# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Fabrizia Grepioni' 'Dario Braga' 'Samipillai Marivel' 'Katia Rubini' _publ_contact_author_name 'Fabrizia Grepioni' _publ_contact_author_email FABRIZIA.GREPIONI@UNIBO.IT _publ_section_title ; Mechanochemical preparation of adducts (co-crystals and molecular salts) of 1,4-diazabicyclo-[2.2.2] octane with aromatic polycarboxylic acids. ; # Attachment '1.cif' data_datam _database_code_depnum_ccdc_archive 'CCDC 753183' #TrackingRef '1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Isophthalic acid DABCO' _chemical_melting_point ? _chemical_formula_moiety 'C6 H12 N2, C8 H6 O4' _chemical_formula_sum 'C14 H18 N2 O4' _chemical_formula_weight 278.30 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 Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 17.216(3) _cell_length_b 6.674(1) _cell_length_c 23.473(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2697.0(8) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2826 _cell_measurement_theta_min 2.5151 _cell_measurement_theta_max 28.4954 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.371 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1184 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.84909 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Goniometer KM4/Xcalibur, detector: Sapphire3' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13073 _diffrn_reflns_av_R_equivalents 0.0518 _diffrn_reflns_av_sigmaI/netI 0.0927 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 28.57 _reflns_number_total 3078 _reflns_number_gt 1276 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^ > 2\s(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^)+(0.0701P)^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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3078 _refine_ls_number_parameters 183 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1838 _refine_ls_R_factor_gt 0.0575 _refine_ls_wR_factor_ref 0.1513 _refine_ls_wR_factor_gt 0.1145 _refine_ls_goodness_of_fit_ref 0.865 _refine_ls_restrained_S_all 0.865 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.13091(15) -0.4395(3) 0.62071(10) 0.0279(6) Uani 1 1 d . . . H1 H 0.1146 -0.3067 0.6203 0.033 Uiso 1 1 calc R . . C2 C 0.14457(16) -0.5387(4) 0.56929(10) 0.0290(7) Uani 1 1 d . . . C3 C 0.16772(17) -0.7377(4) 0.57080(11) 0.0355(7) Uani 1 1 d . . . H3 H 0.1773 -0.8051 0.5369 0.043 Uiso 1 1 calc R . . C4 C 0.17668(17) -0.8369(4) 0.62182(12) 0.0366(7) Uani 1 1 d . . . H4 H 0.1908 -0.9714 0.6222 0.044 Uiso 1 1 calc R . . C5 C 0.16453(17) -0.7354(4) 0.67250(11) 0.0347(7) Uani 1 1 d . . . H5 H 0.1720 -0.8015 0.7069 0.042 Uiso 1 1 calc R . . C6 C 0.14138(16) -0.5364(4) 0.67253(10) 0.0285(7) Uani 1 1 d . . . C7 C 0.13631(17) -0.4324(4) 0.51346(11) 0.0362(7) Uani 1 1 d . . . O1 O 0.15835(15) -0.5100(3) 0.46905(7) 0.0574(7) Uani 1 1 d . . . O2 O 0.10530(14) -0.2576(3) 0.51674(8) 0.0550(7) Uani 1 1 d . . . H20 H 0.1028 -0.2080 0.4848 0.066 Uiso 1 1 calc R . . C8 C 0.13068(17) -0.4265(4) 0.72808(11) 0.0339(7) Uani 1 1 d . . . O3 O 0.14835(15) -0.5086(3) 0.77280(8) 0.0601(7) Uani 1 1 d . . . O4 O 0.10366(14) -0.2492(3) 0.72367(8) 0.0487(6) Uani 1 1 d . . . H40 H 0.0994 -0.1996 0.7555 0.058 Uiso 1 1 calc R . . C9 C 0.1741(2) 0.0095(5) 0.33649(13) 0.0511(9) Uani 1 1 d . . . H9A H 0.2105 0.1198 0.3328 0.061 Uiso 1 1 calc R . . H9B H 0.1900 -0.0962 0.3106 0.061 Uiso 1 1 calc R . . C10 C 0.1745(2) -0.0680(6) 0.39739(13) 0.0689(11) Uani 1 1 d . . . H10A H 0.2012 -0.1959 0.3988 0.083 Uiso 1 1 calc R . . H10B H 0.2024 0.0253 0.4216 0.083 Uiso 1 1 calc R . . C11 C 0.0681(2) 0.2180(4) 0.36653(11) 0.0507(9) Uani 1 1 d . . . H11A H 0.0191 0.2773 0.3550 0.061 Uiso 1 1 calc R . . H11B H 0.1056 0.3250 0.3716 0.061 Uiso 1 1 calc R . . C12 C 0.0577(2) 0.1051(4) 0.42195(12) 0.0648(11) Uani 1 1 d . . . H12A H 0.0801 0.1817 0.4530 0.078 Uiso 1 1 calc R . . H12B H 0.0028 0.0875 0.4297 0.078 Uiso 1 1 calc R . . C13 C 0.04271(19) -0.0972(4) 0.32136(11) 0.0414(8) Uani 1 1 d . . . H13A H 0.0553 -0.1839 0.2895 0.050 