8 C 0.6214(2) 0.57626(11) 0.06540(10) 0.0183(3) Uani 1 1 d . . . H8A H 0.7274 0.6341 0.0712 0.022 Uiso 1 1 calc R . . H8B H 0.5689 0.5615 0.1360 0.022 Uiso 1 1 calc R . . C9 C 0.54818(19) 0.37874(11) 0.00474(11) 0.0185(3) Uani 1 1 d . . . H9A H 0.4927 0.3561 0.0729 0.022 Uiso 1 1 calc R . . H9B H 0.6082 0.3110 -0.0277 0.022 Uiso 1 1 calc R . . O1W O 0.64499(15) 0.19552(10) 0.23772(8) 0.0234(3) Uani 1 1 d . . . H1W1 H 0.729(3) 0.2529(17) 0.2321(14) 0.031(5) Uiso 1 1 d . . . H2W1 H 0.717(3) 0.1340(19) 0.2556(16) 0.042(5) 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 0.0220(5) 0.0200(5) 0.0158(5) 0.0016(4) -0.0043(4) -0.0019(4) O2 0.0264(5) 0.0228(5) 0.0141(5) 0.0021(4) 0.0025(4) -0.0048(4) N1 0.0225(7) 0.0286(7) 0.0166(6) 0.0041(5) -0.0039(5) -0.0032(5) C1 0.0176(6) 0.0152(6) 0.0146(6) -0.0018(5) 0.0006(5) 0.0025(5) C2 0.0184(7) 0.0143(6) 0.0147(6) -0.0009(5) 0.0001(5) 0.0012(5) C3 0.0176(7) 0.0156(6) 0.0170(6) -0.0004(5) 0.0021(5) -0.0007(5) C4 0.0166(6) 0.0147(6) 0.0204(7) -0.0002(5) -0.0033(5) 0.0000(5) C5 0.0223(7) 0.0130(6) 0.0143(6) -0.0006(5) -0.0024(5) 0.0013(5) C6 0.0178(6) 0.0187(7) 0.0153(6) 0.0010(5) 0.0021(5) -0.0026(5) C7 0.0161(6) 0.0172(6) 0.0162(6) -0.0016(5) -0.0019(5) -0.0006(5) N2 0.0156(6) 0.0199(6) 0.0137(5) 0.0020(4) 0.0005(4) 0.0007(4) C8 0.0192(7) 0.0195(7) 0.0162(6) -0.0018(5) -0.0015(5) -0.0011(5) C9 0.0193(7) 0.0162(7) 0.0200(7) 0.0014(5) -0.0009(5) -0.0005(5) O1W 0.0203(5) 0.0218(6) 0.0282(6) 0.0030(4) -0.0022(4) -0.0016(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 O1 C1 1.2676(16) . ? O2 C1 1.2635(16) . ? N1 C5 1.3766(17) . ? N1 H1N1 0.90(2) . ? N1 H2N1 0.89(2) . ? C1 C2 1.4927(18) . ? C2 C3 1.3965(18) . ? C2 C7 1.3976(19) . ? C3 C4 1.3855(19) . ? C3 H3 0.9300 . ? C4 C5 1.3999(19) . ? C4 H4 0.9300 . ? C5 C6 1.4055(19) . ? C6 C7 1.3802(18) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? N2 C8 1.4879(17) . ? N2 C9 1.4938(17) . ? N2 H1N2 0.921(18) . ? N2 H2N2 0.952(19) . ? C8 C9 1.5141(18) 3_665 ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C8 1.5141(18) 3_665 ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? O1W H1W1 0.87(2) . ? O1W H2W1 0.88(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 C5 N1 H1N1 116.5(12) . . ? C5 N1 H2N1 119.1(12) . . ? H1N1 N1 H2N1 116.8(17) . . ? O2 C1 O1 123.46(12) . . ? O2 C1 C2 118.79(12) . . ? O1 C1 C2 117.75(12) . . ? C3 C2 C7 118.30(12) . . ? C3 C2 C1 121.57(12) . . ? C7 C2 C1 120.11(12) . . ? C4 C3 C2 121.10(12) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C4 C5 120.51(12) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? N1 C5 C4 120.72(13) . . ? N1 C5 C6 120.85(12) . . ? C4 C5 C6 118.38(12) . . ? C7 C6 C5 120.66(12) . . ? C7 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C6 C7 C2 121.03(12) . . ? C6 C7 H7 119.5 . . ? C2 C7 H7 119.5 . . ? C8 N2 C9 111.32(10) . . ? C8 N2 H1N2 110.5(10) . . ? C9 N2 H1N2 109.3(11) . . ? C8 N2 H2N2 108.6(11) . . ? C9 N2 H2N2 107.0(11) . . ? H1N2 N2 H2N2 110.2(14) . . ? N2 C8 C9 110.82(11) . 3_665 ? N2 C8 H8A 109.5 . . ? C9 C8 H8A 109.5 3_665 . ? N2 C8 H8B 109.5 . . ? C9 C8 H8B 109.5 3_665 . ? H8A C8 H8B 108.1 . . ? N2 C9 C8 111.12(11) . 3_665 ? N2 C9 H9A 109.4 . . ? C8 C9 H9A 109.4 3_665 . ? N2 C9 H9B 109.4 . . ? C8 C9 H9B 109.4 3_665 . ? H9A C9 H9B 108.0 . . ? H1W1 O1W H2W1 107.4(17) . . ? 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 H1N1 O1 0.90(2) 2.557(19) 3.3108(17) 142.1(15) 4_566 N1 H2N1 O1W 0.89(2) 2.04(2) 2.9297(18) 177.6(17) 4_666 N2 H1N2 O2 0.921(18) 1.797(18) 2.6972(16) 164.9(16) 3_765 N2 H2N2 O1 0.952(19) 1.718(19) 2.6316(16) 159.7(16) . O1W H1W1 O1 0.87(2) 1.95(2) 2.8044(15) 167.5(17) . O1W H2W1 O2 0.88(2) 1.92(2) 2.7889(15) 167.8(18) 2_745 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.264 _refine_diff_density_min -0.248 _refine_diff_density_rms 0.049 # Attachment 'B618207K_m5msad.cif' data_m5msad _database_code_depnum_ccdc_archive 'CCDC 626906' _audit_creation_method SHELXL-97 _chemical_name_systematic ; meso-(5S,12S)-5,7,7,12,14,14-hexamethyl-4,11-diaza-1,8-diazoniacyclotetradecane bis(4-aminobenzoate) hydrate ; _chemical_name_common ; meso-(5S,12S)-5,7,7,12,14,14-hexamethyl-4,11-diaza-1,8- diazoniacyclotetradecane bis(4-aminobenzoate) hydrate ; _chemical_melting_point '270-271 \oC' _chemical_formula_moiety 'C16 H38 N4, 2(C7 H6 N O2), H2 O' _chemical_formula_sum 'C30 H52 N6 O5' _chemical_formula_weight 576.78 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 19.0506(13) _cell_length_b 12.1200(9) _cell_length_c 14.4397(10) _cell_angle_alpha 90.00 _cell_angle_beta 107.7200(10) _cell_angle_gamma 90.00 _cell_volume 3175.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 3244 _cell_measurement_theta_min 2.303 _cell_measurement_theta_max 27.25 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.206 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1256 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.86956 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS - Area-Detector Absorption Correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 90(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13533 _diffrn_reflns_av_R_equivalents 0.0321 _diffrn_reflns_av_sigmaI/netI 0.0323 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3646 _reflns_number_gt 2940 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^+1.4832P] 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_number_reflns 3646 _refine_ls_number_parameters 213 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0619 _refine_ls_R_factor_gt 0.0484 _refine_ls_wR_factor_ref 0.1283 _refine_ls_wR_factor_gt 0.1211 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _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 O1 O 0.42743(6) 0.25354(9) -0.14574(7) 0.0288(3) Uani 1 1 d . . . O2 O 0.34192(6) 0.20107(8) -0.07946(7) 0.0269(2) Uani 1 1 d . . . C1 C 0.37368(7) 0.19207(11) -0.14330(10) 0.0207(3) Uani 1 1 d . . . C2 C 0.34956(7) 0.10337(11) -0.21800(9) 0.0200(3) Uani 1 1 d . . . C3 C 0.38673(8) 0.08266(12) -0.28620(10) 0.0235(3) Uani 1 1 d . . . H3 H 0.4257 0.1280 -0.2878 0.028 Uiso 1 1 calc R . . C4 C 0.36661(8) -0.00375(12) -0.35112(10) 0.0247(3) Uani 1 1 d . . . H4 H 0.3917 -0.0149 -0.3964 0.030 Uiso 1 1 calc R . . C5 C 0.30897(7) -0.07490(11) -0.34982(10) 0.0224(3) Uani 1 1 d . . . C6 C 0.27029(7) -0.05275(12) -0.28280(10) 0.0236(3) Uani 1 1 d . . . H6 H 0.2309 -0.0973 -0.2815 0.028 Uiso 1 1 calc R . . C7 C 0.29057(7) 0.03474(11) -0.21898(10) 0.0222(3) Uani 1 1 d . . . H7 H 0.2642 0.0483 -0.1755 