Uiso 1 1 calc R . . H13B H -0.0106 -0.0525 0.3171 0.050 Uiso 1 1 calc R . . C14 C 0.0518(2) -0.2121(4) 0.37726(12) 0.0560(9) Uani 1 1 d . . . H14A H 0.0009 -0.2431 0.3927 0.067 Uiso 1 1 calc R . . H14B H 0.0787 -0.3373 0.3703 0.067 Uiso 1 1 calc R . . N1 N 0.09575(14) -0.0921(3) 0.41845(9) 0.0322(6) Uani 1 1 d . . . N2 N 0.09558(14) 0.0776(3) 0.32196(8) 0.0309(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0349(16) 0.0252(12) 0.0235(14) 0.0013(12) 0.0028(13) 0.0006(11) C2 0.0322(19) 0.0305(15) 0.0244(15) 0.0003(11) -0.0003(12) 0.0005(13) C3 0.042(2) 0.0383(16) 0.0263(15) -0.0072(13) 0.0026(14) 0.0037(14) C4 0.0454(19) 0.0246(13) 0.0397(17) 0.0000(14) 0.0015(17) 0.0092(12) C5 0.0408(19) 0.0356(16) 0.0277(15) 0.0096(13) -0.0022(14) 0.0016(13) C6 0.0337(18) 0.0296(14) 0.0223(14) 0.0021(11) 0.0028(13) -0.0023(13) C7 0.0447(19) 0.0397(16) 0.0242(15) 0.0019(13) 0.0013(14) 0.0003(16) O1 0.092(2) 0.0564(13) 0.0242(11) -0.0028(10) 0.0128(12) 0.0152(11) O2 0.0935(19) 0.0494(12) 0.0220(11) 0.0111(9) 0.0078(11) 0.0234(13) C8 0.051(2) 0.0315(15) 0.0193(15) 0.0010(12) -0.0003(13) 0.0014(15) O3 0.106(2) 0.0521(13) 0.0226(11) 0.0026(10) -0.0035(12) 0.0226(12) O4 0.0849(18) 0.0399(11) 0.0213(10) -0.0074(8) -0.0046(10) 0.0172(12) C9 0.039(2) 0.069(2) 0.0448(18) 0.0140(16) 0.0017(17) -0.0021(16) C10 0.042(2) 0.116(3) 0.049(2) 0.039(2) -0.0045(18) -0.001(2) C11 0.094(3) 0.0305(15) 0.0278(18) 0.0014(12) 0.0046(17) 0.0120(15) C12 0.117(4) 0.0427(19) 0.0345(19) -0.0019(15) 0.011(2) 0.0223(19) C13 0.051(2) 0.0448(18) 0.0284(16) 0.0046(13) -0.0109(15) -0.0101(15) C14 0.079(3) 0.0472(18) 0.0420(19) 0.0148(16) -0.0124(19) -0.0225(17) N1 0.0441(16) 0.0303(12) 0.0223(12) 0.0004(10) 0.0012(12) 0.0026(11) N2 0.0393(15) 0.0302(12) 0.0232(12) 0.0023(10) -0.0023(11) -0.0013(11) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.389(3) . ? C1 C2 1.396(3) . ? C1 H1 0.9300 . ? C2 C3 1.387(3) . ? C2 C7 1.497(3) . ? C3 C4 1.377(3) . ? C3 H3 0.9300 . ? C4 C5 1.385(3) . ? C4 H4 0.9300 . ? C5 C6 1.386(3) . ? C5 H5 0.9300 . ? C6 C8 1.507(3) . ? C7 O1 1.224(3) . ? C7 O2 1.285(3) . ? O2 H20 0.8200 . ? C8 O3 1.223(3) . ? C8 O4 1.275(3) . ? O4 H40 0.8200 . ? C9 N2 1.466(4) . ? C9 C10 1.520(4) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 N1 1.452(4) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 N2 1.482(3) . ? C11 C12 1.514(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 N1 1.472(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 N2 1.480(3) . ? C13 C14 1.528(4) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 N1 1.466(4) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? 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 C6 C1 C2 121.0(2) . . ? C6 C1 H1 119.5 . . ? C2 C1 H1 119.5 . . ? C3 C2 C1 118.7(2) . . ? C3 C2 C7 120.2(2) . . ? C1 C2 C7 121.1(2) . . ? C4 C3 C2 121.0(2) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C4 C5 119.6(2) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? C4 C5 C6 120.8(2) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C5 C6 C1 118.9(2) . . ? C5 C6 C8 120.1(2) . . ? C1 C6 C8 121.0(2) . . ? O1 C7 O2 124.3(3) . . ? O1 C7 C2 121.0(2) . . ? O2 C7 C2 114.7(2) . . ? C7 O2 H20 109.5 . . ? O3 C8 O4 125.2(2) . . ? O3 C8 C6 119.6(2) . . ? O4 C8 C6 115.2(2) . . ? C8 O4 H40 109.5 . . ? N2 C9 C10 109.2(3) . . ? N2 C9 H9A 109.8 . . ? C10 C9 H9A 109.8 . . ? N2 C9 H9B 109.8 . . ? C10 C9 H9B 109.8 . . ? H9A C9 H9B 108.3 . . ? N1 C10 C9 110.7(3) . . ? N1 C10 H10A 109.5 . . ? C9 C10 H10A 109.5 . . ? N1 C10 H10B 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 108.1 . . ? N2 C11 C12 109.2(2) . . ? N2 C11 H11A 109.8 . . ? C12 C11 H11A 109.8 . . ? N2 C11 H11B 109.8 . . ? C12 C11 H11B 109.8 . . ? H11A C11 H11B 108.3 . . ? N1 C12 C11 110.1(2) . . ? N1 C12 H12A 109.6 . . ? C11 C12 H12A 109.6 . . ? N1 C12 H12B 109.6 . . ? C11 C12 H12B 109.6 . . ? H12A C12 H12B 108.1 . . ? N2 C13 C14 108.9(2) . . ? N2 C13 H13A 109.9 . . ? C14 C13 H13A 109.9 . . ? N2 C13 H13B 109.9 . . ? C14 C13 H13B 109.9 . . ? H13A C13 H13B 108.3 . . ? N1 C14 C13 110.2(2) . . ? N1 