0.027 Uiso 1 1 calc R . . N1 N 0.29234(7) -0.16550(11) -0.40910(10) 0.0289(3) Uani 1 1 d . . . H1N1 H 0.3085(10) -0.1671(14) -0.4585(14) 0.033(5) Uiso 1 1 d . . . H2N1 H 0.2527(11) -0.2043(16) -0.4092(14) 0.042(5) Uiso 1 1 d . . . N2 N 0.58377(6) 0.45908(10) -0.04950(9) 0.0217(3) Uani 1 1 d . . . H1N2 H 0.5589(8) 0.4407(13) -0.1099(12) 0.023(4) Uiso 1 1 d . . . N3 N 0.49637(6) 0.33297(10) 0.03398(8) 0.0205(3) Uani 1 1 d . . . H1N3 H 0.5146(9) 0.4007(15) 0.0201(12) 0.033(4) Uiso 1 1 d . . . H2N3 H 0.4688(10) 0.3027(15) -0.0253(14) 0.039(5) Uiso 1 1 d . . . C8 C 0.61332(8) 0.57052(12) -0.05127(11) 0.0256(3) Uani 1 1 d . . . H8A H 0.6481 0.5699 -0.0883 0.031 Uiso 1 1 calc R . . H8B H 0.6394 0.5936 0.0146 0.031 Uiso 1 1 calc R . . C9 C 0.64150(8) 0.37339(13) -0.01590(11) 0.0273(3) Uani 1 1 d . . . H9 H 0.6751 0.3962 0.0472 0.033 Uiso 1 1 calc R . . C10 C 0.68668(9) 0.35688(15) -0.08686(13) 0.0370(4) Uani 1 1 d . . . H10A H 0.6539 0.3497 -0.1518 0.055 Uiso 1 1 calc R . . H10B H 0.7160 0.2913 -0.0695 0.055 Uiso 1 1 calc R . . H10C H 0.7183 0.4194 -0.0834 0.055 Uiso 1 1 calc R . . C11 C 0.60575(8) 0.26393(12) -0.00251(11) 0.0267(3) Uani 1 1 d . . . H11A H 0.6440 0.2081 0.0149 0.032 Uiso 1 1 calc R . . H11B H 0.5716 0.2429 -0.0648 0.032 Uiso 1 1 calc R . . C12 C 0.56403(8) 0.26074(12) 0.07347(10) 0.0254(3) Uani 1 1 d . . . C13 C 0.53923(9) 0.14250(13) 0.08300(13) 0.0352(4) Uani 1 1 d . . . H13A H 0.5121 0.1404 0.1292 0.053 Uiso 1 1 calc R . . H13B H 0.5817 0.0955 0.1049 0.053 Uiso 1 1 calc R . . H13C H 0.5084 0.1172 0.0210 0.053 Uiso 1 1 calc R . . C14 C 0.61128(9) 0.30528(15) 0.17156(11) 0.0359(4) Uani 1 1 d . . . H14A H 0.6159 0.3839 0.1675 0.054 Uiso 1 1 calc R . . H14B H 0.6593 0.2721 0.1883 0.054 Uiso 1 1 calc R . . H14C H 0.5884 0.2878 0.2205 0.054 Uiso 1 1 calc R . . C15 C 0.44749(8) 0.34882(12) 0.09613(10) 0.0249(3) Uani 1 1 d . . . H15A H 0.4765 0.3756 0.1595 0.030 Uiso 1 1 calc R . . H15B H 0.4262 0.2784 0.1052 0.030 Uiso 1 1 calc R . . O1W O 0.5000 0.62839(13) 0.2500 0.0264(3) Uani 1 2 d S . . H1W H 0.5272(11) 0.6745(17) 0.2221(15) 0.057(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 0.0320(6) 0.0333(6) 0.0233(5) -0.0051(4) 0.0119(4) -0.0110(5) O2 0.0319(6) 0.0284(5) 0.0244(5) -0.0041(4) 0.0145(4) -0.0020(4) C1 0.0228(7) 0.0210(6) 0.0180(6) 0.0029(5) 0.0057(5) 0.0025(5) C2 0.0217(7) 0.0209(6) 0.0176(6) 0.0023(5) 0.0061(5) 0.0022(5) C3 0.0231(7) 0.0259(7) 0.0232(7) 0.0008(6) 0.0096(6) -0.0029(6) C4 0.0253(7) 0.0309(8) 0.0214(7) -0.0026(6) 0.0121(6) 0.0005(6) C5 0.0212(7) 0.0257(7) 0.0194(7) -0.0012(5) 0.0048(5) 0.0038(6) C6 0.0204(7) 0.0268(7) 0.0246(7) -0.0015(6) 0.0081(5) -0.0029(6) C7 0.0220(7) 0.0261(7) 0.0207(7) -0.0006(5) 0.0097(5) 0.0019(6) N1 0.0286(7) 0.0331(7) 0.0277(7) -0.0112(6) 0.0126(6) -0.0060(6) N2 0.0202(6) 0.0250(6) 0.0196(6) -0.0016(5) 0.0057(4) -0.0031(5) N3 0.0214(6) 0.0228(6) 0.0177(6) -0.0005(5) 0.0064(5) -0.0039(5) C8 0.0233(7) 0.0283(7) 0.0277(7) -0.0052(6) 0.0117(6) -0.0073(6) C9 0.0207(7) 0.0351(8) 0.0258(7) 0.0058(6) 0.0068(6) -0.0005(6) C10 0.0288(8) 0.0436(10) 0.0439(10) 0.0125(8) 0.0192(7) 0.0090(7) C11 0.0231(7) 0.0298(8) 0.0279(8) 0.0043(6) 0.0086(6) 0.0038(6) C12 0.0230(7) 0.0283(7) 0.0245(7) 0.0057(6) 0.0064(6) -0.0006(6) C13 0.0343(9) 0.0282(8) 0.0447(10) 0.0108(7) 0.0143(7) 0.0022(7) C14 0.0292(8) 0.0520(10) 0.0235(8) 0.0083(7) 0.0035(6) -0.0015(7) C15 0.0293(8) 0.0264(7) 0.0227(7) -0.0019(6) 0.0136(6) -0.0069(6) O1W 0.0283(8) 0.0296(8) 0.0229(7) 0.000 0.0103(6) 0.000 _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 1.2755(17) . ? O2 C1 1.2519(16) . ? C1 C2 1.4929(19) . ? C2 C7 1.3947(19) . ? C2 C3 1.3995(18) . ? C3 C4 1.380(2) . ? C3 H3 0.9300 . ? C4 C5 1.401(2) . ? C4 H4 0.9300 . ? C5 N1 1.3689(18) . ? C5 C6 1.4091(18) . ? C6 C7 1.3806(19) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? N1 H1N1 0.860(18) . ? N1 H2N1 0.89(2) . ? N2 C8 1.4665(18) . ? N2 C9 1.4828(18) . ? N2 H1N2 0.885(16) . ? N3 C15 1.4892(17) . ? N3 C12 1.5183(18) . ? N3 H1N3 0.936(18) . ? N3 H2N3 0.932(19) . ? C8 C15 1.504(2) 5_665 ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C11 1.530(2) . ? C9 C10 1.539(2) . ? C9 H9 0.9800 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.5386(19) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C14 1.527(2) . ? C12 C13 1.528(2) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C8 1.504(2) 5_665 ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? O1W H1W 0.932(19) . ? 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 O2 C1 O1 122.78(12) . . ? O2 C1 C2 118.91(12) . . ? O1 C1 C2 118.28(12) . . ? C7 C2 C3 117.68(12) . . ? C7 C2 C1 120.44(12) . . ? C3 C2 C1 121.82(12) . . ? C4 C3 C2 121.25(13) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? C3 C4 C5 121.00(12) . . ? C3 C4 H4 119.5 . . ? C5 C4 H4 119.5 . . ? N1 C5 C4 121.24(13) . . ? N1 C5 C6 120.83(13) . . ? C4 C5 C6 117.88(12) . . ? C7 C6 C5 120.41(13) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C6 C7 C2 121.72(12) . . ? C6 C7 H7 119.1 . . ? C2 C7 H7 119.1 . . ? C5 N1 H1N1 117.7(12) . . ? C5 N1 H2N1 117.4(12) . . ? H1N1 N1 H2N1 120.4(17) . . ? C8 N2 C9 113.59(11) . . ? C8 N2 H1N2 107.9(10) . . ? C9 N2 H1N2 105.5(10) . . ? C15 N3 C12 117.59(11) . . ? C15 N3 H1N3 110.8(10) . . ? C12 N3 H1N3 105.0(10) . . ? C15 N3 H2N3 108.9(11) . . ? C12 N3 H2N3 107.1(11) . . ? H1N3 N3 H2N3 106.9(15) . . ? N2 C8 C15 110.90(11) . 5_665 ? N2 C8 H8A 109.5 . . ? C15 C8 H8A 109.5 5_665 . ? N2 C8 H8B 109.5 . . ? C15 C8 H8B 109.5 5_665 . ? H8A C8 H8B 108.0 . . ? N2 C9 C11 109.53(11) . . ? N2 C9 C10 112.51(12) . . ? C11 C9 C10 109.40(13) . . ? N2 C9 H9 108.4 . . ? C11 C9 H9 108.4 . . ? C10 C9 H9 108.4 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 C12 117.28(12) . . ? C9 C11 H11A 108.0 . . ? C12 C11 H11A 108.0 . . ? C9 C11 H11B 108.0 . . ? C12 C11 H11B 108.0 . . ? H11A C11 H11B 107.2 . . ? N3 C12 C14 109.75(12) . . ? N3 C12 C13 108.91(12) . . ? C14 C12 C13 111.04(13) . . ? N3 C12 C11 106.35(11) . . ? C14 C12 C11 111.46(12) . . ? C13 C12 C11 109.19(12) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N3 C15 C8 111.44(11) . 5_665 ? N3 C15 H15A 109.3 . . ? C8 C15 H15A 109.3 5_665 . ? N3 C15 H15B 109.3 . . ? C8 C15 H15B 109.3 5_665 . ? H15A C15 H15B 108.0 . . ? 