C14 H14A 109.6 . . ? C13 C14 H14A 109.6 . . ? N1 C14 H14B 109.6 . . ? C13 C14 H14B 109.6 . . ? H14A C14 H14B 108.1 . . ? C10 N1 C14 108.5(3) . . ? C10 N1 C12 109.6(3) . . ? C14 N1 C12 107.2(2) . . ? C9 N2 C13 109.0(2) . . ? C9 N2 C11 109.0(2) . . ? C13 N2 C11 108.0(2) . . ? _diffrn_measured_fraction_theta_max 0.896 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.286 _refine_diff_density_min -0.240 _refine_diff_density_rms 0.042 # Attachment '2.cif' data_datam2 _database_code_depnum_ccdc_archive 'CCDC 753184' #TrackingRef '2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Dinicotinic acid DABCO' _chemical_melting_point ? _chemical_formula_moiety 'C12 H25 N4, C14 H9 N2 O8' _chemical_formula_sum 'C26 H34 N6 O8' _chemical_formula_weight 558.59 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/m' 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' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 21.223(2) _cell_length_b 6.675(1) _cell_length_c 10.304(1) _cell_angle_alpha 90.00 _cell_angle_beta 116.450(10) _cell_angle_gamma 90.00 _cell_volume 1306.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.419 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.93578 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Goniometer KM4/Xcalibur, detector: Sapphire3' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6270 _diffrn_reflns_av_R_equivalents 0.0312 _diffrn_reflns_av_sigmaI/netI 0.0489 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.23 _diffrn_reflns_theta_max 29.27 _reflns_number_total 1695 _reflns_number_gt 981 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^ > 2\s(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^)+(0.0655P)^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_number_reflns 1695 _refine_ls_number_parameters 140 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0905 _refine_ls_R_factor_gt 0.0428 _refine_ls_wR_factor_ref 0.1136 _refine_ls_wR_factor_gt 0.1030 _refine_ls_goodness_of_fit_ref 0.918 _refine_ls_restrained_S_all 0.918 _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 C1 C 0.28942(12) 0.0000 0.0137(2) 0.0348(6) Uani 1 2 d S . . H1 H 0.3370 0.0000 0.0783 0.042 Uiso 1 2 calc SR . . C2 C 0.24171(11) 0.0000 0.0705(2) 0.0292(5) Uani 1 2 d S . . C3 C 0.17081(12) 0.0000 -0.0260(2) 0.0314(5) Uani 1 2 d S . . H3 H 0.1369 0.0000 0.0079 0.038 Uiso 1 2 calc SR . . C4 C 0.15090(11) 0.0000 -0.1736(2) 0.0298(5) Uani 1 2 d S . . C5 C 0.20356(12) 0.0000 -0.2183(2) 0.0343(5) Uani 1 2 d S . . H5 H 0.1902 0.0000 -0.3174 0.041 Uiso 1 2 calc SR . . C6 C 0.26522(14) 0.0000 0.2316(2) 0.0393(6) Uani 1 2 d S . . C7 C 0.07430(13) 0.0000 -0.2807(2) 0.0363(6) Uani 1 2 d S . . N1 N 0.27208(10) 0.0000 -0.12807(19) 0.0390(5) Uani 1 2 d S . . O1 O 0.33317(9) 0.0000 0.30601(16) 0.0566(5) Uani 1 2 d S . . H1A H 0.3436 0.0088 0.3926 0.085 Uiso 0.50 1 calc PR . . O2 O 0.22293(10) 0.0000 0.28173(18) 0.0559(5) Uani 1 2 d S . . O3 O 0.02900(9) 0.0000 -0.23807(18) 0.0526(5) Uani 1 2 d S . . O4 O 0.06258(8) 0.0000 -0.41423(17) 0.0565(5) Uani 1 2 d S . . H4 H 0.0000 0.0000 -0.5000 0.068 Uiso 1 4 d S . . C8 C 0.41180(10) 0.1815(3) 0.80880(17) 0.0391(4) Uani 1 1 d . . . H8B H 0.3799(8) 0.175(2) 0.8525(17) 0.039(5) Uiso 1 1 d . . . H8A H 0.4442(10) 0.299(3) 0.8426(19) 0.054(5) Uiso 1 1 d . . . C9 C 0.36900(13) 0.1813(4) 0.64358(19) 0.0563(6) Uani 1 1 d . . . H13B H 0.3822(11) 0.299(4) 0.600(2) 0.083(7) Uiso 1 1 d . . . H13A H 0.3214(13) 0.173(4) 0.621(2) 0.086(8) Uiso 1 1 d . . . C10 C 0.50461(12) 0.0000 0.7852(2) 0.0376(6) Uani 1 2 d S . . H10A H 0.5350(9) -0.119(2) 0.8180(16) 0.038(4) Uiso 1 1 d . . . C11 C 0.46081(15) 0.0000 0.6209(3) 0.0485(7) Uani 1 2 d S . . H12A H 0.4707(11) 0.115(3) 0.578(2) 0.073(6) Uiso 1 1 d . . . N2 N 0.45713(9) 0.0000 0.85531(17) 0.0325(5) Uani 1 2 d S . . H2B H 0.5000 0.0000 1.0000 0.039 Uiso 1 4 d S . . N3 N 0.38551(10) 0.0000 0.58269(18) 0.0389(5) Uani 1 2 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0298(12) 0.0375(14) 0.0288(11) 0.000 0.0055(9) 0.000 C2 0.0330(12) 0.0251(12) 0.0250(10) 