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 H1N1 O2 0.860(18) 2.073(19) 2.9230(17) 169.5(17) 6 N1 H2N1 O2 0.89(2) 2.10(2) 2.9877(17) 175.7(17) 4_544 N2 H1N2 O1W 0.885(16) 2.162(17) 3.0397(13) 171.8(14) 5_665 N3 H1N3 N2 0.936(18) 2.014(17) 2.7898(16) 139.1(14) . N3 H2N3 O1 0.932(19) 1.78(2) 2.7039(16) 170.8(16) . O1W H1W O1 0.932(19) 1.818(19) 2.7373(13) 168.1(19) 5_665 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.346 _refine_diff_density_min -0.158 _refine_diff_density_rms 0.047 data_m6sad _database_code_depnum_ccdc_archive 'CCDC 626907' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4,10-diaza-1,7-diazoniacyclododecane bis(4-aminobenzoate) dihydrate ; _chemical_name_common ;4,10-diaza-1,7-diazoniacyclododecane bis(4-aminobenzoate) dihydrate ; _chemical_melting_point '206-207 \oC' _chemical_formula_moiety 'C8 H22 N4, 2(C7 H6 N O2), 2(H2 O)' _chemical_formula_sum 'C22 H38 N6 O6' _chemical_formula_weight 482.58 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 P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.6004(19) _cell_length_b 11.350(2) _cell_length_c 12.088(2) _cell_angle_alpha 90.00 _cell_angle_beta 111.91(3) _cell_angle_gamma 90.00 _cell_volume 1222.0(4) _cell_formula_units_Z 2 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 3262 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 27.20 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_min 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_max 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.802426 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details 'SADABS - Area Detector Absorption Correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 90(2) _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9148 _diffrn_reflns_av_R_equivalents 0.0272 _diffrn_reflns_av_sigmaI/netI 0.0396 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 25.50 _reflns_number_total 4232 _reflns_number_gt 3939 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0550P)^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 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.0(8) _refine_ls_number_reflns 4232 _refine_ls_number_parameters 363 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0400 _refine_ls_R_factor_gt 0.0366 _refine_ls_wR_factor_ref 0.0906 _refine_ls_wR_factor_gt 0.0881 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _refine_ls_shift/su_max 0.001 _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 O1A O -0.25790(16) 0.16326(13) -0.07778(13) 0.0271(3) Uani 1 1 d . . . O2A O -0.13330(16) 0.22889(13) 0.10519(12) 0.0274(3) Uani 1 1 d . . . N1A N -0.4908(2) -0.19352(18) 0.22725(18) 0.0306(4) Uani 1 1 d . . . H1NA H -0.478(2) -0.185(2) 0.308(2) 0.027(6) Uiso 1 1 d . . . H2NA H -0.559(3) -0.243(3) 0.180(3) 0.049(8) Uiso 1 1 d . . . C1A C -0.2267(2) 0.15981(18) 0.03333(17) 0.0212(4) Uani 1 1 d . . . C2A C -0.3009(2) 0.06934(18) 0.08315(18) 0.0207(4) Uani 1 1 d . . . C3A C -0.3930(2) -0.01822(18) 0.01049(18) 0.0217(4) Uani 1 1 d . . . H3A H -0.4128 -0.0176 -0.0709 0.026 Uiso 1 1 calc R . . C4A C -0.4552(2) -0.10581(18) 0.05743(18) 0.0225(4) Uani 1 1 d . . . H4A H -0.5149 -0.1635 0.0073 0.027 Uiso 1 1 calc R . . C5A C -0.4295(2) -0.10867(18) 0.17972(18) 0.0221(4) Uani 1 1 d . . . C6A C -0.3382(2) -0.01974(18) 0.25214(18) 0.0231(4) Uani 1 1 d . . . H6A H -0.3192 -0.0194 0.3334 0.028 Uiso 1 1 calc R . . C7A C -0.2761(2) 0.06711(19) 0.20473(18) 0.0230(4) Uani 1 1 d . . . H7A H -0.2168 0.1251 0.2546 0.028 Uiso 1 1 calc R . . O1B O -0.61732(15) 0.58916(12) -0.50710(12) 0.0238(3) Uani 1 1 d . . . O2B O -0.72115(16) 0.76387(12) -0.50446(13) 0.0271(3) Uani 1 1 d . . . N1B N -1.3097(2) 0.43958(19) -0.69944(17) 0.0293(4) Uani 1 1 d . . . H1NB H -1.310(3) 0.365(3) -0.666(2) 0.041(7) Uiso 1 1 d . . . H2NB H -1.390(3) 0.487(2) -0.706(2) 0.036(7) Uiso 1 1 d . . . C1B C -0.7310(2) 0.65553(18) -0.52465(16) 0.0210(4) Uani 1 1 d . . . C2B C -0.8830(2) 0.59902(18) -0.57235(17) 0.0209(4) Uani 1 1 d . . . C3B C -1.0141(2) 0.66740(19) -0.61078(17) 0.0234(4) Uani 1 1 d . . . H3B H -1.0060 0.7491 -0.6071 0.028 Uiso 1 1 calc R . . C4B C -1.1552(2) 0.6163(2) -0.65401(17) 0.0236(4) Uani 1 1 d . . . H4B H -1.2402 0.6639 -0.6812 0.028 Uiso 1 1 calc R . . C5B C -1.1709(2) 0.49358(19) -0.65702(17) 0.0230(4) Uani 1 1 d . . . C6B C -1.0397(2) 0.42461(19) -0.61970(18) 0.0249(5) Uani 1 1 d . . . H6B H -1.0475 0.3429 -0.6222 0.030 Uiso 1 1 calc R . . C7B C -0.8998(2) 0.47653(18) -0.57953(18) 0.0231(4) Uani 1 1 d . . . H7B H -0.8148 0.4291 -0.5567 0.028 Uiso 1 1 calc R . . N2 N -0.33131(19) 0.62135(16) -0.10108(15) 0.0226(4) Uani 1 1 d . . . H1N2 H -0.407(2) 0.602(2) -0.0852(19) 0.023(6) Uiso 1 1 d . . . N3 N -0.33833(19) 0.61916(16) -0.33941(15) 0.0211(4) Uani 1 1 d . . . H1N3 H -0.336(2) 0.558(2) -0.287(2) 0.025(6) Uiso 1 1 d . . . H2N3 H -0.434(3) 0.624(2) -0.396(2) 0.033(6) Uiso 1 1 d . . . N4 N -0.15393(19) 0.42065(17) -0.26796(16) 0.0246(4) Uani 1 1 d . . . H1N4 H -0.191(2) 0.367(2) -0.320(2) 0.024(6) Uiso 1 1 d . . . N5 N -0.1397(2) 0.42319(16) -0.01901(16) 0.0226(4) Uani 1 1 d . . . H1N5 H -0.134(3) 0.346(3) 0.016(2) 0.038(7) Uiso 1 1 d . . . H2N5 H -0.222(3) 0.4313(19) -0.081(2) 0.019(5) Uiso 1 1 d . . . C8 C -0.0321(2) 0.36709(19) -0.16783(19) 0.0265(5) Uani 1 1 d . . . H8B H 0.0594 0.3672 -0.1841 0.032 Uiso 1 1 calc R . . H8A H -0.0573 0.2860 -0.1582 0.032 Uiso 1 1 calc R . . C9 C -0.0073(2) 0.43497(19) -0.05422(19) 0.0249(4) Uani 1 1 d . . . H9B H 0.0814 0.4052 0.0092 0.030 Uiso 1 1 calc R . . H9A H 0.0092 0.5175 -0.0663 0.030 Uiso 1 1 calc R . . C10 C -0.1506(2) 0.51382(19) 0.06673(18) 0.0251(4) Uani 1 1 d . . . H10B H -0.0544 0.5207 0.1323 0.030 Uiso 1 1 calc R . . H10A H -0.2242 0.4889 0.0992 0.030 Uiso 1 1 calc R . . C11 C -0.1955(2) 0.63318(19) 0.00711(18) 0.0246(4) Uani 1 1 d . . . H11B H -0.2143 0.6876 0.0618 0.029 Uiso 1 1 calc R . . H11A H -0.1143 0.6646 -0.0135 0.029 Uiso 1 1 calc R . . C12 C -0.3672(2) 0.72798(19) -0.17567(18) 0.0242(4) Uani 1 1 d . . . H12B H -0.3365 0.7973 -0.1255 0.029 Uiso 1 1 calc R . . H12A H -0.4747 0.7325 -0.2196 0.029 Uiso 1 1 calc R . . C13 C -0.2868(2) 0.72472(19) -0.26189(18) 0.0232(4) Uani 1 1 d . . . H13B H -0.3089 0.7956 -0.3102 0.028 Uiso 1 1 calc R . . H13A H -0.1791 0.7208 -0.2183 0.028 Uiso 1 1 calc R . . C14 C -0.2417(2) 0.5841(2) -0.40593(18) 0.0250(5) Uani 1 1 d . . . H14B H -0.2101 0.6538 -0.4366 0.030 Uiso 1 1 calc R . . H14A H -0.2987 0.5347 -0.4731 0.030 Uiso 1 1 calc R . . C15 C -0.1053(2) 0.51763(19) -0.32490(18) 0.0246(5) Uani 1 1 d . . . H15B H -0.0494 0.4868 -0.3708 0.030 Uiso 1 1 calc R . . H15A H -0.0401 0.5703 -0.2645 0.030 Uiso 1 1 calc R . . O1W O -0.3788(2) 0.01172(15) -0.26750(16) 0.0331(4) Uani 1 1 d . . . H1W1 H -0.371(4) 0.046(3) -0.331(3) 0.074(11) Uiso 1 1 d . . . H2W1 H -0.330(3) 0.059(3) -0.212(3) 0.062(10) Uiso 1 1 d . . . O2W O -0.45989(19) 0.84394(15) -0.52500(13) 0.0277(3) Uani 1 1 d . . . H1W2 H -0.439(3) 0.920(3) -0.509(2) 0.040(7) Uiso 1 1 d . . . H2W2 H -0.546(4) 0.830(3) -0.511(3) 0.064(10) 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 O1A 0.0311(8) 0.0257(8) 0.0249(8) 0.0025(6) 0.0110(6) 0.0007(6) O2A 0.0307(8) 0.0238(8) 0.0256(7) 0.0012(7) 0.0082(6) -0.0058(7) N1A 0.0339(11) 0.0365(11) 0.0213(10) -0.0020(9) 0.0102(8) -0.0122(9) C1A 0.0213(10) 0.0170(10) 0.0250(11) 0.0018(8) 0.0082(8) 0.0046(8) C2A 0.0185(9) 0.0201(10) 0.0233(10) 0.0026(8) 0.0078(8) 0.0039(8) C3A 0.0223(10) 0.0233(11) 0.0198(10) -0.0013(8) 0.0081(8) 0.0026(9) C4A 0.0216(10) 0.0222(11) 0.0238(10) -0.0047(9) 0.0088(8) -0.0008(8) C5A 0.0171(10) 0.0250(11) 0.0249(11) 0.0021(9) 0.0086(8) 0.0028(8) C6A 0.0234(10) 0.0264(12) 0.0187(10) 0.0009(8) 0.0071(8) 0.0037(9) C7A 0.0168(10) 0.0243(11) 0.0258(11) -0.0026(9) 0.0055(8) 0.0011(8) O1B 0.0209(7) 0.0256(8) 0.0238(7) 0.0002(6) 0.0072(6) 0.0019(6) O2B 0.0250(8) 0.0212(8) 0.0362(9) -0.0014(6) 0.0127(7) -0.0012(6) N1B 0.0207(10) 0.0333(12) 0.0317(10) -0.0011(9) 0.0073(8) -0.0032(9) C1B 0.0233(10) 0.0248(11) 0.0164(9) 0.0004(8) 0.0091(8) 0.0015(9) C2B 0.0215(10) 0.0247(11) 0.0176(9) 0.0020(8) 0.0086(8) 0.0002(8) C3B 0.0273(11) 0.0219(10) 0.0234(10) 0.0028(8) 0.0121(9) 0.0028(9) C4B 0.0215(10) 0.0301(12) 0.0204(10) 0.0046(9) 0.0093(8) 0.0072(9) C5B 0.0229(10) 0.0300(12) 0.0155(10) 0.0003(8) 0.0063(8) -0.0012(9) C6B 0.0275(11) 0.0221(11) 0.0243(10) -0.0027(9) 0.0087(9) -0.0029(9) C7B 0.0223(10) 0.0238(11) 0.0228(11) -0.0002(8) 0.0079(8) 0.0025(8) N2 0.0200(9) 0.0245(9) 0.0241(9) -0.0024(8) 0.0092(7) -0.0025(7) N3 0.0190(9) 0.0240(9) 0.0181(8) 0.0008(8) 0.0043(7) 0.0007(7) N4 0.0237(9) 0.0223(10) 0.0253(9) -0.0039(8) 0.0060(7) -0.0006(8) N5 0.0223(9) 0.0208(9) 0.0224(9) 0.0010(8) 0.0059(8) -0.0015(8) C8 0.0247(11) 0.0234(11) 0.0318(12) 0.0003(9) 0.0112(9) 0.0026(9) C9 0.0212(10) 0.0243(11) 0.0272(10) 0.0012(9) 0.0068(8) -0.0007(9) C10 0.0266(11) 0.0275(11) 0.0211(10) -0.0016(9) 0.0089(8) -0.0039(9) C11 0.0264(11) 0.0237(11) 0.0232(10) -0.0020(9) 0.0089(8) -0.0035(9) C12 0.0241(11) 0.0225(10) 0.0238(10) -0.0003(9) 0.0062(8) 0.0035(9) C13 0.0252(11) 0.0203(10) 0.0220(10) 0.0006(9) 0.0064(8) -0.0013(9) C14 0.0259(11) 0.0298(12) 0.0210(10) -0.0013(9) 0.0106(8) 0.0002(9) C15 0.0224(11) 0.0287(12) 0.0235(10) -0.0039(9) 0.0095(8) -0.0009(9) O1W 0.0437(10) 0.0290(9) 0.0304(9) -0.0030(8) 0.0182(8) -0.0097(8) O2W 0.0287(9) 0.0266(9) 0.0288(8) -0.0019(7) 0.0119(7) -0.0051(7) _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 O1A C1A 1.263(2) . ? O2A C1A 1.262(3) . ? N1A C5A 1.362(3) . ? N1A H1NA 0.94(2) . ? N1A H2NA 0.89(3) . ? C1A C2A 1.498(3) . ? C2A C7A 1.399(3) . ? C2A C3A 1.400(3) . ? C3A C4A 1.386(3) . ? C3A H3A 0.9300 . ? C4A C5A 1.405(3) . ? C4A H4A 0.9300 . ? C5A C6A 1.407(3) . ? C6A C7A 1.382(3) . ? C6A H6A 0.9300 . ? C7A H7A 0.9300 . ? O1B C1B 1.277(2) . ? O2B C1B 1.250(2) . ? N1B C5B 1.380(3) . ? N1B H1NB 0.94(3) . ? N1B H2NB 0.92(3) . ? C1B C2B 1.498(3) . ? C2B C7B 1.399(3) . ? C2B C3B 1.402(3) . ? C3B C4B 1.384(3) . ? C3B H3B 0.9300 . ? C4B C5B 1.400(3) . ? C4B H4B 0.9300 . ? C5B C6B 1.407(3) . ? C6B C7B 1.378(3) . ? C6B H6B 0.9300 . ? C7B H7B 0.9300 . ? N2 C11 1.468(3) . ? N2 C12 1.471(3) . ? N2 H1N2 0.84(2) . ? N3 C13 1.487(3) . ? N3 C14 1.490(3) . ? N3 H1N3 0.94(2) . ? N3 H2N3 0.92(2) . ? N4 C15 1.464(3) . ? N4 C8 1.465(3) . ? N4 H1N4 0.86(2) . ? N5 C9 1.489(3) . ? N5 C10 1.491(3) . ? N5 H1N5 0.97(3) . ? N5 H2N5 0.87(2) . ? C8 C9 1.514(3) . ? C8 H8B 0.9700 . ? C8 H8A 0.9700 . ? C9 H9B 0.9700 . ? C9 H9A 0.9700 . ? C10 C11 1.519(3) . ? C10 H10B 0.9700 . ? C10 H10A 0.9700 . ? C11 H11B 0.9700 . ? C11 H11A 0.9700 . ? C12 C13 1.511(3) . ? C12 H12B 0.9700 . ? C12 H12A 0.9700 . ? C13 H13B 0.9700 . ? C13 H13A 0.9700 . ? C14 C15 1.512(3) . ? C14 H14B 0.9700 . ? C14 H14A 0.9700 . ? C15 H15B 0.9700 . ? C15 H15A 0.9700 . ? O1W H1W1 0.89(3) . ? O1W H2W1 0.85(3) . ? O2W H1W2 0.89(3) . ? O2W H2W2 0.91(4) . ? 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 C5A N1A H1NA 116.9(14) . . ? C5A N1A H2NA 120.3(18) . . ? H1NA N1A H2NA 121(2) . . ? O2A C1A O1A 122.56(19) . . ? O2A C1A C2A 118.14(17) . . ? O1A C1A C2A 119.29(18) . . ? C7A C2A C3A 117.79(19) . . ? C7A C2A C1A 120.98(18) . . ? C3A C2A C1A 121.19(18) . . ? C4A C3A C2A 121.34(18) . . ? C4A C3A H3A 119.3 . . ? C2A C3A H3A 119.3 . . ? C3A C4A C5A 120.92(19) . . ? C3A C4A H4A 119.5 . . ? C5A C4A H4A 119.5 . . ? N1A C5A C4A 121.73(19) . . ? N1A C5A C6A 120.76(19) . . ? C4A C5A C6A 117.52(19) . . ? C7A C6A C5A 121.23(19) . . ? C7A C6A H6A 119.4 . . ? C5A C6A H6A 119.4 . . ? C6A C7A C2A 121.20(19) . . ? C6A C7A H7A 119.4 . . ? C2A C7A H7A 119.4 . . ? C5B N1B H1NB 113.6(15) . . ? C5B N1B H2NB 115.8(16) . . ? H1NB N1B H2NB 115(2) . . ? O2B C1B O1B 123.34(19) . . ? O2B C1B C2B 119.23(18) . . ? O1B C1B C2B 117.43(18) . . ? C7B C2B C3B 117.45(18) . . ? C7B C2B C1B 121.54(18) . . ? C3B C2B C1B 121.01(18) . . ? C4B C3B C2B 121.6(2) . . ? C4B C3B H3B 119.2 . . ? C2B C3B H3B 119.2 . . ? C3B C4B C5B 120.48(19) . . ? C3B C4B H4B 119.8 . . ? C5B C4B H4B 119.8 . . ? N1B C5B C4B 122.1(2) . . ? N1B C5B C6B 119.8(2) . . ? C4B C5B C6B 118.07(19) . . ? C7B C6B C5B 120.9(2) . . ? C7B C6B H6B 119.6 . . ? C5B C6B H6B 119.6 . . ? C6B C7B C2B 121.46(19) . . ? C6B C7B H7B 119.3 . . ? C2B C7B H7B 119.3 . . ? C11 N2 C12 113.43(17) . . ? C11 N2 H1N2 111.9(15) . . ? C12 N2 H1N2 109.0(15) . . ? C13 N3 C14 115.29(16) . . ? C13 N3 H1N3 104.7(14) . . ? C14 N3 H1N3 107.7(14) . . ? C13 N3 H2N3 115.0(16) . . ? C14 N3 H2N3 105.2(15) . . ? H1N3 N3 H2N3 109(2) . . ? C15 N4 C8 113.85(16) . . ? C15 N4 H1N4 108.0(15) . . ? C8 N4 H1N4 107.4(15) . . ? C9 N5 C10 115.18(16) . . ? C9 N5 H1N5 106.9(14) . . ? C10 N5 H1N5 109.1(15) . . ? C9 N5 H2N5 110.1(14) . . ? C10 N5 H2N5 104.4(14) . . ? H1N5 N5 H2N5 111(2) . . ? N4 C8 C9 110.19(18) . . ? N4 C8 H8B 109.6 . . ? C9 C8 H8B 109.6 . . ? N4 C8 H8A 109.6 . . ? C9 C8 H8A 109.6 . . ? H8B C8 H8A 108.1 . . ? N5 C9 C8 110.58(17) . . ? N5 C9 H9B 109.5 . . ? C8 C9 H9B 109.5 . . ? N5 C9 H9A 109.5 . . ? C8 C9 H9A 109.5 . . ? H9B C9 H9A 108.1 . . ? N5 C10 C11 111.49(17) . . ? N5 C10 H10B 109.3 . . ? C11 C10 H10B 109.3 . . ? N5 C10 H10A 109.3 . . ? C11 C10 H10A 109.3 . . ? H10B C10 H10A 108.0 . . ? N2 C11 C10 109.97(17) . . ? N2 C11 H11B 109.7 . . ? C10 C11 H11B 109.7 . . ? N2 C11 H11A 109.7 . . ? C10 C11 H11A 109.7 . . ? H11B C11 H11A 108.2 . . ? N2 C12 C13 109.85(17) . . ? N2 C12 H12B 109.7 . . ? C13 C12 H12B 109.7 . . ? N2 C12 H12A 109.7 . . ? C13 C12 H12A 109.7 . . ? H12B C12 H12A 108.2 . . ? N3 C13 C12 108.58(17) . . ? N3 C13 H13B 110.0 . . ? C12 C13 H13B 110.0 . . ? N3 C13 H13A 110.0 . . ? C12 C13 H13A 110.0 . . ? H13B C13 H13A 108.4 . . ? N3 C14 C15 110.28(17) . . ? N3 C14 H14B 109.6 . . ? C15 C14 H14B 109.6 . . ? N3 C14 H14A 109.6 . . ? C15 C14 H14A 109.6 . . ? H14B C14 H14A 108.1 . . ? N4 C15 C14 109.18(17) . . ? N4 C15 H15B 109.8 . . ? C14 C15 H15B 109.8 . . ? N4 C15 H15A 109.8 . . ? C14 C15 H15A 109.8 . . ? H15B C15 H15A 108.3 . . ? H1W1 O1W H2W1 102(3) . . ? H1W2 O2W H2W2 106(3) . . ? 