0.000 0.0090(9) 0.000 C3 0.0336(12) 0.0302(13) 0.0313(11) 0.000 0.0153(9) 0.000 C4 0.0298(12) 0.0272(12) 0.0271(10) 0.000 0.0079(9) 0.000 C5 0.0366(14) 0.0384(14) 0.0227(10) 0.000 0.0086(9) 0.000 C6 0.0496(16) 0.0340(14) 0.0260(11) 0.000 0.0093(11) 0.000 C7 0.0358(14) 0.0314(14) 0.0347(12) 0.000 0.0093(10) 0.000 N1 0.0338(11) 0.0472(13) 0.0331(10) 0.000 0.0124(8) 0.000 O1 0.0513(12) 0.0814(14) 0.0208(8) 0.000 0.0015(8) 0.000 O2 0.0651(13) 0.0724(14) 0.0351(9) 0.000 0.0267(9) 0.000 O3 0.0319(10) 0.0727(13) 0.0485(10) 0.000 0.0137(8) 0.000 O4 0.0351(10) 0.0900(14) 0.0289(9) 0.000 0.0004(7) 0.000 C8 0.0421(10) 0.0421(11) 0.0354(9) -0.0025(7) 0.0193(7) 0.0042(10) C9 0.0582(14) 0.0636(16) 0.0377(10) 0.0037(9) 0.0130(9) 0.0229(12) C10 0.0283(13) 0.0458(17) 0.0377(13) 0.000 0.0137(10) 0.000 C11 0.0504(17) 0.066(2) 0.0369(14) 0.000 0.0263(12) 0.000 N2 0.0337(10) 0.0397(12) 0.0218(8) 0.000 0.0103(8) 0.000 N3 0.0375(12) 0.0516(13) 0.0227(9) 0.000 0.0089(8) 0.000 _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.338(3) . ? C1 C2 1.377(3) . ? C1 H1 0.9300 . ? C2 C3 1.386(3) . ? C2 C6 1.505(3) . ? C3 C4 1.385(3) . ? C3 H3 0.9300 . ? C4 C5 1.385(3) . ? C4 C7 1.504(3) . ? C5 N1 1.332(3) . ? C5 H5 0.9300 . ? C6 O2 1.219(3) . ? C6 O1 1.297(3) . ? C7 O3 1.222(3) . ? C7 O4 1.285(3) . ? O1 H1A 0.8200 . ? O4 H4 1.2245(15) . ? C8 N2 1.487(2) . ? C8 C9 1.532(2) . ? C8 H8B 0.967(16) . ? C8 H8A 1.00(2) . ? C9 N3 1.475(2) . ? C9 H13B 1.01(2) . ? C9 H13A 0.93(2) . ? C10 N2 1.479(3) . ? C10 C11 1.525(3) . ? C10 H10A 0.983(16) . ? C11 N3 1.466(3) . ? C11 H12A 0.953(19) . ? N2 C8 1.487(2) 6 ? N2 H2B 1.3572(16) . ? N3 C9 1.475(2) 6 ? 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 N1 C1 C2 124.6(2) . . ? N1 C1 H1 117.7 . . ? C2 C1 H1 117.7 . . ? C1 C2 C3 117.62(19) . . ? C1 C2 C6 121.6(2) . . ? C3 C2 C6 120.8(2) . . ? C4 C3 C2 119.4(2) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C3 C4 C5 117.91(19) . . ? C3 C4 C7 120.5(2) . . ? C5 C4 C7 121.62(19) . . ? N1 C5 C4 124.02(19) . . ? N1 C5 H5 118.0 . . ? C4 C5 H5 118.0 . . ? O2 C6 O1 125.7(2) . . ? O2 C6 C2 121.5(2) . . ? O1 C6 C2 112.8(2) . . ? O3 C7 O4 125.2(2) . . ? O3 C7 C4 120.2(2) . . ? O4 C7 C4 114.6(2) . . ? C5 N1 C1 116.5(2) . . ? C6 O1 H1A 109.5 . . ? C7 O4 H4 113.79(17) . . ? N2 C8 C9 109.62(14) . . ? N2 C8 H8B 107.4(10) . . ? C9 C8 H8B 109.0(9) . . ? N2 C8 H8A 106.3(11) . . ? C9 C8 H8A 111.4(10) . . ? H8B C8 H8A 113.0(14) . . ? N3 C9 C8 109.74(16) . . ? N3 C9 H13B 106.7(13) . . ? C8 C9 H13B 110.5(13) . . ? N3 C9 H13A 106.6(15) . . ? C8 C9 H13A 108.3(14) . . ? H13B C9 H13A 115(2) . . ? N2 C10 C11 109.34(19) . . ? N2 C10 H10A 108.5(9) . . ? C11 C10 H10A 111.3(9) . . ? N3 C11 C10 110.55(19) . . ? N3 C11 H12A 108.3(13) . . ? C10 C11 H12A 111.2(13) . . ? C10 N2 C8 109.05(11) . 6 ? C10 N2 C8 109.05(11) . . ? C8 N2 C8 109.07(19) 6 . ? C10 N2 H2B 105.53(14) . . ? C8 N2 H2B 112.02(9) 6 . ? C8 N2 H2B 112.02(9) . . ? C11 N3 C9 108.83(14) . 6 ? C11 N3 C9 108.83(14) . . ? C9 N3 C9 110.2(2) 6 . ? _diffrn_measured_fraction_theta_max 0.878 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.269 _refine_diff_density_min -0.252 _refine_diff_density_rms 0.044 # Attachment '3.cif' data_datam3 _database_code_depnum_ccdc_archive 'CCDC 753185' #TrackingRef '3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Dipicolinic acid DABCO' _chemical_melting_point ? _chemical_formula_moiety 'C6 H13 N2, C7 H4 N O4' _chemical_formula_sum 'C13 H17 N3 O4' _chemical_formula_weight 279.30 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 10.275(1) _cell_length_b 7.122(1) _cell_length_c 17.450(1) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1277.