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 N1A H1NA O2W 0.94(2) 1.99(2) 2.928(3) 176(2) 1_546 N1A H2NA O1A 0.89(3) 2.03(3) 2.911(3) 170(3) 2_445 N1B H1NB O2B 0.94(3) 2.27(3) 3.098(3) 146(2) 2_344 N1B H2NB O1W 0.92(3) 2.14(3) 2.981(3) 152(2) 2_354 N3 H1N3 N4 0.94(2) 2.29(2) 2.796(3) 113.4(17) . N3 H1N3 N2 0.94(2) 2.34(2) 2.857(2) 113.9(17) . N3 H2N3 O1B 0.92(2) 1.82(2) 2.710(2) 164(2) . N4 H1N4 O2B 0.86(2) 2.28(2) 3.116(2) 163(2) 2_444 N5 H1N5 O2A 0.97(3) 1.71(3) 2.656(2) 165(2) . N5 H1N5 O1A 0.97(3) 2.45(3) 3.146(2) 128.6(18) . N5 H2N5 N2 0.87(2) 2.37(2) 2.840(3) 114.4(17) . O1W H1W1 O1B 0.89(3) 1.98(3) 2.850(2) 166(3) 2_444 O1W H2W1 O1A 0.85(3) 1.92(4) 2.753(2) 167(3) . O2W H1W2 O1B 0.89(3) 1.98(3) 2.869(2) 172(2) 2_454 O2W H2W2 O2B 0.91(4) 1.87(4) 2.765(2) 165(3) . _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.212 _refine_diff_density_min -0.168 _refine_diff_density_rms 0.040 # Attachment 'B618207K_M9MSAD.CIF' data_m9msad _database_code_depnum_ccdc_archive 'CCDC 626908' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,7-dioxa-4,10-diazoniacyclododecane bis(4-aminobenzoate) dihydrate ; _chemical_name_common ;1,7-dioxa-4,10-diazoniacyclododecane bis(4-aminobenzoate) dihydrate ; _chemical_melting_point '126-127 \oC' _chemical_formula_moiety 'C8 H20 N2 O2, 2(C7 H6 N O2), 2(H2 O)' _chemical_formula_sum 'C22 H36 N4 O8' _chemical_formula_weight 484.55 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 Pc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' _cell_length_a 10.9044(14) _cell_length_b 9.9475(13) _cell_length_c 12.1429(15) _cell_angle_alpha 90.00 _cell_angle_beta 114.267(2) _cell_angle_gamma 90.00 _cell_volume 1200.8(3) _cell_formula_units_Z 2 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 3496 _cell_measurement_theta_min 2.75 _cell_measurement_theta_max 27.21 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_max 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.340 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.583630 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details 'SADABS - Area Detector Absorption Correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 90(2) _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8749 _diffrn_reflns_av_R_equivalents 0.0267 _diffrn_reflns_av_sigmaI/netI 0.0399 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 25.50 _reflns_number_total 4343 _reflns_number_gt 4062 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0421P)^2^+0.1580P] 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 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1.1(7) _refine_ls_number_reflns 4343 _refine_ls_number_parameters 355 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0381 _refine_ls_R_factor_gt 0.0349 _refine_ls_wR_factor_ref 0.0825 _refine_ls_wR_factor_gt 0.0800 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _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 O1A O 0.79464(14) -0.11559(13) 0.54802(13) 0.0259(3) Uani 1 1 d . . . O2A O 1.00532(13) -0.17521(14) 0.58690(13) 0.0259(3) Uani 1 1 d . . . N1A N 0.6865(2) -0.6238(2) 0.19535(19) 0.0351(5) Uani 1 1 d . . . H1NA H 0.743(2) -0.663(2) 0.175(2) 0.019(5) Uiso 1 1 d . . . H2NA H 0.603(3) -0.633(2) 0.157(2) 0.032(6) Uiso 1 1 d . . . C1A C 0.87899(19) -0.19367(19) 0.53436(17) 0.0214(4) Uani 1 1 d . . . C2A C 0.82794(19) -0.31041(19) 0.44941(17) 0.0211(4) Uani 1 1 d . . . C3A C 0.69047(19) -0.33665(19) 0.38864(18) 0.0226(4) Uani 1 1 d . . . H3AA H 0.6297 -0.2838 0.4051 0.027 Uiso 1 1 calc R . . C4A C 0.6423(2) -0.4388(2) 0.30486(18) 0.0241(4) Uani 1 1 d . . . H4AA H 0.5502 -0.4543 0.2667 0.029 Uiso 1 1 calc R . . C5A C 0.7313(2) -0.5199(2) 0.27654(18) 0.0252(4) Uani 1 1 d . . . C6A C 0.8693(2) -0.49434(19) 0.33757(18) 0.0243(4) Uani 1 1 d . . . H6AA H 0.9303 -0.5469 0.3211 0.029 Uiso 1 1 calc R . . C7A C 0.9162(2) -0.39198(19) 0.42205(19) 0.0227(4) Uani 1 1 d . . . H7AA H 1.0084 -0.3772 0.4614 0.027 Uiso 1 1 calc R . . O1B O 0.43663(14) -0.22404(14) 0.52260(13) 0.0274(3) Uani 1 1 d . . . O2B O 0.36723(15) -0.19652(14) 0.32422(13) 0.0316(3) Uani 1 1 d . . . N1B N 0.11703(19) -0.77222(19) 0.34828(19) 0.0286(4) Uani 1 1 d . . . H1NB H 0.134(2) -0.822(2) 0.411(2) 0.031(6) Uiso 1 1 d . . . H2NB H 0.085(3) -0.805(3) 0.274(3) 0.042(7) Uiso 1 1 d . . . C1B C 0.37357(19) -0.2636(2) 0.41352(18) 0.0244(4) Uani 1 1 d . . . C2B C 0.30576(19) -0.39672(19) 0.39610(18) 0.0218(4) Uani 1 1 d . . . C3B C 0.3168(2) -0.47574(19) 0.49525(18) 0.0239(4) Uani 1 1 d . . . H3BA H 0.3661 -0.4437 0.5730 0.029 Uiso 1 1 calc R . . C4B C 0.2563(2) -0.5996(2) 0.47974(19) 0.0250(4) Uani 1 1 d . . . H4BA H 0.2652 -0.6502 0.5470 0.030 Uiso 1 1 calc R . . C5B C 0.18164(19) -0.6504(2) 0.36417(18) 0.0232(4) Uani 1 1 d . . . C6B C 0.1688(2) -0.5709(2) 0.26425(18) 0.0252(4) Uani 1 1 d . . . H6BA H 0.1179 -0.6018 0.1864 0.030 Uiso 1 1 calc R . . C7B C 0.2311(2) -0.4480(2) 0.28107(18) 0.0246(4) Uani 1 1 d . . . H7BA H 0.2233 -0.3977 0.2139 0.029 Uiso 1 1 calc R . . O3 O 0.78592(13) 0.09036(13) 0.74088(12) 0.0232(3) Uani 1 1 d . . . O4 O 0.67898(14) 0.20914(13) 0.47428(13) 0.0261(3) Uani 1 1 d . . . N3 N 0.95677(18) 0.12037(17) 0.61788(15) 0.0236(4) Uani 1 1 d . . . H3A H 1.027(3) 0.098(2) 0.604(2) 0.028(6) Uiso 1 1 d . . . H3B H 0.893(3) 0.057(3) 0.591(2) 0.041(7) Uiso 1 1 d . . . N4 N 0.54686(17) 0.01592(17) 0.54607(15) 0.0231(4) Uani 1 1 d . . . H4A H 0.631(2) 0.010(2) 0.5487(19) 0.020(5) Uiso 1 1 d . . . H4B H 0.508(2) -0.075(2) 0.529(2) 0.028(6) Uiso 1 1 d . . . C8 C 0.9127(2) 0.2482(2) 0.54798(19) 0.0271(5) Uani 1 1 d . . . H8A H 0.9033 0.2331 0.4660 0.032 Uiso 1 1 calc R . . H8B H 0.9819 0.3158 0.5840 0.032 Uiso 1 1 calc R . . C9 C 0.7813(2) 0.30121(19) 0.54430(19) 0.0261(4) Uani 1 1 d . . . H9A H 0.7853 0.3077 0.6254 0.031 Uiso 1 1 calc R . . H9B H 0.7628 0.3898 0.5077 0.031 Uiso 