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4374 _cell_measurement_theta_min 2.8553 _cell_measurement_theta_max 28.9265 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.453 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 0.109 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.98508 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Goniometer KM4/Xcalibur, detector: Sapphire3' _diffrn_measurement_method 'Omega Scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7919 _diffrn_reflns_av_R_equivalents 0.0184 _diffrn_reflns_av_sigmaI/netI 0.0144 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 28.99 _reflns_number_total 1671 _reflns_number_gt 1292 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0833P)^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_number_reflns 1671 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0541 _refine_ls_R_factor_gt 0.0400 _refine_ls_wR_factor_ref 0.1219 _refine_ls_wR_factor_gt 0.1158 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.01761(15) 0.2500 0.50891(9) 0.0322(4) Uani 1 2 d S . . C2 C -0.08460(16) 0.2500 0.45686(10) 0.0423(5) Uani 1 2 d S . . H2 H -0.1704 0.2500 0.4739 0.048(5) Uiso 1 2 calc SR . . C3 C -0.05705(19) 0.2500 0.37972(11) 0.0464(5) Uani 1 2 d S . . H3 H -0.1236 0.2500 0.3436 0.053(6) Uiso 1 2 calc SR . . C4 C 0.07110(18) 0.2500 0.35724(9) 0.0380(4) Uani 1 2 d S . . H4 H 0.0925 0.2500 0.3055 0.045(5) Uiso 1 2 calc SR . . C5 C 0.16864(15) 0.2500 0.41265(8) 0.0288(4) Uani 1 2 d S . . C6 C 0.30957(16) 0.2500 0.38514(8) 0.0347(4) Uani 1 2 d S . . C7 C -0.01832(16) 0.2500 0.59297(9) 0.0377(4) Uani 1 2 d S . . N1 N 0.14343(12) 0.2500 0.48819(7) 0.0291(3) Uani 1 2 d S . . O1 O -0.13228(12) 0.2500 0.61146(7) 0.0657(6) Uani 1 2 d S . . O2 O 0.07662(11) 0.2500 0.64146(6) 0.0458(4) Uani 1 2 d S . . H2A H 0.0432 0.2500 0.6907 0.050 Uiso 1 2 d S . . O3 O 0.39934(11) 0.2500 0.43457(7) 0.0470(4) Uani 1 2 d S . . O4 O 0.32830(14) 0.2500 0.31529(7) 0.0602(5) Uani 1 2 d S . . C8 C 0.41286(13) 0.0795(2) 0.70249(8) 0.0448(4) Uani 1 1 d . . . C9 C 0.36867(12) 0.0785(2) 0.61903(7) 0.0374(3) Uani 1 1 d . . . C10 C 0.56606(15) 0.2500 0.58494(9) 0.0392(4) Uani 1 2 d S . . C11 C 0.60650(16) 0.2500 0.66903(10) 0.0408(5) Uani 1 2 d S . . N2 N 0.48967(12) 0.2500 0.71917(7) 0.0383(4) Uani 1 2 d S . . N3 N 0.42036(12) 0.2500 0.58108(8) 0.0321(3) Uani 1 2 d S . . H8A H 0.4645(17) -0.032(3) 0.7123(9) 0.068(5) Uiso 1 1 d . . . H8B H 0.3366(15) 0.086(3) 0.7347(9) 0.068(5) Uiso 1 1 d . . . H9A H 0.4026(15) -0.032(2) 0.5925(8) 0.051(4) Uiso 1 1 d . . . H9B H 0.2768(14) 0.082(2) 0.6143(7) 0.044(4) Uiso 1 1 d . . . H10A H 0.5969(14) 0.138(2) 0.5571(8) 0.045(4) Uiso 1 1 d . . . H11A H 0.6578(13) 0.135(2) 0.6795(7) 0.047(4) Uiso 1 1 d . . . H3A H 0.3997(18) 0.2500 0.5247(11) 0.042(5) Uiso 1 2 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0296(8) 0.0360(9) 0.0310(8) 0.000 -0.0006(6) 0.000 C2 0.0289(8) 0.0553(12) 0.0427(10) 0.000 -0.0038(7) 0.000 C3 0.0415(10) 0.0603(13) 0.0373(9) 0.000 -0.0140(8) 0.000 C4 0.0477(10) 0.0412(10) 0.0251(8) 0.000 -0.0055(6) 0.000 C5 0.0339(8) 0.0291(8) 0.0233(7) 0.000 -0.0010(6) 0.000 C6 0.0383(9) 0.0418(10) 0.0239(8) 0.000 0.0032(6) 0.000 C7 0.0293(8) 0.0489(11) 0.0348(9) 0.000 0.0067(6) 0.000 N1 0.0285(6) 0.0367(8) 0.0222(6) 0.000 0.0007(5) 0.000 O1 0.0283(7) 0.1244(16) 0.0445(8) 0.000 0.0097(6) 0.000 O2 0.0297(6) 0.0829(11) 0.0248(6) 0.000 0.0060(4) 0.000 O3 0.0323(6) 0.0801(11) 0.0287(6) 0.000 0.0035(5) 0.000 O4 0.0531(8) 0.1037(14) 0.0237(6) 0.000 0.0093(5) 0.000 C8 0.0383(7) 0.0608(9) 0.0352(6) 0.0114(7) 0.0029(5) -0.0042(6) C9 0.0307(6) 0.0427(7) 0.0388(7) -0.0012(6) -0.0008(5) -0.0012(5) C10 0.0266(8) 0.0627(13) 0.0282(8) 0.000 0.0047(6) 0.000 C11 0.0223(7) 0.0685(14) 0.0314(8) 0.000 -0.0004(6) 0.000 N2 0.0263(7) 0.0645(11) 0.0243(7) 0.000 0.0007(5) 0.000 N3 0.0257(6) 0.0456(8) 0.0249(6) 0.000 -0.0009(5) 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 C1 N1 1.342(2) . ? C1 C2 1.388(2) . ? C1 C7 1.513(2) . ? C2 C3 1.376(3) . ? C3 C4 1.374(3) . ? C4 C5 1.393(2) . ? C5 N1 1.3435(19) . ? C5 C6 1.525(2) . ? C6 O4 1.2339(19) . ? C6 O3 1.263(2) . ? C7 O1 1.215(2) . ? C7 O2 1.291(2) . ? C8 N2 1.4771(16) . ? C8 C9 1.5256(18) . ? C9 N3 1.4872(15) . ? C10 N3 1.499(2) . ? C10 C11 1.525(2) . ? C11 N2 1.485(2) . ? N2 C8 1.4771(16) 7_565 ? N3 C9 1.4872(15) 7_565 ? 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 N1 C1 C2 123.53(15) . . ? N1 C1 C7 119.74(14) . . ? C2 C1 C7 116.73(15) . . ? C3 C2 C1 118.97(16) . . ? C4 C3 C2 118.47(16) . . ? C3 C4 C5 119.44(16) . . ? N1 C5 C4 122.85(15) . . ? N1 C5 C6 119.46(13) . . ? C4 C5 C6 117.69(14) . . ? O4 C6 O3 124.11(15) . . ? O4 C6 C5 117.31(14) . . ? O3 C6 C5 118.58(14) . . ? O1 C7 O2 123.65(15) . . ? O1 C7 C1 119.53(15) . . ? O2 C7 C1 116.82(14) . . ? C5 N1 C1 116.73(13) . . ? N2 C8 C9 110.55(11) . . ? N3 C9 C8 108.36(11) . . ? N3 C10 C11 108.39(13) . . ? N2 C11 C10 110.28(13) . . ? C8 N2 C8 110.56(15) . 7_565 ? C8 N2 C11 108.40(8) . . ? C8 N2 C11 108.40(8) 7_565 . ? C9 N3 C9 110.39(13) . 7_565 ? C9 N3 C10 109.68(8) . . ? C9 N3 C10 109.68(8) 7_565 . ? _diffrn_measured_fraction_theta_max 0.917 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.231 _refine_diff_density_min -0.320 _refine_diff_density_rms 0.059 # Attachment '2bis.CIF' data_[DABCOH]2_[din]_.2H2O _database_code_depnum_ccdc_archive 'CCDC 761019' #TrackingRef '2bis.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H33 N5 O6' _chemical_formula_weight 427.50 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.3743(7) _cell_length_b 10.3573(6) _cell_length_c 12.2042(7) _cell_angle_alpha 84.468(5) _cell_angle_beta 83.268(5) _cell_angle_gamma 67.587(7) _cell_volume 1086.15(12) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.307 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 460 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.89442 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23112 _diffrn_reflns_av_R_equivalents 0.0263 _diffrn_reflns_av_sigmaI/netI 0.0415 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.64 _diffrn_reflns_theta_max 28.00 _reflns_number_total 5046 _reflns_number_gt 2930 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1043P)^2^+0.1323P] 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 5046 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1207 _refine_ls_R_factor_gt 0.0677 _refine_ls_wR_factor_ref 0.1984 _refine_ls_wR_factor_gt 0.1786 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.001 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 N1 N 0.8837(2) 0.86036(19) -0.03628(15) 0.0477(5) Uani 1 1 d . . . C1 C 0.9660(2) 0.7637(2) 0.14240(19) 0.0379(5) Uani 1 1 d . . . C2 C 0.8997(2) 0.8948(2) 0.18362(18) 0.0381(5) Uani 1 1 d . . . H2 H 0.9053 0.9064 0.2574 0.046 Uiso 1 1 calc R . . C3 C 0.8248(2) 1.0090(2) 0.11509(17) 0.0356(5) Uani 1 1 d . . . C4 C 0.8215(3) 0.9844(2) 0.00648(18) 0.0420(5) Uani 1 1 d . . . H4 H 0.7717 1.0610 -0.0403 0.050 Uiso 1 1 calc R . . C5 C 0.9547(3) 0.7529(2) 0.0323(2) 0.0436(6) Uani 1 1 d . . . H5 H 0.9997 0.6646 0.0041 0.052 Uiso 1 1 calc R . . C6 C 0.7495(3) 1.1568(2) 0.1551(2) 0.0499(6) Uani 1 1 d . . . O1 O 0.6862(2) 1.25234(17) 0.08674(18) 0.0741(6) Uani 1 1 d . . . O2 O 0.7607(3) 1.1726(2) 0.25229(19) 0.0911(7) Uani 1 1 d . . . C7 C 1.0420(3) 0.6353(3) 0.2169(3) 0.0545(7) Uani 1 1 d . . . O3 O 1.0963(3) 0.52070(19) 0.1724(2) 0.0844(7) Uani 1 1 d . . . O4 O 1.0440(3) 0.6512(2) 0.3152(2) 0.0887(7) Uani 1 1 d . . . C8 C 1.3367(3) 0.2063(3) 0.2536(3) 0.0638(7) Uani 1 1 d . . . H8A H 1.4104 0.2522 0.2467 0.077 Uiso 1 1 calc R . . H8B H 1.3211 0.1886 0.1801 0.077 Uiso 1 1 calc R . . C9 C 1.3974(3) 0.0686(3) 0.3236(3) 0.0666(8) Uani 1 1 d . . . H9A H 1.4287 -0.0095 0.2763 0.080 Uiso 1 1 calc R . . H9B H 1.4876 0.0635 0.3581 0.080 Uiso 1 1 calc R . . C10 C 1.2063(4) 0.3094(3) 0.4261(3) 0.0702(8) Uani 1 1 d . . . H10A H 1.1105 0.3739 0.4609 0.084 Uiso 1 1 calc R . . H10B H 1.2873 0.3452 0.4296 0.084 Uiso 1 1 calc R . . C11 C 1.2489(5) 0.1656(3) 0.4850(2) 0.0809(10) Uani 1 1 d . . . H11A H 1.3405 0.1454 0.5236 0.097 Uiso 1 1 calc R . . H11B H 1.1650 0.1651 0.5396 0.097 Uiso 1 1 calc R . . C12 C 1.0731(3) 0.2300(3) 0.3052(2) 0.0605(7) Uani 1 1 d . . . H12A H 1.0526 0.2297 0.2291 0.073 Uiso 1 1 calc R . . H12B H 0.9765 0.2818 0.3468 0.073 Uiso 1 1 calc R . . C13 C 1.1413(4) 0.0811(3) 0.3544(3) 0.0762(9) Uani 1 1 d . . . H13A H 1.0647 0.0627 0.4072 0.091 Uiso 1 1 calc R . . H13B H 1.1674 0.0163 0.2961 0.091 Uiso 1 1 calc R . . N2 