1 1 calc R . . C10 C 0.5493(2) 0.2444(2) 0.4684(2) 0.0296(5) Uani 1 1 d . . . H10A H 0.5039 0.3052 0.4015 0.036 Uiso 1 1 calc R . . H10B H 0.5579 0.2884 0.5426 0.036 Uiso 1 1 calc R . . C11 C 0.4705(2) 0.1153(2) 0.4509(2) 0.0283(5) Uani 1 1 d . . . H11A H 0.3848 0.1338 0.4542 0.034 Uiso 1 1 calc R . . H11B H 0.4529 0.0781 0.3720 0.034 Uiso 1 1 calc R . . C12 C 0.5559(2) 0.0468(2) 0.67041(18) 0.0269(4) Uani 1 1 d . . . H12A H 0.5416 0.1421 0.6772 0.032 Uiso 1 1 calc R . . H12B H 0.4869 -0.0023 0.6845 0.032 Uiso 1 1 calc R . . C13 C 0.6923(2) 0.0071(2) 0.76245(18) 0.0279(5) Uani 1 1 d . . . H13A H 0.6982 0.0211 0.8435 0.034 Uiso 1 1 calc R . . H13B H 0.7098 -0.0869 0.7533 0.034 Uiso 1 1 calc R . . C14 C 0.9210(2) 0.0464(2) 0.79804(18) 0.0274(5) Uani 1 1 d . . . H14A H 0.9278 -0.0471 0.7785 0.033 Uiso 1 1 calc R . . H14B H 0.9531 0.0546 0.8850 0.033 Uiso 1 1 calc R . . C15 C 1.0030(2) 0.1334(2) 0.75296(19) 0.0280(5) Uani 1 1 d . . . H15A H 1.0969 0.1076 0.7928 0.034 Uiso 1 1 calc R . . H15B H 0.9953 0.2264 0.7732 0.034 Uiso 1 1 calc R . . O1W O 1.20316(15) 0.09976(15) 0.60235(14) 0.0284(3) Uani 1 1 d D . . H1W1 H 1.251(3) 0.138(3) 0.670(2) 0.051(8) Uiso 1 1 d D . . H2W1 H 1.231(3) 0.016(2) 0.611(3) 0.053(9) Uiso 1 1 d D . . O2W O 1.27730(16) -0.16065(16) 0.64233(15) 0.0350(4) Uani 1 1 d D . . H1W2 H 1.198(2) -0.195(3) 0.618(3) 0.045(8) Uiso 1 1 d D . . H2W2 H 1.318(4) -0.197(4) 0.602(4) 0.108(15) Uiso 1 1 d 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 O1A 0.0233(7) 0.0270(7) 0.0274(8) -0.0060(6) 0.0105(6) 0.0010(6) O2A 0.0220(7) 0.0271(7) 0.0259(7) -0.0007(6) 0.0070(6) -0.0004(6) N1A 0.0279(11) 0.0377(11) 0.0390(12) -0.0137(9) 0.0132(10) -0.0009(9) C1A 0.0218(10) 0.0230(10) 0.0177(9) 0.0048(7) 0.0063(8) 0.0006(8) C2A 0.0231(10) 0.0198(9) 0.0197(9) 0.0039(7) 0.0081(8) 0.0018(8) C3A 0.0191(10) 0.0240(9) 0.0244(10) 0.0019(8) 0.0087(8) 0.0024(8) C4A 0.0203(9) 0.0267(10) 0.0232(10) 0.0004(8) 0.0068(8) -0.0010(8) C5A 0.0310(11) 0.0241(10) 0.0208(10) 0.0017(8) 0.0111(9) -0.0017(8) C6A 0.0253(10) 0.0241(10) 0.0254(11) 0.0022(8) 0.0124(9) 0.0044(8) C7A 0.0186(10) 0.0245(10) 0.0233(10) 0.0047(8) 0.0071(8) 0.0011(8) O1B 0.0265(8) 0.0261(7) 0.0284(8) -0.0037(6) 0.0100(6) -0.0049(6) O2B 0.0321(8) 0.0286(8) 0.0306(8) 0.0064(6) 0.0094(7) -0.0025(6) N1B 0.0336(10) 0.0274(9) 0.0237(10) -0.0017(8) 0.0105(8) -0.0060(8) C1B 0.0204(10) 0.0257(10) 0.0281(11) 0.0018(9) 0.0109(9) 0.0037(8) C2B 0.0187(10) 0.0225(9) 0.0247(10) 0.0001(8) 0.0094(8) 0.0006(7) C3B 0.0229(10) 0.0252(10) 0.0216(10) -0.0028(8) 0.0071(8) -0.0001(8) C4B 0.0270(10) 0.0250(10) 0.0233(11) 0.0026(8) 0.0108(9) 0.0006(8) C5B 0.0204(9) 0.0245(10) 0.0252(11) -0.0013(8) 0.0098(8) 0.0002(8) C6B 0.0252(10) 0.0298(10) 0.0186(10) -0.0024(8) 0.0069(8) 0.0001(8) C7B 0.0269(10) 0.0273(10) 0.0208(10) 0.0038(8) 0.0110(9) 0.0028(8) O3 0.0214(7) 0.0245(7) 0.0233(7) 0.0011(6) 0.0086(6) -0.0001(6) O4 0.0237(7) 0.0251(7) 0.0284(8) -0.0005(6) 0.0097(6) -0.0004(6) N3 0.0208(9) 0.0254(9) 0.0246(9) -0.0032(7) 0.0095(7) -0.0003(7) N4 0.0203(9) 0.0231(9) 0.0258(9) -0.0029(7) 0.0095(7) -0.0031(7) C8 0.0272(11) 0.0233(10) 0.0315(12) 0.0031(9) 0.0129(10) -0.0019(8) C9 0.0292(11) 0.0214(10) 0.0270(11) 0.0012(8) 0.0109(9) -0.0007(8) C10 0.0263(11) 0.0288(11) 0.0336(12) 0.0034(9) 0.0121(9) 0.0069(9) C11 0.0215(10) 0.0304(11) 0.0285(11) 0.0024(9) 0.0058(9) 0.0022(8) C12 0.0249(11) 0.0308(11) 0.0278(11) -0.0070(8) 0.0136(9) -0.0070(8) C13 0.0344(12) 0.0261(10) 0.0239(11) -0.0013(8) 0.0126(9) -0.0026(9) C14 0.0272(11) 0.0317(11) 0.0200(10) -0.0023(8) 0.0063(9) 0.0064(9) C15 0.0206(10) 0.0335(11) 0.0261(11) -0.0063(9) 0.0058(9) 0.0011(9) O1W 0.0261(8) 0.0281(8) 0.0297(8) -0.0015(7) 0.0100(7) -0.0002(6) O2W 0.0305(9) 0.0316(8) 0.0467(10) -0.0073(7) 0.0198(8) -0.0040(7) _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 O1A C1A 1.266(2) . ? O2A C1A 1.271(2) . ? N1A C5A 1.372(3) . ? N1A H1NA 0.85(2) . ? N1A H2NA 0.84(3) . ? C1A C2A 1.500(3) . ? C2A C3A 1.397(3) . ? C2A C7A 1.400(3) . ? C3A C4A 1.380(3) . ? C3A H3AA 0.9300 . ? C4A C5A 1.409(3) . ? C4A H4AA 0.9300 . ? C5A C6A 1.400(3) . ? C6A C7A 1.385(3) . ? C6A H6AA 0.9300 . ? C7A H7AA 0.9300 . ? O1B C1B 1.278(2) . ? O2B C1B 1.250(2) . ? N1B C5B 1.375(3) . ? N1B H1NB 0.86(3) . ? N1B H2NB 0.88(3) . ? C1B C2B 1.489(3) . ? C2B C7B 1.392(3) . ? C2B C3B 1.401(3) . ? C3B C4B 1.373(3) . ? C3B H3BA 0.9300 . ? C4B C5B 1.396(3) . ? C4B H4BA 0.9300 . ? C5B C6B 1.406(3) . ? C6B C7B 1.373(3) . ? C6B H6BA 0.9300 . ? C7B H7BA 0.9300 . ? O3 C14 1.415(2) . ? O3 C13 1.420(2) . ? O4 C9 1.423(2) . ? O4 C10 1.430(2) . ? N3 C8 1.494(3) . ? N3 C15 1.510(3) . ? N3 H3A 0.88(3) . ? N3 H3B 0.90(3) . ? N4 C11 1.488(3) . ? N4 C12 1.504(3) . ? N4 H4A 0.91(2) . ? N4 H4B 0.98(2) . ? C8 C9 1.511(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.510(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.500(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.500(3) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? O1W H1W1 0.86(2) . ? O1W H2W1 0.87(2) . ? O2W H1W2 0.86(2) . ? O2W H2W2 0.87(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 C5A N1A H1NA 118.0(15) . . ? C5A N1A H2NA 117.7(17) . . ? H1NA N1A H2NA 123(2) . . ? O1A C1A O2A 122.78(18) . . ? O1A C1A C2A 118.74(16) . . ? O2A C1A C2A 118.44(16) . . ? C3A C2A C7A 117.38(18) . . ? C3A C2A C1A 121.49(16) . . ? C7A C2A C1A 121.00(17) . . ? C4A C3A C2A 121.85(17) . . ? C4A C3A H3AA 119.1 . . ? C2A C3A H3AA 119.1 . . ? C3A C4A C5A 120.69(18) . . ? C3A C4A H4AA 119.7 . . ? C5A C4A H4AA 119.7 . . ? N1A C5A C6A 120.31(19) . . ? N1A C5A C4A 122.0(2) . . ? C6A C5A C4A 117.67(18) . . ? C7A C6A C5A 121.02(18) . . ? C7A C6A H6AA 119.5 . . ? C5A C6A H6AA 119.5 . . ? C6A C7A C2A 121.38(19) . . ? C6A C7A H7AA 119.3 . . ? C2A C7A H7AA 119.3 . . ? C5B N1B H1NB 117.8(16) . . ? C5B N1B H2NB 116.0(17) . . ? H1NB N1B H2NB 122(2) . . ? O2B C1B O1B 123.30(18) . . ? O2B C1B C2B 120.26(18) . . ? O1B C1B C2B 116.43(17) . . ? C7B C2B C3B 117.71(17) . . ? C7B C2B C1B 121.31(18) . . ? C3B C2B C1B 120.97(18) . . ? C4B C3B C2B 121.24(19) . . ? C4B C3B H3BA 119.4 . . ? C2B C3B H3BA 119.4 . . ? C3B C4B C5B 120.77(19) . . ? C3B C4B H4BA 119.6 . . ? C5B C4B H4BA 119.6 . . ? N1B C5B C4B 120.92(18) . . ? N1B C5B C6B 120.73(19) . . ? C4B C5B C6B 118.29(18) . . ? C7B C6B C5B 120.32(19) . . ? C7B C6B H6BA 119.8 . . ? C5B C6B H6BA 119.8 . . ? C6B C7B C2B 121.66(18) . . ? C6B C7B H7BA 119.2 . . ? C2B C7B H7BA 119.2 . . ? C14 O3 C13 114.30(15) . . ? C9 O4 C10 112.84(15) . . ? C8 N3 C15 115.46(16) . . ? C8 N3 H3A 102.4(14) . . ? C15 N3 H3A 107.4(15) . . ? C8 N3 H3B 111.9(17) . . ? C15 N3 H3B 108.3(17) . . ? H3A N3 H3B 111(2) . . ? C11 N4 C12 115.41(16) . . ? C11 N4 H4A 107.6(14) . . ? C12 N4 H4A 109.2(13) . . ? C11 N4 H4B 113.0(13) . . ? C12 N4 H4B 104.5(13) . . ? H4A N4 H4B 106.9(19) . . ? N3 C8 C9 113.16(16) . . ? N3 C8 H8A 108.9 . . ? C9 C8 H8A 108.9 . . ? N3 C8 H8B 108.9 . . ? C9 C8 H8B 108.9 . . ? H8A C8 H8B 107.8 . . ? O4 C9 C8 107.11(16) . . ? O4 C9 H9A 110.3 . . ? C8 C9 H9A 110.3 . . ? O4 C9 H9B 110.3 . . ? C8 C9 H9B 110.3 . . ? H9A C9 H9B 108.5 . . ? O4 C10 C11 106.98(16) . . ? O4 C10 H10A 110.3 . . ? C11 C10 H10A 110.3 . . ? O4 C10 H10B 110.3 . . ? C11 C10 H10B 110.3 . . ? H10A C10 H10B 108.6 . . ? N4 C11 C10 110.55(17) . . ? N4 C11 H11A 109.5 . . ? C10 C11 H11A 109.5 . . ? N4 C11 H11B 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 108.1 . . ? C13 C12 N4 109.29(16) . . ? C13 C12 H12A 109.8 . . ? N4 C12 H12A 109.8 . . ? C13 C12 H12B 109.8 . . ? N4 C12 H12B 109.8 . . ? H12A C12 H12B 108.3 . . ? O3 C13 C12 106.06(16) . . ? O3 C13 H13A 110.5 . . ? C12 C13 H13A 110.5 . . ? O3 C13 H13B 110.5 . . ? C12 C13 H13B 110.5 . . ? H13A C13 H13B 108.7 . . ? O3 C14 C15 107.39(17) . . ? O3 C14 H14A 110.2 . . ? C15 C14 H14A 110.2 . . ? O3 C14 H14B 110.2 . . ? C15 C14 H14B 110.2 . . ? H14A C14 H14B 108.5 . . ? C14 C15 N3 111.35(17) . . ? C14 C15 H15A 109.4 . . ? N3 C15 H15A 109.4 . . ? C14 C15 H15B 109.4 . . ? N3 C15 H15B 109.4 . . ? H15A C15 H15B 108.0 . . ? H1W1 O1W H2W1 105(3) . . ? H1W2 O2W H2W2 109(3) . . ? 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 N1A H2NA O1B 0.84(3) 2.36(3) 3.069(3) 143(2) 2_544 N1B H1NB O1W 0.86(3) 2.27(3) 3.105(3) 165(2) 1_445 N1B H2NB O2A 0.88(3) 2.08(3) 2.942(3) 163(2) 2_444 N3 H3A O1W 0.88(3) 1.93(3) 2.777(2) 162(2) . N3 H3B O1A 0.90(3) 1.97(3) 2.850(2) 164(2) . N4 H4A O1A 0.91(2) 2.18(2) 2.993(2) 148.3(19) . N4 H4B O1B 0.98(2) 1.66(2) 2.635(2) 169(2) . O1W H1W1 O2B 0.86(2) 1.87(2) 2.725(2) 172(3) 2_655 O1W H2W1 O2W 0.87(2) 1.83(2) 2.698(2) 172(3) . O2W H1W2 O2A 0.86(2) 1.98(2) 2.762(2) 150(2) . O2W H2W2 O1B 0.87(3) 1.92(3) 2.758(2) 162(4) 1_655 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.177 _refine_diff_density_min -0.142 _refine_diff_density_rms 0.036 # Attachment 'B618207K_m8msad.cif' data_m8msad _database_code_depnum_ccdc_archive 'CCDC 626909' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,4,7,10,13-pentaoxa-16-azoniacyclooctadecane 4-aminobenzoate trihydrate ; _chemical_name_common ;1,4,7,10,13-pentaoxa-16-azoniacyclooctadecane 4-aminobenzoate trihydrate ; _chemical_melting_point '111-112 \oC' _chemical_formula_moiety 'C12 H26 N O5, C7 H6 N O2, 3(H2 O)' _chemical_formula_sum 'C19 H38 N2 O10' _chemical_formula_weight 454.51 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 Orthorhombic _symmetry_space_group_name_H-M 'Pca2(1) ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 24.784(4) _cell_length_b 9.6757(17) _cell_length_c 10.0867(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2418.8(7) _cell_formula_units_Z 4 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 4398 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 27.09 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_max 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.248 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 984 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.568287 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details 'SADABS - Area-Detector Absorption Correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 90(2) _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12926 _diffrn_reflns_av_R_equivalents 0.0601 _diffrn_reflns_av_sigmaI/netI 0.0926 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 25.99 _reflns_number_total 3892 _reflns_number_gt 3038 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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 [0.00000+1.00000exp(1.90(sin\q/\l)^2^)]/ [\s^2^(Fo^2^)+0.0000+0.0000*P+(0.0200P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.6(10) _refine_ls_number_reflns 3892 _refine_ls_number_parameters 321 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0575 _refine_ls_R_factor_gt 0.0424 _refine_ls_wR_factor_ref 0.0913 _refine_ls_wR_factor_gt 0.0848 _refine_ls_goodness_of_fit_ref 0.996 _refine_ls_restrained_S_all 0.995 _refine_ls_shift/su_max 0.001 _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 0.60449(8) 0.2857(2) 1.04344(19) 0.0310(4) Uani 1 1 d . . . O2 O 0.51809(8) 0.30682(18) 1.10138(18) 0.0285(4) Uani 1 1 d . . . N1 N 0.58220(11) -0.1927(3) 1.4850(3) 0.0375(6) Uani 1 1 d . . . H1N1 H 0.6144(13) -0.223(3) 1.506(3) 0.031(8) Uiso 1 1 d . . . H2N1 H 0.5529(12) -0.219(3) 1.531(3) 0.023(7) Uiso 1 1 d . . . C1 C 0.56322(11) 0.2490(3) 1.1102(2) 0.0242(5) Uani 1 1 d . . . C2 C 0.56887(11) 0.1297(3) 1.2059(2) 0.0245(5) Uani 1 1 d . . . C3 C 0.61792(10) 0.0627(3) 1.2276(2) 0.0232(5) Uani 1 1 d . . . H3 H 0.6482 0.0899 1.1797 0.028 Uiso 1 1 calc R . . C4 C 0.62253(11) -0.0435(3) 1.3188(3) 0.0267(6) Uani 1 1 d . . . H4 H 0.6558 -0.0863 1.3312 0.032 Uiso 1 1 calc R . . C5 C 0.57778(11) -0.0877(3) 1.3931(3) 0.0256(5) Uani 1 1 d . . . C6 C 0.52839(11) -0.0208(3) 1.3710(3) 0.0275(6) Uani 1 1 d . . . H6 H 0.4981 -0.0477 1.4188 0.033 Uiso 1 1 calc R . . C7 C 0.52421(10) 0.0854(3) 1.2785(3) 0.0260(5) Uani 1 1 d . . . H7 H 0.4910 0.1276 1.2649 0.031 Uiso 1 1 calc R . . N2 N 0.56128(9) 0.4616(2) 0.8562(2) 0.0249(5) Uani 1 1 d . . . H2N2 H 0.5775(11) 0.415(3) 0.917(3) 0.022(7) Uiso 1 1 d . . . H1N2 H 0.5916(11) 0.504(3) 0.808(3) 0.028(8) Uiso 1 1 d . . . O3 O 0.58871(7) 0.75171(19) 0.8919(2) 0.0286(4) Uani 1 1 d . . . O4 O 0.67737(7) 0.87398(19) 0.76452(19) 0.0306(4) Uani 1 1 d . . . O5 O 0.70373(7) 0.7604(2) 0.5152(2) 0.0311(4) Uani 1 1 d . . . O6 O 0.67176(8) 0.4857(2) 0.45603(19) 0.0314(5) Uani 1 1 d . . . O7 O 0.58500(7) 0.35492(18) 0.58810(19) 0.0281(4) Uani 1 1 d . . . C8 C 0.52569(11) 0.5701(3) 0.9144(3) 0.0299(6) Uani 1 1 d . . . H8A H 0.5004 0.5273 0.9752 0.036 Uiso 1 1 calc R . . H8B H 0.5052 0.6141 0.8443 0.036 Uiso 1 1 calc R . . C9 C 0.55804(12) 0.6778(3) 0.9872(3) 0.0316(6) Uani 1 1 d . . . H9A H 0.5342 0.7402 1.0343 0.038 Uiso 1 1 calc R . . H9B H 0.5818 0.6340 1.0511 0.038 Uiso 1 1 calc R . . C10 C 0.61672(13) 0.8648(3) 0.9480(3) 0.0330(6) Uani 1 1 d . . . H10A H 0.6459 0.8315 1.0038 0.040 Uiso 1 1 calc R . . H10B H 0.5924 0.9191 1.0025 0.040 Uiso 1 1 calc R . . C11 C 0.63895(11) 0.9520(3) 0.8388(3) 