N 0.5056(2) 0.7535(2) 0.2145(2) 0.0584(6) Uani 1 1 d . . . N3 N 0.6115(2) 0.5023(2) 0.1705(2) 0.0569(6) Uani 1 1 d . . . H30 H 0.640(3) 0.416(3) 0.147(2) 0.068 Uiso 1 1 d . . . N4 N 1.1876(2) 0.29569(18) 0.31032(17) 0.0474(5) Uani 1 1 d . . . H40 H 1.160(3) 0.380(3) 0.273(2) 0.057 Uiso 1 1 d . . . N5 N 1.2786(3) 0.05812(19) 0.40876(17) 0.0517(5) Uani 1 1 d . . . C14 C 0.5787(3) 0.7378(3) 0.1036(2) 0.0657(8) Uani 1 1 d . . . H14A H 0.6672 0.7655 0.0982 0.079 Uiso 1 1 calc R . . H14B H 0.5062 0.7990 0.0530 0.079 Uiso 1 1 calc R . . C15 C 0.6301(5) 0.5929(4) 0.0715(3) 0.0922(12) Uani 1 1 d . . . H15A H 0.7378 0.5608 0.0422 0.111 Uiso 1 1 calc R . . H15B H 0.5689 0.5877 0.0145 0.111 Uiso 1 1 calc R . . C16 C 0.6197(4) 0.6718(4) 0.2896(3) 0.0789(10) Uani 1 1 d . . . H16A H 0.5701 0.6736 0.3641 0.095 Uiso 1 1 calc R . . H16B H 0.6975 0.7124 0.2891 0.095 Uiso 1 1 calc R . . C17 C 0.6975(5) 0.5200(3) 0.2558(4) 0.0997(13) Uani 1 1 d . . . H17A H 0.8044 0.5007 0.2277 0.120 Uiso 1 1 calc R . . H17B H 0.6962 0.4560 0.3191 0.120 Uiso 1 1 calc R . . C18 C 0.3819(3) 0.6989(2) 0.2250(3) 0.0601(7) Uani 1 1 d . . . H18A H 0.3095 0.7468 0.1701 0.072 Uiso 1 1 calc R . . H18B H 0.3261 0.7168 0.2975 0.072 Uiso 1 1 calc R . . C19 C 0.4467(3) 0.5436(3) 0.2093(3) 0.0634(8) Uani 1 1 d . . . H19A H 0.4348 0.4928 0.2786 0.076 Uiso 1 1 calc R . . H19B H 0.3917 0.5223 0.1554 0.076 Uiso 1 1 calc R . . O5 O 1.2309(4) 0.5949(3) 0.4872(2) 0.1055(9) Uani 1 1 d . . . H50 H 1.154(6) 0.646(5) 0.426(5) 0.158 Uiso 1 1 d . . . H51 H 1.256(6) 0.681(5) 0.488(4) 0.158 Uiso 1 1 d . . . O6 O 0.6494(3) 1.2066(2) 0.46807(18) 0.0798(7) Uani 1 1 d . . . H60 H 0.683(5) 1.105(4) 0.504(3) 0.120 Uiso 1 1 d . . . H61 H 0.752(5) 1.160(4) 0.434(4) 0.120 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 N1 0.0596(12) 0.0370(10) 0.0380(11) -0.0036(8) -0.0041(9) -0.0083(9) C1 0.0293(11) 0.0325(11) 0.0504(14) 0.0106(9) -0.0067(9) -0.0121(9) C2 0.0388(12) 0.0427(12) 0.0359(12) 0.0039(9) -0.0072(9) -0.0192(10) C3 0.0373(11) 0.0291(10) 0.0393(12) -0.0024(8) 0.0000(9) -0.0120(9) C4 0.0492(13) 0.0289(11) 0.0372(13) 0.0046(9) -0.0073(10) -0.0034(9) C5 0.0416(13) 0.0263(10) 0.0550(15) -0.0050(10) 0.0018(11) -0.0048(9) C6 0.0519(15) 0.0398(13) 0.0571(17) -0.0157(11) 0.0093(12) -0.0171(11) O1 0.0875(14) 0.0275(9) 0.0876(15) -0.0081(9) -0.0126(12) 0.0031(9) O2 0.136(2) 0.0734(14) 0.0608(14) -0.0338(11) 0.0072(13) -0.0338(14) C7 0.0404(14) 0.0454(15) 0.074(2) 0.0230(13) -0.0144(13) -0.0160(11) O3 0.0869(15) 0.0345(10) 0.1083(18) 0.0235(10) -0.0140(13) -0.0013(10) O4 0.1019(17) 0.0808(15) 0.0733(16) 0.0357(12) -0.0419(13) -0.0228(13) C8 0.0584(16) 0.0464(14) 0.0746(19) 0.0072(13) 0.0032(14) -0.0114(12) C9 0.0679(18) 0.0330(13) 0.086(2) -0.0010(12) -0.0054(16) -0.0050(12) C10 0.097(2) 0.0359(13) 0.0706(19) -0.0124(12) -0.0226(16) -0.0105(14) C11 0.132(3) 0.0512(16) 0.0480(17) -0.0006(13) -0.0250(17) -0.0164(17) C12 0.0580(16) 0.0618(16) 0.0615(17) 0.0034(13) -0.0216(13) -0.0191(13) C13 0.086(2) 0.0606(17) 0.095(2) 0.0141(16) -0.0258(18) -0.0418(17) N2 0.0483(12) 0.0334(10) 0.0901(18) -0.0139(10) 0.0119(12) -0.0143(9) N3 0.0531(13) 0.0289(10) 0.0838(17) -0.0203(10) -0.0025(11) -0.0067(9) N4 0.0546(13) 0.0241(9) 0.0545(13) 0.0091(8) -0.0134(10) -0.0048(8) N5 0.0715(14) 0.0312(10) 0.0502(12) 0.0070(8) -0.0173(11) -0.0157(9) C14 0.0551(16) 0.0688(18) 0.075(2) 0.0163(15) -0.0089(14) -0.0284(14) C15 0.119(3) 0.103(3) 0.069(2) -0.0343(19) 0.038(2) -0.064(2) C16 0.092(2) 0.103(3) 0.0633(19) -0.0334(18) -0.0076(17) -0.054(2) C17 0.094(3) 0.068(2) 0.131(3) 0.022(2) -0.066(2) -0.0136(19) C18 0.0415(14) 0.0439(14) 0.085(2) 0.0034(13) 0.0100(13) -0.0110(11) C19 0.0528(16) 0.0531(16) 0.091(2) -0.0171(14) 0.0100(14) -0.0284(13) O5 0.167(3) 0.1019(19) 0.0778(16) 0.0176(14) -0.0436(17) -0.0804(19) O6 0.1224(19) 0.0519(12) 0.0660(14) 0.0013(10) -0.0032(13) -0.0360(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 N1 C4 1.323(3) . ? N1 C5 1.330(3) . ? C1 C5 1.379(3) . ? C1 C2 1.378(3) . ? C1 C7 1.516(3) . ? C2 C3 1.380(3) . ? C2 H2 0.9300 . ? C3 C4 1.380(3) . ? C3 C6 1.523(3) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 O2 1.235(3) . ? C6 O1 1.239(3) . ? C7 O4 1.230(3) . ? C7 O3 1.249(3) . ? C8 N4 1.484(3) . ? C8 C9 1.532(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 N5 1.460(4) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 N4 1.471(4) . ? C10 C11 1.518(4) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 N5 1.444(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 N4 1.483(3) . ? C12 C13 1.519(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 N5 1.445(4) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? N2 C14 1.437(4) . ? N2 C16 1.446(4) . ? N2 C18 1.460(3) . ? N3 C17 1.454(4) . ? N3 C19 1.468(3) . ? N3 C15 1.493(4) . ? N3 H30 0.90(3) . ? N4 H40 0.91(3) . ? C14 C15 1.468(4) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.534(5) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.510(3) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? O5 H50 1.05(6) . ? O5 H51 1.01(5) . ? O6 H60 1.04(4) . ? O6 H61 0.96(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 C4 N1 C5 116.21(19) . . ? C5 C1 C2 117.60(18) . . ? C5 C1 C7 121.3(2) . . ? C2 C1 C7 121.1(2) . . ? C1 C2 C3 119.8(2) . . ? C1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? C4 C3 C2 117.05(19) . . ? C4 C3 C6 120.41(19) . . ? C2 C3 C6 122.5(2) . . ? N1 C4 C3 125.02(19) . . ? N1 C4 H4 117.5 . . ? C3 C4 H4 117.5 . . ? N1 C5 C1 124.3(2) . . ? N1 C5 H5 117.8 . . ? C1 C5 H5 117.8 . . ? O2 C6 O1 125.1(2) . . ? O2 C6 C3 117.3(2) . . ? O1 C6 C3 117.5(2) . . ? O4 C7 O3 125.3(2) . . ? O4 C7 C1 118.2(2) . . ? O3 C7 C1 116.4(3) . . ? N4 C8 C9 107.3(2) . . ? N4 C8 H8A 110.3 . . ? C9 C8 H8A 110.3 . . ? N4 C8 H8B 110.3 . . ? C9 C8 H8B 110.3 . . ? H8A C8 H8B 108.5 . . ? N5 C9 C8 110.9(2) . . ? N5 C9 H9A 109.5 . . ? C8 C9 H9A 109.5 . . ? N5 C9 H9B 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 108.1 . . ? N4 C10 C11 107.9(2) . . ? N4 C10 H10A 110.1 . . ? C11 C10 H10A 110.1 . . ? N4 C10 H10B 110.1 . . ? C11 C10 H10B 110.1 . . ? H10A C10 H10B 108.4 . . ? N5 C11 C10 111.6(2) . . ? N5 C11 H11A 109.3 . . ? C10 C11 H11A 109.3 . . ? N5 C11 H11B 109.3 . . ? C10 C11 H11B 109.3 . . ? H11A C11 H11B 108.0 . . ? N4 C12 C13 107.6(2) . . ? N4 C12 H12A 110.2 . . ? C13 C12 H12A 110.2 . . ? N4 C12 H12B 110.2 . . ? C13 C12 H12B 110.2 . . ? H12A C12 H12B 108.5 . . ? N5 C13 C12 111.4(2) . . ? N5 C13 H13A 109.4 . . ? C12 C13 H13A 109.4 . . ? N5 C13 H13B 109.3 . . ? C12 C13 H13B 109.3 . . ? H13A C13 H13B 108.0 . . ? C14 N2 C16 108.5(2) . . ? C14 N2 C18 109.0(2) . . ? C16 N2 C18 108.5(2) . . ? C17 N3 C19 110.4(3) . . ? C17 N3 C15 107.8(3) . . ? C19 N3 C15 109.8(2) . . ? C17 N3 H30 117.2(18) . . ? C19 N3 H30 105.0(18) . . ? C15 N3 H30 106.4(18) . . ? C10 N4 C8 110.7(2) . . ? C10 N4 C12 110.1(2) . . ? C8 N4 C12 108.0(2) . . ? C10 N4 H40 110.3(16) . . ? C8 N4 H40 106.0(16) . . ? C12 N4 H40 111.7(16) . . ? C11 N5 C13 110.6(2) . . ? C11 N5 C9 107.7(2) . . ? C13 N5 C9 107.4(2) . . ? N2 C14 C15 111.6(2) . . ? N2 C14 H14A 109.3 . . ? C15 C14 H14A 109.3 . . ? N2 C14 H14B 109.3 . . ? C15 C14 H14B 109.3 . . ? H14A C14 H14B 108.0 . . ? C14 C15 N3 109.0(2) . . ? C14 C15 H15A 109.9 . . ? N3 C15 H15A 109.9 . . ? C14 C15 H15B 109.9 . . ? N3 C15 H15B 109.9 . . ? H15A C15 H15B 108.3 . . ? N2 C16 C17 110.5(2) . . ? N2 C16 H16A 109.6 . . ? C17 C16 H16A 109.6 . . ? N2 C16 H16B 109.6 . . ? C17 C16 H16B 109.5 . . ? H16A C16 H16B 108.1 . . ? N3 C17 C16 107.7(2) . . ? N3 C17 H17A 110.2 . . ? C16 C17 H17A 110.2 . . ? N3 C17 H17B 110.2 . . ? C16 C17 H17B 110.2 . . ? H17A C17 H17B 108.5 . . ? N2 C18 C19 110.90(19) . . ? N2 C18 H18A 109.5 . . ? C19 C18 H18A 109.5 . . ? N2 C18 H18B 109.5 . . ? C19 C18 H18B 109.5 . . ? H18A C18 H18B 108.0 . . ? N3 C19 C18 108.0(2) . . ? N3 C19 H19A 110.1 . . ? C18 C19 H19A 110.1 . . ? N3 C19 H19B 110.1 . . ? C18 C19 H19B 110.1 . . ? H19A C19 H19B 108.4 . . ? H50 O5 H51 89(4) . . ? H60 O6 H61 76(3) . . ? _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.378 _refine_diff_density_min -0.298 _refine_diff_density_rms 0.044