0.0337(7) Uani 1 1 d . . . H11A H 0.6099 0.9820 0.7811 0.040 Uiso 1 1 calc R . . H11B H 0.6561 1.0335 0.8757 0.040 Uiso 1 1 calc R . . C12 C 0.70016(13) 0.9537(3) 0.6592(3) 0.0369(7) Uani 1 1 d . . . H12A H 0.7207 1.0302 0.6954 0.044 Uiso 1 1 calc R . . H12B H 0.6716 0.9913 0.6041 0.044 Uiso 1 1 calc R . . C13 C 0.73611(12) 0.8636(3) 0.5779(3) 0.0362(7) Uani 1 1 d . . . H13A H 0.7546 0.9184 0.5114 0.043 Uiso 1 1 calc R . . H13B H 0.7630 0.8203 0.6340 0.043 Uiso 1 1 calc R . . C14 C 0.73400(12) 0.6700(3) 0.4328(3) 0.0356(7) Uani 1 1 d . . . H14A H 0.7588 0.6159 0.4862 0.043 Uiso 1 1 calc R . . H14B H 0.7548 0.7230 0.3693 0.043 Uiso 1 1 calc R . . C15 C 0.69562(12) 0.5766(3) 0.3619(3) 0.0346(7) Uani 1 1 d . . . H15A H 0.6679 0.6308 0.3183 0.042 Uiso 1 1 calc R . . H15B H 0.7147 0.5238 0.2949 0.042 Uiso 1 1 calc R . . C16 C 0.63950(11) 0.3800(3) 0.3968(3) 0.0329(6) Uani 1 1 d . . . H16A H 0.6604 0.3303 0.3310 0.039 Uiso 1 1 calc R . . H16B H 0.6085 0.4208 0.3532 0.039 Uiso 1 1 calc R . . C17 C 0.62134(12) 0.2830(3) 0.5034(3) 0.0304(6) Uani 1 1 d . . . H17A H 0.6035 0.2036 0.4643 0.036 Uiso 1 1 calc R . . H17B H 0.6522 0.2505 0.5537 0.036 Uiso 1 1 calc R . . C18 C 0.56628(12) 0.2716(3) 0.6942(3) 0.0300(6) Uani 1 1 d . . . H18A H 0.5964 0.2388 0.7470 0.036 Uiso 1 1 calc R . . H18B H 0.5467 0.1922 0.6604 0.036 Uiso 1 1 calc R . . C19 C 0.52973(11) 0.3607(3) 0.7766(3) 0.0301(6) Uani 1 1 d . . . H19A H 0.5050 0.4100 0.7190 0.036 Uiso 1 1 calc R . . H19B H 0.5086 0.3028 0.8354 0.036 Uiso 1 1 calc R . . O1W O 0.65658(8) 0.5632(2) 0.7249(2) 0.0304(4) Uani 1 1 d . . . H1W1 H 0.6600(18) 0.552(5) 0.639(5) 0.088(16) Uiso 1 1 d . . . H2W1 H 0.6580(16) 0.648(5) 0.735(4) 0.061(12) Uiso 1 1 d . . . O2W O 0.72131(10) 0.3109(3) 0.7561(2) 0.0390(5) Uani 1 1 d . . . H1W2 H 0.7287(19) 0.283(5) 0.830(5) 0.082(16) Uiso 1 1 d . . . H2W2 H 0.7035(14) 0.386(4) 0.755(4) 0.055(12) Uiso 1 1 d . . . O3W O 0.71500(10) 0.2382(3) 1.0243(2) 0.0389(5) Uani 1 1 d . . . H1W3 H 0.7346(17) 0.272(4) 1.081(5) 0.061(13) Uiso 1 1 d . . . H2W3 H 0.6834(16) 0.256(4) 1.027(4) 0.051(11) 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 0.0328(10) 0.0342(10) 0.0261(10) 0.0077(8) 0.0012(9) 0.0005(9) O2 0.0308(10) 0.0285(9) 0.0262(10) 0.0048(8) -0.0009(8) 0.0015(8) N1 0.0317(14) 0.0385(14) 0.0422(16) 0.0196(12) 0.0011(12) 0.0017(12) C1 0.0334(14) 0.0238(12) 0.0153(11) -0.0009(10) -0.0026(11) -0.0033(11) C2 0.0332(14) 0.0211(12) 0.0192(13) -0.0046(10) -0.0041(11) -0.0026(11) C3 0.0300(13) 0.0238(13) 0.0157(11) -0.0008(10) 0.0011(10) -0.0003(10) C4 0.0297(14) 0.0249(13) 0.0255(13) -0.0028(11) -0.0008(11) 0.0037(12) C5 0.0350(13) 0.0200(12) 0.0219(12) 0.0002(10) -0.0002(12) 0.0000(11) C6 0.0296(13) 0.0269(13) 0.0260(13) 0.0009(10) 0.0004(11) -0.0052(11) C7 0.0268(13) 0.0240(12) 0.0271(13) -0.0030(11) -0.0033(11) 0.0012(11) N2 0.0301(12) 0.0278(12) 0.0169(10) 0.0034(9) 0.0001(9) -0.0003(10) O3 0.0354(10) 0.0276(9) 0.0228(9) -0.0045(7) -0.0001(9) -0.0028(8) O4 0.0354(10) 0.0256(9) 0.0309(11) 0.0009(8) 0.0018(9) 0.0006(8) O5 0.0325(10) 0.0274(10) 0.0333(11) 0.0009(8) 0.0025(9) -0.0002(8) O6 0.0415(11) 0.0279(10) 0.0248(10) -0.0015(8) 0.0047(8) -0.0045(9) O7 0.0367(10) 0.0249(9) 0.0225(9) 0.0006(7) 0.0019(8) 0.0024(8) C8 0.0319(14) 0.0279(13) 0.0301(14) 0.0038(11) 0.0064(12) 0.0035(11) C9 0.0387(15) 0.0311(15) 0.0250(13) 0.0001(11) 0.0054(12) 0.0014(12) C10 0.0355(15) 0.0344(16) 0.0290(14) -0.0134(12) -0.0014(12) 0.0028(13) C11 0.0346(15) 0.0249(14) 0.0415(17) -0.0082(12) -0.0054(13) -0.0006(12) C12 0.0520(19) 0.0249(14) 0.0336(16) 0.0034(13) -0.0033(13) -0.0092(13) C13 0.0386(15) 0.0343(15) 0.0355(16) 0.0053(13) -0.0002(13) -0.0119(13) C14 0.0361(16) 0.0332(15) 0.0374(16) 0.0049(12) 0.0124(13) 0.0017(12) C15 0.0445(16) 0.0311(15) 0.0282(15) 0.0042(12) 0.0133(13) 0.0038(13) C16 0.0374(15) 0.0361(16) 0.0252(14) -0.0084(12) 0.0024(13) 0.0000(13) C17 0.0344(14) 0.0280(15) 0.0287(15) -0.0087(12) -0.0008(12) -0.0008(12) C18 0.0395(15) 0.0251(13) 0.0253(14) -0.0012(10) -0.0028(12) -0.0051(12) C19 0.0363(16) 0.0323(14) 0.0216(12) 0.0025(12) 0.0001(12) -0.0060(12) O1W 0.0424(12) 0.0262(11) 0.0226(10) -0.0012(9) 0.0022(9) -0.0014(9) O2W 0.0488(14) 0.0362(12) 0.0321(13) 0.0008(10) -0.0011(11) 0.0056(11) O3W 0.0328(11) 0.0534(14) 0.0307(11) 0.0020(10) -0.0012(11) 0.0020(12) _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 1.275(3) . ? O2 C1 1.254(3) . ? N1 C5 1.380(3) . ? C1 C2 1.511(4) . ? C2 C3 1.395(4) . ? C2 C7 1.395(4) . ? C3 C4 1.384(4) . ? C4 C5 1.405(4) . ? C5 C6 1.403(4) . ? C6 C7 1.391(4) . ? N2 C19 1.486(3) . ? N2 C8 1.492(3) . ? O3 C10 1.414(3) . ? O3 C9 1.419(3) . ? O4 C11 1.428(3) . ? O4 C12 1.430(3) . ? O5 C14 1.421(4) . ? O5 C13 1.429(3) . ? O6 C15 1.423(3) . ? O6 C16 1.429(3) . ? O7 C18 1.418(3) . ? O7 C17 1.424(3) . ? C8 C9 1.506(4) . ? C10 C11 1.494(4) . ? C12 C13 1.493(4) . ? C14 C15 1.494(4) . ? C16 C17 1.496(4) . ? C18 C19 1.502(4) . ? 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 O2 C1 O1 123.6(2) . . ? O2 C1 C2 118.0(2) . . ? O1 C1 C2 118.4(2) . . ? C3 C2 C7 117.8(2) . . ? C3 C2 C1 122.4(2) . . ? C7 C2 C1 119.8(2) . . ? C4 C3 C2 121.4(2) . . ? C3 C4 C5 121.0(2) . . ? N1 C5 C6 121.0(2) . . ? N1 C5 C4 121.3(2) . . ? C6 C5 C4 117.6(2) . . ? C7 C6 C5 120.8(3) . . ? C6 C7 C2 121.3(2) . . ? C19 N2 C8 111.3(2) . . ? C10 O3 C9 112.4(2) . . ? C11 O4 C12 111.6(2) . . ? C14 O5 C13 113.1(2) . . ? C15 O6 C16 113.3(2) . . ? C18 O7 C17 112.45(19) . . ? N2 C8 C9 111.4(2) . . ? O3 C9 C8 107.7(2) . . ? O3 C10 C11 108.8(2) . . ? O4 C11 C10 109.5(2) . . ? O4 C12 C13 109.2(2) . . ? O5 C13 C12 108.4(2) . . ? O5 C14 C15 108.4(2) . . ? O6 C15 C14 108.6(2) . . ? O6 C16 C17 108.5(2) . . ? O7 C17 C16 108.4(2) . . ? O7 C18 C19 106.7(2) . . ? N2 C19 C18 111.0(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 H1N1 O5 0.88(3) 2.22(3) 3.061(3) 161(3) 1_546 N1 H2N1 O2 0.90(3) 2.08(3) 2.962(3) 167(3) 2_655 N2 H2N2 O1 0.86(3) 1.91(3) 2.759(3) 170(3) . N2 H1N2 O1W 0.98(3) 1.90(3) 2.881(3) 171(3) . O1W H1W1 O6 0.88(6) 1.97(6) 2.838(3) 167(5) . O1W H2W1 O4 0.83(4) 2.26(4) 3.077(3) 170(4) . O1W H2W1 O3 0.83(4) 2.54(4) 2.999(3) 116(3) . O2W H1W2 O3W 0.81(5) 2.04(5) 2.799(3) 156(5) . O2W H2W2 O1W 0.85(4) 2.09(4) 2.938(3) 172(4) . O3W H1W3 O2W 0.82(5) 2.11(5) 2.908(3) 164(4) 4_655 O3W H2W3 O1 0.80(4) 1.99(4) 2.784(3) 175(4) . _diffrn_measured_fraction_theta_max 0.835 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.835 _refine_diff_density_max 0.144 _refine_diff_density_min -0.148 _refine_diff_density_rms 0.032